Holiday rentals in West Gloucester

Stay at Little River

Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ Waterfront setting on peaceful Little River with private dock access ✓ Sleeps 7 across 4 bedrooms: king, queen, and 3 twins ✓ Fully renovated with bright interiors, central AC, and modern comforts ✓ Outdoor patio with dining, lounge seating, grill, and river views ✓ Minutes to Stage Fort Park, downtown Gloucester, beaches, and trails See more photos, video tours, and local recommendations on IG

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

Lakefront cottage for a fun, relaxing getaway.

Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

Blue Magnolia

High in the treetops, this spacious apartment is only two blocks from the Atlantic Ocean! You'll enjoy 1400+ square feet with beautiful hardwood floors, an all-new kitchen, and your choice of two comfortable bedrooms -- one king and one queen. With a sleeper sofa, the apartment can sleep six total. This is a 2-flight walkup with private entrance, plus access to a large patio and well-established plantings including roses & a grassy yard. Offstreet parking in back if needed, thru driveway gates.

Heated Pool Firepit Huge Screen Porch King bed

Beautifully renovated New England home with classic charm and modern comfort. Enjoy spacious living room, family room with gas fireplace, and bedrooms with vaulted ceilings. Full kitchen, heated pool (seasonal), large screened porch, outside dining, fire pit, gas grill, and outdoor seating. Heat/AC for year-round comfort. Peaceful setting amid woodlands. Prime location: 15 minutes to Wingaersheek Beach or Crane Beach, 1.5 miles to Conomo Point. We love calling this home, and hope you will too!

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

PVT Waterfront Deck|Firepit|Workspace|Free Parking

Welcome to your waterfront escape in Gloucester! Nestled along the a portion of the tidal Annisquam River, this professionally designed 3-bedroom home offers the perfect mix of relaxation and functionality for families and business travelers. Enjoy stunning tidal views, a private desk for remote work, and a fully loaded kitchen. Unwind by the electric fireplace, gather on the large private deck with a gas firepit, or explore nearby shops, restaurants, and beaches. Free parking included!

Stunning Ocean-View Retreat, Magnolia Beach

Escape to this luxury coastal retreat home overlooking the Atlantic ocean. Stunning newly renovated 2-bedroom, 2-bathroom apartment, offers 1,500 sq feet of bright and sunny living space. Free off street parking for two cars included. Bedrooms both have king size beds. Fully equipped kitchen with high-end appliances. Cable TV & WiFi included. Washer and dryer in unit. Located near Magnolia beach, Coolidge Reservation, Hammond Castle, Stage Fort Park. Beauport Hotel, downtown Gloucester.

The Artist Suite by Toi Moi

Welcome to Toi Moi's latest addition to AirBnb. This art-filled and chic suite with its own entrance and parking area blends influences from the Wabi-sabi philosophy, minimalist design, and old world treasures collected from our trips to create a unique aesthetic experience unavailable anywhere else on the North Shore. The Artist Suite is attached to our private home deep in the woods, creating a space for the solo traveler or romantic couple looking for serenity and inspiration.

R. Hill Tree Top Studio!

Minutes from the coast along a wooded road, this property greets you with nature and art. With a tree top view filtering amazing sunsets you feel away from it all. This property is a place to create. Home of a metal sculptor, art is woven into a lifestyle of art and nature. The nearby studio is an amazing place that welcomes visitors. Wake to the wonderful trees and landscape this property has, while staying in our newly renovated, thoughtfully designed & styled space.

3BR Oceanfront Condo with decks

Have fun with the whole family at our stylish oceanfront condo. Capture exquisite sunrises and sunsets off of the decks overlooking the ocean. Spend time in the spacious arcade/game room with family and friends or listen to some smooth beats using our retro record player. Walk to downtown Gloucester where you will find a number of restaurants and bars or alternatively walk to exquisite beaches or parks all available steps from your front door.

William Haskell House First Period Colonial Home

A First Period Colonial American experience in beautiful Gloucester, Massachusetts! As you step through the threshold of this sensitively restored 1680 residence, you are transported to an earlier time—immersed in the history of the home and the area. This listing reserves all four rooms in the house: Parlor Chamber, North Ell, the Spinning Room and The Gambrell Bedroom. As well as access to the kitchen and lounge area that has a television.