House holiday rentals in Gloucester

Seaside Cottage

Here you are down the street from some of Marblehead's hidden gems such as Redds Pond, Browns Island & Old Burial Hill Cemetery. One car parking. 5 minute walk to the beach, shops & restaurants. Fully fenced in yard with turf grass. One bedroom with a low profile queen sized bed. In unit washer/dryer. Full bath with tub. Newly renovated kitchen with major appliances: stove, oven, dishwasher, fridge, Nespresso maker & microwave. Sheets & bath linens provided. Minisplit A/C. Home is all one level.

Views over Lobster Cove! Fall/Holiday stays

Book fall and holiday stays. Water views/access, sunsets above Lobster Cove on Washington St. Ideal for couple, NEW KING BED in master, queen in 2nd. Fast WiFi./TV. Not suitable for young children. Central A/C. 2nd fl unit large windows. Large living/dining/kitchen area. Comfy new mattresses, 100% cotton sheets,sound machines. Overlooks beautiful Lobster Cove and footbridge. Minutes walk to the village of Annisquam and Lighthouse Beach. Small deck. Swim/kayak out your door. Parking for one car

Gloucester getaway ocean escape

A completely renovated house that is located close to the commuter rail and within walking distance to many shops, the Marina, and whale watching tours. There are many beaches around this area including the pristine Good Harbor and Wingaersheek Beach. Hammond Castle is a ten minute drive, breweries and deep sea fishing options as well. Rockport is close by with many artisan shops. Guests can spend the afternoon eating fresh seafood at famous Woodman's or taking an Essex River Cruise.

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).

Stay at Rocky Neck

Rare Gloucester Waterfront Retreat! ✓ Perched directly on the water with breathtaking ocean views ✓ Expansive deck with outdoor dining – watch boats pass at eye level ✓ Private 30-ft deep-water dock – swim, kayak, paddleboard, or dock your boat (fees apply) ✓ Newly renovated home + detached guest house with modern coastal charm ✓ Wall-to-wall windows & open layout – feel immersed in the sea A one-of-a-kind escape—book now! Visit @stay_collections on IG for a video property tour!

Harbor House with Ocean Views

Welcome to our charming Airbnb in Gloucester, MA! Steps from Stacy Boulevard, our home offers breathtaking views of Gloucester Harbor. Enjoy a stroll to nearby downtown restaurants, shops, and Pavilion Beach, just a 5-minute walk away. We provide private parking for two cars. Stage Fort Park is walkable for kids, and Good Harbor beach and Wingaersheek beach are a short drive away. Whether relaxing by the water or exploring the local scene, our Harbor House is the perfect retreat.

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away!

Gloucester Beach House, near Good Harbor Beach!

Escape to this inviting, and pup friendly 4-bedroom Gloucester home, just a short walk to Good Harbor Beach! This classic coastal home blends comfort & convenience. All 4 bedrooms are air-conditioned, featuring a large eat-in kitchen, covered front porch perfect for relaxing or grilling, full bathroom plus refreshing outdoor shower. Stay connected with high-speed Wi-Fi, & enjoy the ease of on-site laundry. Openings for September and October. Ideal for weekend get aways!

Charming Toe-Hold, A Short Walk to Town and Beach

Toe-Hold is a wonderful year-round 1846 home with plenty of rooms, reading nooks and quiet spaces for family and friends of all backgrounds to eat and play together. The gorgeous beaches and picturesque downtown, great restaurants, art galleries and shops for the whole family, are within 10-15 minute walk. Rockport is one of the oldest art colonies in the US, and home to generations of fishermen. Day trips by car or train to Boston and other beautiful historic towns.