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

Gloucester Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Gloucester holiday rentals

A modern apartment with a dining area, kitchen, living room, and a large window.

1. Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (97 reviews)
"This is our 3rd time and we will be back next year. Love the location, the place is perfect we truly enjoy our time. The response time for any questions is great."
United States
Kim
The price is HK$967
HK$2,614 total
includes taxes & fees
17 Nov - 18 Nov
Long Beach Suites
A living room with a fireplace, a television mounted on the wall, and a variety of decorative items including plants and a large vase.

2. Charming Retreat

Charming Retreat
East Gloucester
10.0 out of 10, Exceptional, (26 reviews)
"Parking was great...easy access to visiting all of Cape Ann"
United States
Margaret
The price is HK$981
HK$2,244 total
includes taxes & fees
14 Nov - 15 Nov
Charming Retreat
A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

3. Long Beach Suites: 3 Mins Toes To Sand!

Long Beach Suites: 3 Mins Toes To Sand!
East Gloucester
8.8 out of 10, Excellent, (21 reviews)
"Had a wonderful visit to the area exploring Gloucester, Rockport, and Salem."
United States
Margaret O.
The price is HK$1,420
HK$3,766 total
includes taxes & fees
15 Nov - 16 Nov
Long Beach Suites: 3 Mins Toes To Sand!
Property grounds

4. Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Gloucester
9.4 out of 10, Exceptional, (6 reviews)
"Lovely, large room with beams on the ceiling and a very comfortable bed. Clean and inviting. Appreciated the detailed, friendly messages from the host. The building is near a pretty pond and the store downstairs sells coffee for a dollar!"
United States
Catherine C.
The price is HK$1,123
HK$1,605 total
includes taxes & fees
8 Nov - 9 Nov
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
A staircase with wooden steps leading to a room with a wooden ceiling.

5. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.8 out of 10, Exceptional, (16 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$1,052
HK$3,254 total
includes taxes & fees
10 Nov - 11 Nov
Oceanside Village Home~Private Fenced Yard~Reserved Parking
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

6. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (18 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$1,312
HK$1,597 total
includes taxes & fees
8 Nov - 9 Nov
The Essex of Gloucester
A wooden staircase with a railing leading to a covered deck area.

7. 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
9.6 out of 10, Exceptional, (24 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$2,114
HK$4,998 total
includes taxes & fees
3 Nov - 4 Nov
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
A residential area with houses, a road, and a body of water in the background.

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, (8 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$1,922
HK$6,870 total
includes taxes & fees
3 Nov - 4 Nov
Classic Coastal Family Home | Walk to Sea;King Bed
A modern staircase with wooden steps and metal railings, leading to a well-lit interior space.

9. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (5 reviews)
"Comfortable, clean and very much natural light. The beds are incredibly comfortable. A great place as a homebase when visiting the area."
United States
Richard B.
The price is HK$1,538
HK$5,722 total
includes taxes & fees
3 Nov - 4 Nov
New England Coastal Residence
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

10. The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard
East Gloucester
10.0 out of 10, Exceptional, (6 reviews)
"We truly enjoyed our time at the Mariner. Its a beautiful home with all the necessary amenities. Rachel is an excellent host. She was extremely responsive throughout our stay. We will definitely be back!!"
United States
Nina R.
The price is HK$2,693
HK$6,055 total
includes taxes & fees
24 Nov - 25 Nov
The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

11. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (65 reviews)
"Very nice little house with all amenities you can ask for. Unfortunately we only had a quick over night stay. Beautiful location. The drive way is a challenge to get out if you are backing out. We certainly would stay again!"
United States
Nicole
Beach Life Bliss - steps to the beach
A wooden deck with a table and chairs, overlooking a body of water and a distant building.

12. 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!
A marina with boats docked, a clear sky, and a street with parked cars.

13. Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
9.8 out of 10, Exceptional, (41 reviews)
"Was a fantastic place to stay. Host was great as well."
United States
Wesley G.
The price is HK$800
HK$2,048 total
includes taxes & fees
3 Nov - 4 Nov
Harborside Oasis ★ Harbor View ★ Heart of Downtown
A waterfront property with a dock, houses in the background, and a clear sky.

14. Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (46 reviews)
"This is a wonderful place to stay! It's super clean, modern amenities, & comfortable and literally steps from Bearskin Neck. The host, Gigi, is awesome and great communication. Such a cool vibe here, i can'twait to return!"
United States
Heidi K.
The price is HK$889
HK$2,158 total
includes taxes & fees
3 Nov - 4 Nov
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
A waterfront property with a dock, a bicycle, and a white chair.

15. Charming Waterfront Home - Patio - AC - Projector - Kitchen - Shops - Dining

Charming Waterfront Home - Patio - AC - Projector - Kitchen - Shops - Dining
Rockport
10.0 out of 10, Exceptional, (5 reviews)
"Cute spot, comfy bed, perfect location!!"
United States
Amelia W.
Charming Waterfront Home - Patio - AC - Projector - Kitchen - Shops - Dining
A kitchen with white cabinets, a stainless steel range hood, and a clock on the wall.

16. 2BR Home Minutes to Downtown Rockport+Beach!

2BR Home Minutes to Downtown Rockport+Beach!
Rockport
10.0 out of 10, Exceptional, (13 reviews)
"Good facilities, clean and tidy, lovely decor. Good location."
United States
Janet C.
The price is HK$956
HK$3,223 total
includes taxes & fees
16 Nov - 17 Nov
2BR Home Minutes to Downtown Rockport+Beach!
A living room with a sofa, a coffee table, a plant, and a view into the kitchen.

17. Fall Asleep to Waves — Steps to Shops & Dining

Fall Asleep to Waves — Steps to Shops & Dining
Rockport
10.0 out of 10, Exceptional, (14 reviews)
"We loved our stay here ! The beach view from the bedroom window is amazing ! The home was so clean and cozy. We walked to breakfast every morning and all the shops were also in walking distance! We will definately be back!!"
United States
Dominique
The price is HK$1,325
HK$2,909 total
includes taxes & fees
3 Nov - 4 Nov
Fall Asleep to Waves — Steps to Shops & Dining
A modern kitchen with white cabinetry, granite countertops, and stainless steel appliances.

18. 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, (45 reviews)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
The price is HK$1,342
HK$3,630 total
includes taxes & fees
3 Nov - 4 Nov
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
A modern kitchen with dark blue cabinets, a white countertop, and a wooden ceiling.

19. The Bookstore · King Beds · Walk to Beach · Private Parking

The Bookstore · King Beds · Walk to Beach · Private Parking
Rockport
10.0 out of 10, Exceptional, (45 reviews)
"Lovely place, very clean and quiet and within walking distance of several restaurants and stores. We had a couple of questions that the host answered very promptly. Certainly one of the nicest places we've stayed at."
United States
Dave
The price is HK$1,535
HK$3,526 total
includes taxes & fees
16 Nov - 17 Nov
The Bookstore · King Beds · Walk to Beach · Private Parking
A modern kitchen with stainless steel appliances, white cabinets, and a large window.

20. NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH

NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH
Ipswich
9.6 out of 10, Exceptional, (38 reviews)
"Great place to stay—loved the renovations, it was very clean and had an exclusive side entrance for coming & going. I would definitely stay there again!"
United States
Dawne
The price is HK$941
HK$1,730 total
includes taxes & fees
22 Nov - 23 Nov
NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH
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

10/10 Excellent
"Loved everything"
Delbert 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Boston North Shore

Find out more about Gloucester

Search for holiday rentals in Gloucester on Expedia! You can easily find your home rentals, villas, holiday apartments in Gloucester using one of the methods below:

  • View our selection of featured holiday rentals in Gloucester
  • Use the map to find apartments and other holiday homes in the Gloucester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Gloucester while they last

Look no further and take a look at our great range of rental properties in Gloucester!

Frequently asked questions

Can I find a holiday rental in Gloucester?

Yes, there are holiday rentals in Gloucester close to Maritime Gloucester, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the scenic seaside and waterfront in Gloucester. Make sure you have time to check out the seafood restaurants and monuments during your trip.

What are some of the best holiday rentals that Gloucester has to offer?

Beach Life Bliss - steps to the beach: This highly rated holiday home rental in Gloucester is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other top choices in Gloucester are Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam and Single Level Home - Steps to Downtown Gloucester & A/C throughout .

How many holiday rentals are there in Gloucester?

Expedia has 174 holiday rentals for your stay in Gloucester.

What can I see and do in Gloucester?

Family-friendly attractions include Maritime Gloucester and Schooner Adventure, whereas Half Moon Beach and Stage Fort Park are a couple of great spots to enjoy the outdoors. Capt Bill & Sons Whale Watch and Cape Ann Museum are other places to visit while you're in town.

What are holiday rentals like in Gloucester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Gloucester. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.