A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

Gloucester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Gloucester vacation rentals

Basic Apartment | Dining room

Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (73 reviews)
"Really good,so close to the beaches"
United States
Oscar
$445 nightly
The price is $497
Jul 20 - Jul 21
Total with taxes and fees
Long Beach Suites
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, (16 reviews)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
$587 nightly
The price is $655
Jul 20 - Jul 21
Total with taxes and fees
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Interior

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Downtown Gloucester
10.0 out of 10, Exceptional, (13 reviews)
"Excellent downtown location! The loft was clean and well stocked. Great communication from the time of booking through check-out. "
United States
Aimee C.
$358 nightly
The price is $399
Jul 20 - Jul 21
Total with taxes and fees
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Smart TV, books

Quaint Neighborhood / Close to Beaches

Quaint Neighborhood / Close to Beaches
East Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"A lovely place! Very clean with very comfortable beds! "
United States
Mariyana K.
$422 nightly
The price is $471
Jul 23 - Jul 24
Total with taxes and fees
Quaint Neighborhood / Close to Beaches
Smart TV, fireplace

Charming Retreat

Charming Retreat
East Gloucester
9.8 out of 10, Exceptional, (17 reviews)
"Nice place to stay, clean and comfortable."
United States
Anonymous traveler
$331 nightly
The price is $370
Jul 22 - Jul 23
Total with taxes and fees
Charming Retreat
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, (48 reviews)
"Beautiful home in a beautiful location!"
United States
Paul H.
$633 nightly
The price is $708
Jul 30 - Jul 31
Total with taxes and fees
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
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, (2 reviews)
"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.
$1,021 nightly
The price is $1,167
Jul 29 - Jul 30
Total with taxes and fees
Classic Coastal Family Home | Walk to Sea;King Bed
Smart TV, books

Cozy two bedroom house in the heart of Gloucester

Cozy two bedroom house in the heart of Gloucester
Gloucester
9.4 out of 10, Exceptional, (17 reviews)
"Wonderful spot to stay and would use it again if I visit later."
United States
Shelley S.
$394 nightly
The price is $440
Jul 29 - Jul 30
Total with taxes and fees
Cozy two bedroom house in the heart of Gloucester
Interior

New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (2 reviews)
"Comfortable, clean and very much natural light. The beds are incredibly comfortable. A great place as a homebase when visiting the area."
United States
Richard B.
$730 nightly
The price is $740
Jul 20 - Jul 21
Total with taxes and fees
New England Coastal Residence
Dining

The Duval House

The Duval House
Downtown Gloucester
9.6 out of 10, Exceptional, (18 reviews)
"We moved our time at Daryl’s rental. Perfect location as we were visiting for a family wedding. He was great and the apartment was really cute and well stocked :)"
United States
Michelle R.
$512 nightly
The price is $572
Jul 29 - Jul 30
Total with taxes and fees
The Duval House
Smart TV, fireplace

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Gloucester
10.0 out of 10, Exceptional, (25 reviews)
"A beautiful cottage with wonderful amenities and host. Couldn’t have asked for a better place to stay!"
United States
Samson L.
$627 nightly
The price is $700
Jul 26 - Jul 27
Total with taxes and fees
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
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, (21 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.
$522 nightly
The price is $583
Jul 26 - Jul 27
Total with taxes and fees
Long Beach Suites: 3 Mins Toes To Sand!
TV, offices

Stay at Little River

Stay at Little River
Gloucester
10.0 out of 10, Exceptional, (6 reviews)
"My friend and I had a great time staying at the house. Beautiful view, close to great attractions, and the kitchen was well appointed."
United States
Caitlin D.
$872 nightly
The price is $974
Jul 23 - Jul 24
Total with taxes and fees
Stay at Little River
Private kitchen

The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (11 reviews)
"Perfect size for two couples! Extremely clean and well stocked!!!!"
United States
Kimberly
$310 nightly
The price is $346
Jul 27 - Jul 28
Total with taxes and fees
The Essex of Gloucester
Beach nearby

Stay at Wingaersheek

Stay at Wingaersheek
Gloucester
$1,450 nightly
The price is $1,620
Jul 27 - Jul 28
Total with taxes and fees
Stay at Wingaersheek
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.
$493 nightly
The price is $550
Jul 29 - Jul 30
Total with taxes and fees
Long Beach Suites: Ocean Views
Beach

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Gloucester
$192 nightly
The price is $215
Jul 23 - Jul 24
Total with taxes and fees
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
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, (40 reviews)
"Perfect house for a stay in Rockport. Clean, well decorated and the perfect location for walking around the town and also exploring the east coast. "
United States
Leanna S.
$328 nightly
The price is $367
Jul 20 - Jul 21
Total with taxes and fees
1BR with Private Deck + Ocean Views· Private Parking · King Bed
Marina

The Bookstore · Private Parking · King Beds · Downtown Rockport

The Bookstore · Private Parking · King Beds · Downtown Rockport
Rockport
10.0 out of 10, Exceptional, (41 reviews)
"Absolutely perfect Stay! Wonderful host and wonderful location. We will definitely be back!"
United States
Shannon R.
$487 nightly
The price is $544
Jul 27 - Jul 28
Total with taxes and fees
The Bookstore · Private Parking · King Beds · Downtown Rockport
Marina

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (37 reviews)
"This is our second year staying at Gigi's place. It's such a great location and value. It offers everything we like during the off season without the crowds and is such a clean and comfortable place to stay."
United States
Victoria P.
$293 nightly
The price is $335
Aug 11 - Aug 12
Total with taxes and fees
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
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

The Northshore Hotel - Boston/Danvers

The Northshore Hotel - Boston/Danvers

8/10 Good
"✌"
Alba 1-night trip
Posted 3 hours ago
The Northshore Hotel - Boston/Danvers

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 $240 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.

Explore a world of travel with Expedia

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?

Lovely 'The Buoys Cottage' on Annisquam River!: This Gloucester vacation home rental is located on a river and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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. 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 170 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.