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. Sands Resort at Hampton Beach

Sands Resort at Hampton Beach
2.0 star property
Hampton Beach
8.4 out of 10, Very good, (53 reviews)
"Great stay"
United States
Phillip
Sands Resort at Hampton Beach

2. Apartments in Salem

Apartments in Salem
3.0 star property
Salem
8.0 out of 10, Very good, (50 reviews)
"Well kept property"
United States
Michelle
The price is NZ$1,325
includes taxes & fees
27 Sept - 28 Sept
Apartments in Salem

3. Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
Coastal Charm Lobster Ch Teau

4. Walk to Public Beach Access! Breezy Hampton Condo

Walk to Public Beach Access! Breezy Hampton Condo
3.0 star property
Hampton Beach
The price is NZ$782
includes taxes & fees
4 Oct - 5 Oct
Walk to Public Beach Access! Breezy Hampton Condo

5. Broom & Board

Broom & Board
3.5 star property
Salem
8.0 out of 10, Very good, (2 reviews)
"Great stay highly recommended!"
United States
Jamie
The price is NZ$1,833
includes taxes & fees
30 Sept - 1 Oct
Broom & Board

6. 7 Beachside Inn

7 Beachside Inn
3.0 star property
Hampton Beach
8.4 out of 10, Very good, (13 reviews)
"Great cottage with all the amenities you could ask for, excellent location. We didn't understand how to use the TV but we were there for the beach so that was fine. The hotel staff was so nice and helpful."
United States
Grace
The price is NZ$422
includes taxes & fees
7 Oct - 8 Oct
7 Beachside Inn

7. 1 Mi to Downtown Salem: Studio w/ Fire Pit Access

1 Mi to Downtown Salem: Studio w/ Fire Pit Access
3.0 star property
Salem
9.6 out of 10, Exceptional, (5 reviews)
"Studio was very nicely laid out and the owner of the property was friendly! Area the house was in was quiet but yet still walkable to downtown Salem. Bagel place across the street was amazing as well"
United States
chris
The price is NZ$719
includes taxes & fees
30 Sept - 1 Oct
1 Mi to Downtown Salem: Studio w/ Fire Pit Access

8. Apt in Historic Lynn Neighborhood: 5 Mi to Salem!

Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
3.0 star property
Lynn
The price is NZ$675
includes taxes & fees
27 Sept - 28 Sept
Apt in Historic Lynn Neighborhood: 5 Mi to Salem!

9. Bell Buoy

Bell Buoy
3.5 star property
Rockport
6.0 out of 10, (1 review)
"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...
United States
Amy
The price is NZ$865
includes taxes & fees
28 Sept - 29 Sept
Bell Buoy

10. Seacity View

Seacity View
2.0 star property
Swampscott
7.0 out of 10, Good, (2 reviews)
"Beautiful house!"
United States
carla n
The price is NZ$1,120
includes taxes & fees
30 Sept - 1 Oct
Seacity View

11. Rockmere Inn

Rockmere Inn
3.5 star property
Marblehead Historic District
Rockmere Inn
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?

Peaceful centrally located home: w/ yard & walking distance to town: This highly rated holiday home rental in Gloucester offers a garden, 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 Single Level Home - Steps to Downtown Gloucester & A/C throughout .

How many holiday rentals are there in Gloucester?

Expedia has 173 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.