Gloucester Holiday Rentals

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Our top choices for Gloucester holiday rentals

Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (10 reviews)
"Lovely home in a great location. Very clean and fit us well. "
United States
Susan A.
The price is NZ$575
includes taxes & fees
30 Mar - 31 Mar
Oceanside Village Home~Private Fenced Yard~Reserved Parking

Long Beach Suites: Ocean Views, Book 2025 Already!

Long Beach Suites: Ocean Views, Book 2025 Already!
East Gloucester
9.2 out of 10, Wonderful, (22 reviews)
"Loved the stay Very close to beaches, beautiful area. "
United States
Jessica P.
The price is NZ$609
includes taxes & fees
30 Mar - 31 Mar
Long Beach Suites: Ocean Views, Book 2025 Already!

The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (4 reviews)
"The Essex was exceptionally clean! The rooms were all beautifully done and the bed was comfortable! We ate at the Blue Marlin for dinner , the food was excellent and the service too!"
United States
Robin
The price is NZ$518
includes taxes & fees
25 Apr - 26 Apr
The Essex of Gloucester

Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (42 reviews)
"A wonderful place to stay!"
United States
rich k.
The price is NZ$620
includes taxes & fees
6 Apr - 7 Apr
Beach Life Bliss - steps to the beach

The Duval House

The Duval House
Downtown Gloucester
9.6 out of 10, Exceptional, (17 reviews)
"We moved our time at Daryl’s rental. Perfect location as we were visiting for a family wedding. He was great and the apartment was really cute and well stocked :)"
United States
Michelle R.
The price is NZ$718
includes taxes & fees
12 Apr - 13 Apr
The Duval House

Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (63 reviews)
"It's amazing & very private, has everything you could need!"
United States
Ashley
The price is NZ$539
includes taxes & fees
29 Mar - 30 Mar
Long Beach Suites

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, (12 reviews)
"Everything about the cottage was amazing. Check in was easy. The house was very clean, the kitchen was well stocked and the back yard was delightful. Even the fur babies loved being able to run in the fenced in yard. Rachel answered all of my questions in a very timely manner. We would absolutely stay here again if we are ever in the area. "
United States
Anita W.
The price is NZ$693
includes taxes & fees
29 Mar - 30 Mar
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
East Gloucester
9.8 out of 10, Exceptional, (46 reviews)
"House was wonderful and had everything we needed. Very clean and homey for three couples. Great location. Great contact with the host. "
United States
Monica W.
The price is NZ$874
includes taxes & fees
28 Mar - 29 Mar
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

Quaint Neighborhood / Close to Beaches

Quaint Neighborhood / Close to Beaches
East Gloucester
10.0 out of 10, Exceptional, (13 reviews)
"Very nice place I loved it"
United States
Erika G.
The price is NZ$583
includes taxes & fees
9 Apr - 10 Apr
Quaint Neighborhood / Close to Beaches

Charming New England Family Home; Harbor View

Charming New England Family Home; Harbor View
Gloucester
The price is NZ$1,787
includes taxes & fees
29 Mar - 30 Mar
Charming New England Family Home; Harbor View

Seaside Home I Sleeps 6 I Plum Cove Beach+Rockport

Seaside Home I Sleeps 6 I Plum Cove Beach+Rockport
Gloucester
Seaside Home I Sleeps 6 I Plum Cove Beach+Rockport

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
The price is NZ$522
includes taxes & fees
27 Mar - 28 Mar
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

The Bookstore · Private Parking · King Beds · Downtown Rockport

The Bookstore · Private Parking · King Beds · Downtown Rockport
Rockport
9.8 out of 10, Exceptional, (35 reviews)
"Clean cozy space. Perfect location, could walk to everything we wanted to do. "
United States
Cara L.
The price is NZ$519
includes taxes & fees
29 Mar - 30 Mar
The Bookstore · Private Parking · King Beds · Downtown Rockport

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!
Rockport
10.0 out of 10, Exceptional, (38 reviews)
"Lovely home - so close to town. We had a wonderful stay. "
United States
Lisa H.
The price is NZ$779
includes taxes & fees
9 Apr - 10 Apr
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (30 reviews)
"This is a really beautiful property that's great for a weekend getaway in an incredible little town!"
United States
Travis G.
The price is NZ$444
includes taxes & fees
27 Mar - 28 Mar
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

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, (14 reviews)
"Cozy house in great location. We would definitely stay here again. "
United States
John D.
The price is NZ$771
includes taxes & fees
30 Mar - 31 Mar
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Hocus Pocus Season is here! Don’t miss it!

Hocus Pocus Season is here! Don’t miss it!
Salem
10.0 out of 10, Exceptional, (7 reviews)
"Great property!!!"
United States
Heather
The price is NZ$477
includes taxes & fees
30 Mar - 31 Mar
Hocus Pocus Season is here! Don’t miss it!

Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
10.0 out of 10, Exceptional, (22 reviews)
"good location"
United States
Bruce S.
The price is NZ$448
includes taxes & fees
31 Mar - 1 Apr
Harborside Oasis ★ Harbor View ★ Heart of Downtown

2 BR City Sanctuary - 5 Mins to Historical Salem!

2 BR City Sanctuary - 5 Mins to Historical Salem!
Beverly
9.0 out of 10, Wonderful, (2 reviews)
"The host was super accommodating with check in time and check out time. This is the perfect location just outside of Salem. You are not too close to the chaos but only 6-8 minute drive to downtown Salem. Highly recommend! "
United States
Kaitlyn F.
The price is NZ$408
includes taxes & fees
29 Mar - 30 Mar
2 BR City Sanctuary - 5 Mins to Historical Salem!

2b apt loft Downtown Ipswich

2b apt loft Downtown Ipswich
Ipswich
9.2 out of 10, Wonderful, (42 reviews)
"This was such a great stay!! Wonderful space, especially for anyone looking to visit Salem, as it was only about a 30 minute drive. The host was extremely responsive as well. Couldn’t recommend this place more, we had a great trip!!"
United States
Faith A.
The price is NZ$367
includes taxes & fees
28 Mar - 29 Mar
2b apt loft Downtown Ipswich
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$327 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?

Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach: 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 11 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 Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

How many holiday rentals are there in Gloucester?

Expedia has 165 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.