Holiday houses in Gloucester

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Top-rated holiday rentals in Gloucester

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Guest favourite

Loft in Rockport

5.0 out of 5 average rating, 198 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

16 – 23 Dec

$2,358 AUD total

Guest favourite

Apartment in Rockport

4.96 out of 5 average rating, 257 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! ⚓

31 Mar – 7 Apr

$2,114 AUD total

Guest favourite

Guest suite in Gloucester

4.98 out of 5 average rating, 376 reviews

SplashLanding Private Beach Getaway in Gloucester

Jan-March 2024 open for monthly rentals. Must Book Summer 2024 via Airbnb website not the APP! *Our 2nd unit SquishInn has openings beginning April 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples. Now another 2 friends can join you!

22 – 29 Apr

$3,703 AUD total

Guest favourite

Loft in Gloucester

4.9 out of 5 average rating, 167 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

1 – 8 Mar

$1,632 AUD total

Guest favourite

Cottage in Gloucester

4.97 out of 5 average rating, 101 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. In the off-season, a quiet escape -perfect for focused work, writing, painting or reading, Please contact host for discounts on longer stays (of a week or more) Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

1 – 8 Nov

$2,300 AUD total

Guest favourite

Apartment in Gloucester

4.94 out of 5 average rating, 109 reviews

Walk to Good Harbor Beach

Newly renovated ground floor efficiency apartment with sliders/walkout to fenced backyard. Wifi and Netflix included. Most dogs okay, some breed restrictions apply. If you want to bring your dog please contact us prior to booking. Three night minimum for all stays. Space includes 1 bedroom with Queen size bed and Living Area with pull out couch. 2 adults will be most comfortable. 5 minute walk to Good Harbor Beach or Bass Rocks. 15 minute walk to Rocky Neck.

8 – 15 Oct

$2,468 AUD total

Guest favourite

Apartment in Beverly

4.97 out of 5 average rating, 182 reviews

Garden City of the Northshore

Our charming newly renovated second floor apartment in Beverly, on Boston's Northshore, is minutes from beautiful beaches, ocean parks, bike trails, commuter rail and restaurants. Convenient to Salem. This comfy apartment has beautiful light and sea breezes to greet you in the morning. Original pine floors, antique furnishings along with updated, full kitchen and new tiled bathroom. Queen size new mattress in the bedroom. 4k TV with free HBO, Showtime, Netflex .

25 Dec – 1 Jan

$1,596 AUD total

Guest favourite

Guest suite in Rockport

4.99 out of 5 average rating, 611 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

2 – 9 Jan

$1,642 AUD total

Guest favourite

Guest suite in Rockport

4.87 out of 5 average rating, 197 reviews

Charming Studio in the Pines

This is a first floor, above ground, garden apartment in a private home and is located in a quiet neighborhood with the backyard nestled in the woods, just out side your sliding door. Flower gardens and bird feeders adds ambiance for relaxing in a private setting. The studio offers a kitchenette, dining nook, a full bathroom, a queen bed, plus a sofa. Also available is CableTV, Netflix and Wi Fi.

6 – 13 May

$1,541 AUD total

Superhost

Apartment in Rockport

4.87 out of 5 average rating, 163 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.

8 – 15 Jan

$2,056 AUD total

Guest favourite

Guesthouse in Gloucester

4.94 out of 5 average rating, 143 reviews

Jestina's Cottage - Next to Rocky Neck

Jestina's Cottage is walking distance to the Rocky Neck Art Colony, Gloucester Stage, restaurants, Niles Beach and a short bike ride to Good Harbor Beach. You’ll love the cottage because of the ambience and the location; you feel like you are lost in the woods of Maine but you are close to everything. The cottage is great for couples, solo adventurers, business travelers, and pet-friendly.

29 Sept – 6 Oct

$2,036 AUD total

Guest favourite

Apartment in Gloucester

4.97 out of 5 average rating, 102 reviews

The Gilbert: 1-Bed downtown suite, walk to beach.

Come stay in Gloucester’s historic downtown district, in St. Peter’s Square, just one block from Pavilion Beach, Stacey Boulevard and the historic West End of Main Street. The Gilbert sleeps two (up to 3 with an air mattress). A perfect getaway for those in love with history and seaside living. The unit has a private entrance, king sized bed, kitchenette and private bath.

28 Mar – 4 Apr

$2,781 AUD total