Vacation Rentals By Owner In Gloucester, MA

Enjoy a memorable family vacation in this fully furnished, 3 bedroom single-family home with deck, yard and marsh views, that is actually walking distance to Good Harbor Beach.brbrComfortably sleeps 8 people, but can easily accommodate up to 10 people with living room pullout. The spacious living room that is open to the dining and kitchen area is furnished with sectional and an entertainment center for your enjoyment. The kitchen with a center island is perfect for dining and entertaining, and is equipped with a stove, microwave and a full refrigerator. Less than 5-minute walk from Good Harbor Beach, with great deck overlooking the marsh.brbrKitchen is fully stocked with dishes, and cookware and offers everything needed for a comfortable and relaxing stay. br

Walk to Good Harbor Beach, pet friendly, family beach home

Gloucester, Massachusetts, United States

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Bath

Sleeps

$865.37

Summary:brbrRare Gloucester Waterfront Retreat!brbrbrbr✓ Rocky Neck Location – Nestled above scenic Smith Cove with breathtaking harbor viewsbrbr✓ Spacious Deck – Outdoor dining with boats passing belowbrbr✓ Open-Concept Living – 17-ft ceilings + floor-to-ceiling windowsbrbr✓ Loft-Style Bedroom – Sweeping water views & private suitebrbrbrbrA one-of-a-kind escape — book your stay today! Visit @stay_collections on IG for a video property tour!brbrbrbrThe Space:brbr☆☆☆ WATERFRONT VIEWS & OUTDOOR LIVING ☆☆☆brbrbrbr→ Oversized deck with front-row harbor views — perfect for coffee at sunrise or sunset cocktailsbrbr→ Outdoor dining table & grill for meals by the waterbrbr→ Perched above Smith Cove and steps from the Rocky Neck Art Colonybrbrbrbr☆☆☆ 1ST FLOOR ☆☆☆brbrbrbr→ Custom chef's kitchen with granite counters, stone finishes & large eat-in islandbrbr→ Expansive windows that fill the home with natural light + panoramic water viewsbrbr→ Spacious living room with plush sofa and Smart TVbrbr→ Dining area with bench seating for up to 8brbr→ Full bathroom conveniently off the kitchen & living areabrbrbrbr☆☆☆ 2ND FLOOR & LOFT ☆☆☆brbrbrbr→ Primary Suite: Queen bed • En-suite bath • Harbor viewsbrbr→ Loft Suite: Two queen beds • Private bath • In-room laundry • Full-length blackout shades • Overlooks living area with sweeping water viewsbrbrbrbr☆☆☆ EXPERIENCE THE BEST OF GLOUCESTER ☆☆☆brbrbrbrThis coastal retreat blends modern style with classic New England charm. With soaring ceilings, an open-concept design, and unmatched waterfront views, it's the ideal setting for relaxation, entertaining, or simply taking in the beauty of Rocky Neck.brbrbrbrBook today and live the waterfront dream.brbrbrbrGuest Access:brbrWe'll send you a key code ahead of check-in for easy access.brbrbrbrThe Neighborhood:brbrFor those familiar with the area, please note that the space formerly occupied by the restaurant below is currently vacant and inactive. This means you can enjoy a peaceful, quiet stay without any of the noise, foot traffic, or kitchen activity typically associated with waterfront properties. It’s the perfect setup for a serene getaway!brbrbrbrThe 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: Please note there are steps leading to the front entrance and a staircase to access the upstairs bedrooms.brbrbrbrFireplaces - Not in use. brbrbrbrLoft Sleeping: The loft features blackout shades that span the entire space, keeping morning light out for a restful sleep.brbrbrbrParking: Parking is easy and convenient here! There is ample free street parking directly in front of the condo on Rocky Neck Avenue. While the neighborhood sees a bit more activity during peak hours, our guests consistently find parking right out front or within a very short, one-block stroll. You'll have no trouble finding a spot nearby at any time of day.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 Smith Cove

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$509.55

Very sunny, clean 4 bedrooms, 2 bath ranch home in a QUIET residential neighborhood, not far from Good Harbor beach and amenities, ABSOLUTELY NO PARTIES or groups of adults who's plan is to spend the time partying at the house.) brThis 4-bed includes one bedroom in separate in-law with bathroom. The layout includes main house, a great deck, with grill, PLUS a separate entry, lower level studio efficiency ~ with additional full size bed, bathroom/shower, sitting area with TV, extra coffee maker, fridge and microwave. This entire property rental includes full backyard access, complete with hammock and extra cafe table/chairs, and 3- 4 parking spaces in driveway. We also provide games, beach chairs (5) and one boogie board! NO SMOKING ALLOWED INSIDE OR ON THE DECK. brWe are only a 6-8 minute walk to Good Harbor Beach. House has a Zen-like vibe, simple, clean with an open, relaxed feeling. 5 minute walk to Shaws, StopnShop, Cape Ann Coffee, Nino's Scoops ice cream, liquor store and pharmacy. The custom deck, with little white lights~ is perfect for grilling and lounging as the sun is setting. The lower level can be separately rented, with a separate entry, studio efficiency, so if you wish to book the entire property, book soon! The studio fills up quickly because of demand for hotel rooms in the area.

~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun

Gloucester, Massachusetts, United States

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Bath

Sleeps

$1170.63

A spacious, beautiful contemporary home on a private oceanfront estate near Gloucester's coveted Annisquam district, with access to two private sandy beaches, boating and a fresh water pond just outside the door. This fully furnished, newly renovated home has four bedrooms, two full bathrooms, hardwood floors, central air conditioning, a large deck with magnificent water views, an outdoor shower and a large yard. Only 150 yards away from two private sandy beaches, this sunny bright house also has access to two tennis courts that overlook the ocean, a play and swing area and acres of land to explore--allowing for lots of fun and relaxation for all!brbrThe house opens to an open plan living room with fifteen foot ceilings, a huge brick fireplace and cozy furnishings with a flat screen TV and dining area surrounded by glass patio doors that lead to a wraparound deck. The open kitchen has two separate sinks (great for more than one cook), granite counters and a breakfast bar. Two bedrooms are on this level: one master king with glorious views on the water side and a flat screen TV, and a second room with two twin beds, as well as a full deluxe bath. On the ground floor there are two twin bedded rooms, a full bath and laundry room, and a young adult/children's play area with full size ping pong table, a flat screen TV, and a door leading to the yard, two hanging swings, hammock and outdoor shower. The house has high speed internet access, three flat screen TVs, gas grill, charcoal grill, fire pit, ping pong table and a fully appointed kitchen with every amenity. Tennis on private courts is available free of charge. Four new kayaks available for use as well: Ocean Kayak Malibu Two (two seater), Ocean Kayak Frenzy (single) & two Lifetime Wave Youth Kayak with paddles and life vests. Four brand new Wavestorm paddle boards available, too.brbrLast but not least, this contemporary home is part of a 50+ acre family estate that dates back to the 1860s. The house looks out onto Ipswich Bay and has great views of sunsets across the water as well as views of Crane's Beach, Plum Island, the New Hampshire coast and Mount Agamenticus Conservation Region in Maine. In addition to the private sandy beaches on the estate, the Gloucester area has many long sandy beaches to explore--some of which are great for surfing, skim boarding, scuba diving, snorkeling and nighttime fishing or stargazing. There are nearby quarries, including one in Halibut Point State Park, which makes for a great kayaking destination on calm days. Finally, downtown Gloucester and Rockport are close at hand with their many wonderful restaurants, boutiques, nautical history and antique stores.brbrThe views and beauty of this oceanside estate are memorable and extraordinary, and difficult to capture in words. It is a place to rebuild, refresh and discover deep pleasure among the flora, fauna and surrounding oceanic habitat. Just a peaceful paradise, and never a dull moment.

Beautiful Oceanfront Home in Estate Setting Gloucester — WINTER RENTAL AVAILABLE

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$339.52

Welcome to your charming waterfront retreat in central downtown Gloucester! This delightful 2-bedroom, 1-bathroom apartment sits right on the channel, offering stunning views and a perfect spot for fishing. brEnjoy a modern, fully equipped kitchen and a cozy living room to unwind. Located near numerous restaurants and shops, and just across the street from the beautiful boulevard. Whether for a romantic getaway, family vacation, or solo retreat, this gem combines tranquility and convenience.brWe are delighted to be pet-friendly and have provided water and food bowls to make your furry friend feel at home. For a wonderful outing, we recommend taking a stroll down the scenic boulevard to Stage Fort Park, where you'll find a fantastic dog park perfect for your pet to enjoy.

Apartment

Fish & Ships on Waterway: Steps to Ocean, Beach, Boulevard, Park, Restaurants

Gloucester, Massachusetts, United States

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Bath

Sleeps

$1058.13

Enjoy this fantastic beach house just a quick 5 minute walk to Coffin's Beach. brbr→ Sleeps 10 br→ 1 King bed, 2 Twin beds, 2 Queen beds, 1 Full bedbr→ 2 Full bathrooms br→ Indoor dining area and outdoor dining areabr→Extremely safe neighborhoodbr→Onsite Parkingbr→Fully Stocked kitchenbr→Shuffle board in Lower Levelbr→ access to Private Coffin's Beachbr→Outdoor showerbrbrWelcome to our charming vacation rental, conveniently located just a 3-minute walk from the picturesque Wingaersheek Beach! This cozy rental is perfect for families and groups of friends seeking a relaxing getaway.brbrAs you enter the rental, you'll feel right at home in the comfortable and inviting living room. The space is furnished with cozy seating, a flat-screen TV, and large windows that fill the room with natural light.brbrThe rental boasts three bedrooms, each with ample space and comfortable beds to accommodate up to 8 guests. brbrThe fully equipped kitchen includes all the amenities needed to prepare delicious meals - perfect for enjoying meals together.brbrThe rental also features a private outdoor space, ideal for relaxing and enjoying the fresh sea breeze. The area includes a table and chairs for outdoor dining and a grill for cookouts.brbrBut the best part of this vacation rental is its proximity to Wingaersheek Beach. Just a short 3-minute walk away, you can spend your days soaking up the sun on the white sand beaches, swimming in the crystal clear waters, and creating unforgettable memories with loved ones.brbrWe provide all the beach essentials, including chairs, an umbrella, and towels, so you can pack light and make the most of your beach vacation.

NEW Rental: 2 min walk to Private Coffin's Beach

Gloucester, Massachusetts, United States

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Bath

Sleeps

$623.66

Cozy beach cottage located on private white dunes on 1.5 mile Wingaersheek beach. Best of both worlds, large green yard with vegetable garden and spacious porch. One minute walk to beach. Home has four bedrooms. Two of the bedrooms are queen sized beds. One has two twins the other has one twin bed. Also has a double pull out couch. Treadmill also available for use! Home has AC throughout. brbrCharming cottage boasts mature plantings, new furniture, outdoor shower and air-conditioning. Ample parking. Washer and dryer, Starlight nights, summer bonfires, fire pit, cookouts on the deck. Runners, walkers, beach bums, outdoor enthusiasts welcome. Well behaved pets are welcome.brbrGloucester, MA is one of the premier destinations for outstanding restaurants, outdoor activities and natural beauty located only 35 minutes from Boston.brbrbrGloucester, Essex, North Shore MA.

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Gloucester, Massachusetts, United States

4

Bed

Bath

8

Sleeps

$650.49

Sitting high above Rocky Neck, Painter’s Perch offers stunning views of the Neck and picturesque Smith Cove. This charming 2-bedroom, 1.5-bathroom retreat is the perfect getaway for art lovers, outdoor enthusiasts, or anyone seeking tranquility near the heart of Gloucester's vibrant arts district.brbrThe home boasts an array of outdoor spaces to enjoy the coastal air; a spacious backyard, a private back patio for al fresco dining, a cozy main-level deck, and a second-floor balcony off the primary bedroom—perfect for sipping morning coffee while taking in the water views.brbrInside, the home combines modern comfort with classic coastal charm. The open living and dining areas feature beautiful exposed beams, a fireplace, and ample natural light, creating a warm and inviting atmosphere. The eat-in kitchen features a breakfast nook and gas stove. There is also a half bath with laundry on the first floor.brbrThe second floor features the primary bedroom with a queen bed and a bonus full bed, perfect for a kid. This room has a large skylight and a small balcony with water views. There is a second queen bedroom and a shared hall bathroom as well.brbrLocated within walking distance of Rocky Neck’s galleries, shops, and restaurants, Painter’s Perch also offers easy access to nearby beaches, Gloucester Harbor, and all the beauty Cape Ann has to offer. Whether you're seeking inspiration or relaxation, this unique home is an ideal base for your Gloucester adventures.brbrThere is only parking for two cars, however, there is both street parking and a lot nearby, but these tend to fill up quickly during peak season.brbrNo smoking. No events or parties.

Painter's Perch: Rocky Neck

Gloucester, Massachusetts, United States

Bed

Bath

5

Sleeps

$396.73

Water Views from EVERY window, DECK & TV room overlooking Annisquam River. Harbor Views from Bedroom & Living room, open Dining/Kitchen/living rooms, 1.5 Full bathrooms (w/ Tub & washer/dryer), OFF-street Prime parking spot, Excellent Location as Walking Distance to Downtown Restaurants, Shops, Beaches, Stage Fort Park & iconic Gloucester attractions & activities. See holiday lights & summer festival fireworks, Schooner festival from window. Direct access to Rt. 128 without crossing bridge/traffic...sunsets & unobstructed views of boats & river/harbor activities. Walk out the door to major city events, and a peaceful setting oasis all in one.

Condo

WATERFRONT- River & Harbors views, Walking Distance to Downtown, Beaches & Park

Gloucester, Massachusetts, United States

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Bath

Sleeps

$1342.67

A unique private estate, rich in history and natural beauty. The home was the residence of Benjamin F. Butler, the colorful Civil War general and Massachusetts governor, still belonging to his descendants. Enjoy fifty-five rolling acres of meadows, forest, marsh grass, and rocky granite shoreline, with a white-sand crescent beach, and a flat mica beach.brYou will have use of the Main House (5BR) and the Maids Quarters (2BR), which is a separate, private residence, with a separate entrance.

The Homestead: Elegant Victorian & Maids Quarters

Gloucester, Massachusetts, United States

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Bath

Sleeps

Select Dates for Price

Apartment

WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT

Gloucester, Massachusetts, United States

Come to the Cape named after a Queen NOT an Ugly Fish!! FABULOUS, quiet, dead end location! Incredible views of the Annisquam River. Wildlife, Boats, Paddle boards, Kayaks (bring yours) and Sunbathers. All seen from your private second floor deck as well as your Huge picture window! We can accommodate up to a 17’ boat on our Tidal Dock for an additional fee. Newly renovated apartment! Very comfortable Queen size bed, as well as a brand new pull out memory foam Full sleep sofa! There is a large Butcher Block counter with stools as well as kitchen table. New 40” flat screen smart TV. Owner occupied. Owners Deb Callahan and Paula Parsons are happy to suggest places to go, places to avoid, and respect your privacy! Laundry on the same floor. brWe were on VRBO for 7 years with over 52-5 Star reviews! We stopped for 2 years because of COVID and we have decided to do this again. Sadly we lost all of our reviews by taking that break! We are happy to answer any questions you may have and hope you choose our home for making a memorable vacation experience! Thank you for viewing our post! brbr* Our cleaning is performed by a professional, bonded, cleaning company.br*** An ADDITIONAL WEEKLY cleaning charge will be charged for multiple full weeks. Example: One week=1 cleaning, 2 weeks=2 cleanings, 3 weeks= 3 cleanings.brbr***Any more than 2 adults needs to be discussed with owners before booking. ***NO SMOKING on premises.

Bed

Bath

Sleeps

$1127.26

Escape to this beautiful historic Gloucester coastal home just steps from the waterfront and minutes from beaches, downtown restaurants, and the harbor. With spacious bedrooms, elegant New England charm, and room for families and small groups to gather comfortably, this home is perfect for beach weekends, wedding stays, family vacations, and North Shore getaways. Enjoy the best of Gloucester with easy access to Good Harbor Beach, Stage Fort Park, downtown Gloucester, and nearby Rockport.brbrWhy Guests Choose Harbor Watch:brbr✓ Walkable waterfront locationbr✓ Comfortably sleeps 10–12 guests across 5 bedroomsbr✓ Private parking for up to 5 vehiclesbr✓ Steps from Fishermen's Memorialbr✓ 5-minute walk to waterfront paths and harbor viewsbr✓ 8-minute drive to Good Harbor Beachbr✓ Minutes to Stage Fort Parkbr✓ Short drive to Bearskin Neck and Front Beachbr✓ Spacious backyard, deck, outdoor dining, and grillingbr✓ Bright sunroom with harbor-view morningsbr✓ Fast WiFi + work-friendly setupbr✓ Fully stocked kitchen for easy family mealsbr✓ High-quality linens and comfortable bedroomsbr✓ Premium bathrooms with bidetbr✓ Professionally cleaned with responsive local hostingbr✓ Quiet residential setting near downtown restaurants, museums, and waterfront parksbrbrFirst floor: kitchen, living room, dining room, full bathroom, front and back porches. Second floor: five bedrooms w king and queen beds, second full bath, and balcony.brbrInside, the home feels warm, bright, and inviting, with sun-filled rooms, comfortable living spaces, and quiet corners for relaxing or remote work. brbrMorning coffee in the sunroom with harbor views, shared dinners on the expansive back deck, and peaceful evenings in the private backyard create the kind of stay guests remember long after checkout.brbrIdeal for respectful family gatherings, wedding weekends, multi-generational trips, and relaxed coastal stays, Harbor Watch offers the rare combination of walkability, privacy, and elevated comfort in one of Gloucester’s most desirable waterfront neighborhoods.

Classic Coastal Family Home | Walk to Sea;King Bed

Gloucester, Massachusetts, United States

5

Bed

Bath

12

Sleeps

$462.48

Looking for a 2-level apartment to yourself for your next getaway This open concept apartment is sure to please! You're in the center of everything: downtown, beaches, souvenir shops, restaurants, and even public transit! Staying in Enjoy a cozy cup of coffee, Wifi, internet streaming on 2 smart TVs, and take in breathtaking views of Gloucester from this 2nd floor beauty!brbrThe spacebrKitchen (1st floor of unit)- Full, Open Concept, with 2 large windows, new cabinets fully stocked (dishes, mugs, drinking glasses and wine glasses), new gas range, granite countertop, 2-in-1 coffeemaker/Keurig, toaster, knife set, cooking utensils, microwave, and flatware. Table set for 4.brbrLiving Room (1st floor of unit)- Full, Open Concept, 2 large windows, complete with loveseat and sofa, 55 smart TV on console, large coffee table. Fully stocked closet: hangers, laundry basket, iron, ironing board, drying rack, vacuum, mop, bucket, dustpan and brush, and broom. Spare light bulb.brbrBathroom (1st floor of unit)- Tub and shower, shower curtain, toilet brush, plunger, towels, wash cloths, men's/women's toiletries, hair dryer, soaps, shampoo, conditioner, body wash, feminine products, shaving cream, hair spray, makeup remover, razors, deodorants, toothpaste, toothbrushes, and mouthwash.brbr1st Floor Bedroom (of unit)- 2 large windows, twin bed with bedding, dresser, end table, and lamp. Extra sheets in living room closet.brbr2nd Floor Master Bedroom (of unit)- 1 large window with views, Queen bed with bedding, small closet, 2 dressers: 1 with mirror. Extra sheets, 43 Roku smart TV, 2 nightstands, 2 lamps.brbrDen (2nd floor of unit)- dedicated workspace complete with office desk chair, pens, pencils, highlighters, pencil sharpener, notepad, notebook, eraser, and lamp with USB port, and closet.brbrPlease note: A twin size roll-out bed is available for a 4th guest upon request.brbrGuest accessbrNo access to attic spaces.brNo access to 2nd exit (located in the kitchen), except for emergencies.brNo access to backyard.brbrOther things to notebrExterior left-side walkway is where trash barrel goes.

Apartment

Open concept, 2-level apartment with scenic view

Gloucester, Massachusetts, United States

Bed

Bath

4

Sleeps

$338.43

Please note that The Gallery has a one month (31 night) minimum rental period.brbrWelcome to The Gallery, a stunning waterfront multi-level property on Rocky Neck, America's oldest art colony. Located above a studio run by the Rocky Neck Art Association, this home puts you in the heart of the action. Enjoy views of Smith Cove and the Gloucester skyline from most of its light filled rooms and its two decks.brbrThe main living area is on the second floor where there is a spacious living room overlooking the Cove. Also on this level is a fully equipped kitchen with granite counter tops and stainless-steel appliances. Past the kitchen is the Queen bedroom with an ensuite bathroom, complete with a jacuzzi tub and standing shower.brbrThe third floor offers a light-filled well-designed waterside King bedroom with ensuite full bath. Down the hall is a versatile office with a magnificent stained-glass window that can double as an additional sleeping area. But the best part is a spectacular waterside rooftop deck where you can enjoy views of the inner harbor perfect for relaxing or entertaining. This space combines comfort and functionality with beautiful coastal surroundings.brbrOn the ground floor there is additional space with a Queen bedroom, kitchen, living area, full bath, and waterside deck, making it the perfect retreat for visiting guests.

The Gallery: Rocky Neck Waterfront

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$1336.89

Summary:brbrThis 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, MA!brbrbrbr• 13-minute drive to Wingaersheek Beachbrbr• 10-minute drive to Downtown Main Street in Gloucesterbrbr• 2 inflatable Paddleboardsbrbr• 4 Kayaks Available!brbr• Outdoor Patio w/ Oceanfront Viewsbrbr• Large Jenga setbrbr• Fully Stocked Kitchenbrbr• Multiple Outdoor Spaces: Balcony/Deckbrbr• Family Friendly- Pack n Play & High Chair brbr• Beach Essentials: Chairs, Umbrellas, Life Vests, TowelsbrbrbrbrThe Space:brbrNestled in the charming coastal town of Gloucester, our exquisite home offers the perfect year-round retreat with breathtaking panoramic water views. With 4 bedrooms and 3 bathrooms, our spacious sanctuary accommodates up to 12 guests, providing ample space for relaxation and adventure. Enjoy direct river and ocean access right from your own dock, where you can even catch striped bass right off the water! You can kayak or paddleboard right over to Wingearsheek Beach, making for a perfect day of exploration. The stunning bluestone patio offers an ideal spot for soaking up the sun.brbrbrbrConveniently located, our home is a gateway to explore the area's natural beauty, vibrant attractions, and delightful dining options. Experience the ultimate coastal getaway at our beautiful waterfront haven.brbrbrbrMAIN SPACES OF THE HOME:brbrbrbr– 4 BEDROOMS & 3 BATHROOMS –brbrbrbrBEDROOM 1:brbr* King-sized Bedbrbr* Twin-sized Trundle Bedbrbr* Smart TVbrbr* Ceiling Fan w/ Lightbrbr* Wooden Drawer w/ Mirrorbrbr* Nightstand and Lampsbrbr* End-of-the Bed Chairsbrbr* Ensuite Bathroom w/ Walk-in showerbrbrbrbrBEDROOM 2:brbr* Full-sized Bedbrbr* Smart TVbrbr* Nightstand and Lampsbrbr* Ceiling Fan w/ Lightbrbr* Plush ChairbrbrbrbrBEDROOM 3:brbr* Full-sized Bedbrbr* Twin-sized Bed brbr* Smart TVbrbr* Ceiling Fan w/ Lightbrbr* Nightstand and LampsbrbrbrbrBEDROOM 4:brbr* Full-sized Sleeper Sofabrbr* Smart TVbrbr* Plush Chairbrbrbrbr– 3 BATHROOMS –brbr* Upper Level : 2 Full Bathroomsbrbr* Main Level: 1 Full Bathroombrbr brbr– CHEF’S KITCHEN –brbr* Fully Stockedbrbr* High-end Stainless Appliancesbrbr* Large Fridgebrbr* Nespresso Coffee Makerbrbr* Tons of Cabinetry & Large Island brbr* Expansive Windowsbrbrbrbr– LIVING ROOM–brbr* 55 Smart TVbrbr* Large Plush Sofa & Chairsbrbr* Hanging Egg Chairbrbr* Open Floor Concept directing to the Kitchen & Dining Areabrbr* Expansive Windowsbrbrbrbr–LOFT LIVING SPACE–brbr* Smart TVbrbr* Plush Chairbrbr* Full-sized Sleeper SofabrbrbrbrGuest Access:brbrThe guest has access to the entire home minus the locked cleaners closet.brbrbrbrThe Neighborhood:brbrBeyond the Property:brbrGloucester is a treasure trove of activities and experiences, perfect for travelers seeking both relaxation and adventure. From beachcombing and whale watching to indulging in local dining and shopping, there's something for everyone.brbrbrbrTop Attractions:brbr- Hammond Castle Museum: Explore medieval architecture, historical exhibits, and breathtaking ocean views.brbr- Good Harbor Beach: White sandy shores, crystal-clear waters, and scenic low-tide walks.brbr- Eastern Point Lighthouse: A photography hotspot with panoramic coastal views.brbr- Stage Fort Park: Perfect for picnics, playgrounds, beaches, and a touch of local history.brbr- Cape Ann Museum: Dive into the region's art and maritime heritage.brbr- Maritime Gloucester: A charming waterfront museum featuring an aquarium and working harbor.brbrbrbrHidden Gems:brbr- Dogtown Commons: Discover abandoned settlements with hiking trails and unique carved boulders.brbr- Rocky Neck Art Colony: Wander through galleries and studios showcasing vibrant local art.brbr- Ravenswood Park: Escape to peaceful trails ideal for hiking and birdwatching.brbrbrbrTop Restaurants:brbr- Azorean: Portuguese-inspired seafood dishes (133 Washington St).brbr- Talise: Creative and locally sourced cuisine.brbr- Tonno: A stylish spot for modern Italian seafood.brbr- 1606 Restaurant & Oyster Bar: Waterfront dining with a refined menu.brbr- Seaport Grille: Fresh seafood and harbor views (6 Rowe Sq).brbr- The Franklin: Seasonal New American dishes in a cozy setting.brbr- Lobstah Land: A casual eatery offering local seafood favorites.brbr- Oak & Ember: Elevated dining with a steakhouse focus.brbrbrbrSeasonal Highlights:brbr- Whale Watching: Embark on unforgettable tours departing from the harbor.brbr- Gloucester Schooner Festival: Experience schooner races and maritime celebrations every Labor Day weekend.brbr- St. Peter's Fiesta: Celebrate Gloucester’s fishing heritage with lively parades and boat races.brbrbrbrGetting Around:brbrBy Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area.brbrbrbrRideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you'll be on your way to your destination in no time.brbrbrbrOther Things to Note:brbrState Tax Number: C0484721070brbrbrbrCheck-in is at 4pmbrbrCheck-out is at 10ambrbrbrbr*NO PETS ALLOWED brbrbrbr- No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors.brbr- Parking in the driveway for 3 cars max. Street parking allowed: NObrbr- Guests must be 21 years or older to book this property.brbrbrbrbrbrGUEST VERIFICATION:brbrTo help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation.brbrbrbrPrior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival.brbrbrbrIncluded with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out.brbrbrbrC0484721070brbrROC-21038977-003

Oceanfront Dock Escape ~ Kayaks & Paddleboards

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$593.45

This recently renovated beach themed 3 level, 3 bedroom, 2.5 baths, fully stocked condo, has 2 unique outdoor spaces, and parking for 4 cars. brbrLocated within walking distance right in between 2 of the most amazing beaches in Cape Ann: Good Harbor Beach in Gloucester, and Long Beach in Rockport. Take your pick, no need to drive and pay to park. It will take you just a few minutes to walk to either.brbrIndoor features include 3 levels of cozy and comfortable living:brbrThe main level has an updated, fully stocked kitchen, with an open concept into the living room, and a 1/2 bathroom on this level. The living room has a gas fireplace, 50+” flat screen tv, 2 full sized couches (1 which pulls out for more sleeping, if needed), and a full sized screen slider with walk out to a front deck.brbrThe 2nd level has 2 bedrooms and 2 bathrooms. Each bedroom has a queen bed, a closet, plenty of storage, and their own full bathroom with bathtub/shower. Linens, bedding and towels are provided during your stay.brbrThere is also a washer and dryer on the lower level for your use, as well as extra beach towels for the days you want to go back to the beach again and again.brbrThe 3rd floor living space has a spiral staircase that leads you up into another living area, with 2 queen beds. This room can also act as another living room, as it will have a tv and lounge area.brbrOutdoor features include unique spaces for relaxing:brbrOn the main level there is a walkout to a front deck with a bistro table and chairs.brbrOff the kitchen is a walk out to the back patio. This patio has a dining table, BBQ, outdoor furniture, fire pit, and an outdoor shower.brbrAbove the back patio you will find the garden ledge, surrounded by beautiful granite rock features. This serene space has a hammock, and a lounging/meditating/relaxing area.brbrYour rental includes cable tv, wi-fi, a fully equipped kitchen, linens, beach cart, beach chairs, classic board games, and plenty of books for lazy days reading on the beach, lounging around, or on the hammock…brbrThis property is half of a duplex house (2 units), and we live in the other half.

Condo

Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$528.03

brWe are offering a 4 night minimum May 29 - June 13 and again from September 12 - October 3.brbrYou can enjoy any 4 - 7 nights between our Saturday - Saturday schedule.brbrBeachcomber Cottage is just a few steps to a lovely white sandy beach, (Long Beach) where you will immediately be drawn to the gorgeous views of 'Twin Lights' Lighthouses and the rocky seashore that surrounds you.brbrGloucester is a place to see, feel and experience history. brIt is America's oldest fishing port!brThe working waterfront and beauty have drawn fisherman, families, artists and visitors for hundreds of years.brbrEnjoy a Whale watching tour and bring your fishing pole and enjoy the freshest catch! Haddock, cod and tuna can be enjoyed from the Whale Watching and Deep Sea Fishing boats.brbrLighthouses date from the 1780's, and the historic downtown has over 75 restaurants serving all kinds of cuisine along with the 'freshest' of seafood.brbrGalleries, world class museums and the period architecture will enthrall you.brMeet artists in America's oldest working artist colony on nearby Rocky Neck.brCome and experience Cape Ann!brbr'Long Beach' is a protected stretch of ocean and white sand, perfect for sunbathing, walking, shelling and even surfing! Great waves and just a 2 minute walk from the cottage.brbrFrom Long Beach, which is steps from the cottage, you can easily see 'Twin Lights' on Thatcher's Island as shown in photo.brbr*'Good Harbor Beach' (walking distance from the cottage) is a 1/2 mile long barrier beach with a rocky shore and a salt marsh which is protected by sand dunes. Small shrub covered rocky 'Salt Island' is accessible at low tide.brbr*These 2 beaches are nestled in secluded coves with white sand and stretch for miles.brbrBeachcomber has 3 bedrooms: 1 King bed, 1 Queen size bed and 2 Twin Size beds.br2 full bathrooms with shower/tub combo (1 on each level)brbrThere is one entrance with steps up to the large deck which opens into the kitchen. (Please see photo) We apologize, but Beachcomber is not handicap accessible.brbrA few things to note:br'Beachcomber Cottage' sleeps a maximum of 6 (Total includes adults/children and toddlers). brbrWe 'ONLY' allow 5 cars in the driveway at any time. brParking is not allowed on Long Beach Road. br(You will be towed and ticketed)brbrWe do not allow parties and expect our guests to be respectful of our wonderful neighbors who we have known for over 50 years. brbrBeachcomber Cottage sits on an extra large, beautifully landscaped double lot filled with flowering trees, shrubs and seasonal flowers which offers a very private setting to enjoy with family and friends.brbrTucked away on the lower ground floor in the rear, is a small apartment which has a very quiet, professional person who works full time.brThe entrances are not shared and are 'not' close together. This does not interfere with the 2 upstairs floors which are 100% designated for your use and enjoyment. brbrWe supply beach chairs, umbrellas and beach towels.brbrDue to weekend traffic on Cape Ann, Check-in time is 3PM and check-out time is 9AM.brbrWeeks run SATURDAY - SATURDAY.brbrDuring the low season, we can offer a 4 night (minimum) stay at a per diem rate. Contact us with days you are interested in visiting and we will do our best to accommodate you.brbrWe require a signed rental agreement which will be emailed to you once you have booked your reservation. Details upon booking.brbrWe offer a moderate cancellation policy however you can purchase VRBO Trip Insurance for the unlikely event you should you have to cancel your reservation during the non-refundable time period (15 days or less from your arrival date).

Long Beach/Gloucester. 1 minute walk to Beach! Large yard, lush gardens. Pup ok!

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$836.23

*NEW: We recently completed a full upgrade and modernization of the kitchen. In addition, we just completed a massive landscape project, which includes outdoor patios with stunning views and a 8,000+ sq ft of lawn perfect for fun and games, outdoor gatherings, and sunbathing. Finally, we just redid all decks (pictures will be updated soon), which are now modern steel cable railing. Feel free to ask for more details. brbr*VIDEO TOUR: Please click the play button on the 3rd photo (right before outdoor shower photo) to see our professional video tour of all rooms and drone footage of property. Note that the video tour is BEFORE recent kitchen and BEFORE all landscaping upgrades.brbrWelcome to Gloucester, America’s oldest seaport! This two acre, family-friendly, contemporary private retreat on Gloucester’s Rust Island offers 4 Bedrooms with stunning panoramic views of hundreds of acres of beautiful unique marshes and the Jones River, which flows into the Annisquam River and Ipswich Bay. The two acre property consists of plentiful indoor and outdoor living space. Surrounded by birch groves and nestled among fine landscaping, this peaceful home offers luxury vacation living only a short drive to several of the best beaches in New England, as well as historic Gloucester Harbor. Once you enter the driveway and proceed up to the house, you will immediately feel like you are on vacation.brbrGloucester, Massachusetts has made a lot of news in recent years: the movie ‘CODA’ – based and filmed in Gloucester – won 3 Oscars at the Academy Awards including Best Picture. brbrAnd, Travel + Leisure recently named Gloucester one of the best places to live on the East Coast and previously listed Gloucester’s Good Harbor Beach one of the best beaches in the United States! USA Today recently ranked Good Harbor Beach in Gloucester as one of the best beaches in the Northeast. CNN recently included Gloucester in the list of “15 of America’s best small towns and cities.”brbrThis home is a bird lovers paradise. brbrThe house is quite spacious and the perfect set-up for the extended family or share with a second family.brbrPlease feel free to contact us with any questions about the home or special requests -- we will do whatever we can to be helpful!brbrA substantial modernization was recently completed. ALL furniture and décor was replaced with contemporary pieces. All 3 bathrooms were modernized (including the spa-like master bathroom), and the home will had new paint and styling throughout. All bedrooms feature brand new hotel-quality linens and bath towels. You won’t be disappointed. Feel free to email us with any questions.brbrThis spacious home features large windows that invite the extraordinary view indoors. The spacious and open floor plan includes a large living room with high ceilings and a fireplace (and flat screen television), and an ample dining area (and outdoor decks). The home’s four bedrooms include a gracious cathedral ceiling master bedroom with King bed and en suite bathroom with soaking tub and separate shower. A second bedroom on the first floor sleeps three, and an additional baby crib is also available. A full bathroom with shower/tub is adjacent. Two additional bedrooms (one queen bed; two twin beds) and a large bathroom on the second floor offer privacy. The first floor of the home is wheelchair accessible. Please contact the host for more details regarding the property. brbrThe entire house is air conditioned. Or, if you prefer, you can enjoy the peaceful breeze air and open the two sets of screened Anderson gliding doors (decks are off the dining room and master bedroom).brbrThe home has gorgeous panoramic views of hundreds of acres of water (during high tides), beautiful marshes and conservation land, and is a 5-minute walk (or a 1-minute drive) to private dock access through the Rust Island Owners Association. There are plenty of spots nearby to launch kayaks (please contact us for details). brbrWingaersheek Beach and Good Harbor Beach – both of which are considered among the best beaches in New England are within a 10-minute drive. Several other smaller beaches are equally close to the property. brbrABOUT GLOUCESTER:brbrWhether you’re a beachgoer, a foodie, an artist or a history buff (or all of the above), the City of Gloucester has it all. Visitors enjoy spectacular beaches (Wingaersheek, Good Harbor and many more) only a 9-minute drive from the home. Gloucester was one of the first English settlements (1623), predating both Salem in 1626 and Boston in 1630, in what would later become the Massachusetts Bay Colony. brbrCLOSE PROXIMITY TO BOSTON AND AIRPORT:brbr Only a 40 minute drive from downtown Boston and Boston’s Logan Airport. While the home feels like a private retreat, you are only 0.3 miles from Route 128 (Crafts Road Rust Island exit) on the west side of Gloucester directly before the Annisquam River Bridge, so you conveniently avoid most summer traffic).brbr Only a 5 minute drive from West Gloucester commuter rail station that goes to Boston’s North Station in ~57 minutes (for those that would need to commute into Boston during your stay). brbrCLOSE PROXIMITY TO WATER:brbr Most windows of the house have gorgeous panoramic views of beautiful marshes and the Jones River, which flows into the Annisquam River.brbr Only a 1 minute drive (or 5 minute walk) to Rust Island Owners private dock water accessbrbr Less than a 10 minute drive to both Wingaersheek Beach and Good Harbor Beach (both of which are widely-considered some of the best beaches in New England). Several other smaller beaches are equally close to the house.brbr Gloucester is America’s oldest seaport and remains among the busiest of fishing ports on the entire Eastern seaboard. The house is only a 8 minute drive to a variety of great boat tour and fishing options, including Lighthouse Cruise, charter tours, and various whale watch tours.brbrGREAT FOOD:brbr Only a 1 minute drive (or less than 5 minute walk) to one of Gloucester’s best breakfast/lunch/dinner restaurants (Lobsta Land), which opens at 7am for breakfast! brbr Some of the best and nearby finer dining options in the area include Duckowrth’s Bistro, Franklin Cafe Cape Ann, and CK Pearl.brbr Numerous other great restaurants are within minutes of the home.brbr Several great grocery stores and farm stands are within minutes of the home, including Marshall’s Farm Stand, Whole Foods and Market Basket.brbrMUSEUMS AND CULTURAL ACTIVITIES:brbr Visit the Cape Ann Museum, Sargent House Museum, White Ellery House, Rocky Neck Art Colony (America’s oldest working art colony), and many other historical or cultural sites.brbr Spend a day 15 miles away visiting historic Salem, Massachusetts (among other things, site of the famous witch trials in 1692, the birthplace of the National Guard in 1637, and also home to the Peabody Essex Museum -- one of the oldest continuously operating museums in the United States).brbr Movies: Gloucester has two movies theaters near the home (Gloucester Cinema and the Cape Ann Cinema)brbrOTHER OUTDOOR AND ATHLETIC ACTIVITIES:brbr Hiking: Our property is 2 acres and filled with fun things to explore. We are also 12 minute drive to Ravenswood Park (10 miles of great hiking trails) and the Cape Ann Discover Center for kids.brbr Kayaks, SUP and Surfing: Cape Ann SUP and Surf in Gloucester and North Shore Adventures in Rockport both offer a variety of great kayak tours, lessons, and rentals. brbr Golf: Three great golf courses nearby the house, including Bass Rocks Golf Club is 9 minute drive, Cape Ann Golf is a 12 minute drive, and Rockport Golf Club is a 18 minute drive.brbr Local gyms include Crossfit Cape Ann, Cape Ann YMCA, and Fitness Zone Gloucester. Gloucester also has numerous yoga studios.brbrRULES:brbrWe have had dozens of amazing guests, partially because we are totally upfront on the house rules in advance (please do not book this home if it will not be a good fit for your group). brbrThis is our family vacation home, so we ask that you treat it as you would treat your own! :)brbrWe have a reasonable set of house rules designed to respect our neighbors, protect our property, and ensure a safe, enjoyable stay for all guests.brbrThe primary renter will be required to sign a strictly worded Short-Term Rental Agreement covering important topics such as noise, occupancy limits, smoking, cleanliness, and property care.brbrA photo ID (scan) and the full names of all occupants are required prior to check-in — this is a requirement of our insurance carrier and is not negotiable.brbrPlease note that the host uses exterior security cameras to monitor activity around the property (never inside) for safety and compliance.brbrHOUSE RULES:br- No parties, events, or large gatheringsbr- No drug use of any kind, including marijuanabr- No smoking, vaping, or burning of any substance (including tobacco or marijuana) anywhere on the property, indoors or outdoorsbr- No alcohol consumption by guests under 21br- No pets of any kindbr- Quiet hours observed 10:00 PM – 7:00 AM (please respect our neighbors)br- Maximum occupancy limited to the number stated in your reservationbr- Primary renter must be 30 years or older to book and present during the staybr- No firearms, fireworks, candles, or hazardous materialsbr- See Short-Term Rental Agreement for other rulesbrbrThank you for partnering with us to maintain a peaceful environment and protect our shared investment — we truly appreciate your cooperation!

PREMIUM PROPERTY - Private 2-Acre Retreat - MODERN 4 Bedrooms - See Video Tour

Gloucester, Massachusetts, United States

Bed

Bath

Sleeps

$713.39

Pristine, serene 2300 sq ft. furnished seaside home with breathtaking views! Stunning open design, vaulted ceilings, central AC. Chef's kitchen. Radiant floors. Two fireplaces. Office, surround sound, wet bar, patio, two decks, lawn. 3-5 min to Plum Cove Beach, Halibut Point, Annisquam Lighthouse, Lobster Pool; 10-15 min to Good Harbor, Wingaersheek, Rockport and Gloucester galleries, restaurants, shopping, theaters. 1 hr to Boston. Specialty market/cafe nearby. Very special home! brbrThis Lanesville mid-century modern home is all about light, open space, and fantastic views from nearly every room, onto the Ipswich Bay and Atlantic Ocean. Wireless, fantastic surround sound throughout. Vaulted ceiling open concept kitchen- dining-living area with a deck for dining as well. Stunning sunset views. Gas fireplace, stone hearth, large comfy window seat, beautiful gardens.brbrOur fully stocked kitchen is designed for serious cooking and entertaining-- with two sinks, two ovens, high end appliances, bamboo cabinetry and a stainless steel/granite island. There is a beautiful kitchen nook, complete with a built-in desk that has a perfectly unobstructed view of the sea-- a great place to work remotely, if one must!brbrThe dining area has sliding glass doors onto the deck for clear sea and sunset view dining and lounging with an open sea air feel.brbrThe primary bedroom has vaulted ceilings, water views, a queen bed and ensuite bath with a tiled shower and sea view. On the same floor, there is a second office/bedroom with a built-in, spacious desk, bookshelves, and a very comfortable Murphy bed with a new full sized hybrid mattress. There is a half bath just outside the bedroom door. brbrThe first floor family suite includes more spectacular water views--another queen bedroom, a large family/TV room equipped with wifi for streaming, a second fireplace, a second full bath with a deep tub/shower, a laundry area, a granite wet bar, a second dishwasher and mini fridge, ample closets and storage, two stone patio areas with a gas grill, an outdoor lounging and dining area, and a very large lawn and gardens.brbrOn the third floor of the home, you will find a sweet upper roof deck/lookout, perfect for sunsets, morning coffee, cocktails, cool breezes.brbrWhether coming to celebrate a holiday with family or friends, work remotely, or to undertake a peaceful retreat in a beautiful home surrounded by sea views and sunsets, we hope you will come to enjoy and appreciate our Cape Ann getaway home as much as we do!

Stunning, contemporary 2300 sq ft home with breathtaking views of Ipswich Bay

Gloucester, Massachusetts, United States

3

Bed