Gloucester Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Gloucester vacation 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 ￥22,859
￥65,917 total
includes taxes & fees
May 17 - May 18
Long Beach Suites: Steps To Beach, Newly Built
Basic Apartment | Dining room

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 ￥17,829
￥50,945 total
includes taxes & fees
May 18 - May 19
Long Beach Suites
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 ￥17,001
￥48,070 total
includes taxes & fees
May 17 - May 18
Quaint Neighborhood / Close to Beaches
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 ￥26,668
￥34,045 total
includes taxes & fees
May 28 - May 29
The Essex of Gloucester
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 ￥17,915
￥57,424 total
includes taxes & fees
May 18 - May 19
Oceanside Village Home~Private Fenced Yard~Reserved Parking
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 ￥26,964
￥80,121 total
includes taxes & fees
May 19 - May 20
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
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, (11 reviews)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
The price is ￥50,489
￥106,931 total
includes taxes & fees
May 19 - May 20
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Sauna

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 ￥21,535
￥63,596 total
includes taxes & fees
May 20 - May 21
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
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 ￥47,622
￥91,139 total
includes taxes & fees
Jun 11 - Jun 12
Beach Life Bliss - steps to the beach
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 ￥50,321
￥153,896 total
includes taxes & fees
May 18 - May 19
Classic Coastal Family Home | Walk to Sea;King Bed
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.
The price is ￥90,006
￥164,723 total
includes taxes & fees
May 21 - May 22
Stay at Smith Cove
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 ￥109,531
￥263,133 total
includes taxes & fees
Jun 9 - Jun 10
Ocean front and 3 beaches across,parks, short walk to historic downtown!
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 ￥26,510
￥68,001 total
includes taxes & fees
May 25 - May 26
Long Beach Suites: Ocean Views
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 ￥30,478
￥78,329 total
includes taxes & fees
May 25 - May 26
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

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 ￥26,964
￥67,887 total
includes taxes & fees
May 21 - May 22
The Bookstore · Private Parking · King Beds · Downtown Rockport
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
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, (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 ￥18,293
￥42,901 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥20,001
￥45,923 total
includes taxes & fees
Jun 3 - Jun 4
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, (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 ￥30,954
￥39,364 total
includes taxes & fees
May 17 - May 18
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
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

avid hotel Boston Logan Airport - Revere by IHG

avid hotel Boston Logan Airport - Revere by IHG

10/10 Excellent
"This hotel was great. Shuttle to and from Logan. Staff is fantastic!"
Stephanie 2-night trip
Posted 3 hours ago
avid hotel Boston Logan Airport - Revere 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 vacation rental in Gloucester?

Yes, we offer vacation rentals in Gloucester close to Maritime Gloucester, or you can choose a more remote option if you'd like a relaxing place to 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 vacation rentals that Gloucester has to offer?

Beach Life Bliss - steps to the beach: This Gloucester vacation home rental is located near the beach and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 vacation rentals are there in Gloucester?

Expedia has 169 vacation 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 vacation rentals like in Gloucester?

Vacation rentals are private properties you can stay in for a short or long stay in Gloucester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.