Vacation rentals in Annisquam River

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

Evensong: Lovely Oceanview Retreat with Dock

Unobstructed water views in this newly renovated "walls of glass" home boasting panoramic views of the Mill River, Anisquam, Wingaersheek Beach & beyond. Enjoy our dock (removed in Winter), shared with our neighbors below, and feel free to bring kayaks or paddleboards along. 1,600 square ft open concept home with 3 beds/3 baths. Large roof deck overlooking the water. Owners live nearby & also have a basement apartment (with separate entrance) at the property. Available for questions/requests.

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!

Oceanfront Stay w/ Deck & Parking

• Private deck with ocean view • Parking • Steps to Front Beach • Walk to Bearskin Neck • Pet friendly • 15-minute walk to commuter rail • Contemporary art gallery on site Beautifully renovated, light-filled top-floor apartment on the water in historic downtown Rockport. Enjoy a private ocean-view deck, one dedicated parking space, and seasonal private access to Front Beach. One of three guest apartments at The Pearl, located just behind Thalassa, our contemporary art gallery.

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

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.

Private Beachfront Property in Gloucester

Experience the ultimate coastal living with this private beachfront property in Gloucester, nestled on the exclusive Coffins Beach-also known as the private section of Wingaersheek Beach. From your expansive beachside deck, take in breathtaking panoramic views: To the right, gaze across Annisquam to Halibut Point, and enjoy sweeping sights over Essex Bay all the way to Portland, Maine. Your reservation is for 10 adult guests.

On the Water Gem - 2 BR -The Cove Lanesville

Enjoy our immaculate 2 BR at The Cove Lanesville, on lovely Ipswich Bay. Two spacious decks overlook spectacular sunsets. You can be as active...or as chill as you desire; great restaurants, world-renowned beaches, shopping, Everything in the Arts, woodland quarry walks. No matter what the season the beauty of this special island does not disappoint.

Gloucester Private Contemporary 4 bedrooms

A contemporary private house with large yard in quiet and exclusive goose cove bay neighborhood offers the perfect space for a summer sojourn. Everyone in your group will love being only minutes away from some of the best beaches, activities, history, and food in New England!