Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

10.0 out of 10, Exceptional, (49)
"Location on Plum Island: beautiful sunsets and beaches and walks in nature. Just a few miles from dntn Newburyport. Lots of great restaurants and shopping and culture."
The price is NZ$796
includes taxes & fees
26 Dec - 27 Dec
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

The widow’s walk your very own spa experience

10.0 out of 10, Exceptional, (6)
"We loved the Widow’s Walk house! It was so extra with 2 spiral staircases, view of the harbor, cozy beds, hammock, towel warmers, hot tub, electric bikes, fancy coffee machine, fire pit, plus friendly neighbor kitty! The neighborhood is classy and quiet, we loved it there so much!"
The widow’s walk your very own spa experience

OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

9.6 out of 10, Exceptional, (9)
"Loved this old historic home and the town. Had everything we needed to make our stay comfortable. Would love to come back again! Everything was walkable. Charming town. Gorgeous ocean all around. In love!"
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

Stunning 2 bed apt in Revere 15 mins to Boston

Stunning 2 bed apt in Revere 15 mins to Boston

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

9.8 out of 10, Exceptional, (73)
"The bed upstairs is so confortable, I slept like a baby! Great location! You can swim nearby, it’s very quiet and in the Rocky Neck art colony district."
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

10.0 out of 10, Exceptional, (3)
"This place was so peaceful and relaxing "
Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!

10.0 out of 10, Exceptional, (19)
"House is so charming and comfy! Well-equipped kitchen for meals in"
Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (221)
"Nice house, close to downtown. Walking distance to most of the attractions. Great place to stay. No complaints! "
Leslie's Retreat: Spacious home ideally located to everything

Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

9.6 out of 10, Exceptional, (34)
"It was nice "
The price is NZ$516
includes taxes & fees
31 Dec - 1 Jan 2025
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

9.6 out of 10, Exceptional, (108)
"It was the best location, just a VERY short walk to all that Salem has to offer! It is right across the street from Jaho, which is an amazing coffee place and access to the lighthouse is directly across the street. The layout of the unit is awesome - the primary is in the basement with its own living area, HUGE walk-in closet, and bathroom, while the two other bedrooms are on the main floor. It felt very private having the whole basement to ourselves. The only downside (and it's a personal...
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Stunning Beach Cottage just steps from Marblehead Harbor and Town

10.0 out of 10, Exceptional, (42)
"Everything about our stay was terrific! The house is old and feels historical, but it's also renovated and has all the modern amenities. It's comfortable and quiet and perfect for relaxing, cooking and enjoying time with the people you love. And it's just a short walk to the ocean and some great local Marblehead shops and restaurants. It is also a quick drive over to Salem, which was great. We also drove up to New Hampshire and Maine for a day trip, and that was a quick drive up as well....
Stunning Beach Cottage just steps from Marblehead Harbor and Town

NEWLY Renovated Luxury Home, Walk To Town & Beach. 5 Bedroom, 3.5 Bath + Office.

9.8 out of 10, Exceptional, (14)
"The house is simply gorgeous, the kitchen is even nicer in person! The spacious living areas accommodated our group wonderfully. The location is great, on a nice quiet street and still so close to the water!"
NEWLY Renovated Luxury Home, Walk To Town & Beach. 5 Bedroom, 3.5 Bath + Office.

Coastal Lynn Escape w/ Fireplace: 3 Mi to Beaches

9.8 out of 10, Exceptional, (8)
"Excellent option to staying at a hotel. Good location near family and away from tourists. Property was as described, clean and well maintained. Only issues were the water pressure in the primary suite shower was tterrible and"
Coastal Lynn Escape w/ Fireplace: 3 Mi to Beaches

NEW Tiny House Walk to Essex Main St+Boat Launch

10.0 out of 10, Exceptional, (4)
"Perfect location, quiet, clean and comfortable! Would recommend! We enjoyed being so close to our family in Ipswich and Hamilton. Thank you!!"
NEW Tiny House Walk to Essex Main St+Boat Launch

The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

2.0 star property
10.0 out of 10, Exceptional, (1)
"The cottage is amazing and so beautiful! The location couldn't have been more perfect, and communicating with the host was a breeze. We had a peaceful and relaxing stay. "
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

Beach House In Hampton Steps To The Sand And Strip!

2.0 star property
The price is NZ$1,731
includes taxes & fees
23 Dec - 24 Dec
Beach House In Hampton Steps To The Sand And Strip!

Massachusetts Abode w/ Deck & Grill: Near Beaches!

10.0 out of 10, Exceptional, (9)
"My husband, sister, and brother in law and I stayed here for 3 nights and were very pleased. The house was cozy and in a peaceful neighborhood. We loved staying here however the water does take a while to heat up and the shower water pressure was very low. Minor details but overall recommended. "
Massachusetts Abode w/ Deck & Grill: Near Beaches!

Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD

10.0 out of 10, Exceptional, (102)
"It’s a fun little cottage and Julie is a wonderful host!"
Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD

Beach Life Bliss - steps to the beach

9.8 out of 10, Exceptional, (23)
"I spent two weeks in the property and loved it. The host was immediately available and one issue with the heat was addressed right away. Cute place with great New England vibes. I was able to work from the property with no issues as well. Beautiful walk down to the cove and a very short drive up the road to the State Park. Great location! "
The price is NZ$623
includes taxes & fees
26 Dec - 27 Dec
Beach Life Bliss - steps to the beach

Sweeping, dog-friendly, waterfront home w/ a sun room, ocean views, & fireplaces

8.6 out of 10, Excellent, (57)
"We all absolutely loved this home. It was the coziest place we have ever stayed. And the location and view were unbelievable, being right on the coast. We read the reviews ahead of time and knew it was an older home, which added to the charm for us. Would definitely stay here again."
Sweeping, dog-friendly, waterfront home w/ a sun room, ocean views, & fireplaces
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Gloucester

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

9.8 out of 10, Exceptional, (73)
"The bed upstairs is so confortable, I slept like a baby! Great location! You can swim nearby, it’s very quiet and in the Rocky Neck art colony district."
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

Beach Life Bliss - steps to the beach

9.8 out of 10, Exceptional, (23)
"I spent two weeks in the property and loved it. The host was immediately available and one issue with the heat was addressed right away. Cute place with great New England vibes. I was able to work from the property with no issues as well. Beautiful walk down to the cove and a very short drive up the road to the State Park. Great location! "
The price is NZ$623
includes taxes & fees
26 Dec - 27 Dec
Beach Life Bliss - steps to the beach

Luxury 1900's romantic retreat steps from the beach - King Suite!

9.6 out of 10, Exceptional, (30)
"Exactly how it was described clean easy to get to! Highly recommended "
Luxury 1900's romantic retreat steps from the beach - King Suite!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.