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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Gloucester holiday homes

1. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (14 reviews)
"The home was warm and inviting upon our arrival. We loved the home. Rachel responds immediately with any questions. Cape Ann is beautiful and convenient to Boston. We loved our visit and felt at home! "
United States
Melenia s.
The price is HK$1,243
HK$3,359 total
includes taxes & fees
28 Sept - 29 Sept
Oceanside Village Home~Private Fenced Yard~Reserved Parking

2. Cozy two bedroom house in the heart of Gloucester

Cozy two bedroom house in the heart of Gloucester
Gloucester
9.4 out of 10, Exceptional, (19 reviews)
"For our one night stay it was perfect, Clean and comfortable, plenty of basic's, bedding, towels and kitchen supply's."
United States
CHARLES
Cozy two bedroom house in the heart of Gloucester

3. 3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
East Gloucester
9.8 out of 10, Exceptional, (49 reviews)
"Beautiful, wonderfully well stocked home with everything anyone would need! And not just starter supplies either! They even have beach necessities in a shed out back! Quality and quantity amazing in everything! Beautiful views, comfortable rocking chairs on front porch. Everything was great!!"
United States
Michele V.
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

4. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (12 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 HK$2,101
HK$2,689 total
includes taxes & fees
29 Sept - 30 Sept
The Essex of Gloucester

5. 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, (4 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 HK$2,459
HK$7,563 total
includes taxes & fees
8 Sept - 9 Sept
Classic Coastal Family Home | Walk to Sea;King Bed

6. 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, (17 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 HK$2,673
HK$5,517 total
includes taxes & fees
9 Sept - 10 Sept
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

7. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (55 reviews)
"A wonderful place to stay!"
United States
rich k.
Beach Life Bliss - steps to the beach

8. Stay at Gloucester Harbor

Stay at Gloucester Harbor
Rocky Neck
10.0 out of 10, Exceptional, (1 review)
"The location is perfect! You can walk into Rocky Neck and can get almost anywhere on Cape Ann in 20 minutes or less. Absolutely beautiful views from the front porch and bedrooms. We stayed with our whole family (6 adults & 2 kids) and had plenty of space to relax and enjoy our vacation. Host was great at communication, house was very clean, and we hope to return. Highly recommend!"
United States
Molly S.
The price is HK$6,775
HK$12,149 total
includes taxes & fees
9 Sept - 10 Sept
Stay at Gloucester Harbor

9. Stay at Good Harbor Beach

Stay at Good Harbor Beach
East Gloucester
10.0 out of 10, Exceptional, (1 review)
"House was incredible and great for a group. Super nice house with everything we needed. Walked to the beach , cooked great meals, Allie was super helpful and accommodating. Would love to come back."
United States
hawley s.
Stay at Good Harbor Beach

10. Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
Gloucester
10.0 out of 10, Exceptional, (1 review)
"We loved our stay. The property is beautiful with wonderful views. Convenient to get most places."
United States
Sara G.
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

11. 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.
The price is HK$1,876
HK$4,898 total
includes taxes & fees
7 Sept - 8 Sept
Historic Renovation, Walk to Front Beach and Shopping

12. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Rockport
10.0 out of 10, Exceptional, (44 reviews)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
The price is HK$2,047
HK$4,397 total
includes taxes & fees
17 Sept - 18 Sept
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

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

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
Rockport
9.8 out of 10, Exceptional, (19 reviews)
"Absolutely loved this home!!! We didn’t want to leave and tried for another night , but unfortunately wasn’t able to stay because it was booked with someone else already! The location was close to down town and everyone here was as absolutely welcoming! Would love to stay again!"
United States
Angela G.
The price is HK$1,868
HK$4,171 total
includes taxes & fees
27 Sept - 28 Sept
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

14. 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 HK$2,762
HK$5,512 total
includes taxes & fees
9 Sept - 10 Sept
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

15. HOT TUB I Downtown Rockport w/parking I Sleeps 8

HOT TUB I Downtown Rockport w/parking I Sleeps 8
Rockport
10.0 out of 10, Exceptional, (2 reviews)
"This beach house was everything we were looking for. We had a great family vacation second year in a row at one of Rachel’s great properties in Rockport.The house was perfectly clean, cool, and well equipped for cooking and grilling and enjoying the beautiful outdoor area. The hot tub was a fun bonus and the best surprise was the outdoor shower which made getting home from the beach trips with little kids breezy.We walked to the beach and Bearskin Neck easily each day.The host is on top of every...
United States
Kelli S.
The price is HK$2,379
HK$5,793 total
includes taxes & fees
9 Sept - 10 Sept
HOT TUB I Downtown Rockport w/parking I Sleeps 8

16. 2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
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 HK$1,064
HK$3,027 total
includes taxes & fees
7 Sept - 8 Sept
2BR Historic Marblehead Home+Minutes to Beach

17. 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
The price is HK$2,416
HK$4,508 total
includes taxes & fees
28 Sept - 29 Sept
Bell Buoy

18. 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 HK$3,458
HK$8,365 total
includes taxes & fees
9 Sept - 10 Sept
Experience Classic New England-walk to beach&shops

19. 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

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

Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
Salisbury Beach
10.0 out of 10, Exceptional, (3 reviews)
"Clean, quiet & quaint! Perfect for a couple’s get away!"
United States
Shannon S.
The price is HK$589
HK$2,945 total
includes taxes & fees
7 Sept - 8 Sept
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Gloucester Hotel Reviews

Find out more about Gloucester

Gloucester Vacation Homes information

Number of reviews
284
Accommodation
516 Vacation Homes
Lowest Price
HK$2,689
Highest Price
HK$12,149

Explore a world of travel with Expedia