Holiday Homes in Gloucester

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Our top choices for Gloucester holiday homes

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Gloucester
10.0 out of 10, Exceptional, (7 reviews)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Gloucester
9.8 out of 10, Exceptional, (11 reviews)
"We loved cooking on the antique stove and hanging out in the sun room. It was a cozy spot close to all the activities in Rockport."
United States
Allyson Y.
The price is €353
includes taxes & fees
3 Feb - 4 Feb
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

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

The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill
2.0 star property
Rockport
9.8 out of 10, Exceptional, (7 reviews)
"We had a great stay! Perfect location and a great setup for our family. Beautiful outdoor area and we were lucky with the weather! "
United States
Matt T.
The price is €317
includes taxes & fees
19 Jan - 20 Jan
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
Rockport
10.0 out of 10, Exceptional, (14 reviews)
"Cozy house in great location. We would definitely stay here again. "
United States
John D.
The price is €327
includes taxes & fees
15 Jan - 16 Jan
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Nothing Fancy Older Pet Friendly Home – near I-95

Nothing Fancy Older Pet Friendly Home – near I-95
Georgetown
9.4 out of 10, Exceptional, (3 reviews)
"Came for a short stay and had absolutely no complaints. Easy entry, great communication and an amazing home to stay in. Would highly recommend:)"
United States
Fedalis R.
The price is €266
includes taxes & fees
19 Jan - 20 Jan
Nothing Fancy Older Pet Friendly Home – near I-95

*NEW Spooky Halloween |2BR|Downtown Salem|Parking

*NEW Spooky Halloween |2BR|Downtown Salem|Parking
Salem
9.2 out of 10, Wonderful, (51 reviews)
"Very clean, quiet and convenient location! The owners checked in with me through the app to make sure we had everything we needed. I would stay again!"
United States
Rebecca T.
The price is €252
includes taxes & fees
15 Jan - 16 Jan
*NEW Spooky Halloween |2BR|Downtown Salem|Parking

Riverside Retreat • Laundry • Work-Friendly

Riverside Retreat • Laundry • Work-Friendly
Newbury
8.4 out of 10, Very good, (6 reviews)
"We loved everything about this place. Walk to the Beach, the sunset Bar and close to Newburyport. The house was perfectly decorated and has a nice little yard and outdoor shower."
United States
Timothy N.
The price is €366
includes taxes & fees
22 Jan - 23 Jan
Riverside Retreat • Laundry • Work-Friendly

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
2.0 star property
Marblehead
9.6 out of 10, Exceptional, (15 reviews)
"Perfect location on Marblehead Neck with stunning views of the harbor. The house was just right for a family of 5 adults. We would come back and would recommend this lovely house to anyone. "
United States
Debbie B.
The price is €454
includes taxes & fees
15 Jan - 16 Jan
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

Pat’s Porch | 3BR Monthly | Walk to Beach | Porch

Pat’s Porch | 3BR Monthly | Walk to Beach | Porch
Hampton Beach
10.0 out of 10, Exceptional, (35 reviews)
"My long time best friend, who lives far from me, and my 2 teenage granddaughters had our 3rd annual beach vacation at Hampton Beach.We plan an doing this each year that we are able and hope to return to the same property next year."
United States
Judith L.
The price is €366
includes taxes & fees
19 Jan - 20 Jan
Pat’s Porch | 3BR Monthly | Walk to Beach | Porch

Home w/firepit l Walk to Bearskin Neck+Beach

Home w/firepit l Walk to Bearskin Neck+Beach
2.0 star property
Rockport
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, lots of places and nooks to sit and enjoy. Great ammenities, very cozy, well stocked. A short walk to the beach to enjoy sunrises..A short walk to city center, friendly people, great art scene. We loved our stay and would love to come again."
United States
gila
The price is €478
includes taxes & fees
19 Jan - 20 Jan
Home w/firepit l Walk to Bearskin Neck+Beach

Circa 1789 • Historic South End Home • Back Patio

Circa 1789 • Historic South End Home • Back Patio
Newburyport
9.8 out of 10, Exceptional, (9 reviews)
"This is a very nice property and host, in a perfect location to the water and downtown restaurants and shops. Highly recommend staying here!!"
United States
Gail C.
Circa 1789 • Historic South End Home • Back Patio

Entire Private home 3BDS 1 and half BTHS/ Pet Friendly with fee

Entire Private home 3BDS 1 and half BTHS/ Pet Friendly with fee
Lynn
9.0 out of 10, Wonderful, (4 reviews)
"Fantastic! The easiest check in and check out I’ve ever had super clean. So close to everything. Would highly recommend "
United States
Amanda W.
The price is €380
includes taxes & fees
26 Jan - 27 Jan
Entire Private home 3BDS 1 and half BTHS/ Pet Friendly with fee

Historic Renovation, Walk to Front Beach and Shopping

Historic Renovation, Walk to Front Beach and Shopping
Rockport
9.6 out of 10, Exceptional, (5 reviews)
"Great house, great location, made for a perfect vacation. Kerin was quick to respond to any of our questions, making check-in super easy. The house is just the right mix of Rockport history and modern amenities, beautifully decorated yet casual and comfortable for a family with two energetic kids. The location was just right as well; a quick walk to the beach, shops and restaurants, while tucked away on a quiet neighborhood street. We felt like locals for the week, popping over to Bearskin Neck...
United States
Christian S.
The price is €532
includes taxes & fees
19 Jan - 20 Jan
Historic Renovation, Walk to Front Beach and Shopping

Blinkin Beach House | 3BR Monthly | Walk to Beach

Blinkin Beach House | 3BR Monthly | Walk to Beach
Hampton Beach
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and nicely furnished. Even though it was just a 2 minute walk to the boardwalk it was still relatively quiet. We had a nice time staying there. Thank you!"
United States
Skip S.
The price is €376
includes taxes & fees
19 Jan - 20 Jan
Blinkin Beach House | 3BR Monthly | Walk to Beach

Historic 1686 Home Near Downtown l 5BR Retreat

Historic 1686 Home Near Downtown l 5BR Retreat
2.0 star property
Beverly
9.4 out of 10, Exceptional, (13 reviews)
"The house was perfect "
United States
Patrick J.
The price is €594
includes taxes & fees
10 Feb - 11 Feb
Historic 1686 Home Near Downtown l 5BR Retreat

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Entire 4BR 2 Bath Home l Minutes to Downtown Salem
2.0 star property
Salem
10.0 out of 10, Exceptional, (18 reviews)
"The house was clean and close to everything!!"
United States
Stephanie D.
The price is €341
includes taxes & fees
15 Jan - 16 Jan
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Entire Lower Level of the House, Across From The Beach

Entire Lower Level of the House, Across From The Beach
Swampscott
9.8 out of 10, Exceptional, (25 reviews)
"Wonderful place! Diana was a wonderful host and provided everything we needed for a cozy stay on our girls trip!"
United States
Dana F.
The price is €312
includes taxes & fees
27 Jan - 28 Jan
Entire Lower Level of the House, Across From The Beach

The widow’s walk your very own spa experience

The widow’s walk your very own spa experience
Marblehead
9.4 out of 10, Exceptional, (20 reviews)
"Great location with incredible views! House is great, lots of amenities - family loved it and already wants to go back!"
United States
Jonathan T.
The price is €498
includes taxes & fees
15 Jan - 16 Jan
The widow’s walk your very own spa experience

Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.
Rockport
10.0 out of 10, Exceptional, (23 reviews)
"The house was beautiful, comfortable, very well equipped, easy walk to town. The host was extremely helpful and responsive. "
United States
chris m.
The price is €1,064
includes taxes & fees
21 Jan - 22 Jan
Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Island Path Escape | 3BR Monthly | Views | Fireplace

Island Path Escape | 3BR Monthly | Views | Fireplace
Hampton Beach
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful place! Will stay again "
United States
Melba K.
The price is €502
includes taxes & fees
19 Jan - 20 Jan
Island Path Escape | 3BR Monthly | Views | Fireplace
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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Top Gloucester Hotel Reviews

Find out more about Gloucester

Gloucester Holiday Homes information

Number of reviews
287
Accommodation
539 Holiday Homes
Lowest Price
€252
Highest Price
€1,064