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

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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, (21 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$1,569
HK$3,180 total
includes taxes & fees
21 Sept - 22 Sept
Cozy two bedroom house in the heart of Gloucester

2. 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$1,779
HK$4,528 total
includes taxes & fees
22 Sept - 23 Sept
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

3. 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$1,255
HK$1,603 total
includes taxes & fees
17 Sept - 18 Sept
The Essex of Gloucester

4. 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$3,486 total
includes taxes & fees
28 Sept - 29 Sept
Oceanside Village Home~Private Fenced Yard~Reserved Parking

5. 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, (18 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$2,495
HK$5,091 total
includes taxes & fees
16 Sept - 17 Sept
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

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$2,360
HK$7,441 total
includes taxes & fees
16 Sept - 17 Sept
Classic Coastal Family Home | Walk to Sea;King Bed

7. 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

8. Stay at Little River

Stay at Little River
Gloucester
10.0 out of 10, Exceptional, (9 reviews)
"My friend and I had a great time staying at the house. Beautiful view, close to great attractions, and the kitchen was well appointed."
United States
Caitlin D.
The price is HK$5,083
HK$8,989 total
includes taxes & fees
15 Oct - 16 Oct
Stay at Little River

9. 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)
"Our family of four humans and two tiny dogs enjoyed our stay at this cozy home. The neighborhood is cute, quiet, and perfectly located to get in and out of town easily. The high appliances made cooking, laundry, and dishes convenient. We‘d love to stay here again."
United States
Bridget H.
The price is HK$1,601
HK$3,794 total
includes taxes & fees
17 Sept - 18 Sept
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

10. 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$2,137
HK$4,831 total
includes taxes & fees
16 Sept - 17 Sept
4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

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$2,052
HK$5,122 total
includes taxes & fees
16 Sept - 17 Sept
Historic Renovation, Walk to Front Beach and Shopping

12. 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$1,869
HK$4,146 total
includes taxes & fees
27 Sept - 28 Sept
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

13. 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$1,982
HK$4,023 total
includes taxes & fees
28 Sept - 29 Sept
Bell Buoy

14. 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$3,966
HK$9,012 total
includes taxes & fees
22 Sept - 23 Sept
Experience Classic New England-walk to beach&shops

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

16. 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$938
HK$3,237 total
includes taxes & fees
16 Sept - 17 Sept
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

17. 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$1,422
HK$3,603 total
includes taxes & fees
20 Sept - 21 Sept
2BR Historic Marblehead Home+Minutes to Beach

18. Historic 1686 Home Near Downtown l 5BR Retreat

Historic 1686 Home Near Downtown l 5BR Retreat
Beverly
9.6 out of 10, Exceptional, (18 reviews)
"Everything was lovely. The home was wonderful and communication with our host was top notch. Thank you so much!"
United States
Terry F.
The price is HK$1,436
HK$4,618 total
includes taxes & fees
16 Sept - 17 Sept
Historic 1686 Home Near Downtown l 5BR Retreat

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

Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing
Salisbury Beach
The price is HK$1,170
HK$4,234 total
includes taxes & fees
22 Sept - 23 Sept
Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

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

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
Marblehead
9.8 out of 10, Exceptional, (23 reviews)
"The property was lovely and well kept! And the location was amazing! Very nice and quiet neighborhood - definitely recommend "
United States
Katherine B.
The price is HK$2,667
HK$5,756 total
includes taxes & fees
21 Sept - 22 Sept
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
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 Vacation Homes information

Number of reviews
5
Accommodation
516 Vacation Homes
Lowest Price
HK$4,023
Highest Price
HK$8,161

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