Gloucester Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Gloucester holiday rentals

Beach

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 HK$1,128
HK$3,349 total
includes taxes & fees
2 May - 3 May
Long Beach Suites: Steps To Beach, Newly Built
Sun-loungers, beach towels

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 HK$627
HK$2,005 total
includes taxes & fees
4 May - 5 May
Ocean Breeze / 8-Minute Walk to Beach
Private kitchen

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 HK$1,253
HK$1,601 total
includes taxes & fees
6 May - 7 May
The Essex of Gloucester
Dining room

Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (64 reviews)
"It's amazing & very private, has everything you could need!"
United States
Ashley
The price is HK$1,008
HK$2,657 total
includes taxes & fees
4 May - 5 May
Long Beach Suites
Smart TV, fireplace

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 HK$1,050
HK$2,442 total
includes taxes & fees
6 May - 7 May
Charming Retreat
Property grounds

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, (9 reviews)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
The price is HK$1,777
HK$4,312 total
includes taxes & fees
4 May - 5 May
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Beach

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 HK$973
HK$2,942 total
includes taxes & fees
5 May - 6 May
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Interior

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 HK$1,241
HK$3,346 total
includes taxes & fees
20 May - 21 May
Oceanside Village Home~Private Fenced Yard~Reserved Parking
Fridge, microwave, oven, stovetop

Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (44 reviews)
"Cozy accommodation..comfortable beds, numerous tvs, lots of extras"
United States
Jo-Ann P.
The price is HK$980
HK$2,757 total
includes taxes & fees
6 May - 7 May
Beach Life Bliss - steps to the beach
Smart TV, books

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.
Quaint Neighborhood / Close to Beaches
Exterior

Classic Coastal Family Home | Walk to Sea;King Bed

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
The price is HK$2,491
HK$7,603 total
includes taxes & fees
4 May - 5 May
Classic Coastal Family Home | Walk to Sea;King Bed
Smart TV, books

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 HK$1,867
HK$4,230 total
includes taxes & fees
4 May - 5 May
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
Beach

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 HK$917
HK$2,858 total
includes taxes & fees
5 May - 6 May
Long Beach Suites: Ocean Views, Book 2025 Already!
Room

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
Beach

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 HK$1,536
HK$3,911 total
includes taxes & fees
14 May - 15 May
Long Beach Suites: 3 Mins Toes To Sand!
Beach

1BR with Private Deck + Ocean Views· Private Parking · King Bed

1BR with Private Deck + Ocean Views· Private Parking · King Bed
Rockport
9.8 out of 10, Exceptional, (35 reviews)
"Nice place, great location. Short walk to restaurants and sights. "
United States
Kathryn
The price is HK$974
HK$2,313 total
includes taxes & fees
14 May - 15 May
1BR with Private Deck + Ocean Views· Private Parking · King Bed
Marina

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (32 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 HK$987
HK$2,240 total
includes taxes & fees
4 May - 5 May
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Property grounds

Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
10.0 out of 10, Exceptional, (23 reviews)
"good location"
United States
Bruce S.
The price is HK$1,070
HK$2,342 total
includes taxes & fees
14 May - 15 May
Harborside Oasis ★ Harbor View ★ Heart of Downtown
Beach nearby, sun-loungers, beach towels

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, (201 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 HK$1,527
HK$1,951 total
includes taxes & fees
5 May - 6 May
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Marina

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, (39 reviews)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
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

Holiday Inn Hotel & Suites Boston - Peabody by IHG

Holiday Inn Hotel & Suites Boston - Peabody by IHG

10/10 Excellent
"Check in was good. Room was clean. Comfortable bed. Next door is Starbucks and a Mediterranean restaurant- amazing.. Great location.. All good"
Eva julie 1-night trip
Posted 2 hours ago
Holiday Inn Hotel & Suites Boston - Peabody by IHG

Find out more about Gloucester

Search for holiday rentals in Gloucester on Expedia! You can easily find your home rentals, villas, holiday apartments in Gloucester using one of the methods below:

  • View our selection of featured holiday rentals in Gloucester
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  • Enter your travel dates to view the best deals on holiday rentals in Gloucester while they last

Look no further and take a look at our great range of rental properties in Gloucester!

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 Steps to Wingaersheek's Private 1.5 Mile White Dune Beach.

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.