Vacation Home Rentals By Owner In Gloucester, MA

Home DeepCleaned w Ozone.brbrNewly available on VRBO! I have a 5 star rating and many reviews on AirBnB. Book now to plan a spectacular Gloucester stay this summer on Cape Ann & enjoy our festive activities. From the private house you have a beautiful walk in to local beaches & Gloucester center; restaurants, museums, galleries & boutiques, sailing charters, rent power boat, whale watch, historic landmarks, seaside restaurants & also ocean front tennis, boce ball and so much more! This place is a happy haven! ♡brbrHouse is built with 2 separate levels. Guests have access to the main house via provided electronic keyless door code for ease of 24 hour check in and check out. The upper yard with two private entrances, outdoor seating areas, and the entire 60 foot upper level deck on the water front side. Owners maintain locked-off attick and basement studio on the lower level with a separate private locked entrance on it's own level. Guests will have completely private access to the main house and all amenities with the benefit of the upper level views to the harbor & private garden. Enjoy.brbr*Home Deep Cleaned, Ozonedbr*Pro cleaning team brbrI, the owner live in the studio and am available for the prearranged check-in phone call / walk through. Please text or call if you need anything or have questions, otherwise I may not see you.brbrThank you for looking at rules & inquire for correct number of guests, as this will directly affect the price.Please look through my entire listing before you book! It explains a-la-carte pricing, rules & suggestions for your best experience and local treats. There are so many. Plus reviews give a better perspective as to what the property is like and me as your host. Thank you!brbrWe are very lucky to be in this private enclave, so close to the beach, harbor, two spectacular parks and town with fantastic neighbors! The house is located on short private road with only a few other houses on the street. The other houses are set further back up the hill away from the harbor offering you plenty of privacy. Please respect neighborly etiquette.brThank you.Parking is available for two specified cars in the driveway. More with written permission and only in the driveway. brbrThe Beach and Park are just across the street so you can walk in for free. All beaches have now resident daily fees $15-30 daily fee. In peak season (June - September) I now recommend to reserve/pre pay, or to go early to be able to park.brbrFor getting around without a car and if you don't want to walk, paddle, bike, motorboat, water taxi (from town) or drive; check out the shuttle service from the park (museum hours) or the CATA (Cape Ann Transportation Authority) shuttle, the MBTA train (Line from Boston is less than 1 hour and continues on to Rockport 8 minutes) or Taxi (they are both very reliable). Uber/Lyft is great from Boston/ Logan international airport but is Not reliable within Gloucester / Cape Ann area.

Beautiful Harbor View Walk to Beach 3b2bKings4beds

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$1294.28

Nestled in a private section of Wingaersheek Beach, this bright Gloucester vacation rental home is a tranquil escape for your upcoming ocean getaway. Offering 5 bedrooms, 2 bathrooms, and 2,500 square feet of beautifully appointed living space, this magnificent residence is perfect for families or a group of friends out for a rejuvenating beach retreat. Sip coffee by the wood-burning stove each morning, followed by a relaxing walk to the beach for a sun-filled day along the shore!brbr-- THE PROPERTY --brbrMassachusetts Tax ID: C0836064320 | Open Layout | Interior Coastal Views | Access to Coffins BeachbrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: Twin Bed w/ Twin Trundle | Living Room: Sleeper SofabrbrINDOOR LIVING: Open concept, wall-to-wall windows, skylights, modern furnishings, formal dining table, 2 living rooms, wood-burning stove, multiple cable TVs, surround sound, Sonos music system, ample natural light, contemporary decor, unique fixtures, pop of colorbrOUTDOOR LIVING: Wraparound porch, ocean views, river & dunes views, private beach accessbrKITCHEN: Fully equipped, top-of-the-line appliances, stainless steel finishes, large kitchen island, dual ovens, 2 dishwashers, drip & single-service Keurig coffee makers, cooking basics, dishware & flatwarebrGENERAL: Free WiFi, linens/towels, air conditioning, first aid kit, hairdryer, in-unit washer & dryerbrFAQ: Access only by stairs, 1 external security camera (facing out)brPARKING: Driveway (5-6 vehicles)brbr-- THE LOCATION --brbrSUN + SEA: Wingaersheek Beach (350 yards away), Clammer's Beach (5.4 miles), Half Moon Beach (5.8 miles), Cressy Beach (5.9 miles), Good Harbor Beach (6.9 miles), Plum Cove Beach (8.1 miles), Singing Beach (8.3 miles), Front Beach (9.1 miles) brGET OUTSIDE: Tompson Street Reservation (3.5 miles), Cape Ann SUP (5.3 miles), Dogtown Commons (7.5 miles), Essex River Cruises & Charters (7.6 miles), Ravenswood Park (7.8 miles), Cape Ann Whale Watch (8.1 miles), Cape Ann Golf Course (8.6 miles), North Shore Kayak Outdoor Center (11.4 miles), Halibut Point State Park (12.3 miles)brPOINTS OF INTEREST: Gloucester HarborWalk (5.2 miles), Cape Ann Museum (5.2 miles), Gloucester Fisherman's Wives Memorial (5.4 miles), Gloucester Crossing (5.6 miles), Maritime Gloucester (5.6 miles), Hammond Castle Museum (7.5 miles), Annisquam Lighthouse (7.9 miles), Eastern Point Lighthouse (9.1 miles), Rockport Music-Shalin Liu Performance Center (9.2 miles), Castle Hill on the Crane Estate (13.2 miles) brDAY TRIPS: Rockport (9.0 miles), Salem (16.3 miles), Boston (38.8 miles), Plymouth Rock (78.3 miles)brFARMERS MARKETS: Annisquam Farmers Market (1.8 miles), Cape Ann Farmers Market (5.8 miles), Magnolia Farmers Market (6.4 miles)brAIRPORT: Boston Logan International Airport (34.4 miles)brbr-- 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- The property requires stairs to accessbr- Your safety matters. This property features 1 exterior security camera located on the exterior, facing outward toward the parking area. It does not look into any interior spaces. The camera records video when activated by motionbr- You will have access to Coffins Beach which is a 2-3 minute walk from the property and is easily accessible from Wyoma/Bungalow Road

Elegant Gloucester Beach Getaway with Ocean Views!

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$1248.05

This large and comfortable vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities.brbrOn the ground floor there is living room with plenty of seating and a 32 tv. The large kitchen has a pass-through to the casual dining room, perfect for easy post-beach meals. There is also a queen bedroom and full bathroom with a shower on the main floor as well as a kid's nook with child-size table & chairs as well as many games and books.brbrUpstairs are 4 additional bedrooms -- three with full-sized beds and one with 3 twin beds. There are also two upstairs bathrooms. One is a small 1/2 bath (powder room) and the other is a full bathroom with shower.brbrThere is a large yard with a swing set, a gas grill and outdoor shower for rinsing off the sand after the beach. A large screened-in porch at the front of the house has a dining table as well as plenty of comfortable chairs for lounging and relaxing. There is parking for 3 cars in the driveway, but you will leave the cars at home and just walk to the beach. Long Beach House is the perfect family beach house getaway!

Long Beach House: Large, comfortable home just 285 ft from the white sands!

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$225.0

October is coming and that means that Haunted Happenings in Salem, Massachusetts is in full swing. come stay in Gloucester and take the train to Salem. It is a 15 to 20 minute train ride from Gloucester and puts you right in the middle of all the spookey action. Bring your costume!brbrIf Salem is not a draw, just come and relax and enjoy all that Gloucester has to offer in the fall. Then this desirable East Gloucester apartment in a historic home is perfect for you! It sits directly across from one of Gloucester's working maritime harbors, Cripple Cove. It is a scenic 15 minute walk (.07 mile) or 5 minute drive to Good Harbor Beach Footbridge and Gloucester's famous Harbor Loop with the Fishermen's Memorial. brbrYou have so many choices: enjoy vibrant downtown Gloucester, Rocky Neck Artist's Colony, golf, so many great restaurants, shopping, museums, art galleries, and the hiking...there are so many beautiful trails, boating, whales watch tours, sailing, and kayaking, and so much more. Easy highway, local ferry, train and bus access.brbrThis unique apartment adorns a lovely garden which serves as entrance to the second floor which leads into a combo kitchen/ living room with harbor views. Full bath with view into the garden is off of the living room. Head up to the third floor and there are two bedrooms, one with a queen bed, the other with two twin beds. Laundry in basement. brbrParking is available in the home's driveway, in front or across at the harbor parking lot. Spend relaxing time reading, playing or just relaxing in one of several garden rooms. brbrA brand new playground just across from the home where you can watch all the harbor activities. brbrSleeps 4.

Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$408.18

Walk to two beaches! Spend your day at the beach or relaxing on the porch with a book.br3 Bedrooms, 2 Baths, (Sleeps 6) Lots of privacy. brEnjoy the decks, porches, with light and bright inside spaces in this 3BR, 2BA home just a short walk to Good Harbor Beach and Long Beach. Also convenient to Rockport, Gloucester Harbor, downtown Gloucester, or take the short train ride to Salem or Boston.brWrap-around porch plus large deck. Beautiful gardens, lawn area, deck with grill area, private outdoor shower, and parking for 2-3 carsbrIndoors, you will find a fully equipped, large kitchen, dining table for 6, plus extra bar seating . There is a water filtration system throughout the house.brNumerous seating areas, with a large and comfortable TV area. Bedroom 1 Queen,Bedroom 2 Queen, Bedroom 3 Two single beds. Renters provide their own sheets and towels. brbr This unit is one of 2 units with lower unit reserved separately.

Walk to Good Harbor and Long Beach -Vacation Home

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$388.72

This darling property is private and steps to everything in Gloucester. We own both upstairs and downstairs units. The VRBO is Unit 1 on the main floor with its own entrance and relaxing yard. Steps to restaurants and downtown activities. Blocks to the beach. Comfortable & clean, AC throughout, with relaxing beach decor.

Single Level Home - Steps to Downtown Gloucester & A/C throughout

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$463.56

Location x3! This classic, cozy, waterfront cottage that sits on a private beach overlooking the Annisquam River in Gloucester, MA (45 min drive north of Boston). Nine foot tides provide for a dynamic scenery and activities with a back drop of marshes, Wingaersheek beach, and the quaint seaside village of Annisquam. At low tide, the beach is immediately accessible via a staircase and walkway. At high tide, water rises all the way under the house. All this can be experienced on a full wrap-around deck with a screened in porch and ample seating for dining, sunbathing, and lounging.brbrThe home itself is a former duck hunting cottage sitting waterside atop stilts. The interior has a vintage feel with wood, bright colors, and ample natural light throughout. Provided are all the necessities for your perfect New England vacation - beach chairs, beach towels, and more. High tide water reaches under the deck with a parade of boats, beaches, and crystal clear blue water in full view. Beach, fish, swim, float, unwind, and have fun!brbrOur family has rented our home to countless families, couples, and travelers for many summer seasons. Here is what past guests have had to say:brbrThis seaside cottage is pure magic. It is everything it appears to be in the photos, is super comfortable, and with an amazing location right on the water where boats pass and birds fish and the air is fresh. We had a memorable happy time here with our young boys and their grandparents. Totally hope to come back, and definitely recommend to people seeking quiet comfort by the seashore. - Stephaniebrbr“Jean’s place is awesome! The location/view is incredible. Sitting on the porch, sipping coffee in the mornings and wine in the evening was so relaxing. Was able to go kayaking in the Harbor out front. The house is adorable and perfectly furnished. You won't be disappointed! Thanks Jean.” - MikebrbrOur family loved our stay at Jean’s place. The home is unique, charming and everything you’d expect from the photos. The views from the porch are tranquil and will consume your whole day! Jean was a fabulous host and very much made us feel at home. Gloucester is a great little town... make sure you also get to Rockport! 5 out of 5 and would recommend it for couples and families! - BillbrbrSeasonally, the peak summer months are July and August when the sun is out and the weather trends around 80. June and September often are equally as beautiful but have a higher chance of colder/rainy weather. May and October can be on the cooler side, but are when the house is most cozy with the heat and fire place on. brbrChildren are welcome, but must be vigilantly watched at all times due to the house’s waterfront location. Pets are family too and are welcome for an additional $100 fee (for cleaning service), provided they are well trained and are good with other dogs as there are many in the neighborhood. Coming by boat We can accommodate vessels up to 15 feet on our half tide mooring or otherwise refer you to a mooring with the local yacht club.brbrFor activities, Cape Ann is a top summer destination with a variety of dining, outdoors, and sightseeing options. The closest major beaches are Wingaersheek and Good Harbor. We are also happy to recommend to you our favorite spots around town. brbrTHIS HOUSE IS NOT FOR EVERYONE. Please note the following if you are going to book:brbr- This is an old house without creature comforts (no AC, dishwasher, laundry, only one bathroom). br- It is 1000 sq ft. The upstairs bedroom walls do not go to the ceiling and there is little overall privacy. br- As with being near a beach/marsh in any New England town, there are greenhead flies and midges/gnats outdoorsbr- It can get hot in the summer. With an ocean breeze it tends to be ~10 degrees cooler than the mainland. There are tons of windows and fans for circulation. The ocean is steps away for a nice dip. But if you can't sleep with all the windows open or without AC, please do not book with us. brbr

Clean Waterfront Classic Cottage with Private Beach

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$721.62

Experience river life at its best along the banks of Mill River when you stay at this spectacular waterfront rental home with exquisite water views, a large back yard, and a private tidal dock for swimming and kayaking.brbrRiver Watch is a charming antique home sun-filled with natural light, and beautiful hardwood floors throughout. From the front door, enter the main living level that includes a large living room, a contemporary kitchen, a dining room, and a den with a glass sliding door accessing the back deck. The three bedrooms, a sitting room, and a full bath make up the third floor.brbrEnjoy the river views sitting on the back deck and or lounging in the back yard on the outdoor furniture. There is a gas grill to barbecue your favorite dish. You are welcome to bring a non-motorized watercraft to launch from the beach or dock.brbrSituated in Gloucester's Riverdale neighborhood, the location is ideal to explore the villages of Annisquam and Lanesville. It's a short drive to Downtown Gloucester and Rockport and Good Harbor Beach. Travel to Boston, Salem, and Beverly is easy with the close proximity to Route 128 and the commuter rail for day trips.brbrThere is one off-street parking space in the driveway.brbrDogs allowed. No smoking. No events or parties.

River Watch: Waterfront home with river views and a private dock.

Gloucester, Massachusetts, United States

Bed

2

Bath

6

Sleeps

$419.38

Look no further! Enjoy being a guest at this stylish beach bungalow! It is the perfect vacation spot for you and your family and friends. It’s impeccably clean, inviting and ready for your stay! brbrWake up from your new, firm, queen size bed early enough to catch the beautiful sunrise at Good Harbor beach! (Only a 5 minute walk away!) On your way back to the house, grab a coffee & danish at Cape Ann Coffees (just across the street) or head next-door for a full size breakfast at Charlie’s. Enjoy take out on the private outdoor patio or inside at the large kitchen island.brbrThe brand new, stylish kitchen offers all the basics you’ll need. The island is large enough to host 6 comfortably and will likely be where you entertain when you’re not outside. brbrThe home is tastefully decorated with warm, earthy tones and a relaxing feel. With a large bay window in the living room and oversized slider in the kitchen, it almost feels like you’re outside! brbrFor all the beach lovers; we provide an umbrella, beach chairs, beach bag, towels, cooler and beach wagon. After a long day in the sun, treat yourself to a delicious ice cream from Good Harbor Ice Cream just steps from the house! Then, rinse off in the private outdoor shower before dinner. brbrWith Stop & Shop across the street and two more grocery stores nearby, you can cook up dinner in the kitchen or on the grille outside. If you’re too relaxed to cook, Gloucester center is only a five minute drive away and has an excellent selection of restaurants, bars & nightlife!brbrUnwind after dinner on the comfortable, sectional sofa. Close the curtains and stream your favorite show or movie on the 65” flatscreen TV before turning in after an ideal vacation day!brbrConveniently located near:brGood Harbor BeachbrCape Ann Coffees (Coffee, Bakery, Sandwhiches)brCharlie’s Place (Breakfast, Lunch, Dinner) Good Harbor Ice CreambrCVSbrStop & ShopbrLaundromat brGloucester Center (Shopping, Dining, Nightlife)brLiquor StorebrStage Fort Park & more!brShort drive to Rockport, Ipswich, Salem & Newburyport Ma!brParking: There is a driveway alongside the home to fit 3 cars comfortably. 4 cars max!brbrNew Central Air Conditioning!brMosquito Misting System installed in backyard! brGreat heating system makes for a cozy home for those staying in the cooler months! brbrPlease let us know if you have any questions! We can’t wait for you to enjoy your stay! brAvailable to rent Spring, Summer & Fall! May-December br*Week rentals only (Sat-Sat) June through Sept. Long Term Rental available Nov/Dec-May. If you can’t find availability, please message us as we have another property in Rockport that is a 5 min walk to Front beach & the train station & 5-10 min walk to Bearskin Neck!

WALK TO BEACH! Great Location! Booking 2026! Close to Salem!!

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$631.05

Discover the historic charm of Bayview, a stunning private estate once home to Civil War General Benjamin F. Butler. Spanning 55 acres of meadows, forest, and rocky shoreline, it features two pristine beaches: a white-sand crescent and a mica-strewn gem. Nestled in the quaint village of Annisquam, this peaceful family compound offers access to Plum Cove Beach, Halibut Point State Park, and vibrant Gloucester and Rockport. Indulge in fresh seafood, coastal beauty, and timeless serenity.brbrImmerse yourself in the beauty of the seaside at this expansive coastal home. Perfect for families or groups, the house comfortably sleeps up to 12 guests across six beautifully appointed bedrooms. For dining, the elegant dining room offers a touch of old-world charm, perfect for hosting memorable meals. The well-equipped galley kitchen provides everything you need to prepare, from simple snacks to gourmet feasts. Your stay includes access to two private beaches and tennis courts overlooking Ipswich Bay, ensuring endless opportunities for recreation and relaxation. For adventure lovers, the property also provides two adult and two child kayaks, inviting you to explore the waters nearby.brbr.

Elegant Bayview Victorian Home; walk to beach

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$742.38

This very private contemporary house is perched on a shady hilltop near Gloucester's sandy Wingaersheek Beach. It's spacious and open plan living/dining room/kitchen is filled with natural light and boasts vaulted ceilings, hardwood floors and large oversized windows. The dining area has an oversized table with plenty of seat. Sliding doors in the living area open open onto a wrap around deck. The eat-in kitchen with breakfast bar has a door to a side deck and yard. brbrAlso on this level is the master bedroom with ensuite bath and walk-in closet, two additional bedrooms and one full bath with tub and shower. The ground floor entrance level features a den and game room with ping pong table, pull out sofa and wide screen TV as well as a half bath and entrance to the oversized garage. br brThe property has deeded rights to the private section of Coffin's Beach as well as easy access to the public Wingaersheek Beach. Access is available to Association tennis courts.

Wingaerchic: Woodsy retreat in West Gloucester

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$505.44

Relaxing spot close to everything in Gloucester. Our three bedroom home is a two level home filled with everything to make your stay perfect. Its is located behind our flower shop. Enjoy the quiet courtyard for breakfast or dinner. The first floor has an open concept kitchen living room with a laundry area. The kitchen has granite countertop and fully stocked with everything you will need with brand new appliances . The living room has an electric fireplace with 60 in smart tv. With two cozy loveseats. The second floor has a master bedroom with vaulted ceiling, queen bed, with a dresser and lots of closet space. It also has a chair that folds into a single bed more suitable for a child. Second bedroom has a queen bed with full closet, third bedroom has a full size bed with dresser and closet. Each bedroom has linens and pillows. The bathroom is on the second floor with walk in shower, large mirror, granite countertop and fully stocked with towels. The outdoor space is perfect’s spot to relax. We are located across the street from the train station to take you to Rockport, Salem, or a day in Boston. We are walking distance to a grocery store, liquor store, and coffee shop. We also have a few great restaurants too try out along with a bar that has live music. We are a five minute walk to stage fort park or a quick drive to the beach. We have lots of great shops on Main Street that is within walking distance. Our home is nested behind our flower shop which shares a driveway. There is one parking spot but plenty of off street parking. During summer months we do need to water the gardens daily but we will be sure not to disturb you and your guest. You will be greeted with fresh flowers when you arrive complements of Audrey's flower shop. We hope you will enjoy our beautiful home.

Downtown Dahlias fully remodeled in the heart of Gloucester

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$410

Take a much-needed break from your day-to-day and book a stay at this 2-bed, 1-bath Gloucester vacation rental! Conveniently located near beaches, fishing, and golfing, this cozy home features an inviting interior, a fully equipped kitchen, and a furnished patio. Catch some rays at Good Harbor Beach, explore the local art galleries in downtown Rockport, or visit Salem’s historic downtown area. After a fun-filled day, return home to grill out on the patio or watch the sunset from the deck!brbr-- THE PROPERTY --brbrC0475761070 | Furnished Patio | Washer & Dryer | Near Grocery Stores, Restaurants & Bus Route brbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed, Full Sleeper SofabrbrOUTDOOR LIVING: Deck, gas grill (propane provided), outdoor seating & dining brINDOOR LIVING: Smart TV, electric fireplace (decorative only), dining table, shower/tub combo, ceiling fansbrKITCHEN: Stove/oven, refrigerator, dishwasher, cooking basics, dishware/flatware, pod coffee maker (Keurig, pods provided), microwave, toaster, knife set brGENERAL: Free WiFi, window A/C, baseboard heating, linens/towels, trash bags/paper towels brFAQ: Homeowner on-sitebrACCESSIBILITY: Single-story home, 3 steps to enter, 2 interior steps required to access bedroom 2brPARKING: Shared driveway (4 vehicles)brbr-- THE LOCATION --brbrATTRACTIONS: Gloucester HarborWalk (2 miles), Downtown Gloucester (2 miles), Stage Fort Park (3 miles), Rockport (3 miles), Rockport Art Association & Museum (3 miles), Eastern Point Lighthouse (4 miles), Hammond Castle Museum (4 miles), Halibut Point State Park (6 miles)brSALEM ADVENTURES (~18 miles): Salem Witch Village, Salem Willows Park, Salem Witch Museum, The Witch House at Salem, Salem Wax Museum, Salem Common, Salem Witch Trials Memorial, Real Pirates Salem, Ropes Mansion and GardenbrSAND & SUN: Good Harbor Beach (1 mile), Niles Beach (3 miles), Half Moon Beach (3 miles), Wingaersheek Beach (7 miles), Singing Beach (10 miles), Crean Beach (14 miles)brOUTDOOR ADVENTURES: Angelica Fisheries Inshore & Offshore Fishing Charters Gloucester MA (2 miles), Gloucester Boat Rental (2 miles), North Shore Kayak & Bike Adventures and Flip-Flop Emporium (4 miles), Essex Marina (9 miles), Plum Island Kayak (25 miles), Gannon Municipal Golf Course (26 miles)brAIRPORT: Boston Logan International Airport (39 miles)brbr-- 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 smoking br- No pets allowedbr- No events, parties, or large gatherings br- Additional fees and taxes may apply br- Photo ID may be required upon check-inbr- NOTE: This single-story home requires 3 steps to enter and 2 interior steps to access bedroom 2br- NOTE: The homeowner lives on-site, in a completely separate unit, and may be present during your staybr- NOTE: The fireplace is not currently available for guest use

Massachusetts Abode w/ Deck & Grill: Near Beaches!

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$1053.18

Summary:brbrRare Gloucester Waterfront Retreat! brbrbrbr✓ Perched directly on the water with breathtaking ocean viewsbrbr✓ Expansive deck with outdoor dining – watch boats pass at eye levelbrbr✓ Private 30-ft deep-water dock – swim, kayak, paddleboard, or dock your boat (fees apply)brbr✓ Newly renovated home + detached guest house with modern coastal charmbrbr✓ Wall-to-wall windows & open layout – feel immersed in the seabrbrbrbrA one-of-a-kind escape—book now! Visit @stay_collections on IG for a video property tour!brbrbrbrThe Space:brbrWelcome to Your Ultimate Waterfront Escape! Step inside and you’ll be met with panoramic water views that make you feel like you’re floating on the ocean. With its rare 30-foot deep-water dock, fully renovated main house, and private guest house, this home offers an unparalleled coastal experience. Multiple decks and outdoor spaces invite you to soak in sunrise coffee, sunset cocktails, and everything in between.brbrbrbr☆☆☆ HIGHLIGHTS ☆☆☆ brbrbrbr→ Expansive deck with front-row ocean views — perfect for morning coffee or evening drinksbrbr→ Private 30-ft deep-water dock (rare in Gloucester!) for swimming, kayaking, paddleboarding, or docking your boat (fees apply)brbr→ Outdoor dining table for memorable meals beside the waterbrbr→ Central AC throughout both the main house and guest house for total comfortbrbr→ Two-car driveway for convenient parkingbrbrbrbr☆☆☆ MAIN HOUSE ☆☆☆ brbrbrbr→ Full kitchen with eat-in island & all cooking essentialsbrbr→ Spacious living room with plush sectional, fireplace & smart TVbrbr→ Dining room with oversized windows framing spectacular water viewsbrbr→ Convenient half bath off the main living areabrbr→ Primary bedroom with spa-style en-suite featuring a custom walk-in showerbrbrbrbr☆☆☆ GUEST HOUSE ☆☆☆ brbrbrbrSteps from the main house, this brand-new guest house is ideal for family or friends.brbr→ Queen bedroom with full water viewsbrbr→ Modern bathroom with walk-in showerbrbr→ Kitchenette for easy meals & coffeebrbr→ Loft with second queen bed (low ceilings — best for kids)brbrbrbrExperience the Best of Gloucester’s WaterfrontbrbrWith rare dock access, luxurious renovations, and multiple ways to enjoy the outdoors, this property is more than a vacation rental — it’s a true coastal retreat. Whether you’re here for boating adventures, beach days, or peaceful relaxation, this Gloucester gem offers an experience like no other.brbrbrbr Book today and live the waterfront dream.brbrbrbrGuest Access:brbrThe home features a private two car driveway. We'll send you a key-code ahead of check-in for easy access.brbrbrbrThe Neighborhood:brbrThe Rocky Neck Art Colony is a charming, walkable neighborhood offering a vibrant mix of galleries, local artists, and charming waterfront cafés — only 10 minutes from downtown Gloucester. For those craving outdoor adventure, Ravenswood Park features serene hiking trails through woodlands and marshes, making it a perfect nature escape. For dining, head to The Causeway for a laid-back spot with hearty seafood dishes, or enjoy an upscale, authentic Italian meal at Tonno in Downtown Gloucester.brbrbrbrGetting Around:brbrLocated steps from the Gloucester Water Shuttle which has different stops throughout the town — a super easy and inexpensive way to explore Gloucester.brbrbrbrOther Things to Note:brbrAccessibility notes: The loft space in the boat house has a low ceiling and is accessed by a pull-down attic ladder. There are steps down to the front door of the main house. 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 Rocky Neck

Gloucester, Massachusetts, United States

Bed

2

Bath

7

Sleeps

$606.25

Unwind in Gloucester at this delightful house. With three cozy bedrooms featuring a queen bed, a full bed, and a bunk bed, guests find plenty of space to relax. Two bathrooms with refreshing showers add to the comfort. The house stays comfortable year-round with heating and air conditioning. Whether you’re gathering for a restful night or enjoying quiet mornings, this soothing retreat offers a perfect balance of convenience and charm. We’ll be available to answer any questions while you stay at our place.

Delightful 3-bedroom house with AC in charming Gloucester.

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$736.68

Escape to Lanesville and enjoy breathtaking ocean views from this charming 3-bedroom, 2-bathroom house. Perfect for families or a group of friends, this home is located on a quiet street and offers all the comforts of home.brbrStep inside to find a spacious and inviting living area, complete with a full bathroom on the first floor. Head outside to the deck and take in the stunning views of the coast stretching up to New Hampshire.brbrUpstairs, you'll find three bedrooms and a full bathroom, including a primary bedroom with a king bed, AC split, and a balcony with ocean views. The second bedroom has twin beds and the third bedroom has a queen bed.brbrLanesville is very quaint, quiet, and beautiful. Book your stay at this lovely vacation rental today and experience the best of Cape Ann living!

Sea for Miles: Ocean Views in Lanesville

Gloucester, Massachusetts, United States

Bed

2

Bath

6

Sleeps

$423.84

Welcome to your relaxing North Shore escape at 10 Loma Drive in Gloucester, Massachusetts. Just minutes from the soft sands and turquoise waters of Good Harbor Beach, this charming 3-bedroom cottage blends a laid-back Southwestern vibe with classic New England coastal living.brbrWhether you’re planning a beach vacation, a family getaway, a fishing trip, or a peaceful retreat by the ocean, you’ll find everything you need to unwind and enjoy one of Gloucester’s most sought-after neighborhoods.brbrThe SpacebrbrStep inside and immediately feel at home in a warm, inviting space featuring rich wood floors, comfortable furnishings, and unique Southwestern-inspired décor. Sunlight pours through the windows, creating a bright and welcoming atmosphere after a day exploring the coast.brbrSleeping Arrangements:brbr* Bedroom 1: Queen Bedbr* Bedroom 2: Queen Bedbr* Bedroom 3: Twin Bedbr* 1 Full BathroombrbrThe home comfortably accommodates couples, small families, beachgoers, and travelers looking for a relaxing coastal stay.brbrWhy Guests Love This Locationbrbr Minutes from Good Harbor Beach – One of Massachusetts’ most beautiful beaches, known for its white sand, gentle surf, and stunning sunsets.brbr Explore Gloucester’s Coastline – Visit picturesque beaches, rocky shorelines, scenic walking trails, and historic fishing harbors.brbr Close to Restaurants & Downtown Gloucester – Enjoy fresh seafood, local coffee shops, boutique shopping, and waterfront dining.brbr Perfect Home Base – Easy access to Rockport, Cape Ann, whale watching tours, boating, kayaking, and coastal adventures.brbrAmenitiesbrbr* Fully equipped kitchenbr* Fast Wi-Fibr* Smart TVbr* Comfortable living roombr* Dining areabr* Free parkingbr* Outdoor space for relaxing after a day at the beachbrbrPerfect Forbrbr* Beach vacationsbr* Family getawaysbr* Couples retreatsbr* Fishing tripsbr* Remote workers seeking coastal inspirationbr* Exploring Cape Ann and the North ShorebrbrGuest FavoritebrbrWake up, grab a coffee, and be on one of New England’s most beautiful beaches within minutes. After a day in the sun, return to your cozy Southwestern-inspired retreat, enjoy a peaceful evening, and experience the relaxed charm that makes Gloucester such a special destination.brbrBook your stay and discover why visitors return to Gloucester year after year.

Southwestern Coastal Retreat • Walk to Good Harbor Beach, 3BR Gloucester Getaway

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$585.36

Vacation time This beach gem awaits you! Be surrounded by rich history, absolutely gorgeous views, a baseball field, tennis court, beaches, and Gloucester's attractive Stacy Boulevard all just around the corner! You're a stroll away from shops, restaurants, stores, and other fun locations that your whole family will love! Enjoy seasonal live entertainment and watch fireworks displays over the water without ever leaving home!

Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!

Gloucester, Massachusetts, United States

Bed

1

Bath

5

Sleeps

$249.73