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, (65 reviews)
"It's amazing & very private, has everything you could need!"
United States
Ashley
The price is NZ$546
includes taxes & fees
12 May - 13 May
Long Beach Suites

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, (10 reviews)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
The price is NZ$819
includes taxes & fees
12 May - 13 May
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Long Beach Suites: Steps To Beach, Newly Built

Long Beach Suites: Steps To Beach, Newly Built
East Gloucester
10.0 out of 10, Exceptional, (8 reviews)
"Clean property. Steps from the beach. Will book again! Only regret is not staying longer!"
United States
Desiree P.
The price is NZ$709
includes taxes & fees
12 May - 13 May
Long Beach Suites: Steps To Beach, Newly Built

The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (5 reviews)
"The host was really accessible and easy to communicate with. We had all the info we needed for an easy check-in. The house was exceptionally clean and quiet. "
United States
Chris K.
The price is NZ$401
includes taxes & fees
9 June - 10 June
The Essex of Gloucester

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$500
includes taxes & fees
17 May - 18 May
Quaint Neighborhood / Close to Beaches

Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (45 reviews)
"A wonderful place to stay!"
United States
rich k.
The price is NZ$835
includes taxes & fees
22 May - 23 May
Beach Life Bliss - steps to the beach

Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.8 out of 10, Exceptional, (11 reviews)
"Lovely home in a great location. Very clean and fit us well. "
United States
Susan A.
The price is NZ$558
includes taxes & fees
12 May - 13 May
Oceanside Village Home~Private Fenced Yard~Reserved Parking

Classic Coastal Family Home | Walk to Sea;King Bed

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
The price is NZ$1,457
includes taxes & fees
12 May - 13 May
Classic Coastal Family Home | Walk to Sea;King Bed

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$963
includes taxes & fees
19 May - 20 May
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
Gloucester
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Stay at Smith Cove

Stay at Smith Cove
Rocky Neck
10.0 out of 10, Exceptional, (8 reviews)
"Very much enjoyed our stay. Property was perfect balance of Gloucester authenticity and modern amenities with stunning views and so much natural light which was so welcome in our December stay."
United States
Daniel M.
The price is NZ$1,705
includes taxes & fees
21 May - 22 May
Stay at Smith Cove

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)
"The house was just what we needed for a family get a way. The dogs and are teens loved it. The weather was cold, rainy and windy but the house kept us nice and warm and cozy. We had everything we needed and more. The sauna was a special treat too:) Thank you for a wonderful visit. We hope to return next year:) "
United States
Christina G.
The price is NZ$799
includes taxes & fees
25 May - 26 May
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Charming Retreat

Charming Retreat
East Gloucester
9.8 out of 10, Exceptional, (15 reviews)
"Nice place to stay, clean and comfortable."
United States
Anonymous traveller
The price is NZ$420
includes taxes & fees
13 May - 14 May
Charming Retreat

Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (18 reviews)
"Excellent location, very clean and good communication. Will definitely stay again when in the area. "
United States
Patrick M.
The price is NZ$432
includes taxes & fees
25 May - 26 May
Ocean Breeze / 8-Minute Walk to Beach

Ocean front and 3 beaches across,parks, short walk to historic downtown!

Ocean front and 3 beaches across,parks, short walk to historic downtown!
Gloucester
10.0 out of 10, Exceptional, (37 reviews)
"The house was beautiful and spacious. The views are incredible."
United States
Mary V.
The price is NZ$2,739
includes taxes & fees
9 June - 10 June
Ocean front and 3 beaches across,parks, short walk to historic downtown!

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 reviews)
"Excellent location. Walkable to Long Beach. Enjoyed daily walks on the beach. Well appointed condo unit. Plenty of towels and kitchen supplies. Two king sized beds was ideal. Would stay here again."
United States
Molly P.
The price is NZ$816
includes taxes & fees
25 May - 26 May
Long Beach Suites: 3 Mins Toes To Sand!

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$731
includes taxes & fees
25 May - 26 May
Long Beach Suites: Ocean Views, Book 2025 Already!

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Rockport
9.8 out of 10, Exceptional, (202 reviews)
"What a wonderful, clean place to stay. The view was amazing and for our first ever experience in Massachusetts just couldn't have been better!!"
United States
Jamie L.
The price is NZ$412
includes taxes & fees
12 May - 13 May
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

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$691
includes taxes & fees
17 May - 18 May
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
Rockport
10.0 out of 10, Exceptional, (35 reviews)
"Great location and the host is very responsive. "
United States
Heather P.
The price is NZ$1,163
includes taxes & fees
14 May - 15 May
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
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$374 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?

Beach Life Bliss - steps to the beach: This highly rated holiday home rental in Gloucester is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 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 Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam and 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8.

How many holiday rentals are there in Gloucester?

Expedia has 169 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.