
Condo vacation rentals in Gloucester
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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🌴🍹.

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!

The Raven!
Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

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.

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.

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!

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.

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

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!

Boho Beach Condo for Ocean Escape
Enjoy a stylish experience at our centrally-located oceanfront condo. We are walkable to exquisite beaches and parks as well as downtown Gloucester where you will find a number of bars and restaurants to explore. If you feel like hanging in, share a meal/cocktail on the private deck. Perfect for a couples getaway or a group of friends looking to explore the North Shore without ever getting in your car.

*2BR Downtown Witch House|Salem+Beverly|Hospitals
❄️ Enjoy your winter escape in Beverly! This charming 2-bedroom condo features cozy living areas, a fully equipped kitchen, and free parking for two cars—just minutes from Salem’s seasonal attractions, shops, and museums. ⛄✨ 🎃 Downtown Salem - 5 min Drive 🕸 Hocus Pocus House - 12 min Drive 🚂 Beverly Train Station - 3 min Walk 🎓 Endicott College - 10 min Drive
Popular amenities for Gloucester condo rentals
Weekly condo rentals

1 Bedroom Apartment in Boston/South End

2 Bedrooms, Steps to Sand, Heart of Hampton Beach

Whole Condo near downtown Salem, Ma

Lovely one bedroom apartment condo, with parking

The Wave • Ocean condo on sands of Hampton Beach •

GREAT LOCATION! Modern 2 BD and 2 BA w/Parking!

Walk to Downtown Salem

Fully-Equipped 2nd Floor 1-Bed 1-Bath Apt
Pet-friendly condo rentals

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

Family Home + Near Downtown + Cool Backyard!

Transit friendly condo on quiet street

Spacious, cozy home near Boston!

New Super Modern 2 bed in Waltham

Penthouse 2 Beds /2 Baths luxury in South Boston

Luxury apt w/ sauna & deck | by airport, downtown

Quaint Garden Condo one block off Atlantic Ave
Condo rentals with a pool

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

Village Hideaway

Beachn' at North Beach
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 $82 CAD 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 and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Gloucester vacation 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!
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