Holiday Rentals in Gloucester

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Holiday Rentals in Gloucester

Long Beach Suites

2.0 star property
9.2 out of 10, Wonderful, (35)
"New build or newly remodeled. Condo was spacious and just a couple minutes walk to the beach. Kitchen lacked some basic equipment such as a pasta strainer and a wine opener (thankfully we had one with us). Would rent again. "
The price is €374
includes taxes & fees
20 Aug - 21 Aug
Long Beach Suites

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

10.0 out of 10, Exceptional, (14)
"We had a great time at Captains lookout. The pictures were accurate and we love the view from the roof. The host was very accommodating and helpful. "
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

9.8 out of 10, Exceptional, (37)
"Very peaceful, quiet neighborhood. Very comfortable and clean house with all of the ammenities that we needed! Would stay again"
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

9.8 out of 10, Exceptional, (76)
"Had the best family vacation at the Rocky Neck Hideaway, from the location, to the host, to the amenities, everything was excellent. The whole stay exceeded our expections and we will be back! "
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

9.4 out of 10, Exceptional, (59)
"Beautiful well maintained home. Walking distance to beach. "
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Luxury 1900's romantic retreat steps from the beach - King Suite!

9.8 out of 10, Exceptional, (45)
"much needed respite!"
Luxury 1900's romantic retreat steps from the beach - King Suite!

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

10.0 out of 10, Exceptional, (3)
"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 €633
includes taxes & fees
16 Sept - 17 Sept
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Peaceful centrally located home: w/ yard & walking distance to town

2.0 star property
9.0 out of 10, Wonderful, (7)
"We love the view outside the back deck, and the town right around the corner. The castle on Gloucester is a must see"
Peaceful centrally located home: w/ yard & walking distance to town

Studio Condo 2 minute walk across the street to the beach.

9.0 out of 10, Wonderful, (28)
"It was a great location and clean and accommodating "
The price is €271
includes taxes & fees
28 Aug - 29 Aug
Studio Condo 2 minute walk across the street to the beach.

7 Beachside Inn

3.0 star property
8.4 out of 10, Very good, (12)
"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."
The price is €269
includes taxes & fees
10 Sept - 11 Sept
7 Beachside Inn

Ocean views from every window. 5min walk to the quiet end of the beach!

9.8 out of 10, Exceptional, (22)
"Relaxing, and very convenient for an easy access to the beach while being a little away from the strip night life :)"
The price is €326
includes taxes & fees
19 Aug - 20 Aug
Ocean views from every window. 5min walk to the quiet end of the beach!

Ocean Air Suites

2.5 star property
9.4 out of 10, Exceptional, (36)
"Great studio efficiency, with all the amenities right in the room, including washer, dryer. View of the ocean from a shared balcony. Excellent view of weekly beach fireworks display. Only suggestion, black out curtains on side facing parking lot and the lot’s lights. Only suggestion "
Ocean Air Suites

Salem Haunted Happenings Retreat

9.4 out of 10, Exceptional, (18)
"The place was great. Clean, comfortable and communication was easy. We enjoyed our 2 day impromptu stay in Salem. "
Salem Haunted Happenings Retreat

Charming 2-Bedroom Getaway A/C, WIFI, Covered porch just 3 Minutes to the Beach!

9.4 out of 10, Exceptional, (6)
"Very short walk to beach and boardwalk, property is very clean and cozy and owner is easy to reach out to response from owner is very quick."
Charming 2-Bedroom Getaway A/C, WIFI, Covered porch just 3 Minutes to the Beach!

Beach front , across the street form the sand

9.4 out of 10, Exceptional, (31)
"We had a great stay"
The price is €274
includes taxes & fees
17 Aug - 18 Aug
Beach front , across the street form the sand

Salem Haunted Happenings Retreat

10.0 out of 10, Exceptional, (4)
"Wonderful time, great location, convenient to Salem attractions. Had a fun time. Thanks "
The price is €207
includes taxes & fees
18 Aug - 19 Aug
Salem Haunted Happenings Retreat

House near down town Salem

9.6 out of 10, Exceptional, (50)
"Had a weekend getaway with my mom and sister for Mothers Day and this was the perfect spot to stay! It was a quick walk across the bridge to get to downtown Salem and all of the shops and museums. Owners were super helpful and responsive, and the house was clean and beautiful. It was nice and quiet and we felt so safe the whole time. Would definitely rebook if we return to the area!! "
The price is €382
includes taxes & fees
18 Aug - 19 Aug
House near down town Salem

Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

9.4 out of 10, Exceptional, (10)
The price is €727
includes taxes & fees
24 Aug - 25 Aug
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (239)
"We rented this house to stay for my son’s wedding in Salem. The house was fantastic and quaint. Megan is a great host and very responsive. Would definitely rent again if we’re in Salem!"
Leslie's Retreat: Spacious home ideally located to everything

Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach!

10.0 out of 10, Exceptional, (22)
"Great location. Easy access. Had a wonde Time"
The price is €346
includes taxes & fees
15 Sept - 16 Sept
Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach!
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?

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach: This highly rated holiday home rental in Gloucester is located near the beach, and has a fireplace, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other top choices in Gloucester are "Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester and Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

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.