Gloucester Vacation Rentals

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Vacation Rentals in Gloucester

Cottage in Gloucester

9.8 out of 10, Exceptional, (49)
"Very nice spot - very clean - nice bathroom"
United States
Mary M.
$277 nightly
The price is $309
Nov 29 - Nov 30
Total with taxes and fees
Luxury 1900's romantic retreat steps from the beach - King Suite!

Vacation Home in Gloucester

9.6 out of 10, Exceptional, (9)
"House was nice, with a great back yard. Just a short walk to beautiful rocks overlooking the ocean."
United States
Jeri S.
$286 nightly
The price is $320
Nov 23 - Nov 24
Total with taxes and fees
Oceanside Village Home~Private Fenced Yard~Reserved Parking

Aparthotel in Gloucester

2.0 star property
9.2 out of 10, Wonderful, (57)
"Best location and it's a very nice place. "
United States
Kylie
Long Beach Suites

Vacation Home in Gloucester

10.0 out of 10, Exceptional, (6)
"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.
$460 nightly
The price is $514
Nov 25 - Nov 26
Total with taxes and fees
The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

Vacation Home in Gloucester

10.0 out of 10, Exceptional, (6)
"We stayed at this house for a week. Great location, quiet neighborhood, beds were confortable and communication with the host was great. We would definitely stay here again"
United States
Am B.
$487 nightly
The price is $544
Dec 17 - Dec 18
Total with taxes and fees
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Vacation Home in Gloucester

9.6 out of 10, Exceptional, (10)
"We loved cooking on the antique stove and hanging out in the sun room. It was a cozy spot close to all the activities in Rockport."
United States
Allyson Y.
$369 nightly
The price is $412
Dec 17 - Dec 18
Total with taxes and fees
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Vacation Home in Rockport

10.0 out of 10, Exceptional, (13)
"The house was clean, inviting, and cozy. The location was great. We very much enjoyed our stay there. "
United States
Launa F.
$299 nightly
The price is $334
Nov 23 - Nov 24
Total with taxes and fees
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Apartment in Swampscott

10.0 out of 10, Exceptional, (2)
"Great spot!"
United States
William
$189 nightly
The price is $201
Nov 25 - Nov 26
Total with taxes and fees
Swampscott! Walk Dtwn and beach

Apartment in Rockport

9.8 out of 10, Exceptional, (29)
"Great place for the two of us, centrally located and met all of our expectations."
United States
Charles S.
$212 nightly
The price is $237
Dec 8 - Dec 9
Total with taxes and fees
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Apartment in Rockport

10.0 out of 10, Exceptional, (22)
"We loved our stay. Seconds away from downtown with a nice view of the harbor. The bed was very comfortable and we had everything we needed."
United States
Amy H.
$211 nightly
The price is $236
Nov 23 - Nov 24
Total with taxes and fees
Harborside Oasis ★ Harbor View ★ Heart of Downtown

Vacation Home in Rockport

2.0 star property
10.0 out of 10, Exceptional, (35)
"This is a great place to stay! It was super clean and comfy. I would go back! "
United States
Amanda C.
$334 nightly
The price is $374
Dec 8 - Dec 9
Total with taxes and fees
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Apartment in Beverly

9.4 out of 10, Exceptional, (10)
"Great location! Big Space! Love it!"
United States
Megan H.
$209 nightly
The price is $222
Dec 1 - Dec 2
Total with taxes and fees
Dwtn Beverly! 5 Min to Salem!

Vacation Home in Newburyport

3.0 star property
10.0 out of 10, Exceptional, (2)
"Clean and well cared for; high end finishes; small but adorable with beautiful views from upstairs bedroom. Good communication with owners. "
United States
Anat
$376 nightly
The price is $420
Dec 18 - Dec 19
Total with taxes and fees
Plovers Nest

Condo in Salisbury Beach

9.8 out of 10, Exceptional, (34)
"Overall was great, liked the grill on the beach"
United States
Benjamin J.
$390 nightly
The price is $436
Dec 4 - Dec 5
Total with taxes and fees
Beachfront Panoramic Views Oceanfront Oasis

Vacation Home in Ipswich

9.4 out of 10, Exceptional, (70)
"Comfortable stay in a great location."
United States
Amanda A.
$257 nightly
The price is $282
Nov 24 - Nov 25
Total with taxes and fees
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

Cottage in Rockport

10.0 out of 10, Exceptional, (12)
"We loved the house and its walkable location to town and the water. "
United States
Kate G.
$342 nightly
The price is $382
Nov 30 - Dec 1
Total with taxes and fees
2BR Home Minutes to Downtown Rockport+Beach!

Condo in Beverly

10.0 out of 10, Exceptional, (19)
"A very nice stay everything is in walking distance. Food very good "
United States
Deanna F.
$316 nightly
The price is $353
Nov 24 - Nov 25
Total with taxes and fees
*NEW Spacious 3BR Downtown|Beverly+Salem|Parking

Apartment in Beverly

8.8 out of 10, Excellent, (5)
"Great location pet friendly and friendly host."
United States
Sandy
$225 nightly
The price is $240
Nov 30 - Dec 1
Total with taxes and fees
Beverly/Salem! Dwtn/Water/Train

Apartment in Beverly

9.2 out of 10, Wonderful, (15)
"Beautiful decor and a fantastic location—just steps from restaurants and shops. We really enjoyed our stay!"
United States
Cheryl S.
$278 nightly
The price is $310
Dec 3 - Dec 4
Total with taxes and fees
Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!

Vacation Home in Newbury

10.0 out of 10, Exceptional, (13)
"Wolf appliances, top notch fixtures, comfortable bed, large deck. Such a comfortable place to stay"
United States
Stephanie R.
$440 nightly
The price is $465
Dec 4 - Dec 5
Total with taxes and fees
Across From Beach | High-End Home | "The Nest"
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 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 $304 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.

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?

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach: This Gloucester vacation home rental is located near the beach and has a fireplace, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Gloucester are Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24 and Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

How many vacation rentals are there in Gloucester?

Expedia has 157 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 Niles 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.