Gloucester Vacation Rentals

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Our top choices for Gloucester vacation rentals

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
$323 nightly
The price is $361
Jun 1 - Jun 2
Total with taxes and fees
Long Beach Suites

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.
$423 nightly
The price is $472
Jun 1 - Jun 2
Total with taxes and fees
Long Beach Suites: Steps To Beach, Newly Built

Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (19 reviews)
"Excellent location, very clean and good communication. Will definitely stay again when in the area. "
United States
Patrick M.
$353 nightly
The price is $394
Jun 10 - Jun 11
Total with taxes and fees
Ocean Breeze / 8-Minute Walk to Beach

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
$270 nightly
The price is $302
Jun 1 - Jun 2
Total with taxes and fees
The Essex of Gloucester

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.
$591 nightly
The price is $660
Jun 1 - Jun 2
Total with taxes and fees
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

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.
$550 nightly
The price is $614
Jun 5 - Jun 6
Total with taxes and fees
Oceanside Village Home~Private Fenced Yard~Reserved Parking

Private 2-Bedroom Gloucester Suite Near Beaches, Downtown & Restaurants

Private 2-Bedroom Gloucester Suite Near Beaches, Downtown & Restaurants
Gloucester
$375 nightly
The price is $419
Jun 2 - Jun 3
Total with taxes and fees
Private 2-Bedroom Gloucester Suite Near Beaches, Downtown & Restaurants

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.
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

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.
$514 nightly
The price is $574
Jun 11 - Jun 12
Total with taxes and fees
Beach Life Bliss - steps to the beach

Quaint Neighborhood / Close to Beaches

Quaint Neighborhood / Close to Beaches
East Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"Very nice place I loved it"
United States
Erika G.
$365 nightly
The price is $408
Jun 3 - Jun 4
Total with taxes and fees
Quaint Neighborhood / Close to Beaches

Charming Retreat

Charming Retreat
East Gloucester
9.8 out of 10, Exceptional, (16 reviews)
"Nice place to stay, clean and comfortable."
United States
Anonymous traveler
$331 nightly
The price is $370
Jun 3 - Jun 4
Total with taxes and fees
Charming Retreat

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.
$979 nightly
The price is $1,119
Jun 1 - Jun 2
Total with taxes and fees
Classic Coastal Family Home | Walk to Sea;King Bed

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.
$398 nightly
The price is $444
Jun 9 - Jun 10
Total with taxes and fees
Long Beach Suites: Ocean Views

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.
$556 nightly
The price is $621
Jun 1 - Jun 2
Total with taxes and fees
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

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.
$402 nightly
The price is $449
Jun 1 - Jun 2
Total with taxes and fees
Long Beach Suites: 3 Mins Toes To Sand!

New England Coastal Residence

New England Coastal Residence
Gloucester
$776 nightly
The price is $787
Jun 1 - Jun 2
Total with taxes and fees
New England Coastal Residence

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.
$1,497 nightly
The price is $1,672
Jun 9 - Jun 10
Total with taxes and fees
Ocean front and 3 beaches across,parks, short walk to historic downtown!

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.
$246 nightly
The price is $274
Jun 2 - Jun 3
Total with taxes and fees
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

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, (204 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.
$223 nightly
The price is $249
May 30 - May 31
Total with taxes and fees
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

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
$327 nightly
The price is $366
Jun 7 - Jun 8
Total with taxes and fees
1BR with Private Deck + Ocean Views· Private Parking · King Bed
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gloucester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Gloucester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $206 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gloucester rentals

At Expedia, we put the best Gloucester vacation 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 vacation.

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 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.