Gloucester Holiday Rentals

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Holiday Rentals in Gloucester

Oceanside Village Home~Private Fenced Yard~Reserved Parking

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.
The price is NZ$642
includes taxes & fees
30 Nov - 1 Dec
Oceanside Village Home~Private Fenced Yard~Reserved Parking

Long Beach Suites

2.0 star property
Gloucester
9.2 out of 10, Wonderful, (55)
"Shannon was a treasure of info for us about the local places to go. Stay was nice. Close to the beach. "
United States
Glenn
Long Beach Suites

Long Beach Suites: 3 Mins Toes To Sand!

Gloucester
8.8 out of 10, Excellent, (18)
"Plenty of room and so close to the beach. We love Long Beach and this is one of the best spots we have stayed at."
United States
John & Clarinda W.
The price is NZ$707
includes taxes & fees
11 Nov - 12 Nov
Long Beach Suites: 3 Mins Toes To Sand!

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Gloucester
9.6 out of 10, Exceptional, (10)
"Worked out perfectly to visit local family."
United States
Heather S.
The price is NZ$712
includes taxes & fees
11 Nov - 12 Nov
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

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.
The price is NZ$1,022
includes taxes & fees
11 Nov - 12 Nov
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

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

Gloucester
10.0 out of 10, Exceptional, (23)
"Even better in person, host had great hospitality, very clean, quiet, and lovely place to stay! We loved it!"
United States
Jesse D.
The price is NZ$964
includes taxes & fees
11 Nov - 12 Nov
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

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.
The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

Comfy King Beds~5 min to Salem

Beverly
10.0 out of 10, Exceptional, (1)
"Lovely second floor apartment! Great for a pet too. Lovely pet friendly small beach side park 8 minute walk away. Great place to stay if you’re looking to visit Salem "
United States
Jaylee G.
The price is NZ$343
includes taxes & fees
11 Nov - 12 Nov
Comfy King Beds~5 min to Salem

NEW 2BR Home Minutes to Downtown Rockport+Beach!

Rockport
10.0 out of 10, Exceptional, (12)
"The house is modestly appointed in the best sense, everything you need, nothing you don’t. Perfect size and space for quiet days and nights and the location can’t be beat. Owner responsive and helpful. Can’t wait to go back next year! "
United States
Andrew M.
The price is NZ$652
includes taxes & fees
11 Nov - 12 Nov
NEW 2BR Home Minutes to Downtown Rockport+Beach!

Swampscott! Walk Dtwn and beach

Swampscott
10.0 out of 10, Exceptional, (1)
"Great spot!"
United States
William
The price is NZ$357
includes taxes & fees
11 Nov - 12 Nov
Swampscott! Walk Dtwn and beach

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Rockport
10.0 out of 10, Exceptional, (13)
"We had a wonderful time! The house was charming and very well equipped! The town of Rockport was wonderful and the restaurants were delicious. We used the house as a home base to explore Boston, Gloucester, Rockport and Freeport. The beaches and other natural areas were beautiful! This amateur photographer and her family will be back! We would stay here again in a heartbeat! Thank you for your kind hospitality!"
United States
Blair G.
The price is NZ$642
includes taxes & fees
12 Nov - 13 Nov
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

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.
The price is NZ$407
includes taxes & fees
11 Nov - 12 Nov
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harborside Oasis ★ Harbor View ★ Heart of Downtown

Rockport
10.0 out of 10, Exceptional, (21)
"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.
The price is NZ$419
includes taxes & fees
11 Nov - 12 Nov
Harborside Oasis ★ Harbor View ★ Heart of Downtown

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
Marblehead
10.0 out of 10, Exceptional, (17)
"The house was so cute and wonderfully decorated. The check in and check out process was easy. The kitchen had everything we needed to make food and store left overs. We often walked into town for coffee, lobster rolls, and to go the beach. We loved staying here and it has everything one could want in a vacation home."
United States
Nicole M.
The price is NZ$642
includes taxes & fees
11 Nov - 12 Nov
NEW 2BR Historic Marblehead Home+Minutes to Beach

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

2.0 star property
Rockport
10.0 out of 10, Exceptional, (34)
"Easy walk to the beach and town. Great family space. "
United States
James H.
The price is NZ$689
includes taxes & fees
7 Dec - 8 Dec
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

Ipswich
9.4 out of 10, Exceptional, (70)
"Great space with amenities needed for an overnight for our family. Clean with linens etc and even a library of books. Great communication by owner. Will visit again if in the area in the future. "
United States
Rana
The price is NZ$501
includes taxes & fees
17 Nov - 18 Nov
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

1 Mi to Downtown: Salem Vacation Rental!

3.0 star property
Salem
10.0 out of 10, Exceptional, (2)
"Great overall stay! "
United States
Tessa
The price is NZ$545
includes taxes & fees
11 Nov - 12 Nov
1 Mi to Downtown: Salem Vacation Rental!

The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

2.0 star property
Rockport
9.8 out of 10, Exceptional, (7)
"Nice place, clean and quaint. Beachy vibe with home like amenities. Odd observation: Toilet and its plumbing are old and only seem to be able to be flushed once every 20 minutes. With multiple people that can be awkward. All else very good. Would stay again. "
United States
Kevin J.
The price is NZ$727
includes taxes & fees
11 Nov - 12 Nov
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

Beachfront | Panoramic Views | "Oceanfront Oasis"

Salisbury Beach
9.8 out of 10, Exceptional, (34)
"A beautiful, peaceful view! We will be back!"
United States
Heather M.
The price is NZ$737
includes taxes & fees
16 Nov - 17 Nov
Beachfront | Panoramic Views | "Oceanfront Oasis"

Across From Beach | High-End Home | "The Nest"

Newbury
10.0 out of 10, Exceptional, (13)
"Nice cottage!Clean, well stocked and comfortable beds.The hosts were very responsive to my questions.Directions to the cottage were very clear and it was easy to find.We would definitely stay again if available!"
United States
Susan W.
The price is NZ$752
includes taxes & fees
13 Nov - 14 Nov
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 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, 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 NZ$433 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. 

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?

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach: This highly rated holiday home rental in Gloucester is located near the beach, and has a fireplace, a selection of games and a BBQ 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 that you can cook with friends or family. Some other top choices in Gloucester are Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam and Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24.

How many holiday rentals are there in Gloucester?

Expedia has 153 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.