House holiday rentals in Gloucester

Find and book unique houses on Airbnb

Top-rated house rentals in Gloucester

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

0 of 0 items showing

1 of 3 pages

Top guest favourite

Home in Somerville

4.96 out of 5 average rating, 292 reviews

Best House Cambridge/Somerville

spacious 1900's mansard Victorian. Bright cheerie & centrally located if you're looking for a pad in Cambridge/Somerville. A 10-12minute walk to Harvard Square & close to the Red Line. Great kitchen, living room & /cablewifi. Three bedrooms--one with a European Queen Bed, one double bed & one single. There is one full bathroom w/a large glass shower & a claw foot tub. There is a half bath on the first floor. There is a front porch to sit & sip wine on & a back deck where you can grill & eat out on. I've been living here 12 years--Its tastefully appointed, eclectic finds & a mid century modern touch--absolutely the best equipted kitchen. I've been a chef in Boston & Cambridge for quite some time!

Guest favourite

Home in Cohasset

4.91 out of 5 average rating, 32 reviews

Village Colonial with Cohasset Harbor Views

Location!! An original Grand Dame of Historical Cohasset Harbor is just waiting for you to come and enjoy all that this historical sea side town has to offer. This newly reno/updated, 1848 village colonial has shows her glory with gorgeous hardwoods, fresh paint, comfortable and stylish decor that reflects the relaxed and beach town style of Cohasset. It has a fabulous third floor suite and a location that can't be beat! Harbor views from top two floors! 1 block to the harbor and walk to town.

Top guest favourite

Home in Rockport

5 out of 5 average rating, 42 reviews

New South End Home Quiet Lane To Old Garden Beach

Newer furnished home, 1/2 mile walk to quaint Bearskin Neck with Rockport shops & galleries. Old Garden Beach 1/4 mile walk down a quiet unpaved lane. 3 BR/3 Bath home available for summer weekly vacations. Family friendly, 3 prkg spaces, 2 decks, new appliances (laundry, microwave & dishwasher), hardwood floors, new rugs & beds, full basement w/ pool table, fenced yard. Several beaches, hiking trails nearby or take a train to Salem, Newburyport, or Boston. Longer term winter rental available

Guest favourite

Home in Salisbury

4.9 out of 5 average rating, 129 reviews

NEW 3BR home, incredible views - Beach across St

Enjoy sunrises and sunsets with an expanse of windows that offer breathtaking views of the river and marsh in a new construction, BEAUTIFUL, single family home. Over 2000 Sq Ft wTile & hardwood floors. 1st level has Open living room/kitchen, half bath & 1 bedroom. 2nd Floor has 2 bedrooms, bath, laundry & Large outdoor deck. Beach is a 2 minute walk across the street. 10 minutes to Browns Seafood restaurant, Ice Cream, Groceries & more. 2+ Parking spots. We follow the Advanced Clean Protocol.

Guest favourite

Home in Derry

4.92 out of 5 average rating, 466 reviews

Little Lake House, the Bungalow

Cozy up during your next trip to southern New Hampshire! The Little Lake house, situated right next to a serene lake, boasted luxury and spectacular water views. It's a perfect place for a peaceful escape or chance to experience the wide variety of seasonal New England activities from swimming and leaf peeping to ice fishing. The Little Lake house is a short drive to Canobie Lake Park and Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Superhost

Home in Wayland

4.78 out of 5 average rating, 486 reviews

Tiny house experience steps from the water!

-Tiny house experience in quiet private neighborhood on its own lot with great backyard & fire pit on private secluded St. -prof cleaned after each guest -High speed internet/ expanded cable -Built in full bed with queen sleeper futon bed that can sleep 2 more -Just a few steps from beautiful Dudley Pond for swimming/fishing and great walking trails Wayland is one of nicest towns in MA yet only a min or two from anything you need and less than half hour from Boston. texts returned instantly

Guest favourite

Home in Hampton Beach

4.94 out of 5 average rating, 105 reviews

Pearls on Perkins, Beautiful Condo!

The Pink Pearl is the downstairs 1100 sqft. condo unit! With 2 bedrooms (1 queen & 1 twin bedroom, includes sheets, blanket & comforter), 2 full baths, with towels for your convenience, there is also a comfortable pull out sleep sofa, TV, WIFI, central air, washer/dryer. A large front to back fully equipped kitchen/living room with pots, pans & dishes for home cooked meals. Large roof top deck to watch the sunset over the Hampton River. Fantastic location, only 1 street from the beach.

Guest favourite

Home in Gloucester

4.97 out of 5 average rating, 117 reviews

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

Top guest favourite

Home in Rockport

5 out of 5 average rating, 14 reviews

Adorable renovated house, steps from Front Beach

This charming home was recently fully renovated. The brand new kitchen features stunning granite countertops and stainless steel appliances. The large living/dining room features a 55" flat-screen TV comfy seatingnd a dining table for 4. There is a king bed in the Master Bedroom, along with a TV, ceiling fan, and air conditioning. The second bedroom has a twin daybed, with a second twin trundle bed underneath. The backyard features a patio with a seating for 4 and a gas grill.

Superhost

Home in Scituate

4.83 out of 5 average rating, 60 reviews

Sand Hills Barker Tavern RiverClub lighthouse -

Walking distance to sand hills beach - super close to BARKER TAVERN! One mile from center of town with restaurants and shops. Nearby basketball court. Grassy backyard . New furnishings new full bath and new mattresses. Freshly painted well maintained by owner bedrooms are upstairs. There is only one full bath upstairs Totally redone 2024. Bungalow beach style home. some guests find stairs to be “ steep” … my 82 year old mom does fine with the stairs and rail!

Guest favourite

Home in Gloucester

4.91 out of 5 average rating, 122 reviews

Gloucester Beach House, near Good Harbor Beach!

Delightful 4 bedroom cape house, with fabulous covered porch, and a corner, flat yard, welcomes you any season of the year! Well situated less than a half mile behind Good Harbor beach in Gloucester, MA. Rockport's Long Beach also nearby this beachy neighborhood. Private off-street parking for multiple cars, full eat-in, well equipped kitchen, laundry, gas grill, outdoor shower, air conditioners, cable, and WiFi round out this cozy well decorated home!

Superhost

Home in Hampton Beach

4.81 out of 5 average rating, 186 reviews

Steps to Beach Fireplace Pat's Porch

Welcome to Pat's Porch, the sister cottage of Lorraine's Landing and a professionally managed beach getaway - Just a 5-minute stroll from the sun-kissed shores and bustling boardwalk of Hampton Beach, this 3-bedroom, 1-bath abode boasts a queen master bedroom and newly updated kitchen. Relax on the expansive porch equipped with a picnic table, lounge chairs, and grill, or unwind indoors with fast wifi and a Samsung Smart TV.