Search Vacation Homes in Gloucester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Gloucester holiday homes

Private kitchen

The Essex of Gloucester

The Essex of Gloucester
2.0 star property
Gloucester
10.0 out of 10, Exceptional, (2 reviews)
"The host was really accessible and easy to communicate with. We had all the info we needed for an easy check-in. The house was exceptionally clean and quiet. "
United States
Chris K.
The price is HK$1,079
HK$1,380 total
includes taxes & fees
3 Feb - 4 Feb
The Essex of Gloucester
Property grounds

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.
The price is HK$1,466
HK$3,963 total
includes taxes & fees
20 Jan - 21 Jan
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Beach

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, (12 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 HK$1,056
HK$3,105 total
includes taxes & fees
9 Feb - 10 Feb
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Outdoor dining

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 HK$835
HK$2,814 total
includes taxes & fees
19 Jan - 20 Jan
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill
Interior

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 HK$1,474
HK$4,224 total
includes taxes & fees
19 Jan - 20 Jan
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
Smart TV, books

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 HK$951
HK$2,987 total
includes taxes & fees
19 Jan - 20 Jan
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
Property grounds

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 HK$1,540
HK$4,237 total
includes taxes & fees
21 Jan - 22 Jan
Home w/firepit l Walk to Bearskin Neck+Beach
Property grounds

*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 HK$936
HK$2,237 total
includes taxes & fees
19 Jan - 20 Jan
*NEW Spooky Halloween |2BR|Downtown Salem|Parking
Dining

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 HK$842
HK$2,371 total
includes taxes & fees
27 Jan - 28 Jan
Nothing Fancy Older Pet Friendly Home – near I-95
Beach

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 HK$1,544
HK$2,770 total
includes taxes & fees
17 Jan - 18 Jan
Entire Lower Level of the House, Across From The Beach
Aerial view

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 HK$1,248
HK$3,247 total
includes taxes & fees
19 Jan - 20 Jan
Riverside Retreat • Laundry • Work-Friendly
Beach nearby

Hampton Beach Cottage: Walk to Beach, Porch, BBQ

Hampton Beach Cottage: Walk to Beach, Porch, BBQ
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 HK$1,248
HK$3,240 total
includes taxes & fees
17 Jan - 18 Jan
Hampton Beach Cottage: Walk to Beach, Porch, BBQ
Fridge, microwave, oven, stovetop

The Nest | High-End Kitchen | Steps to Beach | A/C

The Nest | High-End Kitchen | Steps to Beach | A/C
Newbury
10.0 out of 10, Exceptional, (14 reviews)
"Perfect spot for beach, restaurants and Newbury port See you next summer!"
United States
Sebastien L.
The Nest | High-End Kitchen | Steps to Beach | A/C
Dining

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)
"Our stay was fantastic. Great location, only an 8 minute walk to Essex st. Great host as well! "
United States
Adam R.
The price is HK$1,098
HK$3,360 total
includes taxes & fees
26 Jan - 27 Jan
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
TV, offices

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.
The price is HK$1,427
HK$3,905 total
includes taxes & fees
3 Feb - 4 Feb
Circa 1789 • Historic South End Home • Back Patio
TV, offices

The Salty Dog | Pet-Friendly | Private Yard | MTR

The Salty Dog | Pet-Friendly | Private Yard | MTR
Hampton Beach
9.8 out of 10, Exceptional, (31 reviews)
"We had a nice stay. It had everything we needed and is close to beach. Shower is tight but doable. Fenced in yard is nice and great for the dog. We would stay again."
United States
Ralph L.
The price is HK$1,419
HK$3,308 total
includes taxes & fees
2 Feb - 3 Feb
The Salty Dog | Pet-Friendly | Private Yard | MTR
Beach nearby

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 HK$1,248
HK$3,333 total
includes taxes & fees
17 Jan - 18 Jan
Blinkin Beach House | 3BR Monthly | Walk to Beach
Smart TV, books

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 HK$1,957
HK$5,269 total
includes taxes & fees
10 Feb - 11 Feb
Historic 1686 Home Near Downtown l 5BR Retreat
Smart TV, books

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 HK$1,942
HK$4,965 total
includes taxes & fees
27 Jan - 28 Jan
Historic Renovation, Walk to Front Beach and Shopping
Fridge, microwave, oven, stovetop

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
Marblehead
10.0 out of 10, Exceptional, (27 reviews)
"great place and location"
United States
Kacey C.
The price is HK$3,119
HK$4,973 total
includes taxes & fees
31 Jan - 1 Feb
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gloucester Hotel Reviews

Hawthorne Hotel

Hawthorne Hotel

10/10 Excellent
"Very kind staff, especially with my dog. Very helpful. Room was very clean"
Jessica L 1-night trip
Posted 2 days ago
Hawthorne Hotel

Find out more about Gloucester

Gloucester Vacation Homes information

Number of reviews
283
Accommodation
539 Vacation Homes
Lowest Price
HK$2,237
Highest Price
HK$5,269

Explore a world of travel with Expedia