A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Gloucester vacation homes

A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

1. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (62 reviews)
"Nice home with great kitchen and all the amenities."
United States
rick b.
The price is ￥78,220
￥130,087 total
includes taxes & fees
Nov 1 - Nov 2
Beach Life Bliss - steps to the beach
A wooden staircase with a railing leading to a covered deck area.

2. 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
9.6 out of 10, Exceptional, (21 reviews)
"Rachel was very responsive and attentive, excellent host. The house was in a great location, clean, and very comfortable. Would stay there again should the need arise."
United States
Betty
The price is ￥39,451
￥102,913 total
includes taxes & fees
Oct 21 - Oct 22
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

3. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"Very clean and perfect place to stay while we were in a wedding at the Beauport! The host checked in often and made us feel very welcomed and at home"
United States
Katie B.
The price is ￥35,238
￥45,008 total
includes taxes & fees
Nov 4 - Nov 5
The Essex of Gloucester
A two-story house with a wrap-around porch, a curved driveway, and a view of a large body of water.

4. Classic Coastal Family Home | Walk to Sea;King Bed

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
10.0 out of 10, Exceptional, (6 reviews)
"Property was excellent, beautifully decorated with good taste, location was beautiful, everyone enjoyed the weekend stay. Rooms were clean, beds were comfortable."
United States
Maarij K.
The price is ￥51,568
￥155,066 total
includes taxes & fees
Oct 19 - Oct 20
Classic Coastal Family Home | Walk to Sea;King Bed
A beach with people sunbathing and swimming, a rocky outcrop in the foreground, and a small island in the background.

5. Bell Buoy

Bell Buoy
3.5 star property
Rockport
6.0 out of 10, (1 review)
"The property is nicely located but in need of updates. A lot of the lamps are plug in vs light switch and there were some flickering lights behind the TV. One lamp was missing a light bulb. No outlet in the bathroom for a hair dryer. The second bathroom is missing a door handle making it hard to open and close. We were unable to reach the ceiling fan chain without having to get on the bed, The Air Conditioner wasn't working on he first floor which made it a bit stuff but with open windows at...
United States
Amy
Bell Buoy
A wooden deck with wicker furniture and a white chair, overlooking a beach with a rocky shoreline and a clear blue sky.

6. Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
Rockport
10.0 out of 10, Exceptional, (38 reviews)
"Great spot right on Long Beach! Has great views of the ocean right on the water. We definitely stay there again pet friendly."
United States
Emmy D.
The price is ￥57,466
￥124,049 total
includes taxes & fees
Oct 21 - Oct 22
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
A spacious living room with a high ceiling, wooden beams, a sofa, a blue armchair, a coffee table, and a dining area with a table and chairs.

7. Historic Renovation, Walk to Front Beach and Shopping

Historic Renovation, Walk to Front Beach and Shopping
Rockport
9.8 out of 10, Exceptional, (9 reviews)
"This house worked well for our family with seven people of all ages and really enjoyed our first trip to the Rockport/Gloucester area. Hopefully we'll get a chance to return and would highly recommend the area and property."
United States
Dan K.
Historic Renovation, Walk to Front Beach and Shopping
A large, two-story house with a steeply pitched roof, surrounded by lush greenery and a view of the sea.

8. Experience Classic New England-walk to beach&shops

Experience Classic New England-walk to beach&shops
Rockport
10.0 out of 10, Exceptional, (1 review)
"Property was extremely clean. Comfortably fit my group of 8 adults. The deck hot tub was the biggest hot tub I have ever seen. Such a great place! Victor was extremely nice and responsive. "
United States
Danielle L.
The price is ￥57,045
￥152,505 total
includes taxes & fees
Nov 11 - Nov 12
Experience Classic New England-walk to beach&shops
A stone fire pit surrounded by Adirondack chairs in a landscaped area with a stone wall and a large tree.

9. Home w/firepit l Walk to Bearskin Neck+Beach

Home w/firepit l Walk to Bearskin Neck+Beach
Rockport
9.6 out of 10, Exceptional, (8 reviews)
"Home was beautiful decorated and had everything we needed for a relaxing weekend. Host communicated well. Walking distance to the beach and town, and a short drive to Gloucester and Boston. Fantastic!"
United States
Juliet S.
Home w/firepit l Walk to Bearskin Neck+Beach
A beach with a wooden fence, sand, and the ocean.

10. Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
Salisbury Beach
9.8 out of 10, Exceptional, (8 reviews)
"I booked a last minute stay for some time at the ocean. The booking/check in process was so easy with very detailed instructions sent the day of my arrival. The place was exactly as pictured, a well-appointed, clean cottage, with everything I needed. The host also left a welcome gift that was thoughtful and useful. I walked the few blocks to the ocean everyday, multiple times a day to walk for hours on the beaches. I got food from a nice little Italian restaurant (Capri) just a block away. The...
United States
Maura
The price is ￥15,974
￥64,266 total
includes taxes & fees
Oct 19 - Oct 20
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
A modern kitchen with a large island, white cabinets, and a view of a garden through a sliding glass door.

11. Historic Marblehead Nautical Home • Minutes to Salem

Historic Marblehead Nautical Home • Minutes to Salem
Marblehead Historic District
10.0 out of 10, Exceptional, (25 reviews)
"We enjoyed our stay at this property. It is in a great location. Easy to walk to restaurants and stores in Marblehead. It was nice to not have to spend more time in our car after driving from Georgia. Property had everything we needed to live comfortably during our stay."
United States
Kevin H.
The price is ￥32,246
￥79,439 total
includes taxes & fees
Oct 19 - Oct 20
Historic Marblehead Nautical Home • Minutes to Salem
A two-story beach house with a balcony, a deck, and a sign reading "Plovers Nest".

12. Plovers Nest

Plovers Nest
3.0 star property
Newburyport
10.0 out of 10, Exceptional, (2 reviews)
"Clean and well cared for; high end finishes; small but adorable with beautiful views from upstairs bedroom. Good communication with owners. "
United States
Anat
The price is ￥24,686
￥61,941 total
includes taxes & fees
Nov 17 - Nov 18
Plovers Nest
A comfy queen bed - the perfect size for snuggling!

13. Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing
Salisbury Beach
10.0 out of 10, Exceptional, (1 review)
The price is ￥15,919
￥73,524 total
includes taxes & fees
Oct 25 - Oct 26
Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing
A modern kitchen with a central island, stainless steel appliances, and a view to the outside.

14. 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, (15 reviews)
"Perfect spot for beach, restaurants and Newbury port See you next summer!"
United States
Sebastien L.
The price is ￥25,283
￥70,151 total
includes taxes & fees
Oct 19 - Oct 20
The Nest | High-End Kitchen | Steps to Beach | A/C
A modern interior with a kitchen, dining area, and living space, featuring wooden floors, a large TV, and a view of the outdoors.

15. Plum Puddin | Pet-Friendly | Screened Porch | Deck

Plum Puddin | Pet-Friendly | Screened Porch | Deck
Newburyport
9.8 out of 10, Exceptional, (10 reviews)
"Very clean and charming. We enjoyed our stay!"
United States
amy t.
The price is ￥19,911
￥68,829 total
includes taxes & fees
Nov 1 - Nov 2
Plum Puddin | Pet-Friendly | Screened Porch | Deck
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

Holiday Inn Hotel & Suites Boston - Peabody by IHG

Holiday Inn Hotel & Suites Boston - Peabody by IHG

8/10 Good
"This property was pretty good for our weekend trip, our only gripes were the toilet being very low and our bathroom door not being able to lock. Otherwise everything else about this property was good."
Maliya 3-night trip
Posted less than an hour ago
Holiday Inn Hotel & Suites Boston - Peabody by IHG

Find out more about Gloucester

Gloucester Vacation Homes information

Number of reviews
177
Accommodation
515 Vacation Homes
Lowest Price
￥45,008
Highest Price
￥155,066