Gloucester Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Gloucester vacation rentals

Property grounds

1. 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.
The price is AEDĀ 526
AEDĀ 751 total
includes taxes & fees
14 Nov - 15 Nov
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
A staircase with wooden steps leading to a room with a wooden ceiling.

2. 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.
The price is AEDĀ 719
AEDĀ 1,844 total
includes taxes & fees
18 Nov - 19 Nov
Oceanside Village Home~Private Fenced Yard~Reserved Parking
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

3. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (19 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.
The price is AEDĀ 771
AEDĀ 935 total
includes taxes & fees
1 Dec - 2 Dec
The Essex of Gloucester
A wooden staircase with a railing leading to a covered deck area.

4. 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, (25 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
A modern staircase with wooden steps and metal railings, leading to a well-lit interior space.

5. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (6 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.
The price is AEDĀ 720
AEDĀ 2,679 total
includes taxes & fees
11 Nov - 12 Nov
New England Coastal Residence
A residential area with houses, a road, and a body of water in the background.

6. 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, (9 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.
The price is AEDĀ 900
AEDĀ 3,217 total
includes taxes & fees
11 Nov - 12 Nov
Classic Coastal Family Home | Walk to Sea;King Bed
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

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

The Mariner Ā· Walk to Beach+Rocky Neck Ā· 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.
The price is AEDĀ 1,306
AEDĀ 2,891 total
includes taxes & fees
24 Nov - 25 Nov
The Mariner Ā· Walk to Beach+Rocky Neck Ā· Fenced Backyard
A waterfront property with a dock, houses in the background, and a clear sky.

8. Harbor Retreat ā˜… Ocean View ā˜… Heart of Downtown ā˜…

Harbor Retreat ā˜… Ocean View ā˜… Heart of Downtown ā˜…
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.
The price is AEDĀ 337
AEDĀ 915 total
includes taxes & fees
16 Nov - 17 Nov
Harbor Retreat ā˜… Ocean View ā˜… Heart of Downtown ā˜…
A marina with boats docked, a clear sky, and a street with parked cars.

9. Harborside Oasis ā˜… Harbor View ā˜… Heart of Downtown

Harborside Oasis ā˜… Harbor View ā˜… 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.
The price is AEDĀ 354
AEDĀ 935 total
includes taxes & fees
11 Nov - 12 Nov
Harborside Oasis ā˜… Harbor View ā˜… Heart of Downtown
A modern kitchen with dark cabinets, a wooden dining table, and a hanging light fixture.

10. Downtown Rockport Ā· King Bed w/Parking Ā· Walk to Train

Downtown Rockport Ā· King Bed w/Parking Ā· Walk to Train
Rockport
9.8 out of 10, Exceptional, (45 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.
The price is AEDĀ 447
AEDĀ 1,118 total
includes taxes & fees
11 Nov - 12 Nov
Downtown Rockport Ā· King Bed w/Parking Ā· Walk to Train
12 foot long couch for two people to stretch out on.

11. Apartment with private rooftop deck with ocean views

Apartment with private rooftop deck with ocean views
Rockport
10.0 out of 10, Exceptional, (26 reviews)
"Friendly helpful and responsive host. Place was clean, convenient, quiet."
United States
Eli T.
The price is AEDĀ 551
AEDĀ 1,005 total
includes taxes & fees
1 Dec - 2 Dec
Apartment with private rooftop deck with ocean views
A kitchen with white cabinets, a stainless steel range hood, and a clock on the wall.

12. 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.
The price is AEDĀ 538
AEDĀ 1,641 total
includes taxes & fees
16 Nov - 17 Nov
2BR Home Minutes to Downtown Rockport+Beach!
A modern kitchen with dark blue cabinets, a white countertop, and a wooden ceiling.

13. The Bookstore Ā· King Beds Ā· Walk to Beach Ā· Private Parking

The Bookstore Ā· King Beds Ā· Walk to Beach Ā· 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
The price is AEDĀ 583
AEDĀ 1,483 total
includes taxes & fees
1 Dec - 2 Dec
The Bookstore Ā· King Beds Ā· Walk to Beach Ā· Private Parking
A covered outdoor deck with a grill, a table with chairs, and an umbrella.

14. 2b apt loft Downtown Ipswich

2b apt loft Downtown Ipswich
Ipswich
9.2 out of 10, Wonderful, (54 reviews)
"Everything was fabulous, but the access via the spiral staircase was a not for someone physically compromised."
United States
Helen M.
2b apt loft Downtown Ipswich
A living room with a sofa, a coffee table, a plant, and a view into the kitchen.

15. Fall Asleep to Waves ā€” Steps to Shops & Dining

Fall Asleep to Waves ā€” 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
The price is AEDĀ 620
AEDĀ 1,382 total
includes taxes & fees
11 Nov - 12 Nov
Fall Asleep to Waves ā€” Steps to Shops & Dining
A wooden deck with wicker furniture and a white chair, overlooking a beach with a rocky shoreline and a clear blue sky.

16. Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
Rockport
10.0 out of 10, Exceptional, (38 reviews)
"Great spot right on Long Beach! Has great views of the ocean right on the water. We definitely stay there again pet friendly."
United States
Emmy D.
The price is AEDĀ 899
AEDĀ 2,202 total
includes taxes & fees
11 Nov - 12 Nov
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
A modern kitchen with stainless steel appliances, light grey cabinets, and a tiled backsplash.

17. 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.
The price is AEDĀ 422
AEDĀ 899 total
includes taxes & fees
15 Nov - 16 Nov
Riverview charming apt near beach
A bedroom with a bed, a painting, and a view of the outdoors.

18. Balcony ā€¢ KING Suite ā€¢ Walk2Beach+Bearskin ā€¢ Parking

Balcony ā€¢ KING Suite ā€¢ Walk2Beach+Bearskin ā€¢ Parking
Rockport
9.8 out of 10, Exceptional, (50 reviews)
"We loved this property. It was very clean and had great amenities. The location is perfect for walking into town and seeing all the sites."
United States
Laura W.
The price is AEDĀ 764
AEDĀ 1,846 total
includes taxes & fees
15 Nov - 16 Nov
Balcony ā€¢ KING Suite ā€¢ Walk2Beach+Bearskin ā€¢ Parking
A modern kitchen with stainless steel appliances, white cabinets, and a large window.

19. 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 stayā€”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
The price is AEDĀ 606
AEDĀ 1,007 total
includes taxes & fees
11 Dec - 12 Dec
NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH
A modern kitchen with white cabinetry, granite countertops, and stainless steel appliances.

20. 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.
The price is AEDĀ 583
AEDĀ 1,611 total
includes taxes & fees
11 Nov - 12 Nov
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
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

Two individuals in white robes by a window overlooking a body of water with a distant shoreline.
Beauport Hotel Gloucester

Beauport Hotel Gloucester

Beauport Hotel Gloucester
Downtown Gloucester

10/10 Excellent

The beach is out the door and to the left. Perfect location.
United States
Kim
Reviewed June 24, 2025
Beauport Hotel Gloucester

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.