
Condo holiday rentals in Gloucester
Find and book unique condos on Airbnb
Quick stats about condo rentals in Gloucester

Total holiday rentals
Explore 20 holiday rentals in Gloucester

Nightly prices starting at
Gloucester holiday rentals start at $139 NZD per night before taxes and fees

Verified guest reviews
Over 2,090 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Gloucester holiday 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🌴🍹.

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.

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!

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

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.

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.!

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!

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.

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!

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.

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.

Luxurious beach house w/ harbor views & near beach
There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!
Popular amenities for Gloucester condo rentals
Weekly condo rentals

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

Ocean View Coastal Retreat | Walk to Beach | Salem

1742 Marblehead Studio|Minutes to Salem|Parking

Modern Downtown Salem 3 Bedroom | Park & Play

Harbor View Suite

Modern Farmhouse Condo in Salem

The Day-Burrill-Wadsworth-La Voix House

Downtown beautiful renovation with parking
Pet-friendly condo rentals

Condo in downtown Boston

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

Family Home + Near Downtown + Cool Backyard!

Beautiful Apartment in Nice Salem Area

Boston Townhouse - 3BR/2.5BA - Seaport BCEC

Spacious, cozy home near Boston!

Penthouse 2 Beds /2 Baths luxury in South Boston

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

Vitamin Sea

Hampton 100 yards to beach

Serenity by the Sea

Ocean View - Steps to the Beach!

Hampton Beach Bailey's Resort

Steps from Beach | Pool | Parking | Large Deck

406 Co. Seascape

Neighborhood Nest | 10 minutes to Beach & Downtown
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- Fenway Park
- Harvard University
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- TD Garden
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