Vacation rentals in West Gloucester

All New Private Country Setting (2 Level-No Share)

We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

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

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.

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.

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).

Sunset Serenity-Entire Cozy Home-30 min to Salem

Imagine yourself waking up to the waves, enjoying a cup of coffee and watching boats travel between the Annisquam River and Gloucester Harbor. It’s an invitation to an unparalleled waterfront experience. Sunset Serenity offers 1,000 Sq Ft 2 beds 2 baths with one vehicle driveway. Our 1st floor features a spacious kitchen, open concept dining and living area. Upstairs offers 2 bedrooms with water view and full bath with clawfoot tub. Just minutes to downtown and 30 minutes to Salem.

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!

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.

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

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.

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.