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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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, (78 reviews)
"Really good,so close to the beaches"
United States
Oscar
The price is AED 714
AED 1,516 total
includes taxes & fees
2 Sep - 3 Sep
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.
The price is AED 780
AED 1,581 total
includes taxes & fees
12 Aug - 13 Aug
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.
The price is AED 540
AED 1,526 total
includes taxes & fees
1 Sep - 2 Sep
Oceanside Village Home~Private Fenced Yard~Reserved Parking
Smart TV, books

4. 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.
3BR/2 BA Harborside Home · Fenced Backyard+Grill · 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.
The Duval House
Beach

6. 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 AED 848
AED 1,869 total
includes taxes & fees
2 Sep - 3 Sep
Long Beach Suites: Ocean Views
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
The price is AED 948
AED 1,210 total
includes taxes & fees
7 Sep - 8 Sep
The Essex of Gloucester
Smart TV, fireplace

8. 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 AED 1,319
AED 2,388 total
includes taxes & fees
13 Aug - 14 Aug
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Property grounds

9. 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
The price is AED 1,336
AED 2,690 total
includes taxes & fees
12 Aug - 13 Aug
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Interior

10. 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 AED 1,462
AED 3,291 total
includes taxes & fees
1 Sep - 2 Sep
New England Coastal Residence
Interior

11. 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 AED 1,453
AED 2,559 total
includes taxes & fees
28 Aug - 29 Aug
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Exterior

12. 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 AED 1,660
AED 4,158 total
includes taxes & fees
9 Sep - 10 Sep
Classic Coastal Family Home | Walk to Sea;King Bed
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.
Stay at The Neck
Outdoor dining

14. 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 AED 2,503
AED 4,125 total
includes taxes & fees
6 Sep - 7 Sep
Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!
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.
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.
The price is AED 542
AED 807 total
includes taxes & fees
10 Sep - 11 Sep
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.
Long Beach Suites: 3 Mins Toes To Sand!
Property grounds

18. 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
The price is AED 540
AED 1,188 total
includes taxes & fees
2 Sep - 3 Sep
Harborside Oasis ★ Harbor View ★ Heart of Downtown
Marina

19. 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.
The price is AED 486
AED 1,114 total
includes taxes & fees
7 Sep - 8 Sep
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Beach nearby, sun loungers, beach towels

20. 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, (214 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 AED 716
AED 915 total
includes taxes & fees
18 Aug - 19 Aug
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
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

8/10 Good
"My boyfriend and I had a one night stay here that we overall enjoyed very much. The pool and hot tub are great. The sauna was out of order. The waterpark is also really nice, we did not use it, but we did walk in and check it out and it looked like it would be a really good time! The room was very clean, comfortable bed, and amazing pillows. Overall the property is beautiful and has a lot to offer. The staff is where we ran into issues. I booked a king room and when we got to our room, it was two DOUBLE beds, not even queens. Also, somehow we were put in a handicapped room and the shower was for someone with a wheelchair (not what we wanted or asked for.) The following morning, we called down to order room service for breakfast as I had paid for the package. Hours on Sunday are 7am-11an. My boyfriend and I called down at 9:30am and no one answered. I gave it 15 minutes and called back, still nothing. I did this a few times, until I finally called the front desk. I asked the gentleman if room service is available for breakfast and he said it is. I told him I had been calling the restaurant for an hour with no response, and he said he would transfer me himself, still nothing. When I called him back, he didn’t even say hello, he just said in an annoyed tone “still not answering you??” And I told him no. He said well there’s nothing I can do, sorry, and hung up. To me this is very unprofessional. If not for the staff, would have been a 5."
Shannon 1-night trip
Posted 6 hours ago
DoubleTree by Hilton Boston North Shore

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 171 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.