
Apartment holiday rentals in Gloucester
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Gloucester
Guests agree: these apartments 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🌴🍹.

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!

1 Bedroom Waterview Downtown w/ Parking
Steps to ocean, steps to restaurants and shops. Quiet and quaint. Enjoy this centrally-located unit with all the town of Rockport has to offer right out the front door. Clean and fresh, with ocean views from the kitchen and living room. Unit has been renovated and updated with fresh paint, new appliances, new mattress and new sleeper sofa for guests. Enjoy the town shops, restaurants, sights, and beach all with a short scenic walk. This is Main Street, USA. Desirable Downtown Parking spot.

Quintessential Charm, Private, Walk to Beach/Town
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.!

Rockport Oceanfront Apartment Heart of Downtown
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. Steps to shopping, dining, art galleries, Front Beach and Motif #1. A short drive to Halibut Point for wonderful walks and an easy train ride or drive to Salem. Make a trip to this delightful 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 N.E. coast. Come fall in love with charming Rockport!

Boston Rooftop Retreat
A beautiful, fully renovated historic brownstone with a private rooftop deck overlooking the city. Come be inspired by this colorful and romantic artist studio filled with books, records, art and all the comforts of home in a quiet neighborhood with lovely views. Conveniently located a short walk from public transportation, world class universities, medical institutions and museums. About a 22 minute walk to Fenway Park, MGM Music Hall and other great attractions!

Downtown Salem - Park & Play Modern 3 Bedroom Unit
With off street parking , park your car and play! Located in downtown Salem, steps from restaurants, shopping, museums, haunted happenings and commuter rail, enjoy all that Salem has to offer. A quick walk to the commuter rail gives you access to Boston, Rockport and Newburyport. Or take a 3 mile drive that lands you in historic Marblehead. Located on the 2rd floor this Condo is convenient and private -Enjoy central AC, high speed WiFi & smart tv.

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.

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!

Modern Farmhouse Condo in Salem
Welcome to your modern farmhouse retreat! - Newly renovated condo in a quiet neighborhood - Elegant design with shiplap and bold decor - Private master with en-suite bathroom - Comfortable beds and central air - Smart TVs for entertainment - Close to Peabody Essex Museum and Salem Witch Museum (~15-20 minute walk) - No parties allowed
Popular amenities for Gloucester apartment rentals
Weekly apartment rentals

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

Badgers Island Condo-Sweeping Portsmouth Views #3

2 min. walk to beach strip, 2 parking spots & WiF

Private studio w/ parking by MIT/Harvard/BU/Fenway

Sunny Condo

Retreat to tranquility - water views

Oceanfront Penthouse at Salisbury Beaches

The Green Suite, Private Parking Included
Pet-friendly apartment rentals

Condo in downtown Boston

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

New Super Modern 3 Bed in Waltham

Transit friendly condo on quiet street

Harbor View Suite

Historic JP Brownstone with Parking. Pets Welcome!

Spacious, cozy home near Boston!

Boston Townhouse - 3bd / 2.5ba - Central Location
Apartment rentals with a pool

Lovely 2 BR beach condo with inground pool

2BR Balcony, Parking, Pool, Hot Tub, Tennis!

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
Quick stats about apartment rentals in Gloucester

Total holiday rentals
Explore 20 holiday rentals in Gloucester

Nightly prices starting at
Gloucester holiday rentals start at € 51 per night before taxes and fees

Verified guest reviews
Over 2,170 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Gloucester holiday rentals include wifi 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- House rentals Gloucester
- Rentals with an EV charger Gloucester
- Rentals with beach access Gloucester
- Beachfront rentals Gloucester
- Rentals with a washing machine and dryer Gloucester
- Rentals with a firepit Gloucester
- Waterfront rentals Gloucester
- Rentals with a patio Gloucester
- Private suite rentals Gloucester
- Rentals with outdoor seating Gloucester
- Fitness-friendly rentals Gloucester
- Rentals with breakfast Gloucester
- Rentals with a fireplace Gloucester
- Rentals with a kayak Gloucester
- Family-friendly rentals Gloucester
- Pet-friendly rentals Gloucester
- Flat rentals Gloucester
- Apartment rentals Essex County
- Apartment rentals Massachusetts
- Apartment rentals United States
- Hampton Beach
- TD Garden
- Fenway Park
- Ogunquit Beach
- Boston Common
- Harvard University
- Wells Beach
- Revere Beach
- New England Aquarium
- MIT Museum
- Long Sands Beach
- Freedom Trail
- Boston University
- York Harbor Beach
- Canobie Lake Park
- Boston Seaport
- Crane Beach
- Duxbury Beach
- Boston Convention and Exhibition Center
- Quincy Market
- Museum of Fine Arts
- North Hampton Beach
- Prudential Center
- Gillette Stadium




