Apartment holiday rentals in Gloucester

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Top-rated apartment rentals in Gloucester

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Guest favourite
Apartment in Gloucester
4.96 out of 5 average rating, 179 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
A spacious living area is highlighted by framed windows that provide ample natural light and offer views of the sky. A modern couch and an antique roll-top desk are present, accompanied by a cozy armchair. A decorative star design in the area rug adds a unique touch.
Apartment in Peabody
4.94 out of 5 average rating, 107 reviews

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!

Top guest favourite
A modern kitchen is presented with crisp white cabinetry and sleek stainless steel appliances. A large island with seating for four is featured, providing a space for casual dining. Bright overhead lighting enhances the clean lines and organized layout of the kitchen.
Apartment in Rockport
4.98 out of 5 average rating, 126 reviews

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.

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, 110 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.!

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, 111 reviews

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!

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 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, 210 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
The private rooftop deck features a shaded seating area with sectional sofas adorned with cushions. Potted plants add greenery, while views of neighboring buildings and trees are visible in the background under a partially cloudy sky.
Apartment in Fort Hill
4.94 out of 5 average rating, 341 reviews

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!

Top guest favourite
An open-concept living area is visible, featuring a modern dining table surrounded by chairs on a textured rug. A kitchenette is equipped with sleek cabinets and appliances. Natural light floods the space, highlighting wooden flooring and an art piece on the wall.
Apartment in Salem
4.96 out of 5 average rating, 185 reviews

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.

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, 136 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.

Guest favourite
Apartment in Gloucester
4.95 out of 5 average rating, 139 reviews

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!

Top guest favourite
A modern living space is presented with bright walls and stylish furnishings. A large dining table is positioned in the foreground, surrounded by dark chairs. The seating area features a light-colored sofa and an accent chair, complemented by artwork and a decorative wall-mounted antler.
Apartment in Salem
4.83 out of 5 average rating, 389 reviews

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

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!