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

Gloucester Vacation Rentals

Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Gloucester vacation rentals

Basic Apartment | Dining room

1. Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (76 reviews)
"Really good,so close to the beaches"
United States
Oscar
$389 nightly
The price is $435
Sep 1 - Sep 2
Total with taxes and fees
Long Beach Suites
Coffee/tea maker, fridge, microwave, oven

2. 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, (56 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.
$397 nightly
The price is $444
Aug 12 - Aug 13
Total with taxes and fees
Luxury 1900's romantic retreat steps from the beach - King Suite!
Interior

3. 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.
$384 nightly
The price is $429
Aug 26 - Aug 27
Total with taxes and fees
Oceanside Village Home~Private Fenced Yard~Reserved Parking
Beach

4. 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.
$438 nightly
The price is $489
Sep 1 - Sep 2
Total with taxes and fees
Long Beach Suites: Ocean Views
Dining

5. 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.
$495 nightly
The price is $552
Aug 17 - Aug 18
Total with taxes and fees
The Duval House
Smart TV, fireplace

6. 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, (27 reviews)
"A beautiful cottage with wonderful amenities and host. Couldn’t have asked for a better place to stay!"
United States
Samson L.
$582 nightly
The price is $650
Aug 10 - Aug 11
Total with taxes and fees
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Private kitchen

7. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (11 reviews)
"Perfect size for two couples! Extremely clean and well stocked!!!!"
United States
Kimberly
$302 nightly
The price is $337
Aug 31 - Sep 1
Total with taxes and fees
The Essex of Gloucester
Interior

8. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (2 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.
$879 nightly
The price is $892
Sep 1 - Sep 2
Total with taxes and fees
New England Coastal Residence
Exterior

9. 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.
$1,066 nightly
The price is $1,219
Sep 2 - Sep 3
Total with taxes and fees
Classic Coastal Family Home | Walk to Sea;King Bed
Coffee/tea maker, fridge, microwave, oven

10. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (50 reviews)
"A wonderful place to stay!"
United States
rich k.
$577 nightly
The price is $645
Aug 10 - Aug 11
Total with taxes and fees
Beach Life Bliss - steps to the beach
Property grounds

11. 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, (16 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
$681 nightly
The price is $761
Aug 12 - Aug 13
Total with taxes and fees
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Interior

12. 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.
$663 nightly
The price is $741
Aug 28 - Aug 29
Total with taxes and fees
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Marina

13. Stay at The Neck

Stay at The Neck
Rocky Neck
10.0 out of 10, Exceptional, (3 reviews)
"This was an amazing place! Great views and right beside an excellent restaurant. Will stay here again!"
United States
Jack J.
$1,069 nightly
The price is $1,194
Aug 18 - Aug 19
Total with taxes and fees
Stay at The Neck
Beach nearby

14. Stay at Wingaersheek

Stay at Wingaersheek
Gloucester
$1,605 nightly
The price is $1,793
Aug 10 - Aug 11
Total with taxes and fees
Stay at Wingaersheek
Terrace/patio

15. 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.
$1,719 nightly
The price is $1,920
Aug 22 - Aug 23
Total with taxes and fees
Private Beach! Dream vacation at your private beach in Gloucester
Beach

16. 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.
$200 nightly
The price is $224
Aug 27 - Aug 28
Total with taxes and fees
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Beach

17. 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.
$490 nightly
The price is $547
Sep 2 - Sep 3
Total with taxes and fees
Long Beach Suites: 3 Mins Toes To Sand!
TV, fireplace, offices

18. Stay at Smith Cove

Stay at Smith Cove
Rocky Neck
10.0 out of 10, Exceptional, (10 reviews)
"Great place clean convenient, great veiw, recommend "
United States
Justin l.
$1,149 nightly
The price is $1,283
Aug 15 - Aug 16
Total with taxes and fees
Stay at Smith Cove
Property grounds

19. Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
9.8 out of 10, Exceptional, (35 reviews)
"Very clean property located on the rock port harbor and downtown. Amazing view of the harbor. Enjoyed watching the lobster boats leaving early in the morning. Our host was very gracious and accommodating. Very walkable location with lots to do. Enjoyed our stay very much."
United States
Linda
$273 nightly
The price is $312
Sep 2 - Sep 3
Total with taxes and fees
Harborside Oasis ★ Harbor View ★ Heart of Downtown
Marina

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

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (40 reviews)
"This is our second year staying at Gigi's place. It's such a great location and value. It offers everything we like during the off season without the crowds and is such a clean and comfortable place to stay."
United States
Victoria P.
$296 nightly
The price is $338
Sep 2 - Sep 3
Total with taxes and fees
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
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

Best Western Plus North Shore Hotel

Best Western Plus North Shore Hotel

10/10 Excellent
"It was clean and very comfortable. Great breakfast!"
Audra sue 1-night trip
Posted 3 hours ago
Best Western Plus North Shore Hotel

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Gloucester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $174 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Peaceful centrally located home: w/ yard & walking distance to town: This Gloucester vacation home rental offers a garden, a barbecue grill, 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 Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

How many vacation rentals are there in Gloucester?

Expedia has 170 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 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 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.