Holiday rentals in West Gloucester

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

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.

Shore Cottage • Peaceful Coastal Retreat

Tucked away in a quiet, private residential neighborhood, our cozy cottage offers the ideal home base for your Gloucester getaway. Located just steps from the city’s famous boulevard, beautiful beaches, and a variety of local hotspots, you’ll have the best of Cape Ann at your fingertips. The cottage sits behind the main house on the property, offering a peaceful retreat with all the comforts of home. Whether you’re out exploring or simply kicking back and relaxing, this is your place to unwind.

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 its location for your visit.

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).

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.

Stay at Little River

✔ Waterfront Location – Nestled on picturesque Little River with peaceful views ✔ Sleeps 7 – 1 King • 1 Queen • 3 Twins ✔ Private Dock – Swim, fish, kayak, or simply relax by the water ✔ Modern Comforts – Fully renovated with bright, open interiors ✔ Easy Access – Minutes to Stage Fort Park, Downtown Gloucester & local beaches A tranquil escape for families and groups, this fully renovated home blends modern comforts with classic charm. Visit @staycapeann on IG for a video tour!

Oceanfront Dock Escape ~ Kayaks & Paddleboards

This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, MA! • 13-minute drive to Wingaersheek Beach • 10-minute drive to Downtown Main Street in Gloucester • 2 inflatable Paddleboards • 4 Kayaks Available! • Outdoor Patio w/ Oceanfront Views • Large Jenga set • Fully Stocked Kitchen • Multiple Outdoor Spaces: Balcony/Deck • Family Friendly- Pack n Play & High Chair • Beach Essentials: Chairs, Umbrellas, Life Vests, Towels

French Flair "Pied a Terre" Cottage on the Marsh

Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

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.

Ipswich Waterfront Getaway

Welcome to Eagle Hill House in beautiful Ipswich, perched on a waterfront bluff, with amazing views of Plum Island Sound. Watch herons wade and osprey dive for fish as you relax. Private stairs lead down to a rocky beach. It’s the perfect place to bring a kayak or SUP board. You have exclusive use of lower level walkout apartment with private entrance.

Quirky room above convenience store, near water.

Gorgeous view of the Mill River just behind the house. Hiking, boating, marine activities and city life just minutes away. Spacious, bright, private room in funky apartment building, with grocery/convenience store right downstairs. Private entrance (from common hallway), private bath. Best suited for easy going, laidback people.