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Top Holiday Rentals in Gloucester

Beach Life Bliss - steps to the beach

9.6 out of 10, Exceptional, (35)
"Loved this comfortable home! Well located and great host."
The price is £486
includes taxes & fees
23 Jul - 24 Jul
Beach Life Bliss - steps to the beach

Stay at Niles Beach

10.0 out of 10, Exceptional, (35)
" Allies ,Communication was excellent, house was clean cozy and peaceful, would definitely suggest if in Gloucester area!"
The price is £799
includes taxes & fees
22 Jul - 23 Jul
Stay at Niles Beach

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

10.0 out of 10, Exceptional, (2)
"We stayed at this house for a week. Great location, quiet neighborhood, beds were confortable and communication with the host was great. We would definitely stay here again"
The price is £526
includes taxes & fees
30 Jul - 31 Jul
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Private Beach! Dream vacation at your private beach in Gloucester

9.8 out of 10, Exceptional, (12)
"Unique property with an awesome private beach."
The price is £1,332
includes taxes & fees
12 Aug - 13 Aug
Private Beach! Dream vacation at your private beach in Gloucester

Love Shack

3.0 star property
8.0 out of 10, Very good, (1)
"Very nice"
Love Shack

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
10.0 out of 10, Exceptional, (7)
"My family stayed in October for a quick weekend getaway. Great location and easy to get to from Boston. Would definitely book again. "
The price is £356
includes taxes & fees
31 Jul - 1 Aug
NEW 2BR Historic Marblehead Home+Minutes to Beach

Bell Buoy

3.5 star property
6.0 out of 10, (1)
"The property is nicely located but in need of updates. A lot of the lamps are plug in vs light switch and there were some flickering lights behind the TV. One lamp was missing a light bulb. No outlet in the bathroom for a hair dryer. The second bathroom is missing a door handle making it hard to open and close. We were unable to reach the ceiling fan chain without having to get on the bed, The Air Conditioner wasn't working on he first floor which made it a bit stuff but with open windows at...
Bell Buoy

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

2.0 star property
10.0 out of 10, Exceptional, (18)
"Easy walk to the beach and town. Great family space. "
The price is £387
includes taxes & fees
20 Jul - 21 Jul
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had a great stay! Perfect location and a great setup for our family. Beautiful outdoor area and we were lucky with the weather! "
The price is £403
includes taxes & fees
10 Aug - 11 Aug
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

9.6 out of 10, Exceptional, (80)
"This property is perfect for 2 travelers or for a small family. Close to everything, very clean and easy to get to. Would 100% stay here again!"
The price is £223
includes taxes & fees
23 Jul - 24 Jul
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Central Beverly! 5 min to Salem!

The price is £238
includes taxes & fees
20 Jul - 21 Jul
Central Beverly! 5 min to Salem!

Rockmere Inn

3.5 star property
Rockmere Inn

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

9.8 out of 10, Exceptional, (10)
"The house was clean, inviting, and cozy. The location was great. We very much enjoyed our stay there. "
The price is £469
includes taxes & fees
6 Aug - 7 Aug
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2.0 star property
10.0 out of 10, Exceptional, (5)
"Great property. Can walk to many things and was a great hub to see beautiful Maine Owner was helpful and quick to respond. "
The price is £408
includes taxes & fees
22 Jul - 23 Jul
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Plovers Nest

3.0 star property
Plovers Nest

Historic home w/ charming courtyard

10.0 out of 10, Exceptional, (2)
"The home was exactly what we needed for our weekend. The kitchen was well stocked, beds comfortable and location convenient to explore downtown. "
The price is £428
includes taxes & fees
3 Aug - 4 Aug
Historic home w/ charming courtyard

Comfortable spacious house, easy access to all

8.6 out of 10, Excellent, (11)
"House is clean, large, and in a nice quiet neighborhood. Coffee is provided, kitchen is a good size, however we did not cook. Its about 40 minutes to walk downtown, and 5 minute drive. "
The price is £284
includes taxes & fees
18 Jul - 19 Jul
Comfortable spacious house, easy access to all

Entire Lower Level of the House, Across From The Beach

10.0 out of 10, Exceptional, (15)
"Loved getting to visit the beach and the short drive to Salem!"
The price is £297
includes taxes & fees
31 Jul - 1 Aug
Entire Lower Level of the House, Across From The Beach

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

9.6 out of 10, Exceptional, (124)
"We stayed here for four days. It’s very clean nice beautiful place."
The price is £241
includes taxes & fees
28 Jul - 29 Jul
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Nothing Fancy Older Pet Friendly Home – near I-95

The price is £265
includes taxes & fees
24 Jul - 25 Jul
Nothing Fancy Older Pet Friendly Home – near I-95
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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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?

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester: This highly rated holiday home rental in Gloucester offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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 holiday rentals are there in Gloucester?

Expedia has 156 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 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 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.