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

Gloucester Holiday Rentals

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Our top choices for Gloucester holiday rentals

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 NZ$357
includes taxes & fees
14 Nov - 15 Nov
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

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 NZ$709
includes taxes & fees
11 Nov - 12 Nov
Oceanside Village Home~Private Fenced Yard~Reserved Parking

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 NZ$451
includes taxes & fees
1 Dec - 2 Dec
The Essex of Gloucester

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
The price is NZ$1,096
includes taxes & fees
11 Nov - 12 Nov
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

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 NZ$1,237
includes taxes & fees
11 Nov - 12 Nov
New England Coastal Residence

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 NZ$1,513
includes taxes & fees
11 Nov - 12 Nov
Classic Coastal Family Home | Walk to Sea;King Bed

7. 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.
The price is NZ$1,383
includes taxes & fees
24 Nov - 25 Nov
The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

8. 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.
The price is NZ$437
includes taxes & fees
19 Nov - 20 Nov
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

9. 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.
The price is NZ$484
includes taxes & fees
23 Nov - 24 Nov
Harborside Oasis ★ Harbor View ★ Heart of Downtown

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

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

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 NZ$476
includes taxes & fees
1 Dec - 2 Dec
Apartment with private rooftop deck with ocean views

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 NZ$935
includes taxes & fees
23 Nov - 24 Nov
2BR Home Minutes to Downtown Rockport+Beach!

13. 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
The price is NZ$838
includes taxes & fees
23 Nov - 24 Nov
The Bookstore · King Beds · Walk to Beach · Private Parking

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.
The price is NZ$384
includes taxes & fees
11 Nov - 12 Nov
2b apt loft Downtown Ipswich

15. 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
The price is NZ$726
includes taxes & fees
23 Nov - 24 Nov
Fall Asleep to Waves — Steps to Shops & Dining

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 NZ$1,052
includes taxes & fees
11 Nov - 12 Nov
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

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 NZ$435
includes taxes & fees
15 Nov - 16 Nov
Riverview charming apt near beach

18. 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.
Balcony • KING Suite • Walk2Beach+Bearskin • Parking

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 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
The price is NZ$386
includes taxes & fees
22 Nov - 23 Nov
NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH

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 NZ$788
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

Find out more about Gloucester

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gloucester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gloucester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Gloucester. Seeing all the best attractions is bound to make you fall in love with Gloucester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Gloucester short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a holiday rental in Gloucester?

Yes, there are holiday rentals in Gloucester close to Maritime Gloucester, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Gloucester has to offer?

Beach Life Bliss - steps to the beach: This highly rated holiday home rental in Gloucester is located near the beach, and has a patio, a garden and a BBQ 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 holiday with amenities such as 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 holiday rentals are there in Gloucester?

Expedia has 174 holiday 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 holiday rentals like in Gloucester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Gloucester. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.