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

Gloucester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Gloucester vacation rentals

A bedroom with a bed, bedside tables, a desk, and a bench.

1. 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.
The price is ￥41,083
￥108,644 total
includes taxes & fees
Oct 26 - Oct 27
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
A wooden staircase with a railing leading to a covered deck area.

2. 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
9.8 out of 10, Exceptional, (20 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 ￥51,847
￥113,461 total
includes taxes & fees
Oct 7 - Oct 8
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
A two-story house with a wrap-around porch, a curved driveway, and a view of a large body of water.

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, (5 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 ￥61,072
￥167,154 total
includes taxes & fees
Oct 6 - Oct 7
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.

4. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (4 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 ￥53,053
￥143,110 total
includes taxes & fees
Oct 6 - Oct 7
New England Coastal Residence
A cozy living room with a wooden ceiling, a sofa, a coffee table, and a door with glass panels.

5. Quaint Neighborhood / Close to Beaches

Quaint Neighborhood / Close to Beaches
East Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"A lovely place! Very clean with very comfortable beds! "
United States
Mariyana K.
The price is ￥38,556
￥75,412 total
includes taxes & fees
Oct 21 - Oct 22
Quaint Neighborhood / Close to Beaches
A living room with a fireplace, a television mounted on the wall, and a variety of decorative items including plants and a large vase.

6. Charming Retreat

Charming Retreat
East Gloucester
10.0 out of 10, Exceptional, (22 reviews)
"Parking was great...easy access to visiting all of Cape Ann"
United States
Margaret
The price is ￥26,769
￥56,270 total
includes taxes & fees
Oct 6 - Oct 7
Charming Retreat
A spacious living room with a large TV, comfortable seating, and large windows offering a view of the outdoors.

7. Stay at Little River

Stay at Little River
Gloucester
10.0 out of 10, Exceptional, (9 reviews)
"My friend and I had a great time staying at the house. Beautiful view, close to great attractions, and the kitchen was well appointed."
United States
Caitlin D.
The price is ￥101,976
￥180,354 total
includes taxes & fees
Oct 15 - Oct 16
Stay at Little River
A kitchen with white cabinets, a dining table with chairs, and a hanging light fixture.

8. The Duval House

The Duval House
Downtown Gloucester
9.4 out of 10, Exceptional, (20 reviews)
"We had a wonderful stay. The house was very nice and the room was very clean. Can’t wait to come back!"
United States
Jennifer H.
The price is ￥36,014
￥81,185 total
includes taxes & fees
Oct 21 - Oct 22
The Duval House
A living room with a wooden coffee table, two wine glasses, a black textured wall, a green sofa, and a door leading to a garden.

9. Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Downtown Gloucester
10.0 out of 10, Exceptional, (13 reviews)
"Everything was great! Felt like I was in my own house"
United States
Bill D.
The price is ￥30,585
￥69,144 total
includes taxes & fees
Oct 13 - Oct 14
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
A crowded beach with people swimming and sunbathing, tents, and beach chairs.

10. Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (21 reviews)
"Very clean and quaint. There is definitely noise you can hear from upstairs but not in a way that was bothersome. We enjoyed our stay!"
United States
Jessica M.
The price is ￥23,457
￥54,161 total
includes taxes & fees
Oct 15 - Oct 16
Ocean Breeze / 8-Minute Walk to Beach
A waterfront property with a dock, a small house with a balcony, and a larger house with a garage.

11. Stay at Rocky Neck

Stay at Rocky Neck
Rocky Neck
10.0 out of 10, Exceptional, (15 reviews)
"Our host was amazing and this was the perfect getaway for us in a beautiful location!"
United States
Joy B.
The price is ￥169,960
￥267,013 total
includes taxes & fees
Oct 12 - Oct 13
Stay at Rocky Neck
A sunset over a beach with trees and a rocky shoreline.

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

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Gloucester
10.0 out of 10, Exceptional, (3 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 ￥24,644
￥36,492 total
includes taxes & fees
Oct 29 - Oct 30
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

13. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (14 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 ￥40,759
￥52,031 total
includes taxes & fees
Oct 7 - Oct 8
The Essex of Gloucester
A staircase with wooden steps leading to a room with a wooden ceiling.

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

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (15 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 ￥33,907
￥83,401 total
includes taxes & fees
Oct 22 - Oct 23
Oceanside Village Home~Private Fenced Yard~Reserved Parking
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

15. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (57 reviews)
"Nice home with great kitchen and all the amenities."
United States
rick b.
The price is ￥21,245
￥57,306 total
includes taxes & fees
Oct 20 - Oct 21
Beach Life Bliss - steps to the beach
A wooden deck with wicker furniture and a white chair, overlooking a beach with a rocky shoreline and a clear blue sky.

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 spot right on Long Beach! Has great views of the ocean right on the water. We definitely stay there again pet friendly."
United States
Emmy D.
The price is ￥69,787
￥134,203 total
includes taxes & fees
Oct 25 - Oct 26
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
An aerial view of a coastal town with a marina filled with boats, surrounded by residential buildings and a clear blue sky.

17. The Bookstore · Private Parking · King Beds · Downtown Rockport

The Bookstore · Private Parking · King Beds · Downtown Rockport
Rockport
10.0 out of 10, Exceptional, (44 reviews)
"It’s the cutest; has everything you’ll need and only a five minute walk to downtown and on-site parking is a plus! The host is attentive and check-in was a breeze."
United States
Nicki B.
The price is ￥33,907
￥76,548 total
includes taxes & fees
Oct 21 - Oct 22
The Bookstore · Private Parking · King Beds · Downtown Rockport
A beach with houses in the background and people engaging in various activities.

18. Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Rockport
9.8 out of 10, Exceptional, (222 reviews)
"Excellent above garage large studio in a superb Rockport location central to everything. Hosts were gracious and warm and made the overnight stay a good one. Highly recommend."
United States
Eugene
The price is ￥30,687
￥39,024 total
includes taxes & fees
Oct 15 - Oct 16
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
A coastal town with a marina filled with boats, surrounded by residential buildings and a large green area.

19. 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, (44 reviews)
"Our family of four humans and two tiny dogs enjoyed our stay at this cozy home. The neighborhood is cute, quiet, and perfectly located to get in and out of town easily. The high appliances made cooking, laundry, and dishes convenient. We‘d love to stay here again."
United States
Bridget H.
The price is ￥32,113
￥80,695 total
includes taxes & fees
Oct 4 - Oct 5
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
12 foot long couch for two people to stretch out on.

20. Apartment with private rooftop deck with ocean views

Apartment with private rooftop deck with ocean views
Rockport
10.0 out of 10, Exceptional, (23 reviews)
"A beautiful home clean with everything we needed for our stay. We enjoyed our stay and I would definitely book again!"
United States
Ellen W.
The price is ￥27,540
￥50,099 total
includes taxes & fees
Oct 4 - Oct 5
Apartment with private rooftop deck with ocean views
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

The Cove At Salem

The Cove At Salem

8/10 Good
"I liked this property. Stayed in a themed room but it was really dark the whole time with all the lights on and the room needed a little TLC but I would stay again"
Paul 3-night trip
Posted less than an hour ago
The Cove At Salem

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:

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

Frequently asked questions

Can I find a vacation rental in Gloucester?

Yes, we offer vacation rentals in Gloucester close to Maritime Gloucester, or you can choose a more remote option if you'd like a relaxing place to 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 vacation rentals that Gloucester has to offer?

Beach Life Bliss - steps to the beach: This Gloucester vacation home rental is located near the beach and has a patio, a garden, and a barbecue grill 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 vacation with amenities like 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 vacation rentals are there in Gloucester?

Expedia has 174 vacation 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 vacation rentals like in Gloucester?

Vacation rentals are private properties you can stay in for a short or long stay in Gloucester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.