
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🌴🍹.

Samuel Tucker House - Downtown Luxury 2 Bed Condo
Presenting the newly restored Samuel Tucker House. Located in the heart of Marblehead's downtown and walking distance to local shops, restaurants and beaches, this bright and charming newly renovated 2 bedroom and 2 bath condo is a masterful blend of historic detail and modern design. Amenities include a private entrance, open concept living and dining areas that connect to a nicely appointed kitchen, fireplace, workspace, washer/dryer, central A/C, exterior dining area, and dedicated parking.

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.

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!

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.

*NEW Downtown Retreat|2BR|Salem+Beverly|Parking
❄️ Welcome to your Beverly winter getaway! This cozy 2-bedroom condo offers comfortable living spaces, a fully equipped kitchen, and free parking for two cars—just minutes from Salem’s festive 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

Historic JP Brownstone with Parking. Pets Welcome!
Located in one of Boston's best neighborhoods, this 1200 square foot bright sun filled corner unit in a 120 year old historic Brownstone is the perfect retreat. Its excellent location is just steps from the T and a short walk to Centre Street shops and restaurants. Good for couples, solo adventurers, business travelers, and furry friends (pets).

Downtown beautiful renovation with parking
*Perfect location to enjoy Salem according to all of our reviews! Walk to every attraction in just a few minutes!* This second floor apartment is in the best location in town on Charter street, steps to all of the attractions. This apartment was lovingly restored maintaining it's historic charm, but with modern touches.
Popular amenities for Gloucester condo rentals
Weekly condo rentals

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee
Victorian Charm, Modern Style w/Private Entrance

Sunny Condo

Lovely Studio - Spotless, W/D, Parking, Private

Retreat to tranquility - water views

Fairies Nest (full unit w/ desk & kitchen)

Downtown Loft Boston - Close to everything

Pretty private garden-level condo+parking near MIT
Pet-friendly condo rentals

Condo in downtown Boston

Family Home + Near Downtown + Cool Backyard!

Leafy & Tranquil, Artist house. Easy access Boston

Transit friendly condo on quiet street

Spacious, cozy home near Boston!

Harbor Hideaway

New Super Modern 2 bed in Waltham

Penthouse 2 Beds /2 Baths luxury in South Boston
Condo 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

Village Hideaway
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 G$12,547 GYD 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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