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

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Our top choices for Gloucester holiday rentals

1. Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (80 reviews)
"Really good,so close to the beaches"
United States
Oscar
The price is £277
includes taxes & fees
1 Sept - 2 Sept
Long Beach Suites

2. Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

Cripple Cove Apartment in historic home across from harbour in Gloucester, MA
East Gloucester
9.6 out of 10, Exceptional, (37 reviews)
"Linda was so kind and what a fun little home she opened up to us! "
United States
Hillary M.
The price is £321
includes taxes & fees
2 Sept - 3 Sept
Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

3. Long Beach Suites: Ocean Views

Long Beach Suites: Ocean Views
East Gloucester
9.2 out of 10, Wonderful, (22 reviews)
"Loved the stay Very close to beaches, beautiful area. "
United States
Jessica P.
The price is £331
includes taxes & fees
2 Sept - 3 Sept
Long Beach Suites: Ocean Views

4. 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 £327
includes taxes & fees
27 Aug - 28 Aug
Oceanside Village Home~Private Fenced Yard~Reserved Parking

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 £351
includes taxes & fees
30 Aug - 31 Aug
Quaint Neighborhood / Close to Beaches

6. The Duval House

The Duval House
Downtown Gloucester
9.6 out of 10, Exceptional, (19 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 £342
includes taxes & fees
23 Aug - 24 Aug
The Duval House

7. 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)
"Excellent downtown location! The loft was clean and well stocked. Great communication from the time of booking through check-out. "
United States
Aimee C.
The price is £410
includes taxes & fees
28 Aug - 29 Aug
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

8. Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (20 reviews)
"Excellent location, very clean and good communication. Will definitely stay again when in the area. "
United States
Patrick M.
The price is £322
includes taxes & fees
13 Sept - 14 Sept
Ocean Breeze / 8-Minute Walk to Beach

9. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (11 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 £186
includes taxes & fees
15 Sept - 16 Sept
The Essex of Gloucester

10. Luxury 1900's romantic retreat steps from the beach - King Suite!

Luxury 1900's romantic retreat steps from the beach - King Suite!
Gloucester
9.8 out of 10, Exceptional, (58 reviews)
"This was such a cute little place! We enjoyed our Birthday getaway! It was easy to get around the area too. Parking was small, but thanks to the other reviews we brought the car so we were ok. "
United States
Jennifer B.
The price is £348
includes taxes & fees
4 Sept - 5 Sept
Luxury 1900's romantic retreat steps from the beach - King Suite!

11. Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Gloucester
9.8 out of 10, Exceptional, (28 reviews)
"A beautiful cottage with wonderful amenities and host. Couldn’t have asked for a better place to stay!"
United States
Samson L.
The price is £476
includes taxes & fees
25 Aug - 26 Aug
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

12. 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, (49 reviews)
"Beautiful home in a beautiful location!"
United States
Paul H.
The price is £446
includes taxes & fees
22 Sept - 23 Sept
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

13. 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, (17 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 £553
includes taxes & fees
23 Aug - 24 Aug
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

14. 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 £787
includes taxes & fees
24 Aug - 25 Aug
Classic Coastal Family Home | Walk to Sea;King Bed

15. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (3 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 £713
includes taxes & fees
23 Aug - 24 Aug
New England Coastal Residence

16. 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.
The price is £634
includes taxes & fees
24 Aug - 25 Aug
Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

17. Stay at Good Harbor Beach

Stay at Good Harbor Beach
East Gloucester
10.0 out of 10, Exceptional, (1 review)
"House was incredible and great for a group. Super nice house with everything we needed. Walked to the beach , cooked great meals, Allie was super helpful and accommodating. Would love to come back."
United States
hawley s.
The price is £2,008
includes taxes & fees
21 Sept - 22 Sept
Stay at Good Harbor Beach

18. 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.
Private Beach! Dream vacation at your private beach in Gloucester

19. 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)
"Excellent location. Walkable to Long Beach. Enjoyed daily walks on the beach. Well appointed condo unit. Plenty of towels and kitchen supplies. Two king sized beds was ideal. Would stay here again."
United States
Molly P.
Long Beach Suites: 3 Mins Toes To Sand!

20. 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, (1 review)
"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 £160
includes taxes & fees
26 Aug - 27 Aug
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
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

Find out more about Gloucester

Everything you need to know about Gloucester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gloucester holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gloucester holiday rentals we have selected for you start as low as £111 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 holiday 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 holiday.

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. 

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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?

Peaceful centrally located home: w/ yard & walking distance to town: This highly rated holiday home rental in Gloucester offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Some other top choices in Gloucester are Steps to Wingaersheek's Private 1.5 Mile White Dune Beach and Classic Coastal Family Home | Walk to Sea;King Bed.

How many holiday rentals are there in Gloucester?

Expedia has 170 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 Pavilion Beach and Half Moon Beach 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.