Gloucester Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

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$3,394 total
includes taxes & fees
25 May - 26 May
Long Beach Suites: Steps To Beach, Newly Built
Dining room

Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (66 reviews)
"the house was well kept"
United States
Oluwakemi
The price is HK$917
HK$2,555 total
includes taxes & fees
26 May - 27 May
Long Beach Suites
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$666
HK$2,056 total
includes taxes & fees
25 May - 26 May
Ocean Breeze / 8-Minute Walk to Beach
Interior

Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.8 out of 10, Exceptional, (12 reviews)
"Lovely home in a great location. Very clean and fit us well. "
United States
Susan A.
The price is HK$884
HK$2,896 total
includes taxes & fees
27 May - 28 May
Oceanside Village Home~Private Fenced Yard~Reserved Parking
Private kitchen

The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (6 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 HK$1,873
HK$2,389 total
includes taxes & fees
26 May - 27 May
The Essex of Gloucester
Smart TV, fireplace

Charming Retreat

Charming Retreat
East Gloucester
9.8 out of 10, Exceptional, (16 reviews)
"Nice place to stay, clean and comfortable."
United States
Anonymous traveller
The price is HK$1,403
HK$2,897 total
includes taxes & fees
3 Jun - 4 Jun
Charming Retreat
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, (46 reviews)
"A wonderful place to stay!"
United States
rich k.
The price is HK$2,350
HK$4,498 total
includes taxes & fees
11 Jun - 12 Jun
Beach Life Bliss - steps to the beach
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$1,152
HK$3,169 total
includes taxes & fees
25 May - 26 May
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Exterior

Classic Coastal Family Home | Walk to Sea;King Bed

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
10.0 out of 10, Exceptional, (1 review)
"Property was excellent, beautifully decorated with good taste, location was beautiful, everyone enjoyed the weekend stay. Rooms were clean, beds were comfortable."
United States
Maarij K.
The price is HK$2,499
HK$7,614 total
includes taxes & fees
26 May - 27 May
Classic Coastal Family Home | Walk to Sea;King Bed
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.
The price is HK$1,481
HK$3,194 total
includes taxes & fees
3 Jun - 4 Jun
Quaint Neighborhood / Close to Beaches
TV, fireplace, offices

Stay at Smith Cove

Stay at Smith Cove
Rocky Neck
10.0 out of 10, Exceptional, (9 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.
Stay at Smith Cove
Beach

Long Beach Suites: Ocean Views

Long Beach Suites: Ocean Views
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$1,018
HK$2,988 total
includes taxes & fees
26 May - 27 May
Long Beach Suites: Ocean Views
Interior

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 HK$5,406
HK$13,102 total
includes taxes & fees
9 Jun - 10 Jun
Ocean front and 3 beaches across,parks, short walk to historic downtown!
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.
Long Beach Suites: 3 Mins Toes To Sand!
Exterior

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
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.
The price is HK$1,241
HK$3,364 total
includes taxes & fees
27 May - 28 May
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Marina

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (33 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$905
HK$2,148 total
includes taxes & fees
11 Jun - 12 Jun
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, (24 reviews)
"good location"
United States
Bruce S.
The price is HK$987
HK$2,266 total
includes taxes & fees
4 Jun - 5 Jun
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, (203 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$1,528
HK$1,951 total
includes taxes & fees
26 May - 27 May
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Marina

The Bookstore · Private Parking · King Beds · Downtown Rockport

The Bookstore · Private Parking · King Beds · Downtown Rockport
Rockport
9.8 out of 10, Exceptional, (37 reviews)
"We were so happy we stayed at The Library! As soon as we walked in, we felt welcomed, comfortable - it was amazing! Definitely worth staying here. Our host, Rachel, was so helpful and friendly. Five Star all the way!"
United States
Lauren A.
The price is HK$1,331
HK$3,350 total
includes taxes & fees
25 May - 26 May
The Bookstore · Private Parking · King Beds · Downtown Rockport
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

Beauport Hotel Gloucester

Beauport Hotel Gloucester

10/10 Excellent
"From the front desk to the dinning room everything was great. Everyone was helpful and what an amazing hotel"
mark 3-night trip
Posted less than an hour ago
Beauport Hotel Gloucester

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.