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

Holiday Homes in Gloucester

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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 AU$645
includes taxes & fees
31 Aug - 1 Sept
Oceanside Village Home~Private Fenced Yard~Reserved Parking

2. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (11 reviews)
"Perfect size for two couples! Extremely clean and well stocked!!!!"
United States
Kimberly
The price is AU$448
includes taxes & fees
31 Aug - 1 Sept
The Essex of Gloucester

3. 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, (3 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 AU$1,492
includes taxes & fees
17 Aug - 18 Aug
Classic Coastal Family Home | Walk to Sea;King Bed

4. Stay at The Neck

Stay at The Neck
Rocky Neck
10.0 out of 10, Exceptional, (3 reviews)
"This was an amazing place! Great views and right beside an excellent restaurant. Will stay here again!"
United States
Jack J.
The price is AU$1,612
includes taxes & fees
18 Aug - 19 Aug
Stay at The Neck

5. 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 AU$3,737
includes taxes & fees
8 Sept - 9 Sept
Stay at Good Harbor Beach

6. Private Beach! Dream vacation at your private beach in Gloucester

Private Beach! Dream vacation at your private beach in Gloucester
Gloucester
9.8 out of 10, Exceptional, (12 reviews)
"Unique property with an awesome private beach."
United States
William M.
The price is AU$2,712
includes taxes & fees
22 Aug - 23 Aug
Private Beach! Dream vacation at your private beach in Gloucester

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

Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing
Salisbury Beach
The price is AU$708
includes taxes & fees
9 Sept - 10 Sept
Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

8. The Sail Boat: Heart of Hampton Beach

The Sail Boat: Heart of Hampton Beach
Hampton Beach
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,391
includes taxes & fees
8 Sept - 9 Sept
The Sail Boat: Heart of Hampton Beach

9. Hampton Beach getaway steps from the Beach & Blvd, Weekly rent Saturday Check in

Hampton Beach getaway steps from the Beach & Blvd, Weekly rent Saturday Check in
Hampton Beach
The price is AU$852
includes taxes & fees
23 Aug - 24 Aug
Hampton Beach getaway steps from the Beach & Blvd, Weekly rent Saturday Check in

10. 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)
"Cozy house in great location. We would definitely stay here again. "
United States
John D.
The price is AU$855
includes taxes & fees
27 Aug - 28 Aug
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

11. 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 location and the host is very responsive. "
United States
Heather P.
The price is AU$1,086
includes taxes & fees
9 Sept - 10 Sept
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

12. 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 AU$1,021
includes taxes & fees
9 Sept - 10 Sept
Historic Renovation, Walk to Front Beach and Shopping

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 AU$904
includes taxes & fees
27 Aug - 28 Aug
Bell Buoy

14. 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 AU$1,011
includes taxes & fees
9 Sept - 10 Sept
HOT TUB I Downtown Rockport w/parking I Sleeps 8

15. 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 AU$1,490
includes taxes & fees
9 Sept - 10 Sept
Experience Classic New England-walk to beach&shops

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)
"Enjoyed our stay. "
United States
Mary D.
The price is AU$566
includes taxes & fees
1 Sept - 2 Sept
2BR Historic Marblehead Home+Minutes to Beach

17. 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
9.6 out of 10, Exceptional, (10 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 AU$1,053
includes taxes & fees
19 Aug - 20 Aug
4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

18. 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)
"Deck fire place perfect for nice evening with family!"
United States
Calvert G.
The price is AU$1,560
includes taxes & fees
21 Aug - 22 Aug
Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed

19. 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, (21 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 AU$846
includes taxes & fees
1 Sept - 2 Sept
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

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, (1 review)
"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 AU$674
includes taxes & fees
20 Aug - 21 Aug
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.
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Top Gloucester Hotel Reviews

Find out more about Gloucester

Gloucester Holiday Homes information

Number of reviews
146
Accommodation
520 Holiday Homes
Lowest Price
AU$468
Highest Price
AU$3,737

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