Holiday Rentals in Gloucester

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Our top choices for Gloucester holiday rentals

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

Luxury 1900's romantic retreat steps from the beach - King Suite!
Gloucester
9.8 out of 10, Exceptional, (51 reviews)
"We enjoyed every bit of our stay."
United States
Kathy B.
The price is €296
includes taxes & fees
18 Apr - 19 Apr
Luxury 1900's romantic retreat steps from the beach - King Suite!

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.
Long Beach Suites: Steps To Beach, Newly Built

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 €335
includes taxes & fees
28 Apr - 29 Apr
Oceanside Village Home~Private Fenced Yard~Reserved Parking

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 €227
includes taxes & fees
16 Apr - 17 Apr
The Essex of Gloucester

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 €277
includes taxes & fees
20 Apr - 21 Apr
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)
"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 €299
includes taxes & fees
16 Apr - 17 Apr
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 €433
includes taxes & fees
16 Apr - 17 Apr
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

Charming New England Family Home; Harbor View

Charming New England Family Home; Harbor View
Gloucester
The price is €917
includes taxes & fees
16 Apr - 17 Apr
Charming New England Family Home; Harbor View

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 €304
includes taxes & fees
4 May - 5 May
Ocean Breeze / 8-Minute Walk to 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 €334
includes taxes & fees
16 Apr - 17 Apr
Long Beach Suites: 3 Mins Toes To Sand!

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

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 €310
includes taxes & fees
20 Apr - 21 Apr
Long Beach Suites: Ocean Views, Book 2025 Already!

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 €259
includes taxes & fees
28 Apr - 29 Apr
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

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 €224
includes taxes & fees
22 Apr - 23 Apr
Harborside Oasis ★ Harbor View ★ Heart of Downtown

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 €240
includes taxes & fees
16 Apr - 17 Apr
1BR with Private Deck + Ocean Views· Private Parking · King Bed

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)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
The price is €390
includes taxes & fees
16 Apr - 17 Apr
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!

Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!
Beverly
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful decor and a fantastic location—just steps from restaurants and shops. We really enjoyed our stay!"
United States
Cheryl S.
The price is €262
includes taxes & fees
16 Apr - 17 Apr
Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!

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, (8 reviews)
"Great property!!!"
United States
Heather
The price is €248
includes taxes & fees
27 Apr - 28 Apr
Hocus Pocus Season is here! Don’t miss it!

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead Historic District
10.0 out of 10, Exceptional, (72 reviews)
"Super convenient location; quaint old building; spacious apartment with comfortable bed, seating, and well appointed kitchen and bath. Easy checkin, checkout, and access. Thanks for a great stay!"
United States
Barbara D.
The price is €227
includes taxes & fees
27 Apr - 28 Apr
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Fresh Design-Walk to Salem-Food-Train Station

Fresh Design-Walk to Salem-Food-Train Station
Beverly
10.0 out of 10, Exceptional, (13 reviews)
"Darryl is a great host and the apartment is lovely. We would definitely stay here again."
United States
Timothy G.
The price is €231
includes taxes & fees
23 Apr - 24 Apr
Fresh Design-Walk to Salem-Food-Train Station
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, apart-hotels, 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 €165 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. Some other top choices in Gloucester are Beach Life Bliss - steps to the beach and Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

How many holiday rentals are there in Gloucester?

Expedia has 167 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.