Beachfront holiday rentals in Gloucester

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Gloucester

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

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Guest favourite

Loft in Rockport

5 out of 5 average rating, 237 reviews

Chic Downtown Loft ☆ Private Parking ☆ Ocean View

Enjoy the coastal and seaside views from the renovated and bright "jewel" located in the charming seaside New England town of Rockport on Cape Ann. The loft is centrally located is literally steps to the beaches, the Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu. 1-min walk to Bearskin Neck & Motif No.1 5-min walk to Front Beach + easy access to many others 8-min drive to Halibut Point Park 25-min drive to Salem 1-hour drive to Boston 15-min walk MBTA Train Station

Guest favourite

Rental unit in Rockport

4.96 out of 5 average rating, 290 reviews

Harbor Retreat | Ocean View | Heart of Downtown

Discover Rockport's Harbor View Apartment! 🌊 This newly renovated 1-bedroom on the second level boasts stunning harbor views from a private deck. Steps from Bearskin Neck, enjoy proximity to unique shops 🛍️, fine dining 🍽️, and beaches 🏖️. Equipped with high-speed WiFi, a 55" Smart TV, and a Murphy couch. Perfect for experiencing Rockport's vibrant atmosphere. Note: Guests must climb stairs and the downtown location can be lively and noisy 🌆. Book your unforgettable seaside escape today! ⚓

Guest favourite

Guest suite in Gloucester

4.98 out of 5 average rating, 283 reviews

PrivateBeach for 2 Adults, Gloucester MA SquishInn

SquishInn & SplashLanding are quiet, couples beach getaways. 2 adults/unit. No pets. Enjoy the pristine 1 1/4 mile private beach on our beach chairs/towels. SquishInn - hotel room-style unit. Large walk-in shower, vanity, private toilet, small sized refrigerator, Keurig & micro. FULL access to private beach & off street parking. * Combine w/ SplashLanding for a full kitchen, oceanside deck & accommodations for 4 adults. Splashlanding: copy and paste airbnb.com/h/splashlanding-gloucester-ma

Guest favourite

Rental unit in Gloucester

4.96 out of 5 average rating, 111 reviews

Beautifully remodeled unit in heart of Gloucester

Enjoy your stay in the heart of Gloucester close to everything this great town has to offer. This unit was completely remodeled in 2022. Two shorts blocks from Main Street in Gloucester and all of its wonderful restaurants and shops. Three blocks from the Beauport Hotel - perfect for wedding guests not staying at that location. This unit has new floors, countertops, appliances and fixtures and is freshly painted (no VOC paint). You will love this unit and location for your visit.

Guest favourite

Loft in Gloucester

4.9 out of 5 average rating, 194 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2024! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

Guest favourite

Rental unit in Rockport

4.94 out of 5 average rating, 178 reviews

Mary's By The Sea

A unique 650 square foot ground floor apt across the street from Front Beach. 6 minute walk from the Rockport MBTA . There is a separate bedroom with a queen mattress and a pullout sofa bed in the living area. The pullout sofa is best for teens or smaller kids .There is a bathroom with a sink and toilet. There is another room with a sink and shower. The kitchen area is more like a kitchenette than a full-size kitchen. We provide one parking spot next door at The Cove parking lot.

Guest favourite

Apartment in Rockport

4.98 out of 5 average rating, 107 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 favourite

Guest suite in Marblehead

4.9 out of 5 average rating, 263 reviews

Ocean Park Retreat

Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

Guest favourite

Guest suite in Rockport

4.98 out of 5 average rating, 126 reviews

Large Suite in the Historic District of Rockport.

This large suite is the entire top floor of a Historic home, approx. 750 sq. feet. Enjoy a short walk to Old Garden Beach , Front beach, Heath’s Tea Room , Shalin Liu Performance Center and all of downtown Rockport many shops, restaurants and art galleries. You will enter your suite via a keyless door up a private “good morning” staircase to the third floor. Includes use of a screened porch, side porch with rockers and grilling area.

Guest favourite

Home in Gloucester

4.97 out of 5 average rating, 115 reviews

Harbor View Walk to Town&Beach, 6 Guests King beds

Spectacular Gloucester home. Book this Fall to stay on Cape Ann. From the private oasis, you have a beautiful walk to local beaches & Gloucester center, restaurants, museums, galleries & boutiques, sailing and whaling charters, power boat rentals, SUP, kayaking, historic landmarks, seaside restaurants & also ocean front tennis, boce ball and so much more! or just come for happy relaxing! This place is a happy haven! ♡

Superhost

Rental unit in Rockport

4.88 out of 5 average rating, 177 reviews

"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven

Experience the beauty of Rockport's waterfront at this 2 bed/1 bath oceanfront haven. Located on Bearskin Neck, this historic building was once the Sail Loft and is now your perfect getaway. Enjoy the convenience of being close to the ocean, restaurants, shops, and beaches. Come and make lasting memories at this charming Rockport escape. Don't forget to take advantage of the small patio and kitchen.

Guest favourite

Rental unit in Magnolia

4.88 out of 5 average rating, 136 reviews

Bright One Bedroom Apartment 5 Min Walk From Beach

Welcome to the Oak Grove House! Originally built as a twenty-one room Inn and Hotel in 1860 - This beautiful and sunny getaway is as rich with its history as it is with its location. Minutes walk from the beautiful Magnolia Beach and only walking distance to many shops and restaurants in Magnolia - you can truly get away from the hustle and bustle of the city and enjoy a quiet evening in paradise.