Gloucester Holiday Rentals

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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."
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 AU$1,995
includes taxes & fees
4 Aug - 5 Aug
Stay at Niles Beach

Oceanside Village Home~Private Fenced Yard~Reserved Parking

9.6 out of 10, Exceptional, (9)
"House was nice, with a great back yard. Just a short walk to beautiful rocks overlooking the ocean."
The price is AU$737
includes taxes & fees
19 Aug - 20 Aug
Oceanside Village Home~Private Fenced Yard~Reserved Parking

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 AU$1,052
includes taxes & fees
30 July - 31 July
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 AU$2,678
includes taxes & fees
12 Aug - 13 Aug
Private Beach! Dream vacation at your private beach in Gloucester

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 AU$879
includes taxes & fees
6 Aug - 7 Aug
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"The cottage is amazing and so beautiful! The location couldn't have been more perfect, and communicating with the host was a breeze. We had a peaceful and relaxing stay. "
The price is AU$809
includes taxes & fees
10 Aug - 11 Aug
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

Tuna Wharf Townhouse has been sold and is no longer available to rent.

10.0 out of 10, Exceptional, (78)
"Place was great, can’t beat the location, and Jonathan is honestly just the best. Top notch host and will definitely be staying at TWT again"
The price is AU$929
includes taxes & fees
6 Aug - 7 Aug
Tuna Wharf Townhouse has been sold and is no longer available to rent.

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 AU$983
includes taxes & fees
7 Aug - 8 Aug
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

9.0 out of 10, Wonderful, (2)
"Our multi-generational group loved the relaxed vibe of this home. Decor was beachy without being kitsch; tons of games, water equipment and fully-stocked kitchen. Everything worked (dishwasher, washing machine, A/C) and made for a fun and carefree experience. "
The price is AU$1,218
includes taxes & fees
13 Aug - 14 Aug
4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

10.0 out of 10, Exceptional, (17)
"We had a great stay. Home was well appointed. Thank you!"
The price is AU$2,156
includes taxes & fees
29 July - 30 July
Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

9.6 out of 10, Exceptional, (26)
"Great stay"
The price is AU$1,164
includes taxes & fees
6 Aug - 7 Aug
❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

2.0 star property
9.6 out of 10, Exceptional, (10)
"We had a lovely weekend! The views were beautiful and the location was great for our day trips. We will definitely be looking to rebook! "
The price is AU$1,229
includes taxes & fees
18 Aug - 19 Aug
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

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 AU$695
includes taxes & fees
31 July - 1 Aug
NEW 2BR Historic Marblehead Home+Minutes to Beach

Downtown Marblehead 2brm/1.5bath w/ deck

10.0 out of 10, Exceptional, (1)
"The property was large with lots of natural light. Very clean and fully stocked for the stay."
Downtown Marblehead 2brm/1.5bath w/ deck

Bright & Stylish 2BD/1BA in Town Center w Parking!

10.0 out of 10, Exceptional, (16)
"Definitely will be staying there again!"
The price is AU$601
includes taxes & fees
5 Aug - 6 Aug
Bright & Stylish 2BD/1BA in Town Center w Parking!

Prime location in town w parking! Walk to beach, shops & harbor-Sleeps 8

10.0 out of 10, Exceptional, (14)
"Property as advertised. Great walkable location"
The price is AU$1,318
includes taxes & fees
5 Aug - 6 Aug
Prime location in town w parking! Walk to beach, shops & harbor-Sleeps 8

Best location in Old Town home, 5 minutes to everything, enjoy the difference!

10.0 out of 10, Exceptional, (3)
"We are long time visitors of Marblehead and this has been one of, if not the best place we’ve stayed so far. The property was well appointed from the kitchen all the way to linens. A great central home that you will love!"
The price is AU$1,419
includes taxes & fees
28 July - 29 July
Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Authentic Rustic Single Family Home in Old Town

10.0 out of 10, Exceptional, (53)
"Natasha was excellent host. The house is perfect. Very cozy, clean and loved how it’s decorated. Close to everything. Adorable. "
The price is AU$844
includes taxes & fees
31 July - 1 Aug
Authentic Rustic Single Family Home in Old Town
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

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 157 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.