Gloucester Vacation Rentals

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Our top choices for Gloucester vacation rentals

1. Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (97 reviews)
"In a very convenient location. Not far from the train station. Walking dust to the beach. Room was very clean and comfortable."
United States
Jessie
Long Beach Suites

2. Charming Retreat

Charming Retreat
East Gloucester
10.0 out of 10, Exceptional, (26 reviews)
"Parking was great...easy access to visiting all of Cape Ann"
United States
Margaret
$256 nightly
The price is $286
Nov 14 - Nov 15
Total with taxes and fees
Charming Retreat

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

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Gloucester
9.4 out of 10, Exceptional, (6 reviews)
"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.
$183 nightly
The price is $205
Nov 8 - Nov 9
Total with taxes and fees
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

4. 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)
"Had a wonderful visit to the area exploring Gloucester, Rockport, and Salem."
United States
Margaret O.
Long Beach Suites: 3 Mins Toes To Sand!

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

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.8 out of 10, Exceptional, (16 reviews)
"Sparking clean property. Plenty of main floor gathering space (kitchen/dining/livingroom) with good separation of sleeping quarters, giving the opportunity for privacy and rest. Pretty back yard with Adirondack chairs to enjoy while reading or just resting. Easy drive to the main attractions of Gloucester and/or Rockport. All this and responsive owners too! "
United States
Karen T.
$359 nightly
The price is $411
Nov 10 - Nov 11
Total with taxes and fees
Oceanside Village Home~Private Fenced Yard~Reserved Parking

6. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (5 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.
$658 nightly
The price is $735
Nov 10 - Nov 11
Total with taxes and fees
New England Coastal Residence

7. 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, (8 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.
$766 nightly
The price is $876
Nov 8 - Nov 9
Total with taxes and fees
Classic Coastal Family Home | Walk to Sea;King Bed

8. 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
9.6 out of 10, Exceptional, (24 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
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

9. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (18 reviews)
"Very clean and perfect place to stay while we were in a wedding at the Beauport! The host checked in often and made us feel very welcomed and at home"
United States
Katie B.
$245 nightly
The price is $274
Dec 2 - Dec 3
Total with taxes and fees
The Essex of Gloucester

10. The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard
East Gloucester
10.0 out of 10, Exceptional, (6 reviews)
"We truly enjoyed our time at the Mariner. Its a beautiful home with all the necessary amenities. Rachel is an excellent host. She was extremely responsive throughout our stay. We will definitely be back!!"
United States
Nina R.
$688 nightly
The price is $787
Nov 24 - Nov 25
Total with taxes and fees
The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

11. Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
9.8 out of 10, Exceptional, (41 reviews)
"Was a fantastic place to stay. Host was great as well."
United States
Wesley G.
$222 nightly
The price is $254
Nov 9 - Nov 10
Total with taxes and fees
Harborside Oasis ★ Harbor View ★ Heart of Downtown

12. Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (46 reviews)
"This is a wonderful place to stay! It's super clean, modern amenities, & comfortable and literally steps from Bearskin Neck. The host, Gigi, is awesome and great communication. Such a cool vibe here, i can'twait to return!"
United States
Heidi K.
$216 nightly
The price is $247
Nov 13 - Nov 14
Total with taxes and fees
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

13. 2BR Home Minutes to Downtown Rockport+Beach!

2BR Home Minutes to Downtown Rockport+Beach!
Rockport
10.0 out of 10, Exceptional, (13 reviews)
"Good facilities, clean and tidy, lovely decor. Good location."
United States
Janet C.
$377 nightly
The price is $432
Nov 8 - Nov 9
Total with taxes and fees
2BR Home Minutes to Downtown Rockport+Beach!

14. Fall Asleep to Waves — Steps to Shops & Dining

Fall Asleep to Waves — Steps to Shops & Dining
Rockport
10.0 out of 10, Exceptional, (14 reviews)
"We loved our stay here ! The beach view from the bedroom window is amazing ! The home was so clean and cozy. We walked to breakfast every morning and all the shops were also in walking distance! We will definately be back!!"
United States
Dominique
$341 nightly
The price is $381
Nov 11 - Nov 12
Total with taxes and fees
Fall Asleep to Waves — Steps to Shops & Dining

15. The Bookstore · King Beds · Walk to Beach · Private Parking

The Bookstore · King Beds · Walk to Beach · Private Parking
Rockport
10.0 out of 10, Exceptional, (45 reviews)
"Lovely place, very clean and quiet and within walking distance of several restaurants and stores. We had a couple of questions that the host answered very promptly. Certainly one of the nicest places we've stayed at."
United States
Dave
$379 nightly
The price is $434
Nov 9 - Nov 10
Total with taxes and fees
The Bookstore · King Beds · Walk to Beach · Private Parking

16. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Rockport
10.0 out of 10, Exceptional, (45 reviews)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
$425 nightly
The price is $487
Nov 9 - Nov 10
Total with taxes and fees
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

17. Balcony • KING Suite • Walk2Beach+Bearskin • Parking

Balcony • KING Suite • Walk2Beach+Bearskin • Parking
Rockport
9.8 out of 10, Exceptional, (50 reviews)
"The perfect location/The perfect apartment layout./The perfect amenities. It really was all perfect!"
United States
Dale k.
$426 nightly
The price is $487
Nov 8 - Nov 9
Total with taxes and fees
Balcony • KING Suite • Walk2Beach+Bearskin • Parking

18. NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH

NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH
Ipswich
9.6 out of 10, Exceptional, (38 reviews)
"Great place to stay—loved the renovations, it was very clean and had an exclusive side entrance for coming & going. I would definitely stay there again!"
United States
Dawne
$201 nightly
The price is $221
Nov 22 - Nov 23
Total with taxes and fees
NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH

19. Riverview charming apt near beach

Riverview charming apt near beach
Ipswich
9.6 out of 10, Exceptional, (46 reviews)
"Comfortable and clean"
United States
DAVID A.
$223 nightly
The price is $245
Nov 15 - Nov 16
Total with taxes and fees
Riverview charming apt near beach

20. 2b apt loft Downtown Ipswich

2b apt loft Downtown Ipswich
Ipswich
9.2 out of 10, Wonderful, (53 reviews)
"Everything was fabulous, but the access via the spiral staircase was a not for someone physically compromised."
United States
Helen M.
$207 nightly
The price is $227
Nov 8 - Nov 9
Total with taxes and fees
2b apt loft Downtown Ipswich
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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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 $204 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. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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 Single Level Home - Steps to Downtown Gloucester & A/C throughout .

How many vacation rentals are there in Gloucester?

Expedia has 174 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 Half Moon Beach and Stage Fort Park 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.

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