Beach house holiday rentals in Gloucester

4.95 out of 5 average rating, 133 reviews

Views over Lobster Cove! Book spring weekends

Booking summer and fall 2025. 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

4.99 out of 5 average rating, 195 reviews

Rocky Neck Retreat

.Relaxing private location .4 beds 2 baths with full kitchen/pans/Dishwasher/Wash/Dryer.Renovated organic design integrates historic architecture with modern touches.If you come for hikes, beach/music/food scene, you will enjoy the Rocky Neck District .The unique home has 4 bedrooms /4 Queen Beds. Speedy WIFI .Parking is up a steep narrow drive . NO trucks or Large SUVs. 2 cars max. Note* Kitchen and LR are upstairs.There are stairs. Contact owner for questions re:parking or limited mobility.

4.93 out of 5 average rating, 29 reviews

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.

4.98 out of 5 average rating, 196 reviews

Home in Ipswich

Stagehill Beach House

Spectacular water views from every room! 5 min walk to the beach and Pirate Park playground. Well stocked spacious kitchen, two family rooms, 4 BRs , dining room, deck and screened-in sun porch. Happily welcomes families, wedding guests and friends to enjoy my informal, livable, light infused beach house. Located on Great Neck in historic Ipswich, 4 miles to the charming downtown and a 15 minute drive to Crane Beach. Relax and enjoy! Ping pong table, corn hole, campfire! 2 driveways!

5 out of 5 average rating, 8 reviews

Stay at Rocky Neck

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

4.94 out of 5 average rating, 36 reviews

Townhouse #3 in Downtown with Parking

Welcome to Gloucester, the beautiful fisherman city. This townhouse offers a beautiful and unique living space with an eat-in kitchen, and a loft style bedroom. The home boasts numerous features including in-unit laundry and 1 free off street parking spot. Enjoy the convenience of being close to the beach, downtown, and the prestigious Beauport Hotel. Indulge in the vibrant culinary scene with many restaurants just steps away. Don't miss this opportunity to stay in this coastal paradise.

Superhost

5 out of 5 average rating, 3 reviews

Refreshing Ocean and Sunset View

Escape to this homey 3-bedroom retreat in Lanesville. Just a 5-minute walk to the ocean, where waves crash on massive boulders, enjoy stunning ocean views from the porch. Enjoy a fully equipped kitchen and bar area, with cozy living spaces perfect for unwinding. A dedicated desk makes remote work easy. Outside, a large yard offers outdoor games and dining space for al fresco meals. Whether sipping coffee on the porch or exploring the shore, this getaway is perfect to relax and recharge.

4.98 out of 5 average rating, 124 reviews

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).

4.97 out of 5 average rating, 34 reviews

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.

4.91 out of 5 average rating, 126 reviews

Gloucester Beach House, near Good Harbor Beach!

Make your July escape to this inviting 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. 📅 Weekly rentals available only for early July—book now before it’s gone!

4.98 out of 5 average rating, 82 reviews

Overlook Gloucester's Inner Harbor, Walk to Town

VACATION or WORK or a bit of both if it means you'll have longer to play here on Cape Ann! The preferred spot for all things is the sunroom chaise overlooking the harbor, but there are also two spacious desk areas including one in the living room which can be closed off for privacy while your family enjoys the rest of the house! (Then, of course, go to the beach!) Flexible cancel policy. We clean & disinfect with a passion that considers you 'family'. Vaccinations preferred.