Gloucester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Gloucester holiday rentals

Holiday 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.
The price is AU$563
includes taxes & fees
16 Dec - 17 Dec
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Holiday Home in Gloucester

2.0 star property
The price is AU$279
includes taxes & fees
11 Dec - 12 Dec
The Essex of Gloucester

Holiday 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.
The price is AU$786
includes taxes & fees
11 Dec - 12 Dec
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Holiday 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.
The price is AU$563
includes taxes & fees
16 Dec - 17 Dec
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Holiday Home in 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 AU$528
includes taxes & fees
11 Dec - 12 Dec
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Holiday Home in Marblehead

2.0 star property
10.0 out of 10, Exceptional, (18)
"Enjoyed our stay. "
United States
Mary D.
The price is AU$528
includes taxes & fees
11 Dec - 12 Dec
2BR Historic Marblehead Home+Minutes to Beach

Holiday Home in Rockport

2.0 star property
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 AU$531
includes taxes & fees
11 Dec - 12 Dec
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

Apartment in Beverly

9.4 out of 10, Exceptional, (20)
"So comfortable, clean, and cozy. Remarkably central location and really thoughtful touches throughout the apartment. We traveled with our toddler and it was super friendly space for our family. We will be back again!"
United States
Rachel B.
The price is AU$391
includes taxes & fees
11 Dec - 12 Dec
Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Holiday 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
Plovers Nest

Apartment in Rockport

10.0 out of 10, Exceptional, (22)
"We had such a good time in Rockport! We stayed two weeks, and Gigi's place was perfect for us. It couldn't have been in a more convenient location, close to everything! Shopping, restaurants, the harbor. We could walk everywhere and it was a great home base for day trips through all of Cape Ann. Definitely recommend!"
United States
Lesley B.
Harborside Oasis ★ Harbor View ★ Heart of Downtown

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.
The price is AU$360
includes taxes & fees
11 Dec - 12 Dec
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Apartment in Salem

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great overall stay! "
United States
Tessa
The price is AU$497
includes taxes & fees
14 Dec - 15 Dec
1 Mi to Downtown: Salem Vacation Rental!

Apartment in Rockport

9.8 out of 10, Exceptional, (33)
"Nice place, great location. Short walk to restaurants and sights. "
United States
Kathryn
1BR with Private Deck + Ocean Views· Private Parking · King Bed

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.
The price is AU$428
includes taxes & fees
11 Dec - 12 Dec
Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!

Apartment in Rockport

10.0 out of 10, Exceptional, (31)
"We loved our stay at The Bookstore-can’t wait to come back! You can’t beat the location-we walked to everything! The accommodations were 10/10-absolutely beautiful and had everything we needed for a quick getaway!"
United States
Shauna W.
The price is AU$516
includes taxes & fees
11 Dec - 12 Dec
The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·

Condo in 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 AU$445
includes taxes & fees
11 Dec - 12 Dec
*NEW 2BR Downtown Getaway|Salem+Beverly|Parking

Apartment in Ipswich

9.2 out of 10, Wonderful, (40)
"My son and I took a quick trip to Ipswich with a visit to Crane Beach, great accommodations for two."
United States
Tara D.
The price is AU$292
includes taxes & fees
11 Dec - 12 Dec
2b apt loft Downtown Ipswich

Holiday Home in Ipswich

9.4 out of 10, Exceptional, (70)
"Comfortable stay in a great location."
United States
Amanda A.
The price is AU$399
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

Apartment in Salem

9.6 out of 10, Exceptional, (61)
"Small house in a great location. Host and neighbors are friendly and respectful of privacy."
United States
Evan B.
The price is AU$350
includes taxes & fees
2 Jan - 3 Jan 2026
Lovely 1.5 bedroom in the great historic town

Apartment in Beverly

8.6 out of 10, Excellent, (12)
"Great location! Big Space! Love it!"
United States
Megan H.
The price is AU$414
includes taxes & fees
4 Jan - 5 Jan 2026
Dwtn Beverly! 5 Min to Salem!
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favourite 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 depend 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 AU$446 per night. Entering your travel dates in the search wizard might find you 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?

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24: This highly rated holiday home rental in Gloucester offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other top choices in Gloucester are Steps to Wingaersheek's Private 1.5 Mile White Dune Beach and 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.