Vakantiewoningen in Gloucester

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

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.

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.

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!

Walk to DNTN/Beach/Beauport, Boat Island, New Home

Welcome to The Captain's Quarters! This charming retreat in Gloucester, Massachusetts, features three cozy bedrooms, each with a queen bed, and two modern baths. Enjoy a fully equipped kitchen, smart TV, new appliances, and a private balcony. Centrally located near St. Peter's Park, The Beauport, Pavilion Beach, and the waterfront. Relax in the outdoor spaces, with private parking and pet-friendly accommodations. Book now at this stylish place for a perfect getaway at The Captain's Quarters!

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!

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).

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!

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