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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Gloucester vacation 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)
"In a very convenient location. Not far from the train station. Walking dust to the beach. Room was very clean and comfortable."
United States
Jessie
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 CA $175
CA $400 total
includes taxes & fees
Nov 14 - Nov 15
Charming Retreat
Property grounds

3. 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 CA $200
CA $283 total
includes taxes & fees
Nov 8 - Nov 9
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

4. 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.
Long Beach Suites: 3 Mins Toes To Sand!
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 CA $205
CA $615 total
includes taxes & fees
Nov 11 - Nov 12
Oceanside Village Home~Private Fenced Yard~Reserved Parking
A modern staircase with wooden steps and metal railings, leading to a well-lit interior space.

6. 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 CA $281
CA $1,024 total
includes taxes & fees
Nov 10 - Nov 11
New England Coastal Residence
A residential area with houses, a road, and a body of water in the background.

7. 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 CA $342
CA $1,208 total
includes taxes & fees
Nov 8 - Nov 9
Classic Coastal Family Home | Walk to Sea;King Bed
A wooden staircase with a railing leading to a covered deck area.

8. 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 CA $394
CA $919 total
includes taxes & fees
Nov 11 - Nov 12
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

9. 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 CA $277
CA $320 total
includes taxes & fees
Dec 1 - Dec 2
The Essex of Gloucester
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 CA $497
CA $1,098 total
includes taxes & fees
Nov 24 - Nov 25
The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard
A marina with boats docked, a clear sky, and a street with parked cars.

11. 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 CA $135
CA $356 total
includes taxes & fees
Nov 9 - Nov 10
Harborside Oasis ★ Harbor View ★ Heart of Downtown
A waterfront property with a dock, houses in the background, and a clear sky.

12. 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 CA $127
CA $345 total
includes taxes & fees
Nov 13 - Nov 14
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
A kitchen with white cabinets, a stainless steel range hood, and a clock on the wall.

13. 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 CA $187
CA $599 total
includes taxes & fees
Nov 8 - Nov 9
2BR Home Minutes to Downtown Rockport+Beach!
A living room with a sofa, a coffee table, a plant, and a view into the kitchen.

14. 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 CA $236
CA $531 total
includes taxes & fees
Nov 11 - Nov 12
Fall Asleep to Waves — Steps to Shops & Dining
A modern kitchen with dark blue cabinets, a white countertop, and a wooden ceiling.

15. 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 CA $256
CA $605 total
includes taxes & fees
Nov 9 - Nov 10
The Bookstore · King Beds · Walk to Beach · Private Parking
A modern kitchen with white cabinetry, granite countertops, and stainless steel appliances.

16. 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 CA $256
CA $679 total
includes taxes & fees
Nov 9 - Nov 10
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
A bedroom with a bed, a painting, and a view of the outdoors.

17. Balcony • KING Suite • Walk2Beach+Bearskin • Parking

Balcony • KING Suite • Walk2Beach+Bearskin • Parking
Rockport
9.8 out of 10, Exceptional, (50 reviews)
"The perfect location/The perfect apartment layout./The perfect amenities. It really was all perfect!"
United States
Dale k.
The price is CA $273
CA $675 total
includes taxes & fees
Nov 8 - Nov 9
Balcony • KING Suite • Walk2Beach+Bearskin • Parking
A modern kitchen with stainless steel appliances, white cabinets, and a large window.

18. 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 CA $168
CA $308 total
includes taxes & fees
Nov 22 - Nov 23
NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH
A modern kitchen with stainless steel appliances, light grey cabinets, and a tiled backsplash.

19. Riverview charming apt near beach

Riverview charming apt near beach
Ipswich
9.6 out of 10, Exceptional, (46 reviews)
"Comfortable and clean"
United States
DAVID A.
The price is CA $161
CA $342 total
includes taxes & fees
Nov 15 - Nov 16
Riverview charming apt near beach
A covered outdoor deck with a grill, a table with chairs, and an umbrella.

20. 2b apt loft Downtown Ipswich

2b apt loft Downtown Ipswich
Ipswich
9.2 out of 10, Wonderful, (53 reviews)
"Everything was fabulous, but the access via the spiral staircase was a not for someone physically compromised."
United States
Helen M.
The price is CA $175
CA $314 total
includes taxes & fees
Nov 8 - Nov 9
2b apt loft 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

Beauport Hotel Gloucester

Beauport Hotel Gloucester

10/10 Excellent
"Beauport rang all the bells for understated North Shore Elegance. Meals( lunch & drinks were delish) Afternoon 10/27 server was a gem. ( local lady who provided helpful tips & is a single Mom so hope you can identify her.) Very Clean room. Comments: my ocean view rm selection On reserving, yielded some water, & a lot of Endicott Coll. Building view. Hmm? Good idea to add a sensor type night light in bathroom, that is commonplace at your tier hotel. Your walkability to area trails , shops, etc was a plus. All Doorman deserve applause. NB with thanks"
Nancy 2-night trip
Posted less than an hour ago
Beauport Hotel Gloucester

Find out more about Gloucester

Everything you need to know about Gloucester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gloucester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gloucester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gloucester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gloucester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gloucester vacation rentals we have selected for you start as low as CA $339 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gloucester rentals

At Expedia, we put the best Gloucester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gloucester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gloucester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gloucester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

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.