Condo vacation rentals in Gloucester

Find and book unique condos on Airbnb

Quick stats about condo rentals in Gloucester

  • Total vacation rentals

    Explore 20 vacation rentals in Gloucester

  • Nightly prices starting at

    Gloucester vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 2,090 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Gloucester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Gloucester rentals

  • 4.9 Average rating

    Gloucester stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated condo rentals in Gloucester

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Top guest favorite
Condo in Gloucester
4.96 out of 5 average rating, 197 reviews

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

🏖️Looking for the perfect Gloucester retreat for your group or family?🌴 Look no further than this spacious and inviting 2-bedroom unit🛏️, ideal for families and groups seeking comfort, style, and ample room to relax🛋️✨. Step inside and be greeted by a bright and airy living area🛋️, perfect for gathering together after a day of exploring all that Gloucester has to offer 🚤🏞️. With comfortable furnishings 🪑 and modern amenities📺🍽️, this unit provides the ultimate vacation experience🌴🍹.

ValueFamilyLayout

Top guest favorite
An open-concept living and dining area is showcased, featuring a wooden dining table with chairs, a comfortable sofa, and a flat-screen TV mounted on the wall. Natural light enters through multiple windows, enhancing the bright and airy feel of the space.
Condo in Marblehead
4.99 out of 5 average rating, 147 reviews

Samuel Tucker House - Downtown Luxury 2 Bed Condo

Presenting the newly restored Samuel Tucker House. Located in the heart of Marblehead's downtown and walking distance to local shops, restaurants and beaches, this bright and charming newly renovated 2 bedroom and 2 bath condo is a masterful blend of historic detail and modern design. Amenities include a private entrance, open concept living and dining areas that connect to a nicely appointed kitchen, fireplace, workspace, washer/dryer, central A/C, exterior dining area, and dedicated parking.

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Guest favorite
A spacious living area is highlighted by framed windows that provide ample natural light and offer views of the sky. A modern couch and an antique roll-top desk are present, accompanied by a cozy armchair. A decorative star design in the area rug adds a unique touch.
Condo in Peabody
4.93 out of 5 average rating, 121 reviews

Peabody Penthouse Top of the World Sunset View

Enjoy sunrise/sunset panoramic view from the new 6th floor Penthouse Sanctuary, the highest point in Peabody! This thoughtfully decorated spacious Penthouse open floor plan is a place to retreat, recharge, write, envision, and to enjoy the best of life. A walk away from the NS Mall/Borders Books where the Logan Express arrives. Also a mile away are the running trails, lovely ponds and apple picking at the city run Brooksby farm and six miles away from historic Salem. You will love it here!

FamilyLocationSolo travel

Top guest favorite
A comfortable living room features a soft gray sofa flanked by two armchairs. A round coffee table sits in the center, adorned with a decorative bowl. Natural light enters through a window adorned with white shutters, and a cozy rug enhances the inviting ambiance.
Condo in Marblehead
4.98 out of 5 average rating, 208 reviews

Harbor Hideaway

A uniquely detailed single-floor unit in a 2 unit house featuring a large kitchen/dining room, living room, and a private cozy veranda. Queen Bedroom & additional sleeping for 2 with a deluxe air mattress. This space is perfect for couples, families with young children, or a single person. Only one dog allowed no cats. This unit is on the lower floor of a two-family house occasionally you can hear steps from the upstairs. PLEASE note parking on site is very tight small cars compact SUVs only.

LocationValueIndoor spaces

Guest favorite
A comfortable living area features a large sectional sofa with an orange accent pillow. A wooden coffee table sits in front, complemented by a light-colored media console housing a mounted TV. Natural light enters through multiple windows, illuminating the gray walls.
Condo in Beverly
4.93 out of 5 average rating, 125 reviews

Downtown Beverly| Water view| 2 BR| Steps 2 beach

Welcome to beautiful Beverly, MA! —> Perfect North Shore getaway —> Views of Danvers River with outdoor deck and patio furniture —> Steps to Pleasant View Beach & Gillis Park —> Walking distance to restaurants, shops, beaches, and breweries —> Walking distance to new restaurant on the Beverly harbor —> 5 minute walk for train to Boston —> 1 mile to downtown Salem —> 2 Miles to Endicott, 3 miles to Landmark, 5.5 miles to Gordon College, 1 mile to Montserrat College —> Fully equipped kitchen

LocationValueBeach

Top guest favorite
Condo in Hampton Beach
4.98 out of 5 average rating, 349 reviews

Seacoast Getaway

Seacoast, NH’s popularity is well-earned, with museums, the finest restaurants, spas and shopping that blend perfectly with the Seacoast landscape. From our beautiful beaches and coastline combined with plentiful outdoor recreation, including fishing and whale watching, kite flying and more with Portsmouth, Rye, Exeter and Kittery Maine, all a short ride our beachfront condo has something for all. After a day of outdoor activity and exploring, come retire and rest in our place with a view.

FamilyValueLaundry

Guest favorite
A well-lit studio space features a colorful floral bedspread on a spacious bed. Windows provide natural light, with a small table set against the wall and a comfortable loveseat nearby. Modern appliances are present in the kitchen area, complemented by a stylish ceiling fan.
Condo in Rockport
4.89 out of 5 average rating, 118 reviews

Downtown Rockport, Parking, Walk to Beach/Train

This is a sweet studio lit well by two French doors & windows that bring the outside greenery into your homestead. Built for those looking for a tranquil retreat w/o the bustle of downtown. Proximity to the charm of downtown is 4-5 minutes walk including the beach, Shalin Lou performing arts center, train station, grocers, Bearskin Neck and Main Street galleries & artisan shops. Full kitchen, cutleries, utensils, pots and pans for those who love to cook. Perfectly fresh and clean space.!

FamilyLocationCondition

Top guest favorite
A view of a waterfront building is framed by leafy tree branches. A staircase leads to a second-floor entrance. Brightly colored kayaks are lined up along the calm water's edge, with a wooden dock visible in the background.
Condo in Rockport
4.99 out of 5 average rating, 134 reviews

Harbor Place - Airy hideaway over Rockport Harbor

Enjoy stunning views of Rockport Harbor and the Atlantic from Harbor Place, a breezy, quiet open-floorplan bnb on Tuna Wharf, steps from the galleries, shops and restaurants of bustling Bearskin Neck. You'll be within easy strolling distance of several beaches, the train station, the Shalin Liu Performance Center, kayak rentals, walking paths, parks and boat tours. Relax and enjoy the view, eat in or out, lounge on our private beach! Access to Harbor Place is via staircase.

ValueLocationAccess

Top guest favorite
A private deck overlooks Rockport Harbor, featuring two white Adirondack chairs with turquoise cushions. The calm water is dotted with boats, and the iconic Motif #1 is visible in the background, enhancing the coastal ambiance.
Condo in Rockport
4.99 out of 5 average rating, 223 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

From the deck of this New England vacation retreat enjoy amazing views of Rockport Harbor and the iconic Motif #1. Steps from delightful shops, restaurants, and ice cream/coffee, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport on Bearskin Neck. Enjoy beautiful ocean breezes with coffee or cocktails on the deck of this sweet beach retreat nestled on the New England coast. Come fall in love with charming Rockport!

LocationCheckoutCondition

Top guest favorite
A charming three-story house features a light yellow exterior with large windows and a pitched roof. A welcoming front porch offers a mix of outdoor seating. Lush greenery and trees surround the property, creating a serene atmosphere.
Condo in Rockport
5 out of 5 average rating, 109 reviews

Rockport Getaway near ocean, music hall & downtown

This private, newly-renovated, well-appointed entire two-bedroom garden apartment comfortably sleeps four with full kitchen, bathroom, washer/dryer, central A/C. Desirably located, just steps to Rockport Harbor, restaurants, shopping, Shalin Liu Performance Center and short walk to beaches. Free onsite parking for two cars. Exclusive side yard use with patio, outdoor furniture and table. Bright & airy, it's a quiet, restorative getaway. Available for longer winter rental too.

ValueLocationAmenities

Top guest favorite
A spacious game room features a stylish hanging chair and a classic arcade machine in the background. Natural light illuminates the wood-paneled ceiling and bright walls, creating a welcoming space ideal for family fun or relaxation.
Condo in Gloucester
4.99 out of 5 average rating, 161 reviews

3BR Oceanfront Condo with decks

Have fun with the whole family at our stylish oceanfront condo. Capture exquisite sunrises and sunsets off of the decks overlooking the ocean. Spend time in the spacious arcade/game room with family and friends or listen to some smooth beats using our retro record player. Walk to downtown Gloucester where you will find a number of restaurants and bars or alternatively walk to exquisite beaches or parks all available steps from your front door.

LocationFamilyRiver

Top guest favorite
A cozy living space features a queen bed with an orange throw blanket, complemented by natural light filtering through double windows. A mounted TV is positioned above a brick fireplace, while a comfortable sofa and a coffee table enhance the inviting layout.
Condo in Salem
4.97 out of 5 average rating, 246 reviews

The Green Suite, Private Parking Included

Welcome to The Green Suite, a private condo within a historic home. The whole group will enjoy easy access to everything from this centrally located place. Just under a half a mile to all tourist attractions in Downtown Salem, but far enough away to be peaceful at night. Also a half mile from the commuter rail and a 40 minute ride from the airport. This listing includes one parking spot in an on site privately owned parking lot.

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Popular amenities for Gloucester condo rentals