Gloucester Vacation Rentals

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Our top choices for Gloucester vacation rentals

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.
$384 nightly
The price is $429
May 8 - May 9
Total with taxes and fees
Long Beach Suites: Steps To Beach, Newly Built

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.
$183 nightly
The price is $204
May 12 - May 13
Total with taxes and fees
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
$308 nightly
The price is $344
May 10 - May 11
Total with taxes and fees
Long Beach Suites

Charming Retreat

Charming Retreat
East Gloucester
9.8 out of 10, Exceptional, (15 reviews)
"Nice place to stay, clean and comfortable."
United States
Anonymous traveler
$248 nightly
The price is $277
May 10 - May 11
Total with taxes and fees
Charming Retreat

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.
$461 nightly
The price is $515
May 11 - May 12
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, (11 reviews)
"Lovely home in a great location. Very clean and fit us well. "
United States
Susan A.
$370 nightly
The price is $413
May 11 - May 12
Total with taxes and fees
Oceanside Village Home~Private Fenced Yard~Reserved Parking

Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (45 reviews)
"A wonderful place to stay!"
United States
rich k.
$421 nightly
The price is $470
May 22 - May 23
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, (13 reviews)
"Very nice place I loved it"
United States
Erika G.
$271 nightly
The price is $303
May 17 - May 18
Total with taxes and fees
Quaint Neighborhood / Close to Beaches

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.
$413 nightly
The price is $462
May 11 - May 12
Total with taxes and fees
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

Classic Coastal Family Home | Walk to Sea;King Bed

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
$834 nightly
The price is $953
May 11 - May 12
Total with taxes and fees
Classic Coastal Family Home | Walk to Sea;King Bed

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.
$424 nightly
The price is $473
May 20 - May 21
Total with taxes and fees
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

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.
$327 nightly
The price is $365
May 10 - May 11
Total with taxes and fees
Long Beach Suites: Ocean Views, Book 2025 Already!

Stay at Smith Cove

Stay at Smith Cove
Rocky Neck
10.0 out of 10, Exceptional, (8 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.
$934 nightly
The price is $1,043
May 21 - May 22
Total with taxes and fees
Stay at Smith Cove

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.
$373 nightly
The price is $416
May 11 - May 12
Total with taxes and fees
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

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
$376 nightly
The price is $412
May 9 - May 10
Total with taxes and fees
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, (24 reviews)
"good location"
United States
Bruce S.
$259 nightly
The price is $289
May 8 - May 9
Total with taxes and fees
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
$251 nightly
The price is $280
May 11 - May 12
Total with taxes and fees
1BR with Private Deck + Ocean Views· Private Parking · King Bed

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.
$259 nightly
The price is $289
May 10 - May 11
Total with taxes and fees
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (20 reviews)
"Location and amenities were great! Close to everything , yet private. Comfortable and clean . Host was most helpful.Will definitely try to stay again when traveling to the area ."
United States
George G.
$319 nightly
The price is $357
May 11 - May 12
Total with taxes and fees
2BR Historic Marblehead Home+Minutes to Beach
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 $183 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.