House vacation rentals in Gloucester

4.99 out of 5 average rating, 205 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.

Home in Lakeside Marblehead

5 out of 5 average rating, 141 reviews

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.

4.96 out of 5 average rating, 135 reviews

Home in Annisquam

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

Home in Lakeside Marblehead

4.98 out of 5 average rating, 214 reviews

Authentic Rustic Single Family Home in Old Town

Restored 1800's little single family home. Cozy, clean and artistically renovated to retain authenticity. Located in Old Town - walk to everything! Back yard patio with BBQ, perfect for morning coffee. Off street Parking! 4.6 miles to salem witch museum. Boston is 19 miles. Starbucks is a 2 minute WALK. Explore our little town and fall in love. Please this is not a party house. It is in a tiny little neighborhood. Quiet time 10pm - 8am. I want my precious home back in clean condition. Thx

Superhost

4.77 out of 5 average rating, 162 reviews

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.

4.93 out of 5 average rating, 165 reviews

Wonderful Rocky Neck home on Gloucester harbor

2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.

4.97 out of 5 average rating, 135 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).

5 out of 5 average rating, 15 reviews

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!

4.98 out of 5 average rating, 318 reviews

Home in Rye

*Beachfront* Vintage Coastal Cottage - Relaxation

It's always about the view and this place will leave you feeling energized and calm. Situated on premium beachfront property, this single family home has luxurious amenities like super plush towels, organic cotton bedding and touches to make your getaway feel that much Take a virtual tour here: https://bit.ly/3vK5F0G We've outfitted it with an extra screen and a setup to get you up and running. Google home and Sonos systems bring this 100 year old beauty into this century.

4.92 out of 5 average rating, 132 reviews

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!

4.96 out of 5 average rating, 341 reviews

Home in Rockport

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.