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. 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, (20 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
The price is HK$1,568
HK$3,179 total
includes taxes & fees
21 Sept - 22 Sept
Cozy two bedroom house in the heart of Gloucester

2. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (13 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$1,905
HK$2,435 total
includes taxes & fees
5 Oct - 6 Oct
The Essex 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.
The price is HK$1,600
HK$4,292 total
includes taxes & fees
14 Sept - 15 Sept
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

4. 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
7 Oct - 8 Oct
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

5. 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)
"Sparking clean property. Plenty of main floor gathering space (kitchen/dining/livingroom) with good separation of sleeping quarters, giving the opportunity for privacy and rest. Pretty back yard with Adirondack chairs to enjoy while reading or just resting. Easy drive to the main attractions of Gloucester and/or Rockport. All this and responsive owners too! "
United States
Karen T.
The price is HK$1,332
HK$3,397 total
includes taxes & fees
28 Sept - 29 Sept
Oceanside Village Home~Private Fenced Yard~Reserved Parking

6. 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$2,474
HK$7,589 total
includes taxes & fees
14 Sept - 15 Sept
Classic Coastal Family Home | Walk to Sea;King Bed

7. 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.
The price is HK$12,703
HK$21,029 total
includes taxes & fees
21 Sept - 22 Sept
Stay at Good Harbor Beach

8. 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$1,782
HK$4,775 total
includes taxes & fees
15 Sept - 16 Sept
Historic Renovation, Walk to Front Beach and Shopping

9. 4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included
Rockport
9.8 out of 10, Exceptional, (11 reviews)
"House worked great for traveling with teenagers- they had their own space to hang out. Very clean and well designed/ decorated. "
United States
Denitsa a.
The price is HK$2,136
HK$4,830 total
includes taxes & fees
14 Sept - 15 Sept
4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

10. 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$1,958
HK$4,262 total
includes taxes & fees
17 Sept - 18 Sept
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

11. 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$2,544
HK$6,047 total
includes taxes & fees
4 Oct - 5 Oct
HOT TUB I Downtown Rockport w/parking I Sleeps 8

12. 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.
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

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. 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$1,779
HK$4,028 total
includes taxes & fees
20 Sept - 21 Sept
2BR Historic Marblehead Home+Minutes to Beach

15. Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed

Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed
Manchester-by-the-Sea
9.2 out of 10, Wonderful, (14 reviews)
"Great house, great location, wonderful kitchen. Friends all had a great time"
United States
Colorado B.
The price is HK$2,315
HK$5,065 total
includes taxes & fees
13 Sept - 14 Sept
Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed

16. 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$3,543
HK$8,477 total
includes taxes & fees
14 Sept - 15 Sept
Experience Classic New England-walk to beach&shops

17. 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.
The price is HK$2,047
HK$5,116 total
includes taxes & fees
15 Sept - 16 Sept
Home w/firepit l Walk to Bearskin Neck+Beach

18. 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$2,306
HK$4,384 total
includes taxes & fees
28 Sept - 29 Sept
Bell Buoy

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

Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
Salisbury Beach
9.6 out of 10, Exceptional, (5 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 HK$752
HK$3,152 total
includes taxes & fees
20 Sept - 21 Sept
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

20. Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!

Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!
Newburyport
9.8 out of 10, Exceptional, (88 reviews)
"Perfect for a two person stay to relax and enjoy the local activities!"
United States
Tom B.
Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!
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
324
Accommodation
516 Vacation Homes
Lowest Price
HK$2,435
Highest Price
HK$21,029

Explore a world of travel with Expedia