
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.

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🌴🍹.
FamilyLocationLong stay

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.
LocationFamilyCheckout

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
FamilyLocationAccuracy

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.
ValueFamilyQuiet

The Raven!
Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!
LocationFamilyComfort

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.!
ValueLocationGetting around

Waterfront Downtown Apartment • Walk Everywhere
Dreaming of a magical seaside getaway? Our charming eco-apartment in the Dream House awaits you! A beach lover's paradise, we're located directly on the ocean in the heart of downtown on Bearskin Neck. Watch the sunset from our amazing windows overlooking the harbor. Park the car and walk to shopping, dining, art galleries, Front Beach and Motif #1. Accessible by train and easy to get to from Boston and Salem. Make a trip to this charming New England seaside village a priority!
FamilyLocationAir conditioning

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.
LocationFamilyBeach

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!
LocationCheckoutAccess

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.
FamilyLocationCheck-in

The Blue Suite, Private Parking Included
Welcome to The Blue 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.
FamilyValueTV

Ocean View Coastal Retreat | Walk to Beach | Salem
Stay steps from the ocean in beautiful Swampscott, just a 3-minute walk to Fisherman’s Beach with front porch ocean views. Only 7 minutes to historic Salem, 5 minutes to the commuter rail, and about 30 minutes to Boston. Perfect for families, couples, girls trips, Salem visitors, and relaxing beach getaways looking to explore the North Shore and Boston while staying in a peaceful seaside neighborhood. Inhale the ocean air.
FamilyLocationHeating
Popular amenities for Gloucester condo rentals
Weekly condo rentals

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee
ValueLocationTV

1742 Marblehead Studio|Minutes to Salem|Parking
LocationValueIndoor spaces

Beautiful Apartment in Nice Salem Area
ValueFamilyCheckout

My Place - 2 Bedroom Condo with Parking
FamilyLocationLong stay

The Merchant's Carriage House - Downtown Salem
FamilyValueCheck-in

Samuel Tucker House - Downtown Luxury 2 Bed Condo
ValueLocationParking

One bedroom apartment near Boston and Salem.
FamilyValueSolo travel

Charter Street: Historic Charm, Modern Comfort
LocationValueAmenities
Pet-friendly condo rentals

A Cozy 3BR Home Close To Train + Boston & Parking
FamilyLocationGetting around

Condo in downtown Boston
FamilyLocationNearby

Family Home + Near Downtown + Cool Backyard!
FamilyValueOutdoor spaces

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

Spacious, cozy home near Boston!
FamilyLocationWalkability

The Day-Burrill-Wadsworth-La Voix House
FamilyLocationEV charging

Penthouse 2 Beds /2 Baths luxury in South Boston
LocationValueTV

Luxury apt w/ sauna & deck | by airport, downtown
LocationFamilyParks
Condo rentals with a pool

Vitamin Sea
LocationValueCheckout

Hampton 100 yards to beach
LocationValuePool

Serenity by the Sea
ValueLocationCleanliness

Ocean View - Steps to the Beach!
FamilyLocationAccuracy

Hampton Beach Bailey's Resort
LocationBathroomCleanliness

Steps from Beach | Pool | Parking | Large Deck
LocationValueHospitality

406 Co. Seascape
FamilyValueWalkability

Neighborhood Nest | 10 minutes to Beach & Downtown
LocationValueIndoor spaces
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