Vacation Rentals By Owner In Gloucester, MA

Just steps to Long Beach, or a 10 minute walk to Good Harbor Beach, enjoy this clean, modern new single family home with views of Long Beach. Take in breathtaking sunrises and sunsets from the upper deck, living room or master bedroom all overlooking views of the beach. In Summer season, there is an outdoor patio and grill, and enclosed outdoor shower. The house also comes equipped with beach chairs, beach cart, and umbrella, and beach toys!brThere are 4 floors of living space with master suite and a guest bedroom on 2 nd floor. All bedrooms have private bathrooms. On the top floor there are twin over double bunks which lead out to a spacious upper deck with outdoor seating overlooking Long Beach. There is a downstairs family/ entertainment room that serves as a 4th bedroom with a tv, bathroom, and additional kitchen.

Spacious Modern Beach House- Steps to Long Beach and Good Harbor

Gloucester, Massachusetts, United States

Bed

Bath

10

Sleeps

$1569.85

☀ Sleeps up to 19 guestsbr☀Plenty of driveway parkingbr☀ Prime location on the Back Shore ~ 1 mile or 5min drive to Good Harbor Beach - beach gear included!br☀ Private pickleball and/or tennis courtbr☀ Ocean views on 3rd floor br☀ Sprawling lawn+multiple decks to enjoy ocean breezes br☀ Private au-pair suite perfect for an additional familybr☀ Family friendly amenities included - toys, pack and play, boosterbr☀ Multiple living spaces to gather on first floorbr☀ Hi-Speed WiFi and Smart TVs throughout brbrWelcome to Bell View, a spacious, family‑friendly coastal getaway in Gloucester — just a five minute walk from the sparkling Atlantic and the beauty of the rocky coastline known as Bass Rocks. brWelcome to Bell View, a spacious family home tucked away in Gloucester's coveted Back Shore neighborhood. This almost 5000 sq ft home was carefully crafted for groups to enjoy the 2 acres of rare space in this seaside community. Enjoy no shortage of living spaces from sun room, game room, to formal living and dining rooms. A private in-law suite with kitchenette makes this the perfect spot for groups looking for their own space. Conveniently just minutes to Rocky Neck, Bass Rocks Golf Club, and Good Harbor Beach. Perfect for families, friends, and groups, this home blends seaside New England charm with comfort and fun.brbr5 Min Drive to Good Harborbr5-10 Min Drive to Gloucester's Main Street (Beauport Hotel, Cruiseport, etc)br30 Min Drive to SalembrbrExperience Bell View With Us & Learn More Below!brbr☆☆ FIRST IMPRESSION ☆☆brNestled in the quant neighborhood of East Gloucester you'll pass Rocky Neck art colony on your way into this quiet street. The long driveway provides plenty of privacy as well as parking for multiple cars. brbr☆☆ FIRST FLOOR ☆☆brInside, a one-of-a-kind waterfront scene, hand painted along the staircase by a local artist, greets you as you enter via the formal foyer. Pick your hangout spot from two comfortable living rooms, a game room with a ping-pong table, the sunroom, the cheerful and well equipped kitchen, the umbrellaed patio, or the multiple decks and porches. brbr☆☆ SECOND FLOOR☆☆brHead upstairs and you'll find a common full bathroom as well as a bedroom with 2 full beds and a bunkbed room. This floor also boasts 2 king suites each with en-suite bathrooms. One of these suites features a desk for remote work and the other has convenient laundry machines in the bathroom as well as a private balcony.brbr☆☆ THIRD FLOOR ☆☆brThis bonus loft style floor is perfect for kids! Carpeting throughout makes it a safe place to play and there's plenty of room and toys to spread out. Four twin beds are comfortable for kids or adult guests! This floor also gets amazing ocean views. brbr☆☆ PRIVATE SUITE ☆☆brThe in-law suite is located on the east wing of the house. Head up stairs to a cozy apartment - the perfect place for a family or couple to have their our private space! A sofa bed also pulls out to a full sized mattress to sleep 1 or 2 additional guests. A bistro set and kitchenette gives you the option of to have some nights in to yourself. Unwind in front of the smart TV or enjoy your own private balcony after a day of north shore exploring!brbr☆☆ OUTSIDE ☆☆brSet on a spacious lot with plenty of level lawn space, Bell View also boasts a tennis court with equipment to double as a pickleball court. The shed is contains all kinds of sports equipment and outdoor toys - perfect for guests of all ages. In addition, a slate patio in front and a wraparound deck in the back are delightful spots to gather and relax.brbrBell View is just a stone's throw from Bass Rocks on Gloucester's Back Shore where you can enjoy looking out at the scenic surf or a leisurely walk listening to the sounds of waves. It's about a mile to Niles Beach and 2 miles from the white sands and surf of Good Harbor Beach. The home is also about a mile to Rocky Neck, the oldest art colony in the U.S. and home to many galleries, shops and great restaurants.brbr★☆ Book Today & Let Us Take Care Of You at Bell View! ☆★ brbrYou'll have access to the entire property and grounds except the garage. brPlease remember that you're staying in a house, not a hotel. Treat the space with respect. If any problems arise, we will do our best to take action ASAP. brbrI am here for you during your stay, but our level of interaction is up to you. I'm only a phone call/message away. brbr• Check-in is anytime after 4:00 PMbr• Check-out is 11:00 AM or earlierbr• No early check-in or late check outbr• Quiet hours is from 10:00 PM to 8:00 AM

Bell View: Private tennis court and an in-law

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$1113.33

Location, location, location! This vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so close to Cape Ann's most popular beach and also has water views of Bass Rocks.brbrThe front of the house has a full-length porch from which you can view the sea in comfortable shade and enjoy a beverage or meal in the fresh ocean breezes.brbrFrom the porch, enter into the living room with a flat screen TV and plenty of seating. The adjoining den has a pullout sofa, a TV, and games, which makes the room serve double-duty as a kid (or adult) getaway or semi-private additional sleeping space. The recently renovated granite kitchen is eat-in and fully applianced. The butler's pantry offers more storage and prep space in addition to a half bath.brbrUpstairs are 4 bedrooms (3 of which are air conditioned) and two more full baths.The master bath offers an oversized jetted tub, double sinks and a separate glass-enclosed shower and the hall bath also has a full size jetted tub with a shower.brbrThe house will comfortably sleep 10 with enough room for your family and the folks that will want to visit you in this wonderful beach house. Leave your car in the driveway (and avoid the beach parking fees) and walk to Good Harbor Beach.brbrThis dramatic rocky bit of coastline is a destination for those looking for views of the Atlantic at its most intense. The popular Back Shore walk is one of the most scenic walks on the eastern seaboard and the sidewalk begins in front of Seaside House and continues for 1.5 miles one way (or 3 miles round trip back to the house).brbrNote: The house has two other occupied units with separate entrances and parking.brbr2,500 SF. No pets. No smoking. No events or parties.

Seaside House: Walk to Good Harbor Beach

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$454.37

Close to Gloucester's sandy Good Harbor Beach, Joseph's Way is delightful two bedroom property is nestled on a quiet wooded lot on a hidden side street with just 4 other houses.brbrEnjoy the ease of one-level living with a spacious open plan dining/living room which expands to the fully applianced kitchen with breakfast bar, two bedrooms, and a second sitting area that opens to the deck. Dine al fresco on the spacious deck which overlooks a pretty and private wooded lot.brbrMAIN LEVELbrbrLIVING/DINING/KITCHEN: The living area has a couch, chair, and a mounted large flatscreen TV. The dining area has a high-top table with barstools accommodating up to 4, and expands into the well-applianced kitchen with breakfast bar, and beautiful granite counter tops.brbrBEDROOM 1: The room has a Queen bed and TV.brbrBEDROOM 2: This corner room has a Queen bed and TV.brbrDEN: This sitting area has a pullout sofa and TV with access to the back deck and yard.brbrBATH: The full bath has walk-in shower and includes the laundry room.brbrEXTERIORbrbrRelax or dine outdoors on the spacious back deck overlooking the backyard and woods.brbrPARKINGbrbrThere is parking for up to 2 cars in the driveway.

Joseph's Way: Quiet Beach Retreat

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$528.18

Single family house, over one hundred years old, accommodates ten. Three queen beds, one double bed with a trundle, and two sets of bunk beds allow for comfortable sleeping for ten. A large eat-in kitchen and large dining room makes entertaining a delight. brbrThe beach is accessed by crossing a narrow road and a foot bridge over a sandy creek. The house has a first floor wrap around porch, and a second floor veranda that overlook the beach. brbrFour bedrooms and the kitchen have a ceiling fan.Towels and bed linens are available in a linen closet off the kitchen. One full bath has an old claw tub for those who enjoy an old fashioned bath. The other full bath has a shower.brbrKeywords: House

Good Harbor Beachfront at the Footbridge

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$383.08

Welcome to our charming 1900's cottage, a hidden gem nestled in the heart of Gloucester's coastal paradise. Completely renovated in 2006, this quaint retreat offers a perfect blend of historic charm and modern luxury, promising an unforgettable getaway for discerning travelers.brbrStep inside and be greeted by the warmth of our meticulously crafted interiors. The full gourmet kitchen, boasting granite counters and stainless steel appliances, invites culinary adventures and memorable meals shared with loved ones. Indulge in relaxation in our spa shower, or ascend the maple spiral stairs to discover a romantic bedroom adorned with three skylights, bathing the space in natural light and creating a dreamy ambiance.brbrOutside, seasonal ocean views await, offering glimpses of the majestic Atlantic that lies just 500 feet away at Plum Cove Beach. Sit back and watch as the sun dips below the horizon, painting the sky in hues of crimson and gold—an experience lauded as one of the world's best by none other than National Geographic.brbrBut the allure of our cottage extends far beyond its walls. As the premier location to begin your exploration of Cape Ann, we offer unrivaled access to Gloucester's rich tapestry of experiences. Immerse yourself in the town's storied New England history, wander through charming streets lined with historic architecture, and discover hidden gems in local art galleries.brbrFor nature enthusiasts, extraordinary beaches beckon, each offering its own unique charm and opportunities for seaside adventures. Embark on thrilling whale watching excursions, where the chance to encounter these majestic creatures up close awaits. Visit iconic lighthouses that stand as beacons of hope along the rugged coastline, or embark on enchanting fall foliage tours that showcase the area's natural beauty in all its splendor.brbrAnd let's not forget about Gloucester's culinary scene, where fresh seafood reigns supreme. Indulge in the catch of the day at renowned seafood restaurants, savoring every bite of lobster, scallops, and more.brbrWith so much to see and do, our cottage serves as the perfect home base for your Cape Ann getaway. Whether you're seeking relaxation, adventure, or a bit of both, we invite you to make yourself at home and create memories to last a lifetime. Book your stay with us today and embark on an unforgettable journey into the heart of Gloucester's coastal magic.brbrNeed more space : If you need additional space for your family you can also rent our sister property right next door; a charming colonial 2 bedroom home. See property # 238293 on this website.brbrEven more space required : If you need additional space for your family, you can also rent the property around the corner; a delightful 1860's 3 bedroom home. See property # 133898 on this website.

Cottage

Luxury 1900's romantic retreat steps from the beach - King Suite!

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$475.42

Summary:brbrCharming East Gloucester Home - 15-Minute Walk to Good Harborbrbrbrbr✓ Prime Location – Walk to Good Harbor Beach & local attractionsbrbr✓ Outdoor Retreat – Private fenced yard with trellis + seatingbrbr✓ Peaceful & Convenient – Quiet neighborhood close to dining & maritime landmarksbrbr✓ Room to Gather – Spacious eat-in kitchen + formal dining roombrbrbrbrA charming family escape — book now! Visit @stay_collections on IG for a video property tour!brbrbrbrThe Space:brbr☆☆☆ FIRST FLOOR ☆☆☆brbrbrbr→ Kitchen: Bright, open space with new appliances + eat-in area overlooking the backyardbrbr→ Dining Room: Welcoming, formal dining for memorable shared mealsbrbr→ Living Room: Coastal-inspired with Smart TV — perfect for movie nightsbrbr→ Half Bath: Includes brand-new washer & dryerbrbr→ Outdoor Deck: Lounge seating, trellis, & refreshing outdoor showerbrbrbrbr☆☆☆ SECOND FLOOR ☆☆☆brbrbrbr→ Primary Bedroom: Spacious retreat with plush queen bedbrbr→ Bedroom #2: Nautical-inspired queen roombrbr→ Bedroom #3: Cozy twin bedroom with closet spacebrbr→ Bedroom #4: Twin bed + twin trundle — ideal for kids or extra guestsbrbr→ Bathroom: Full bath with shower/tub combo for relaxing after a beach daybrbrbrbrStay cool during your summer visit! Each of the four upstairs bedrooms is equipped with a dedicated AC window unit. Please note the first floor is typically comfortable but does not have AC.brbrbrbr☆☆☆ EXPERIENCE EAST GLOUCESTER ☆☆☆brbrbrbrThis thoughtfully appointed home blends coastal charm with family-friendly comfort. With multiple gathering spaces, private outdoor seating, and a walkable location near beaches and local attractions, it’s the perfect base for exploring Gloucester.brbrbrbrBook today and make East Gloucester your next getaway!brbrbrbrGuest Access:brbrWe'll send you a key code ahead of check-in for easy access.brbrbrbrThe Neighborhood:brbrNestled in the historic East Gloucester neighborhood, this area is centrally located and is surrounded on three sides by the Atlantic Ocean and offers a perfect mix of charm and convenience. Quiet streets connect you easily to downtown, shopping, dining, beaches, and parks. The neighborhood features classic New England architecture and sits within a historic district that reflects Gloucester’s rich maritime heritage. It’s also close to Rocky Neck, the nation’s oldest working art colony, making it a vibrant hub for culture and creativity.brbrbrbrGetting Around:brbrCentrally located, you can walk (13 minutes) to Good Harbor Beach, quick drives to Rocky Neck, the Back Shore, Niles Beach, downtown and more! If you are looking to venture outside of Cape Ann, we are just a 7-minute drive from the Gloucester train station, making it easy to explore the North Shore or head into Boston.brbrbrbrOther Things to Note:brbrAccessibility Notes: Access to the entrance involves a few steps, and the bedrooms are located upstairs via a staircase.brbrbrbrOnce a booking is confirmed, the following cancellation policy is immediately in effect. Due to automatic platform processing fees, full refunds cannot be issued for same-day cancellations. Cancellations made more than 30 days before check-in are eligible for a 50% refund. Cancellations made within 30 days of the check-in date are non-refundable. No-shows are not eligible for any refund.brbrbrbrInteraction with Guests:brbrWe are here to help! We’re available 24/7 via phone, email, or the booking platform’s app.

Stay at East Gloucester

Gloucester, Massachusetts, United States

Bed

7

Sleeps

Exceptional(18)

$773.77

Enjoy the wooded setting, beautiful gardens and privacy of our family vacation home. Our 4 bedroom, 2 bathroom home includes a large family room, well appointed eat-in kitchen, basement rec room with pool table and queen sofa bed, spacious deck and huge yard. We're a 15 minute drive from two of the most beautiful beaches in New England, Wingaersheek and Good Harbor. Whale watch, deep sea fishing, museums, shops and restaurants in downtown Gloucester are a 10 minute ride.brbrThe large, well stocked eat-in kitchen has both a dining table and an island, a double oven, four burner stovetop, microwave, toaster oven, toaster, coffee maker, dishwasher and kid's dishes. Whether you are an avid cook or prefer to throw something on the grill, you will find everything you need.brbrThe comfortable, vaulted ceiling family room has a Smart TV and is stocked with games and books for adults and children, and has plenty of room to relax. Large windows and sliding glass doors allow the sun to pour in, and provides views of the variety of birds that love the birdbaths and trees that surround the house.brbrYou will want to spend a lot of time on the large deck which is a great place to read a book, have cocktails or a serve a meal. In addition to patio furniture, there is a built-in picnic table that seats 10 and a gas grill. The deck overlooks a beautiful yard with gardens, a Koi pond, a big grassy area to play games on, and our own wiffle ball field. We have cornhole, bocce and other yard games available.brbrThe Primary bedroom has a King bed and large jetted tub. The other three bedrooms have queen beds. All rooms have closets and dressers. There is also a queen sofa bed in the lower level rec roombrbrEnjoy the quiet residential neighborhood. Take a short walk to sunsets on Magnolia Pier, walks on Magnolia Beach, strolls along the ocean on Shore Road and to visit shops and restaurants on Lexington Avenue.brbrIf you want to explore the area, you will have easy access to the historic towns of Salem, Manchester-by-the-Sea, Rockport, Essex, Ipswich and Boston.brbrWe have available for your use plenty of things you'll need for the beach including beach chairs, beach umbrella, cooler bag, kid's beach toys, beach games, boogie boards and plenty of beach towels. Wingaersheek Beach, Good Harbor Beach and Stage Fort Park all allow you to reserve a parking space up to 10 days in advance. Visit the City of Gloucester official website for more information. brbrBedrooms and BathroomsbrThe first floor of the house has two bedrooms and a full bathroom.brbrBedroom 1: Large Primary bedroom has a King bed, closet, dresser and desk for remote work. It also has a large jetted tub to relax in or bathe the kids.brbrBedroom 2: This bedroom has a Queen bed, dresser and closet.brbrBathroom 1: The full bathroom on this floor has double sinks, and a shower with a rainshower head, regular head and removable wand. It also converts to a steamroom.brbrThe walk-out lower level has two bedrooms and a bathroom, a rec room with a pool/ping-pong table and a queen sleeper sofa. There is a TV with a Fire TV Stick so you can log into your accounts, connect a gaming console or attach the DVD player to watch movies.brbrBedroom 3: This bedroom has a Queen bed and dresser/closet wardrobe.brbrBedroom 4: This bedroom has a Queen bed and a dresser and closet.brbrThere is also a queen sleeper sofa in the Rec Room.brbrLinens, blankets, duvets, pillows and towels are provided.br--------------------------------------------------------------------------------------------------------brThere is parking for 3 cars.brbrChildren are welcome but please note that the house and grounds are not childproofed.brbr

Magnolia By The Sea-Attractive home, large yard & deck. Walk to Magnolia Beach

Gloucester, Massachusetts, United States

Bed

Bath

10

Sleeps

$300.45

We want your departure to feel easy and hassle free without a cleaning fee! brbrQuick Glance: brMax Capacity: 2br1 Queen Bedbr2 FloorsbrSmall ApartmentbrCentral Gloucester NeighborhoodbrbrEnjoy 2 floors of living space overlooking the changing tides and natural wildlife of the Green Landing Salt Marsh. This stylish and cozy one bedroom apartment is located on a scenic edge of Central Gloucester, just a short drive to Gloucester’s iconic beaches. Being within easy walking distance to the train station means guests can access Gloucester, as well Rockport, Salem and Boston, with or without a car.brbrThe Apartment at Green Landing is a cozy 1 bedroom, designed to inspire relaxation on your adventure to Gloucester, Cape Ann, or Boston’s North Shore. The apartment is on two floors with scenic views of the Green Landing Salt Marsh. It is accessed through it’s own dedicated entrance and side garden. brbrOutside:brThe cozy garden has enough space for lounging and grilling. br- Seating br- Propane Grill (propane and cooking utensils included)br- Coffee table brbrThe first floor is only one room. It contains the living, dining, and kitchen areas.brbrKitchen Area:brThe kitchen utilizes open shelving and natural wood countertop for a modern and open feel. The kitchen contains most equipment to prepare food. brbr- A glass-top electric stove/oven. br- Microwave br- Toasterbr- Apartment sized fridge/freezerbr- Coffee and Drinks Barbr- Coffee, sugar, tea, filters, sugar substitutes br- Standard coffee makerbr- Tea kettlebr- Dishes, bowls, mugs, glasses, utensils, and simple cooking equipmentbrbrDining Area: br- Table and chairs br- Seats two peoplebrbrLiving Area: br- A couch for twobr- Smart TV with free Roku channels (bring your passwords if you would like to use the other apps or streaming)brbrUpstairs, guests will find one bedroom with views of the Green Landing Salt Marsh and a petite full bathroom. brbrBathroom: br- Small petite-sized full bathroom with shower and tub.br- Towels (indoor only)br- Additional vanity space is available in bedroom.brbrBedroom: br- Window unit A/C (8,000BTU) seasonally approximately May until mid-October. br- Queen bed with high quality 100% cotton beddingbr- Wall mounted USB plug, phone shelf, directional light, and side table on either side of bedbr- Vanity/desk area with mirrorbr- Armoire with ample storage and an enclosed Smart TV br- Closet with hangers, extra bedding br- Clothing iron and ironing boardbr- Floor fanbr- Hair dryerbrbrHassle-Free Check out procedure: brSimply keep the place in a reasonably tidy condition. For the safety of cleaners, do not leave any sharp objects in the sink. Lock up on the way out. Check out by 11:00am.

Apartment

Cozy Apartment at Green Landing - AC - No Cleaning Fee - Hassle Free Check Out

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$563.0

KEY FEATURES:br*4 season sunroom with panoramic ocean viewsbr*Primary loft bedroom with ensuite bath and dedicated work spacebr*Updated and fully equipped kitchenbr*3 spacious bedrooms & 2.5 bathroomsbr* Located lovely LANESVILLE walkable to Lanes Covebr* Private outdoor patio with seating and BBQ grillbr* Comfortable living area with fireplace & Smart TVbr*Washer/dryerbr* Washer and dryerbr*High-speed wifi brbrThe spacebr☆☆UPPER FLOOR☆☆ brStep inside and head up the stairs where you'll feel right at home in the welcoming main open concept living area. The first floor features a comfortable living room with a Smart TV and a cozy and convenient gas fireplace, perfect for relaxing after a day exploring Gloucester. The fully equipped kitchen provides everything you need to prepare meals during your stay, with space to gather and enjoy time together. Choose to enjoy your meals at the breakfast bar, the dining table for 6, or the sunroom! brbrThe sunroom is the gem of this home with panoramic ocean views. It's warm and cozy in the cooler seasons and in the summer enjoy it screened in for ocean breezes. A convenient half bathroom is also located on this level with a smart toilet. This luxurious amenity includes a bidet and heated seat feature!brbrStep into the primary suite and you'll find a queen bed, and plenty of space to unpack and unwind in front of the smart TV. This suite features a dedicated workspace with pristine ocean views. The en-suite bathroom is fully updated with a walk in shower and plenty of space to get ready.brbr☆☆LOWER FLOOR☆☆brHead downstairs to find two more comfortable bedrooms, a full bedroom and a bedroom with 2 twin, offering various options to accommodate families or groups. All bedrooms feature their own smart TV. This floor also includes a full bathroom with shower/tub combo and a laundry room so you can pack light! You'll also find a pack and play and high chair to make traveling with little ones easier. brbr☆☆OUTDOOR SPACE☆☆brStep outside to enjoy the private backyard area with zero gravity chairs to relax and sunbathe. The home also features a BBQ grill and outdoor dining set, making it easy to enjoy outdoor meals during warmer months. In the garage you'll also find beach chairs and toys and lawn games like corn hole and badminton. There's no shortage of summer fun to be had!brbrBook today and let us take care of you at the Lanes Cove Cottage! brbr☆☆HOME AMENITIES☆☆brThe home includes high-speed WiFi, central heating and air conditioning, and a washer and dryer available for guest use. You'll also find thoughtful touches such as a hair dryer, hot water, and safety features including smoke detectors, a carbon monoxide detector, fire extinguisher, and first aid kit to ensure a safe and comfortable stay.brbrGuest accessbrYou'll have access to the entire house and property with the exception of one owner's closet in the downstairs back bedroom. Please remember that you're staying in a house, not a hotel. Please treat the space with respect. If any problems arise, we will do our best to take action ASAP.brbrOther things to notebr• Check-in is anytime after 4:00 PMbr• Check-out is 11:00 AM or earlierbr• No early check-in or late check outbr• Quiet hours is from 10:00 PM to 8:00 AMbrbrWalking/Driving Distance: br• Good Harbor Beach -12 min. drivebr• Downtown Rockport & Train Station to Boston: - 5 min. drivebr• Downtown Gloucester: 15 min. Drive br• Children's Playground - 5 min. walkbr• Lanes Cove - 5 min. walkbr• Plum Cove Beach - 15 min. walk or 3 min. drive (on-street parking only)

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$475.65

VACATION or WORK or do a bit of both if it means you'll have longer to play here on Cape Ann! The preferred spot for all things is the sunroom chaise overlooking the harbor, but there are also two spacious desk areas including one in the living room which can be closed off for privacy while your family enjoys the rest of the house! (Then, of course, go to the beach!) Vaccination preferred, though no longer required. brbrWELCOME brFrom this convenient in-town location enjoy restful refinement while also delighting in being part of the Gloucester experience. This 2800 sq ft, easy-to-live-in home is perched above the sparkling waters of Gloucester's inner harbor. Watch the gulls soar and fishing boats return from the comfort of your enclosed sunporch or adjacent outdoor deck, family room or spacious, fully-equipped kitchen. Or fire up some tasty burgers on our new gas grill on the patio overlooking the garden. brbrWalk an easy five to ten minutes to great restaurants, our favorite whale watch boat, schooner sailing, harbor water shuttle, fun and funky shops, and maritime and art museums. In a five minute drive, you can also be at Good Harbor Beach, Niles Beach, Rocky Neck Art Colony or the commuter rail to Boston.brbrWith a peaceful décor and open floor plan, guests tell us this is an especially comfortable place to call home. On the main floor, all overlooking Gloucester's inner harbor are the sunroom, adjacent outdoor porch, family room and fully-equipped kitchen; plus there are a half bath, formal dining room and living room with a baby grand piano. Upstairs are three bedrooms, two full baths, and laundry. The master bedroom with en suite bath overlooks the inner harbor and has a king bed, reading chairs and desk area. Your other two bedrooms include one with a queen bed, and one with two twins. These rooms share the adjacent hall bath with double vanity sinks. Ceiling vented, room-controlled Air Conditioning and ceiling fans in all bedrooms. Family Room/Kitchen area also has a ceiling fan and split AC/Heat unit for any unusually hot days. brbrBASIC DETAILSbrWhen you arrive, on the kitchen island you’ll find a garage door opener, extra keys, house and travel directions (including wifi code); a list of favorite restaurants, activities, and links to explore local events, plus brochures for fun activities around town and in Boston.brbrFAMILY ROOMbrEnjoy wireless internet, a 55 flat-screen Smart TV in the family room, books and games, Bose wireless speakers to listen to your favorite music from your phone or computer. Smart TV is loaded with Netflix and Amazon Prime free videos and music. Or load your subscription streaming services. (Be sure to log out when you depart.)brbrKITCHEN & DININGbrOur kitchen is well-equipped so it's easy to 'eat-in' if you wish. brSeating for four on the kitchen island; seating for six in the dining room. Lovely linens, dishes, silver, glassware...brYou are welcome to use the spices you'll find in the kitchen. brThere's also a Weber gas grill on the patio in the back yard - available early Spring thru late Fall.brbrGARAGE & PARKINGbrThe garage under the house holds two carefully parked medium-sized cars or one larger car. There is also easy, free, on-street parking on Friend St. Beach equipment is in the garage for you. (Beach chairs, 2 kid chairs, coolers, toys and pails, noodles, boogie boards for the kids.) Beach towels are in the linen closet upstairs. brbrTELL US ABOUT YOU!brWhen inquiring please tell me something about yourself, what brings you to Gloucester, and what you love to do. It will help me know you a bit better and it also helps me have some sense of the kinds of activities I might recommend for you while visiting. About a week before your reservation I'll send you a welcome note with Arrival Tips (address, unloading, parking . . . ) plus highlights of Special Events happening while you are with us. Nice people of all races, cultures, faiths, sexual preference and political views are welcome here. brbrCHECK-IN & DEPARTURE: Check-in any time after 3PM / Check-out by 11 AM. brbrRESERVATIONS & PAYMENT: Available online via VRBO. They will add a 4-9% service fee to your rental fee. 25% of fees are due at time of reservation. Balance due 60 days prior to arrival. VRBO will send you payment reminders. brbrLIABILITY & DAMAGES: You agree that the homeowner is not responsible for any accident, injury or illness that occurs to you or anyone in your party. Only guests or visitors agreed to at the time of your making the reservation are to be on the property. No parties without approval prior to reservation. Any visitors are solely your responsibility. You also agree that you are solely responsible for the safekeeping of your personal belongings. In the unusual event of any damage you cause, you agree to pay for the entire repair. brbrWE ARE HERE TO HELP: I’m happy to answer any questions you may have and to help you in any way prior to or during your visit to assure your stay is most enjoyable. Be in touch any time. brbrWINTER VISITORS: Please be aware that we have a petite well-behaved seal point Birman cat who lives with us here typically January/February, though our home is available for guests throughout the entire year. (When guests are here we live in Rockport, the town next door. )You'll find the house super clean, but if you have severe cat allergies, please be aware of this and do what works for you.brbrWelcome to Gloucester!

WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC

Gloucester, Massachusetts, United States

Bed

Bath

6

Sleeps

$461.57

Relax on the Deck | Peaceful Surroundings | Great Location Near Train StationbrbrSeeking a coastal adventure in New England You’ll love this charming Gloucester vacation rental! With easy access to beaches, eateries, and shops, this home is perfect for families looking to explore the best of the city. Catch some rays at Half Moon Beach or check out the Hammond Castle Museum. As evening falls, return home to unwind and enjoy a movie night. Your next seaside getaway awaits!brbr-- THE PROPERTY --brbrC0514521070brbrSLEEPING ARRANGEMENTbr- Bedroom 1: 1 king bed br- Bedroom 2: 1 queen bedbr- Bonus Room: 1 twin bunk bedbrbrMAIN FEATURESbr- 2 Smart TVs, 2 living spacesbr- 6-person dining tablebr- Private yardbr- Fireplace (decorative only)brbrKITCHENbr- Cooking basics, refrigerator, stove/oven, microwave, dishwasherbr- Coffee maker, toasterbrbrGENERALbr- Free WiFibr- Central A/Cbr- Linens/towels, in-unit washer/dryer (small loads only)br- Hair dryer, hangers, complimentary toiletriesbrbrFAQbr- 3 exterior security cameras (facing out)br- Infant supplies not providedbr- Not child-proofedbrbrACCESSIBILITYbr- Single-story, 4 steps required to enterbr- 1 interior step to access the family roombrbrPARKINGbr- Driveway (3 vehicles)brbr-- THE LOCATION --brbr- Easy access to Half Moon Beachbr- 1 mile to Gloucester Fisherman's Memorial & Stage Fort Parkbr- 2 miles to Maritime Gloucester Museum, Cape Ann Museum & Gloucester HarborWalkbr- 3-4 miles to Ravenswood Park & Mount Ann Parkbr- 5 miles to Good Harbor Beach & Wingaersheek Beachbr- 8 miles to Halibut Point State Parkbr- 36 miles to Boston Logan International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story property requires 4 steps to enter and 1 interior step to access the family roombr- The fireplace is decorative only and not for guest usebr- Although the property welcomes children, parents should note that the home is not childproof and not equipped for infants. Children should always be supervised by responsible adults on our property to ensure their safety. If you require further information, kindly contact the Guest Contactbr- While the property has a washer/dryer combo, it is only suitable for small loadsbr- Your safety matters. The property features 3 exterior security cameras: camera 1 is located on the front door and faces the driveway, camera 2 is located above the garage facing the driveway, and camera 3 is located on the side of the garage and faces the garbage cans. The cameras do not look into any interior spaces. The cameras record video and sound when motion is detected

1 Mi to Beach! Family Gloucester Gem w/ Yard

Gloucester, Massachusetts, United States

Bed

Bath

6

Sleeps

$489.45

- Sunny and cheerful home with direct views of harbor, boating activity & glorious sunsets from your private deck & living spacebr- 1 mile to all the attractions of Downtown Gloucesterbr- Located in the quaint East Gloucester neighborhood walking distance to Rocky Neck art galleries and restaurantsbr- 1 mile to either Good Harbor Beach OR Niles Beachbr- Hi-speed WiFibr- 2 off street parking spotsbr- Free washer/dryerbr- Fully equipped + stocked kitchenbrbrThe spacebrRare opportunity to experience an authentic Gloucester vacation right on the harbor! Conveniently pull into the 2 provided parking spots and step up to your front deck overlooking the specular harborside. Upon entering the recently updated duplex you'll immediately be greeted by all the light and bright coastal colors and details.brbrOn the first floor you'll find a newly renovated and fully equipped kitchen complete with stainless appliances and complementary coffee and tea. Head into a comfortable living room with pull-out sofa and large smart TV. The first floor also has a full bathroom which conveniently includes a washer and dryer. perfect. The first floor bedroom is furnished with its own smart TV and cozy bay window sitting area.brbrHead up the stairs and you'll find 2 more coastal style bedrooms with queen beds. This floor also boasts a large bathroom with double vanity, shower, and separate whirlpool tub. In the backyard you'll find a lovingly cared for lawn with gardens and private deck for al fresco dining & summer grilling.brbrOther things to notebr• This is a duplex but you will have hour own fenced in backyard with private patiobr• The home is very quiet but there is a busy road outside so parents should stay attentive of children when enteringbr• Quiet hours are from 10:00 PM to 8:00 AM

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$323.74

Annisquam Bridge House-a renovated second floor unit high above Lobster Cove, Perfect getaway for a couple. It can accommodate up to 4 guests. Not suitable for young children. Water views, amazing sunsets! Blow up location map to see exact location. Unit features a recently renovated open living space with 2 bedrooms. Master bedroom has a new KING bed, second bedroom has a queen. New comfy mattresses, 100% cotton sheets, sound machines in bedrooms. Central AC throughout. Kitchen, living and dining area all overlook beautiful Lobster Cove and the Annisquam footbridge. Small deck overlooking the cove. Washer/Dryer in basement. Beach towels, chairs and small cooler provided. Just a few minutes walk to the village of Annisquam over the footbridge and to stunning Lighthouse Beach. Swim/Kayak outside your door off the public dock, walk to Lighthouse beach, kayak to Wingaersheek beach. brBring your boat, slips available within walking distance through Dockwa. Rentals in July and August limited to a minimum of 5 days. Book your vacation now, so much to do... boating, whale watching, fishing, swimming at breathtaking beaches or jumping off the bridge and swimming laps in Lobster Cove right outside your door. Enjoy sea kayaking, biking, hiking, a vibrant art and music community and not to be missed sunsets over Ipswich Bay. Minutes to Rockport, and easily accessible by commuter rail from Boston. Boston & Salem MA -- less than an hour away.brA short 10 minute drive will put you into downtown Gloucester where you will find an array of fine dining options and music venues as well as Main Street which boasts dozens of shops and boutiques. If history is your thing, be sure to visit the Cape Ann Museum and the Gloucester Maritime Museum, both located in downtown Gloucester. Take a stroll along beautiful Stacy Boulevard where you will view the Outer Harbor and the open ocean beyond. See the historic Gloucester Fisherman Statue, which memorializes they who have gone down to the bottom of the sea in ships. Continue down the boulevard and cross the historic Cut Bridge where you'll find Stage Fort Park-- a scenic outcropping with incredible views of not only Gloucester water line but on a clear day of the Boston skyline.brWe are a short 8 minute walk across the historic pedestrian bridge to magnificent Lighthouse Beach, and less that a 5 minute walk to the Market Restaurant in the village of Annisquam and the Annisquam Yacht Club. The unit it is perfect for one or two couples or a small family. There is parking for one car only. Additional street parking is available.

Apartment

VIEWS! Annisquam Bridge House at Lobster Cove. Booking Spring and Summer.

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$306.0

Relax at Captain’s Lookout, a charming harbor-view townhouse apartment on Gloucester’s historic Rocky Neck. Enjoy spectacular water views from the rooftop deck, sea breezes, and walkable access to beaches, galleries, restaurants, and live music. This cozy coastal retreat features three outdoor spaces, a queen Tempur-Pedic bed, strong WiFi, private parking, and easy access to scenic Wonson Cove for kayaking and paddleboarding.brbrThe SpacebrbrThis bright loft-style apartment features an open-concept living, dining, and kitchen area on the first floor, with a private upstairs bedroom and adjoining bath.brbrEnjoy water views from every level:br• Rooftop deck with spectacular water views, outdoor dining table and seating for four — perfect for cocktails, dinner, or stargazingbr• Private “coffee deck” off the bedroombr• Ground-floor deck off the living area with outdoor table and seating for fourbrbrSleeping Arrangementsbr• Upstairs bedroom with queen Tempur-Pedic mattress and adjoining bathroombr• Queen sleeper sofa in the living roombrbrPlease note that the upstairs bathroom is accessed through the bedroom, making the space best suited for couples or close friends rather than multiple couples or families with young children.brbrAmenities Includebr• Quality linens and blackout shadesbr• Samsung 34 Smart TV with streaming access for your favorite servicesbr• Keurig coffee makerbr• Strong WiFibr• Beach chairsbr• Private parking for one vehiclebr• Central air conditioning and heatbr• Ceiling fan and natural ocean breezesbr• Gas grillbr• Guest information book with local recommendationsbrbrNeighborhood Highlightsbr• A short walk to a small swimmable beachbr• Small public launch area approximately 130 feet from the house for SUPs, kayaks, and canoesbr• Easy access to scenic Wonson Cove, a peaceful and fun part of Gloucester HarborbrbrWonson Cove is tidal, creating a unique coastal experience. At low tide you can walk out onto the flats, while mid-to-high tide is ideal for launching kayaks, canoes, and paddleboards.brbr• Walkable restaurants, galleries, and live music on Rocky Neckbr• Nearby theater company and cultural events throughout Gloucester and Cape AnnbrbrGloucester and nearby Rockport offer whale watches, sailing excursions, beaches, hiking, art galleries, live music, and coastal New England charm throughout the summer season. Guests can explore Bearskin Neck, Halibut Point State Park, the Shalin Liu Performance Center, and seasonal events including Saint Peter’s Fiesta and the Gloucester Schooner Festival.brbrParkingbr• One private off-street parking space includedbr• Due to the narrow layout of this historic waterfront neighborhood, additional parking is not available directly on the street near the propertybr• Additional vehicles may park nearby on adjacent streets or in the free municipal parking lot approximately a 4-minute walk awaybrbrLaundrybr• The basement and laundry area are not part of the standard rental spacebr• Laundry access may be available for guests staying one week or longer upon requestbr• A nearby laundromat is located approximately ½ mile away (about a 3-minute drive)brbrAvailabilitybr• 4-night minimum for weekendsbr• 2-night minimum during weekdaysbr• Weekly rentals available at discounted ratesbr• Available June 6 through October 31

Captain’s Lookout with Harbor Views & Roof Deck

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$1313.7

Let us host your Micro-Wedding this summer! PRIME LOCATION IN GLOUCESTER WITH WATER VIEWS & EVENT-FRIENDLY YARD! A 5-bedroom, 3-bath charming coastal home perfectly positioned in the heart of Gloucester for unforgettable summer stays. With spacious rooms, warm character, and plenty of room for families or wedding groups, it’s the ideal home base for a week of celebration, relaxation and seaside adventure. Steps from beaches, tennis courts, Stacy Boulevard, downtown shops and restaurants! Let us host your authentic Gloucester experience!brbr-Large backyard for photosbr- Expansive deck for rehearsal cocktailsbr- Multiple bathrooms for getting readybr- Walk-able to harbor and restaurantsbr- Parking for several carsbr-Classic New England architecturebrbr* Minutes from The Beauport Hotelbr* Steps from hidden gem Half Moon Beach, Crab Beach, Pavillion Beach, Tennis Courts, Bocce Ball, Stage Fort Park, Stacy Boulevard, Mile Marker One, Cape Ann Marina, Gloucester Cinema, Train stationbr* Prime locations for all things Gloucester!brbr**please reach out to host to customize your authentic Gloucester experience!brbr***First Floor***brbr**Primary bedroom with handicap accessible shower br-Living Roombr-Dining Roombr-Kitchenbr-Officebr-Laundrybr-Deckbrbr***Second Floor***br-Bedroom #2: Queen with full bathbr-Bedroom #3: Full , Crib br-Bedroom #4: 2 Fullbr-Bedroom #5 : Queenbr-Full BathroombrbrBasementbr-Barbr-Loungebr-PlayroombrbrOutdoor Spacebr-Furnished Deck, expansive private yard, parking for 4 vehicles, additional parking available by requestbrbr*6/20-6/21–Battle of Gloucester Reenactment (Stage Fort Park)brbr*6/24-6/28–St. Peter’s Fiesta/Greasy Polebrbr*7/3–Fishtown Horribles Parade/Fireworks (Watch fireworks from the front yard!)brbr*7/11–Block Party Downtownbrbr*7/18–Blackburn Brew Festbrbr*7/21-7/23–Bluefin Blowout (Mile Marker One)brbr*8/9–Blues Festival (Stage Fort Park)brbr*8/15-8/16–Gloucester’s Waterfront Festivalbrbr*9/3-9/6–Schooner Fest brbr*Sundays—Live Bands At the Gazebo (Stage Fort Park)br*Mondays—Magnolia Farmer’s Marketbr*Wednesdays—Harbor Walk Outdoor Moviesbr*Thursdays—Farmers Market (Stage Fort Park), Harbor Loop Outdoor Concerts

NEW 5 BEDROOM-PRIME LOCATION IN GLOUCESTER WITH EVENT SPACE AVAILABLE

Gloucester, Massachusetts, United States

5

Bed

Bath

12

Sleeps

$772.67

New for 2026! Stroll to Long Beach or Good Harbor Beach, or simply relax on the large deck. Nestled between the two beaches, it's just a few hundred yards from Long Beach, with Dairy Maid, serving ice cream and sandwiches, just around the corner.brbrThis inviting coastal home offers an ideal blend of comfort, space, and proximity to the area’s most beloved beaches. Inside, you’ll find a bright and modern open-concept kitchen, living, and dining area, perfect for gathering after a day at the beach. The fully air conditioned house has three bedrooms all thoughtfully arranged for restful stays.brbrA cozy den provides additional living space with a futon, TV, and sliding doors that lead directly to the deck. The deck and large yard are true highlights, offering ample seating for outdoor dining and relaxation. The basement includes a sectional sofa, a desk and a half bathroom. Below the deck, there's a large fully enclosed outdoor shower.brbrWith multiple living spaces, excellent outdoor amenities, and unbeatable beach access, this beach retreat is perfectly suited for families and groups looking to enjoy a classic coastal getaway.brbrNo Smoking. No Events or Parties.

Life on Deck - Spacious Coastal Home & Easy Beach Access

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$578.48

This quiet summer cottage was built in the 1890's, its original charm has been retained, while updates have made it a comfortable, easy home to vacation in. The house faces west, providing the most amazing sunsets over Ipswich Bay every evening.brbrA 4 bedroom summer cottage with beautiful water views from every room. The eat-in kitchen has an induction stove, microwave, refrigerator, toaster, coffee maker, and dishwasher. Off the kitchen is a small porch, there is a Weber grill for charcoal grilling available. brbrThere is a comfortable living room with smart TV, an inside porch with a cozy daybed, and a dining area that leads outside to a huge wrap-around porch overlooking Ipswich Bay. The porch has a 2 big round tables, lots of nice teak chairs and side tables.brbrUpstairs there are 4 bedrooms and 1 full bath: brAll beds have new luxury mattresses (Saatva), and linens.br3 queen bedroomsbr1 king bedroombrAll rooms have water views, including the bathroom.brbrThere is a 1/2 bath off the kitchen and an outdoor hot water shower under the porch with an ocean view, alongside a very comfy hammock!brbrPlease be aware that this is an old cottage. It is not wheelchair accessible, and has different levels within the house. Also please be aware that this is a private home owned by my elderly mother who uses the property regularly. She is extremely allergic to animals, where reactions are extreme and debilitating at her age. Please understand the house is not suitable for a service or emotional support animal. Thanks for your understanding. brbrThere is good, strong wifi in the whole house and yard.brbrGuests have access to the entire house except for the attic, inner cellar and the upstairs back closet.brPlease observe the condition of the house at the beginning of your stay, if there is anything out of order let us know right away. We thank you very much for leaving the cottage as it was when you arrived. brbrMost nights get cooled down by ocean breezes, but if you do need the air conditioning , we appreciate that you only run it when needed. There are often drought conditions in the summer months, so please be careful with your water use when possible. brThere is an additional refrigerator in the basement you are free to use, as well as the washer and dryer. Please take advantage of the breeze and the sun and hang your clothes outside, they will smell amazing! If you do use the dryer, please be sure to clean the lint trap.brbrAlso in the basement are floaties, coolers & beach chairs, lawn games, fishing and snorkeling things... help yourself, just be sure to rinse anything you use with fresh water, and return them in good condition please.brbrBe very careful on the rocks they can very slippery at low tide and may be tippy, please watch and accompany small children at all times. Also be careful along the edge where the grass and the rocks meet, there has been erosion over the years and can be steep in spots. This being said, we swam and boated off these rocks our whole lives, at high tide there is a great pool area that fills up, the water is warmed by the rocks, it is perfect for kids or just for floating :)brbrFeel free to use any of the pantry foods, spices, condiments, etc. We are careful to dispose of anything old or stale, so anything that is here is still good stuff, please use it! This is an extremely well stocked kitchen, there is everything you could possibly need to prepare and serve any meal. There will be toilet paper, paper towels, trash bags, laundry & dish soap to start you off, there is a Market Basket right off the rotary at route 128 for anything you may need. It's ok to leave behind any food or drink items that are sealed and in good condition, please dispose of anything else.brbrKitchen trash bags can go into the big barrels in the basement. Please be sure to keep the basement door closed, as raccoons and bats can get into the house if left open! There are several recycling bins in the basement; please recycle cardboard & newspaper in one, and empty cans, bottles, and plastic in the other.brbrBefore checking out:br-Please strip all beds, stuff the dirty sheets from each bed used bed in to one of the pillow cases, and leave with all dirty towels on the laundry table in the basementbr-Please do all dishes and run the dishwasher before leavingbrbrThank you so much and enjoy your stay!

Cottage

Summer Cottage on Ipswich Bay

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$439.77

New to New England Come stay at this peaceful, central, ground-level suite in downtown Gloucester! Enjoy walks to historic locations, public transit, as well as beaches, restaurants, and stores! Just an hour commute away from Boston, consider this as your new vacation home!

Apartment

Glorious Suite near Downtown with washer/dryer

Gloucester, Massachusetts, United States

Bed

Bath