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. 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 NZ$528
includes taxes & fees
31 Aug - 1 Sept
The Essex 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 home in a beautiful location!"
United States
Paul H.
The price is NZ$1,232
includes taxes & fees
19 Aug - 20 Aug
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

3. 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, (16 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 NZ$1,269
includes taxes & fees
3 Sept - 4 Sept
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

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)
"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 NZ$672
includes taxes & fees
9 Sept - 10 Sept
Oceanside Village Home~Private Fenced Yard~Reserved Parking

5. Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!
Gloucester
10.0 out of 10, Exceptional, (15 reviews)
"Wonderful views, great location, easy access to all of Cape Ann."
United States
Stacey W.
Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

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 NZ$3,223
includes taxes & fees
22 Aug - 23 Aug
Private Beach! Dream vacation at your private beach in Gloucester

7. 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 NZ$2,024
includes taxes & fees
18 Aug - 19 Aug
Stay at The Neck

8. 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 NZ$1,919
includes taxes & fees
30 Aug - 31 Aug
Classic Coastal Family Home | Walk to Sea;King Bed

9. Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Downtown Salem
9.6 out of 10, Exceptional, (111 reviews)
"This place was perfect. Clean, a saved parking spot, within walking distance of everything you could want in Salem as well as the train station. Will definitely be looking into this if we decide to come back"
United States
Jacob
The price is NZ$795
includes taxes & fees
16 Aug - 17 Aug
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

10. Cozy Salem Getaway. Historic Home Near All the Sights

Cozy Salem Getaway. Historic Home Near All the Sights
Salem
9.6 out of 10, Exceptional, (59 reviews)
"Beautiful 2 bedroom, close to everything , host was wonderful, we will be back. "
United States
Charlene
The price is NZ$706
includes taxes & fees
16 Aug - 17 Aug
Cozy Salem Getaway. Historic Home Near All the Sights

11. 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 NZ$725
includes taxes & fees
1 Sept - 2 Sept
2BR Historic Marblehead Home+Minutes to Beach

12. Moody Salem Home Away From Home

Moody Salem Home Away From Home
Salem
9.8 out of 10, Exceptional, (29 reviews)
"Host was very nice we enjoyed our stay at your bra home thank your for having us "
United States
Chris M.
The price is NZ$544
includes taxes & fees
20 Aug - 21 Aug
Moody Salem Home Away From Home

13. 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 NZ$1,001
includes taxes & fees
1 Sept - 2 Sept
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

14. The Thomas Honeycomb Inn w/ Tiki Bar and Roof Deck

The Thomas Honeycomb Inn w/ Tiki Bar and Roof Deck
Salem
The price is NZ$2,068
includes taxes & fees
30 Aug - 31 Aug
The Thomas Honeycomb Inn w/ Tiki Bar and Roof Deck

15. Hampton Beach Seaside Villa Unit 2

Hampton Beach Seaside Villa Unit 2
Hampton Beach
10.0 out of 10, Exceptional, (13 reviews)
"Perfect location across the beach, lovely porch to sit outside, just enough room to comfortable for 5 friends for girls weekend beach day owner very responsive! "
United States
Shayna N.
The price is NZ$677
includes taxes & fees
23 Aug - 24 Aug
Hampton Beach Seaside Villa Unit 2

16. 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 NZ$1,324
includes taxes & fees
9 Sept - 10 Sept
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

17. Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Hampton Beach
10.0 out of 10, Exceptional, (21 reviews)
"Great location, clean, well equipped kitchen and very nicely decorated. Would stay again!"
United States
Lyn F.
The price is NZ$1,063
includes taxes & fees
10 Sept - 11 Sept
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

18. The Perkins Surfside | 4BR Hampton Beach Escape | Heart of Hampton

The Perkins Surfside | 4BR Hampton Beach Escape | Heart of Hampton
Hampton Beach
The price is NZ$1,258
includes taxes & fees
8 Sept - 9 Sept
The Perkins Surfside | 4BR Hampton Beach Escape | Heart of Hampton

19. The widow’s walk your very own spa experience

The widow’s walk your very own spa experience
Marblehead
9.4 out of 10, Exceptional, (21 reviews)
"Great! Lots of activities on property. House is beautiful! You can access the wrap around deck around the widows walk"
United States
Lucy Danielle R.
The price is NZ$1,170
includes taxes & fees
1 Sept - 2 Sept
The widow’s walk your very own spa experience

20. Spacious Ocean Home Only One Block Away From the Beach

Spacious Ocean Home Only One Block Away From the Beach
Hampton Beach
10.0 out of 10, Exceptional, (44 reviews)
"Absolutely had one of the best weekends with family and friends. The house had everything we needed and the beds were so comfy. Will definitely rent here again!"
United States
dawn b.
The price is NZ$1,339
includes taxes & fees
2 Sept - 3 Sept
Spacious Ocean Home Only One Block Away From the Beach
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
355
Accommodation
518 Holiday Homes
Lowest Price
NZ$528
Highest Price
NZ$3,223

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