Gloucester Holiday Rentals

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Holiday Rentals in Gloucester

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

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Gloucester
9.8 out of 10, Exceptional, (39)
"We had a great stay here - the house was very comfortable and welcoming and just steps away from the beach! The owner is very responsive and helpful. Would absolutely stay here again!"
United States
Piper T.
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

Gloucester
10.0 out of 10, Exceptional, (37)
"Pat was a fantastic host. The house was very clean, comfortable and well equipped. The location is awesome. 5 minute walk from Good Harbor Beach and equally close to an excellent ice cream/pizza/lobster roll place. I hope to stay again in the future. "
United States
Adam S.
Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Gloucester
10.0 out of 10, Exceptional, (3)
"It was a beautiful home. Clean, up-to-date, and conveniently located. The host was very attentive and helpful. "
United States
Charlie L.
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Gloucester
9.4 out of 10, Exceptional, (61)
"House and location supported a relaxing stay with family. "
United States
Joe P.
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Luxury 1900's romantic retreat steps from the beach - King Suite!

Gloucester
9.8 out of 10, Exceptional, (49)
"Had a great cozy weekend near the ocean! Planning to stay here again!"
United States
Ryan W.
Luxury 1900's romantic retreat steps from the beach - King Suite!

Peaceful centrally located home: w/ yard & walking distance to town

2.0 star property
Gloucester
8.6 out of 10, Excellent, (11)
"We had a great stay! We had everything we needed and it wasn’t far from Salem which is what we came for. We’d stay again. Thank you! "
United States
Adam T.
Peaceful centrally located home: w/ yard & walking distance to town

Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Hampton Beach
10.0 out of 10, Exceptional, (99)
"This is an amazing property to stay at! The property owner is extremely responsive to ALL texts and requests. I highly recommend staying here!"
United States
Darlene S.
The price is NZ$1,102
includes taxes & fees
10 Nov - 11 Nov
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Apartments in Salem

3.0 star property
Salem
8.0 out of 10, Very good, (48)
"This was a great spacious place! It was a great location to all the attractions and restaurants! We walked everywhere! "
United States
Janet
Apartments in Salem

Cozy Salem Getaway. Historic Home Near All the Sights

Salem
9.6 out of 10, Exceptional, (58)
"it was very nice and cozy definitely go back there again "
United States
Doreen
The price is NZ$737
includes taxes & fees
17 Nov - 18 Nov
Cozy Salem Getaway. Historic Home Near All the Sights

Quiet neighborhood and Walking destination to Downtown Salem

Salem
9.4 out of 10, Exceptional, (24)
"Easy instructions to get into the apartment, we were on the third floor. Great amenities, and it was a nice quiet place. Nice furnishings as well."
United States
Brandon R.
Quiet neighborhood and Walking destination to Downtown Salem

2 Bed/2 Bath Private Beach House One Block from the ocean.

Hampton Beach
10.0 out of 10, Exceptional, (18)
"Truly enjoyed staying at the house. Parking was good. Thank you for a wonderful stay. "
United States
Karen k.
2 Bed/2 Bath Private Beach House One Block from the ocean.

Coastal Charm: Lobster Châto

2.0 star property
Swampscott
8.8 out of 10, Excellent, (5)
"I was quite disappointed with my recent stay. The hot tub was not as advertised; it was empty, not able to be used and the cleanliness left much to be desired. I also experienced issues with the Wi-Fi connection, making it difficult to stay connected for work. Additionally, the bed broke nearly caused an injury to my family. Overall, I expected a more comfortable and smooth experience given the price. Unfortunately, I left feeling unsatisfied. "
United States
Jessica G.
The price is NZ$1,075
includes taxes & fees
10 Nov - 11 Nov
Coastal Charm: Lobster Châto

Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!

Salem
9.6 out of 10, Exceptional, (146)
"We loved our stay at this property. It was so convenient to walking around Salem and the apartment was very comfortable and had everything we needed."
United States
Brigette P.
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!

Ocean views from every window. 5min walk to the quiet end of the beach!

Hampton Beach
9.6 out of 10, Exceptional, (28)
"We had a great long weekend . The location was perfect ."
United States
Anonymous traveller
Ocean views from every window. 5min walk to the quiet end of the beach!

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

Downtown Salem
9.8 out of 10, Exceptional, (60)
"Amazing place to stay! Love the attention to decorating details, from the spooky lighting to the Alexa “Scroll of Spells” and it’s within close walking distance to many Salem attractions! Would recommend to anyone!"
United States
More M.
The price is NZ$1,336
includes taxes & fees
11 Nov - 12 Nov
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

NEW Historic 1803 Salem 1BR l Walk to Haunted Happenings l SMALL DOG friendly

Salem
10.0 out of 10, Exceptional, (1)
"Property was amazing; Easy check in and out, clean, well kept, plenty of accommodations, an easy walk into Salem and great communication with the host. A would rent again."
United States
Blaine M.
The price is NZ$433
includes taxes & fees
12 Nov - 13 Nov
NEW Historic 1803 Salem 1BR l Walk to Haunted Happenings l SMALL DOG friendly

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Salem
9.6 out of 10, Exceptional, (145)
"Great place The one and only negative was the smell of POT when you opened door to unit. Otherwise, what a great place, beautiful, clean, close to everything. Would definitely stay again "
United States
HEATHER
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2.0 star property
Salem
10.0 out of 10, Exceptional, (17)
"Great property. Can walk to many things and was a great hub to see beautiful Maine Owner was helpful and quick to respond. "
United States
Michelle B.
The price is NZ$809
includes taxes & fees
12 Nov - 13 Nov
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

NEW 1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking

Salem
10.0 out of 10, Exceptional, (24)
"Was a lovely place and perfect for me and my girlfriend especially after it being so hot while we were in town "
United States
Merrick P.
The price is NZ$471
includes taxes & fees
10 Nov - 11 Nov
NEW 1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking
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.