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

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Gloucester vacation homes

Smart TV, books

1. 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, (48 reviews)
"Beautiful home in a beautiful location!"
United States
Paul H.
The price is AED 1,043
AED 2,387 total
includes taxes & fees
19 Aug - 20 Aug
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
Beach nearby, sun loungers, beach towels

2. Single Level Home - Steps to Downtown Gloucester & A/C throughout

Single Level Home - Steps to Downtown Gloucester & A/C throughout
Downtown Gloucester
10.0 out of 10, Exceptional, (56 reviews)
"I am a senior and traveled to Gloucester with my middle age daughter. This rental was perfect with 2 separate bedroom on each end of the house. The location was within walking distance for restaurants, pubs, CVS, Dunks etc. I would gladly stay there again."
United States
Ken T.
Single Level Home - Steps to Downtown Gloucester & A/C throughout
Property grounds

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 AED 1,587
AED 3,012 total
includes taxes & fees
23 Aug - 24 Aug
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Exterior

4. 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 AED 1,441
AED 3,924 total
includes taxes & fees
3 Aug - 4 Aug
Classic Coastal Family Home | Walk to Sea;King Bed
Private kitchen

5. 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 AED 1,043
AED 1,333 total
includes taxes & fees
31 Aug - 1 Sep
The Essex of Gloucester
Interior

6. 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 AED 791
AED 1,844 total
includes taxes & fees
26 Aug - 27 Aug
Oceanside Village Home~Private Fenced Yard~Reserved Parking
Coffee/tea maker, fridge, microwave, oven

7. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (50 reviews)
"A wonderful place to stay!"
United States
rich k.
The price is AED 1,458
AED 2,564 total
includes taxes & fees
10 Aug - 11 Aug
Beach Life Bliss - steps to the beach
3 bedrooms, iron/ironing board, WiFi (free), bed sheets

8. 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
Terrace/patio

9. 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 AED 3,489
AED 6,921 total
includes taxes & fees
22 Aug - 23 Aug
Private Beach! Dream vacation at your private beach in Gloucester
Property grounds

10. Stay at Gloucester Harbor

Stay at Gloucester Harbor
Rocky Neck
Stay at Gloucester Harbor
Marina

11. 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, (43 reviews)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
The price is AED 1,336
AED 2,538 total
includes taxes & fees
13 Aug - 14 Aug
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Smart TV, books

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, (18 reviews)
"Cozy house in great location. We would definitely stay here again. "
United States
John D.
The price is AED 1,084
AED 2,221 total
includes taxes & fees
23 Aug - 24 Aug
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
House (Bell Buoy) | Exterior

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 AED 1,196
AED 2,178 total
includes taxes & fees
5 Aug - 6 Aug
Bell Buoy
Exterior

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 AED 1,914
AED 4,296 total
includes taxes & fees
4 Aug - 5 Aug
Experience Classic New England-walk to beach&shops
Smart TV, books

15. 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, (9 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 AED 1,754
AED 3,223 total
includes taxes & fees
19 Aug - 20 Aug
4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included
Interior

16. 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
Beach nearby, sun loungers, beach towels

17. 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.
Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed
Interior

18. 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 AED 1,286
AED 2,440 total
includes taxes & fees
2 Aug - 3 Aug
The widow’s walk your very own spa experience
TV

19. 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, (109 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
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Interior

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

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
Marblehead
9.6 out of 10, Exceptional, (20 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 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

Hawthorne Hotel

Hawthorne Hotel

10/10 Excellent
"Central location. Easy to walk to all restaurants and stores. Free parking which is great"
Jessica L 2-night trip
Posted less than an hour ago
Hawthorne Hotel

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