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Gloucester Holiday Rentals

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Our top choices for Gloucester holiday rentals

Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (60)
"Beautiful clean and spacious condo right near long beach in Gloucester. The property management company is friendly and is very responsive. The room I had was newly renovated. It had 2 big smart tvs and a fully stocked kitchen. The keypad door lock is nice as well. I'd definitely stay here again the next time I'm in Gloucester. There's plenty of restaurants and even a shaws right up the road. George's is a great restaurant/cafe up the street with great service and food."
United States
Alexander
Long Beach Suites

The Essex of Gloucester

The Essex of Gloucester
2.0 star property
Gloucester
The price is NZ$314
includes taxes & fees
27 Dec - 28 Dec
The Essex of Gloucester

Long Beach Suites: 3 Mins Toes To Sand!

Long Beach Suites: 3 Mins Toes To Sand!
East Gloucester
8.8 out of 10, Excellent, (19)
"After a conference in Boston, we wanted go stay a few days in a relaxed area near the sea. It was lovely and quiet, and a short walk to the beach."
United States
Jennifer T.
Long Beach Suites: 3 Mins Toes To Sand!

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, (7)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
The price is NZ$1,056
includes taxes & fees
30 Dec - 31 Dec
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Gloucester
9.8 out of 10, Exceptional, (11)
"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.
The price is NZ$656
includes taxes & fees
6 Jan - 7 Jan 2026
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Townhouse in Downtown Gloucester #2

Townhouse in Downtown Gloucester #2
Downtown Gloucester
Townhouse in Downtown Gloucester #2

Long Beach Suites: Ocean Views, Book 2025 Already!

Long Beach Suites: Ocean Views, Book 2025 Already!
East Gloucester
9.2 out of 10, Wonderful, (21)
"The location was perfect- couldn't have been any better. Clean and stocked kitchen. Great communication. Really enjoyed our stay here!!"
United States
Alex R.
The price is NZ$598
includes taxes & fees
27 Dec - 28 Dec
Long Beach Suites: Ocean Views, Book 2025 Already!

Oceanfront, private balcony, stunning panoramic views of the Atlantic

Oceanfront, private balcony, stunning panoramic views of the Atlantic
Hampton
9.8 out of 10, Exceptional, (46)
"Wish we stayed longer . Beautiful location..ocean across the street was amazing.Wendy is a great host and responded quickly "
United States
amanda L.
The price is NZ$563
includes taxes & fees
4 Jan - 5 Jan 2026
Oceanfront, private balcony, stunning panoramic views of the Atlantic

2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
2.0 star property
Marblehead
10.0 out of 10, Exceptional, (18)
"Enjoyed our stay. "
United States
Mary D.
The price is NZ$656
includes taxes & fees
28 Dec - 29 Dec
2BR Historic Marblehead Home+Minutes to Beach

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

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
Rockport
10.0 out of 10, Exceptional, (13)
"Cozy house in great location. We would definitely stay here again. "
United States
John D.
The price is NZ$612
includes taxes & fees
29 Dec - 30 Dec
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

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

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
2.0 star property
Rockport
10.0 out of 10, Exceptional, (35)
"Everything about our stay was perfect ! The house, its location to the beaches, town and the idyllic Millbrook Meadow Park. The check in was seamless, the house was very clean and had everything we needed. We are definitely going back! "
United States
Tammi M.
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

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

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)
"We had a great stay! Perfect location and a great setup for our family. Beautiful outdoor area and we were lucky with the weather! "
United States
Matt T.
The price is NZ$666
includes taxes & fees
19 Jan - 20 Jan 2026
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
10.0 out of 10, Exceptional, (22)
"good location"
United States
Bruce S.
The price is NZ$428
includes taxes & fees
29 Dec - 30 Dec
Harborside Oasis ★ Harbor View ★ Heart of Downtown

Riverview charming apt near beach

Riverview charming apt near beach
Ipswich
9.8 out of 10, Exceptional, (32)
"Very clean, owner was responsive and helpful, location was excellent. Would stay there again!"
United States
Max G.
The price is NZ$438
includes taxes & fees
11 Jan - 12 Jan 2026
Riverview charming apt near beach

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

Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6
Ipswich
9.4 out of 10, Exceptional, (70)
"Comfortable stay in a great location."
United States
Amanda A.
The price is NZ$385
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

Comfy King Beds~5 min to Salem

Comfy King Beds~5 min to Salem
Beverly
10.0 out of 10, Exceptional, (2)
"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$408
includes taxes & fees
14 Jan - 15 Jan 2026
Comfy King Beds~5 min to Salem

*NEW Downtown Getaway|2BR|Salem+Beverly|Parking

*NEW Downtown Getaway|2BR|Salem+Beverly|Parking
Beverly
10.0 out of 10, Exceptional, (32)
"The home was nicely renovated and comfortable and our hosts were quick to respond to questions. Check in and out was easy and we had a nice stay and will return. "
United States
Lawrence D.
The price is NZ$501
includes taxes & fees
29 Dec - 30 Dec
*NEW Downtown Getaway|2BR|Salem+Beverly|Parking

1880 updated Victorian 1st floor. Harbor view. 20% off NEW special til 12/30/25.

1880 updated Victorian 1st floor. Harbor view. 20% off NEW special til 12/30/25.
2.0 star property
Salem
10.0 out of 10, Exceptional, (4)
"This house is absolutely beautiful, perfect location for all the convince of down town and the host was a sweetheart! "
United States
Shelby L.
The price is NZ$490
includes taxes & fees
27 Dec - 28 Dec
1880 updated Victorian 1st floor. Harbor view. 20% off NEW special til 12/30/25.

Hampton Beach Suite | Mins to Maine | Pet Friendly

Hampton Beach Suite | Mins to Maine | Pet Friendly
Hampton Beach
9.0 out of 10, Wonderful, (12)
"Our stay was great. The location was perfect, right across the street from the beach."
United States
Bryan S.
The price is NZ$372
includes taxes & fees
27 Dec - 28 Dec
Hampton Beach Suite | Mins to Maine | Pet Friendly

1 Mi to Downtown: Salem Vacation Rental!

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$565
includes taxes & fees
28 Dec - 29 Dec
1 Mi to Downtown: Salem Vacation Rental!
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$490 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?

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam: This highly rated holiday home rental in Gloucester is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Another good choice for your trip to Gloucester is Peaceful centrally located home: w/ yard & walking distance to town.

How many holiday rentals are there in Gloucester?

Expedia has 158 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 Half Moon Beach and Stage Fort Park 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.