
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 $80 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.

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🌴🍹.
ValueFamilyDecor

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!
LocationValueAir conditioning

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.
ValueFamilyAccess

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
ValueLocationAmenities

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.
LocationValueDecor

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.!
ValueFamilyKitchen

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.
ValueFamilyAccuracy

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!
LocationCheck-inCleanliness

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.
LocationFamilyIndoor spaces

Charter Street: Historic Charm, Modern Comfort
*Perfect location according to our reviews: Walk to all of Salem's, restaurants, attractions and walking areas* Park your car and walk to all of Salem's main attractions! The Gilbert Chadwick House on Charter Street is a renovated, centrally located apartment perfect for visiting all of Salem's sites and having a nice place to relax at the end of the day. Previously owned by the Peabody Essex Museum, this property was lovingly restored with a modern look.
FamilyValueCheckout

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.
FamilyValueKitchen

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.
FamilyValueGetting around
Popular amenities for Gloucester condo rentals
Weekly condo rentals

Family Home + Near Downtown + Cool Backyard!
FamilyLocationIndoor spaces

1742 Marblehead Studio|Minutes to Salem|Parking
FamilyValueAmenities

Hampton Beach Hideaway | 1 Block to Beach |Parking
ValueFamilyWalkability

My Place - 2 Bedroom Condo with Parking
ValueLocationBathroom

The Merchant's Carriage House - Downtown Salem
ValueLocationComfort

Samuel Tucker House - Downtown Luxury 2 Bed Condo
FamilyValueHospitality

Artsy Condo | High Ceilings | Modern Industrial
ValueLocationWifi

Boston Rooftop Retreat
LocationFamilyWalkability
Pet-friendly condo rentals

Condo in downtown Boston
LocationValueCleanliness

Beautiful Apartment in Nice Salem Area
ValueFamilyAmenities

Right Near Convention Center and Train Station
FamilyValueAccess

Boston Townhouse - 3BR/2.5BA - Seaport BCEC
FamilyValueDecor

Spacious, cozy home near Boston!
LocationFamilyTV

The Day-Burrill-Wadsworth-La Voix House
FamilyLocationCleanliness

Gorgeous Huge Duplex 3 baths sleeps 6 Parking

Penthouse 2 Beds /2 Baths luxury in South Boston
LocationFamilyAir conditioning
Condo rentals with a pool

Vitamin Sea
ValueFamilyTV

Hampton 100 yards to beach
FamilyValueLayout

Serenity by the Sea
LocationValuePool

Ocean View - Steps to the Beach!
LocationFamilyIndoor spaces

Hampton Beach Bailey's Resort
LocationPoolHospitality

Steps from Beach | Pool | Parking | Large Deck
ValueLocationHot tub

406 Co. Seascape
LocationValueSleep quality

Plum Pad: Watch Fireworks Overlooking the Ocean
ValueLocationNearby
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