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

Gloucester Vacation Rentals

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Gloucester vacation rentals

Basic Apartment | Dining room

1. Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (80 reviews)
"Really good,so close to the beaches"
United States
Oscar
$381 nightly
The price is $426
Sep 2 - Sep 3
Total with taxes and fees
Long Beach Suites
Marina

2. Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

Cripple Cove Apartment in historic home across from harbour in Gloucester, MA
East Gloucester
9.6 out of 10, Exceptional, (36 reviews)
"Linda was so kind and what a fun little home she opened up to us! "
United States
Hillary M.
$400 nightly
The price is $447
Sep 2 - Sep 3
Total with taxes and fees
Cripple Cove Apartment in historic home across from harbour in Gloucester, MA
Beach

3. 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.
$430 nightly
The price is $480
Sep 2 - Sep 3
Total with taxes and fees
Long Beach Suites: Ocean Views
Interior

4. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (14 reviews)
"The home was warm and inviting upon our arrival. We loved the home. Rachel responds immediately with any questions. Cape Ann is beautiful and convenient to Boston. We loved our visit and felt at home! "
United States
Melenia s.
$393 nightly
The price is $439
Aug 31 - Sep 1
Total with taxes and fees
Oceanside Village Home~Private Fenced Yard~Reserved Parking
Smart TV, books

5. 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.
$433 nightly
The price is $484
Aug 30 - Aug 31
Total with taxes and fees
Quaint Neighborhood / Close to Beaches
Dining

6. The Duval House

The Duval House
Downtown Gloucester
9.6 out of 10, Exceptional, (19 reviews)
"We had a wonderful stay. The house was very nice and the room was very clean. Can’t wait to come back!"
United States
Jennifer H.
$460 nightly
The price is $513
Aug 23 - Aug 24
Total with taxes and fees
The Duval House
Interior

7. 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.
$513 nightly
The price is $573
Aug 28 - Aug 29
Total with taxes and fees
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Sun loungers, beach towels

8. Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (20 reviews)
"Excellent location, very clean and good communication. Will definitely stay again when in the area. "
United States
Patrick M.
$404 nightly
The price is $451
Sep 13 - Sep 14
Total with taxes and fees
Ocean Breeze / 8-Minute Walk to Beach
Private kitchen

9. 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
$293 nightly
The price is $327
Aug 31 - Sep 1
Total with taxes and fees
The Essex of Gloucester
Coffee/tea maker, fridge, microwave, oven

10. 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, (58 reviews)
"This was such a cute little place! We enjoyed our Birthday getaway! It was easy to get around the area too. Parking was small, but thanks to the other reviews we brought the car so we were ok. "
United States
Jennifer B.
$452 nightly
The price is $505
Sep 4 - Sep 5
Total with taxes and fees
Luxury 1900's romantic retreat steps from the beach - King Suite!
Smart TV, fireplace

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

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Gloucester
9.8 out of 10, Exceptional, (28 reviews)
"A beautiful cottage with wonderful amenities and host. Couldn’t have asked for a better place to stay!"
United States
Samson L.
$582 nightly
The price is $650
Aug 25 - Aug 26
Total with taxes and fees
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Smart TV, books

12. 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, (49 reviews)
"Beautiful home in a beautiful location!"
United States
Paul H.
$712 nightly
The price is $795
Aug 25 - Aug 26
Total with taxes and fees
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
Property grounds

13. 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, (17 reviews)
"Rachel was very responsive and attentive, excellent host. The house was in a great location, clean, and very comfortable. Would stay there again should the need arise."
United States
Betty
$656 nightly
The price is $732
Sep 3 - Sep 4
Total with taxes and fees
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Exterior

14. 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, (3 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.
$978 nightly
The price is $1,118
Sep 9 - Sep 10
Total with taxes and fees
Classic Coastal Family Home | Walk to Sea;King Bed
Interior

15. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (3 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.
$904 nightly
The price is $916
Aug 30 - Aug 31
Total with taxes and fees
New England Coastal Residence
Outdoor dining

16. Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!
Gloucester
10.0 out of 10, Exceptional, (15 reviews)
"Wonderful views, great location, easy access to all of Cape Ann."
United States
Stacey W.
$815 nightly
The price is $910
Aug 24 - Aug 25
Total with taxes and fees
Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!
TV, offices

17. Stay at Good Harbor Beach

Stay at Good Harbor Beach
East Gloucester
10.0 out of 10, Exceptional, (1 review)
"House was incredible and great for a group. Super nice house with everything we needed. Walked to the beach , cooked great meals, Allie was super helpful and accommodating. Would love to come back."
United States
hawley s.
$2,403 nightly
The price is $2,748
Sep 8 - Sep 9
Total with taxes and fees
Stay at Good Harbor Beach
Terrace/patio

18. Private Beach! Dream vacation at your private beach in Gloucester

Private Beach! Dream vacation at your private beach in Gloucester
Gloucester
9.8 out of 10, Exceptional, (12 reviews)
"Unique property with an awesome private beach."
United States
William M.
$1,757 nightly
The price is $1,963
Aug 22 - Aug 23
Total with taxes and fees
Private Beach! Dream vacation at your private beach in Gloucester
Beach

19. 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.
$519 nightly
The price is $579
Sep 2 - Sep 3
Total with taxes and fees
Long Beach Suites: 3 Mins Toes To Sand!
Beach

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

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Gloucester
10.0 out of 10, Exceptional, (1 review)
"Lovely, large room with beams on the ceiling and a very comfortable bed. Clean and inviting. Appreciated the detailed, friendly messages from the host. The building is near a pretty pond and the store downstairs sells coffee for a dollar!"
United States
Catherine C.
$192 nightly
The price is $215
Aug 26 - Aug 27
Total with taxes and fees
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
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

Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG

10/10 Excellent
"."
Chester 1-night trip
Posted 3 hours ago
Holiday Inn Express Boston - Saugus by IHG

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 $135 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?

Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!! : This Gloucester vacation home rental is located on the beach and has a patio, a garden, and air-conditioning 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. Some other top choices in Gloucester are Steps to Wingaersheek's Private 1.5 Mile White Dune Beach and Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

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.