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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Gloucester vacation homes

Private kitchen

The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (5 reviews)
"The host was really accessible and easy to communicate with. We had all the info we needed for an easy check-in. The house was exceptionally clean and quiet. "
United States
Chris K.
The price is AED 863
AED 1,100 total
includes taxes & fees
3 May - 4 May
The Essex of Gloucester
Property grounds

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, (9 reviews)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
The price is AED 1,001
AED 2,230 total
includes taxes & fees
4 May - 5 May
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Beach

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Gloucester
9.8 out of 10, Exceptional, (12 reviews)
"The house was just what we needed for a family get a way. The dogs and are teens loved it. The weather was cold, rainy and windy but the house kept us nice and warm and cozy. We had everything we needed and more. The sauna was a special treat too:) Thank you for a wonderful visit. We hope to return next year:) "
United States
Christina G.
The price is AED 498
AED 1,435 total
includes taxes & fees
4 May - 5 May
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Interior

Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.8 out of 10, Exceptional, (11 reviews)
"Lovely home in a great location. Very clean and fit us well. "
United States
Susan A.
The price is AED 582
AED 1,569 total
includes taxes & fees
20 May - 21 May
Oceanside Village Home~Private Fenced Yard~Reserved Parking
Fridge, microwave, oven, stovetop

Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (44 reviews)
"Cozy accommodation..comfortable beds, numerous tvs, lots of extras"
United States
Jo-Ann P.
Beach Life Bliss - steps to the beach
3 bedrooms, iron/ironing board, free WiFi, bed sheets

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
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
Exterior

Classic Coastal Family Home | Walk to Sea;King Bed

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
The price is AED 1,205
AED 3,612 total
includes taxes & fees
4 May - 5 May
Classic Coastal Family Home | Walk to Sea;King Bed
Smart TV, books

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, (46 reviews)
"House was wonderful and had everything we needed. Very clean and homey for three couples. Great location. Great contact with the host. "
United States
Monica W.
The price is AED 791
AED 1,963 total
includes taxes & fees
19 May - 20 May
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
TV, offices

Plum Puddin | Pet-Friendly | Screened Porch | Deck

Plum Puddin | Pet-Friendly | Screened Porch | Deck
Newburyport
9.8 out of 10, Exceptional, (8 reviews)
"Our stay was excellent. We will definitely be back soon. "
United States
Edmond B.
The price is AED 610
AED 1,768 total
includes taxes & fees
3 May - 4 May
Plum Puddin | Pet-Friendly | Screened Porch | Deck
Lake

Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6
Ipswich
9.4 out of 10, Exceptional, (70 reviews)
"Comfortable stay in a great location."
United States
Amanda A.
The price is AED 459
AED 947 total
includes taxes & fees
3 May - 4 May
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6
TV, offices

Circa 1789 • Historic South End Home • Back Patio

Circa 1789 • Historic South End Home • Back Patio
Newburyport
9.8 out of 10, Exceptional, (9 reviews)
"This is a very nice property and host, in a perfect location to the water and downtown restaurants and shops. Highly recommend staying here!!"
United States
Gail C.
The price is AED 738
AED 1,982 total
includes taxes & fees
3 May - 4 May
Circa 1789 • Historic South End Home • Back Patio
Terrace/patio

Riverside Retreat • Cozy Coastal Cottage • Yard

Riverside Retreat • Cozy Coastal Cottage • Yard
Newbury
8.4 out of 10, Very Good, (6 reviews)
"We loved everything about this place. Walk to the Beach, the sunset Bar and close to Newburyport. The house was perfectly decorated and has a nice little yard and outdoor shower."
United States
Timothy N.
The price is AED 584
AED 1,572 total
includes taxes & fees
4 May - 5 May
Riverside Retreat • Cozy Coastal Cottage • Yard
Fridge, microwave, oven, stovetop

2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. "
United States
Mary D.
The price is AED 498
AED 1,472 total
includes taxes & fees
13 May - 14 May
2BR Historic Marblehead Home+Minutes to Beach
Fridge, microwave, oven, stovetop

The Nest | High-End Kitchen | Steps to Beach | A/C

The Nest | High-End Kitchen | Steps to Beach | A/C
Newbury
10.0 out of 10, Exceptional, (14 reviews)
"Perfect spot for beach, restaurants and Newbury port See you next summer!"
United States
Sebastien L.
The price is AED 771
AED 1,829 total
includes taxes & fees
7 May - 8 May
The Nest | High-End Kitchen | Steps to Beach | A/C
Marina

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, (39 reviews)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
The price is AED 791
AED 1,844 total
includes taxes & fees
3 May - 4 May
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
TV, offices

The Salty Dog | Pet-Friendly | Private Yard

The Salty Dog | Pet-Friendly | Private Yard
Hampton Beach
9.8 out of 10, Exceptional, (32 reviews)
"Location, location, location! This little gem of a property has a direct walking path through town to the sandy beach! Great for leased dog walks! It is very clean, comfy and well-stocked with things you may need, including laundry facilities, and parking on-site in the driveway. During our stay a 'Nor Easter rainstorm hit, but we were tight and cozy inside the Salty Dog property. A fun, little place to stay to enjoy Hampton Beach and its coastal amenities!"
United States
Katherine P.
The price is AED 610
AED 1,538 total
includes taxes & fees
3 May - 4 May
The Salty Dog | Pet-Friendly | Private Yard
Dining

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Entire 4BR 2 Bath Home l Minutes to Downtown Salem
Salem
10.0 out of 10, Exceptional, (20 reviews)
"Our stay was fantastic. Great location, only an 8 minute walk to Essex st. Great host as well! "
United States
Adam R.
The price is AED 582
AED 1,672 total
includes taxes & fees
6 May - 7 May
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
Beach nearby

Lorraine's Landing | 2 Min to Beach | Pet-Friendly

Lorraine's Landing | 2 Min to Beach | Pet-Friendly
Hampton Beach
9.4 out of 10, Exceptional, (13 reviews)
"We had a great time, they really maxed out and made the space flexible for visitors. We also had a large dog. Neighborhood was great and with the AC you really couldn’t hear traffic.You can fit six but I think five would make it most comfortable. "
United States
Kathryn C.
The price is AED 558
AED 1,475 total
includes taxes & fees
3 May - 4 May
Lorraine's Landing | 2 Min to Beach | Pet-Friendly
Fridge, microwave, oven, stovetop

Comfortable spacious house, easy access to all

Comfortable spacious house, easy access to all
Newburyport
8.8 out of 10, Excellent, (13 reviews)
"A big, comfortable house. The owner was quick to answer the questions that I had and resolved everything nicely."
United States
William
The price is AED 853
AED 1,490 total
includes taxes & fees
3 May - 4 May
Comfortable spacious house, easy access to all
Terrace/patio

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, (34 reviews)
"Great location and the host is very responsive. "
United States
Heather P.
The price is AED 1,420
AED 2,763 total
includes taxes & fees
4 May - 5 May
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
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

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

6/10 Okay
"The overall condition of the hotel is just okay. Everything seems pretty old and outdated. The carpet in our room had seen better days and the room could haven been cleaned better. The breakfast selection was good."
Priscilla 1-night trip
Posted 9 hours ago
DoubleTree by Hilton Boston North Shore

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