Apartment holiday rentals in Gloucester

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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 $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,070 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!

Top-rated apartment rentals in Gloucester

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

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Top guest favourite
Apartment in Gloucester
4.96 out of 5 average rating, 193 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🌴🍹.

Top guest favourite
The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.
Apartment in Winthrop
4.98 out of 5 average rating, 111 reviews

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

Top guest favourite
Apartment in Hampton Beach
4.98 out of 5 average rating, 336 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.

Guest favourite
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.
Apartment in Rockport
4.88 out of 5 average rating, 111 reviews

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.!

Top guest favourite
The exterior of the historic building features a grey façade with distinctive architectural details, including prominent window frames and a central entryway adorned with two potted plants. Soft hues of the sunset cast a warm glow on the structure, highlighting its classic lines.
Apartment in Salem
4.91 out of 5 average rating, 124 reviews

Miskatonic Academy Suite

Live out your New England dreams in this well appointed suite on the Historic Salem Common. This garden level unit is outfitted with a luxurious canopy bed with green velvet curtains. Loosely inspired by HP Lovecraft's Miskatonic University, this suite is full of decor and details reminiscent of the early 1900s. The location cannot be beat with all of what Downtown Salem has to offer so close by. One bedroom off of a spacious living, dining, and kitchen space can easily accommodate 4.

Top guest favourite
Seating for two is positioned by expansive windows, offering views of the ocean and harbor at sunset. Natural light enhances the inviting atmosphere, while curtains frame the scene, highlighting the serene coastal setting.
Apartment in Rockport
4.95 out of 5 average rating, 113 reviews

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!

Top guest favourite
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.
Apartment in Rockport
4.98 out of 5 average rating, 123 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.

Top guest favourite
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.
Apartment in Rockport
5 out of 5 average rating, 100 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.

Top guest favourite
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.
Apartment in Rockport
4.99 out of 5 average rating, 214 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 N.E. coast. Come fall in love with charming Rockport!

Top guest favourite
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.
Apartment in Gloucester
4.99 out of 5 average rating, 152 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.

Top guest favourite
The living area features a mix of comfortable seating, including a floral-patterned sofa and a plaid armchair. A round coffee table sits atop a light blue area rug, and large windows allow natural light to fill the space, enhancing the cozy ambiance.
Apartment in Marblehead
4.99 out of 5 average rating, 255 reviews

Harbor View Suite

Harbor View Suite is a beautifully decorated two story Unit within a newly renovated Victorian house on the harbor located in Historic Old Town Marblehead, Massachusetts. This accommodation offers a rooftop terrace with panoramic views of the Harbor. Views of the harbor also from the kitchen deck. Perfect for families & friends.​ One dog allowed no cats please PLEASE note - parking on site is very tight small cars compact SUVs only

Top guest favourite
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.
Apartment in Salem
4.96 out of 5 average rating, 217 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.

Popular amenities for Gloucester apartment rentals