Condo vacation rentals in Gloucester

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Top-rated condo rentals in Gloucester

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Top guest favorite
Condo in Gloucester
4.96 out of 5 average rating, 181 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 favorite
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.
Condo in Peabody
4.94 out of 5 average rating, 108 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 favorite
Condo in Hampton Beach
4.98 out of 5 average rating, 320 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 favorite
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.
Condo 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 favorite
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.
Condo 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 favorite
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.
Condo 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.

Guest favorite
A sandy pathway leads to the beach, flanked by tall grass and a low fence. A wooden bench provides a resting spot along the way. The ocean stretches into the distance under a clear blue sky, inviting relaxation and exploration.
Condo in Seabrook Beach
4.8 out of 5 average rating, 189 reviews

Welcome to the Beach Escape! Seabrook, NH

Come stay in the BEACH ESCAPE! Walk 1,000 feet to Seabrook Beach in New Hampshire. After a day at the beach, come back to relax on the balcony overlooking the marsh, watch the sunsets and fireworks. The condo sleeps up to 3-4 people with a full sized bed and full sleeper sofa, TV, WiFi, kitchenette, central AC, and 2 chairs. Walk to amazing restaurants steps away. Our goal is for you to have an amazing time on the New Hampshire Seacoast! We have a check in time of 2PM.

Top guest favorite
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.
Condo 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 favorite
A spacious living area features a modern gray sectional sofa with an accent pillow. Two windows provide natural light, framed by elegant window treatments. A flat-screen TV is mounted on the wall opposite a small coffee table set on a textured area rug, enhancing the inviting atmosphere.
Condo in Salem
4.98 out of 5 average rating, 310 reviews

Charter Street: Historic Charm, Modern Comfort

*Perfect location according to our reviews: Walk to all of Salem's, restaurants, attractions and walking areas* Park your car and walk to all of Salem's main attractions! The Gilbert Chadwick House on Charter Street is a renovated, centrally located apartment perfect for visiting all of Salem's sites and having a nice place to relax at the end of the day. Previously owned by the Peabody Essex Museum, this property was lovingly restored with a modern look.

Top guest favorite
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.
Condo in Gloucester
4.99 out of 5 average rating, 139 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 favorite
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.
Condo in Lakeside Marblehead
4.99 out of 5 average rating, 247 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 favorite
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.
Condo in Salem
4.97 out of 5 average rating, 180 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 condo rentals

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 € 52 per night before taxes and fees

  • Verified guest reviews

    Over 2,170 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!

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