Gloucester Holiday Rentals

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Holiday Rentals in Gloucester

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

10.0 out of 10, Exceptional, (192)
"House was exactly as described. Super clean, big enough for the entire group and a beautiful view in the back! Close to everything!"
Good Harbor Beach House - walk to beach, close to restaurants and shopping!

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

9.8 out of 10, Exceptional, (73)
"The bed upstairs is so confortable, I slept like a baby! Great location! You can swim nearby, it’s very quiet and in the Rocky Neck art colony district."
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

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

9.6 out of 10, Exceptional, (29)
"Exactly how it was described clean easy to get to! Highly recommended "
Luxury 1900's romantic retreat steps from the beach - King Suite!

Beach Life Bliss - steps to the beach

9.8 out of 10, Exceptional, (22)
"We really enjoyed our stay. The community is beautiful."
Beach Life Bliss - steps to the beach

Charming Downtown Gloucester Retreat. Walk to Restaurants, Museums, Waterfront

9.2 out of 10, Wonderful, (27)
"We were attending a wedding nearby. It was clean, convenient, comfortable and exactly as pictured. "
Charming Downtown Gloucester Retreat. Walk to Restaurants, Museums, Waterfront

Beautiful, Cozy Ultra Convenient Salem Home

8.2 out of 10, Very good, (32)
"Overall the house was fine. The location was perfect (close to Salem, but the neighborhood was quiet) and the beds were super comfortable. My recommendations would be to have a tv in the first floor living area and tvs in the bedrooms as well. Also some kind of curtain or frosted glass in the upstairs bathroom for privacy, since it looks right out onto the Salem State fields."
The price is AU$472
includes taxes & fees
24 Nov - 25 Nov
Beautiful, Cozy Ultra Convenient Salem Home

The Great Escape on Hampton Beach. Beach directly across the street.

10.0 out of 10, Exceptional, (60)
"From start to finish it was exceptional. Scott was a great host, checked in to see if we needed anything. The place was clean and had everything we could ever ask for. It was an amazing stay and we will definitely be back!"
The Great Escape on Hampton Beach. Beach directly across the street.

The Warlock House: Speak Spells, Wave Wands, Ride Brooms - 5min Walk to Salem, Big TV, WiFi, Parking

9.8 out of 10, Exceptional, (36)
"Super unique! Very walkable to all the fun stuff downtown. I give this place 4.5 stars. My only beef is its terribly expensive for a 1 bathroom and the living room is cool, but uncomfortable. Great for insta pics and all that, but if you think you're gonna unwind an watch a scary movie its not gonna happen. The couches are more decorative. Big kitchen with everything that you'd have at home. And whoever was the decorator...the detail is impeccable. "
The price is AU$1,370
includes taxes & fees
10 Dec - 11 Dec
The Warlock House: Speak Spells, Wave Wands, Ride Brooms - 5min Walk to Salem, Big TV, WiFi, Parking

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (218)
"This house was perfect for us. Plenty of room, comfortable beds, quiet neighborhood, and an easy walk to downtown. The host was very responsive and friendly. I would highly recommend starting at this property. "
Leslie's Retreat: Spacious home ideally located to everything

Oceanfront, private porch,unobstructed amazing panoramic views of Atlantic Ocean

9.8 out of 10, Exceptional, (21)
"We stayed only for 1 night way off season. Beautiful view of the sunrise. This place would be great in the summer."
The price is AU$791
includes taxes & fees
26 Nov - 27 Nov
Oceanfront, private porch,unobstructed amazing panoramic views of Atlantic Ocean

Spectacular OCEANFRONT apt near BOSTON, SALEM + Logan Airport

9.8 out of 10, Exceptional, (90)
"You will like this property if you value a nice host, peace and quiet, and gorgeous views, with easy walking distance to the beach and the very good Tides restaurant. The home is comfortable, easy to access, and just as advertised. If you are looking for brand new, high end amenities, you might want to look elsewhere. We enjoyed our stay and would stay here again should we return to this area. Thank you Liz and safe travels to all."
Spectacular OCEANFRONT apt near BOSTON, SALEM + Logan Airport

Dog-friendly home with a partial river view & deck - steps from park & beach

8.8 out of 10, Excellent, (12)
"The location was perfect! A 4 minute drive to Salem and was xlose wnto the interstate but yet far enough away that you didn't hear the traffic. The house was across the street feom a park and had eaa path to walk down to thw shoreline."
Dog-friendly home with a partial river view & deck - steps from park & beach

Lovely 3-Bedroom in Historic Downtown Ipswich

9.6 out of 10, Exceptional, (19)
"Very convenient to the train station where you can park for free. Good property , well stocked kitchen and comfortable beds. The town was nice but the neighborhood was a bit noisy very early before dawn. Also there is no way to comfortably watch tv with the setup . The tv should be moved to the other wall. Overall a good stay and clean property."
The price is AU$516
includes taxes & fees
24 Nov - 25 Nov
Lovely 3-Bedroom in Historic Downtown Ipswich

Walk to the ocean, very private. Secluded, woodsy location.

9.8 out of 10, Exceptional, (19)
"Beautiful, cozy stay near the ocean. Beautiful views a short walk away. Because of the weather we didn't get to use much of the outdoor space, but several nice chairs outside. Felt pretty private, separate entrance from rest of house. The grill was a nice touch, but nowhere to sit and eat inside (other than the bed) so we didn't get a chance to cook. Thanks for the lovely stay!"
Walk to the ocean, very private. Secluded, woodsy location.

Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.

9.6 out of 10, Exceptional, (58)
"Sandra was a great host and IMMEDIATELY responded to ally our inquiries. The fenced in yard was great for the dog! Plenty of places to enjoy morning coffee outside. It was an easy walk to beach! We even found a bagel shop! "
Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.

House near down town Salem

9.8 out of 10, Exceptional, (39)
"Super fun!!"
The price is AU$692
includes taxes & fees
23 Dec - 24 Dec
House near down town Salem

The Lobster Claw - Perfect Location Near Beach/Boardwalk

10.0 out of 10, Exceptional, (15)
"Great place for a New England fall long weekend. Easy to find, great for beach walks. "
The price is AU$491
includes taxes & fees
24 Nov - 25 Nov
The Lobster Claw - Perfect Location Near Beach/Boardwalk

Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach

8.8 out of 10, Excellent, (20)
"The property is very close to the beach which is terrific. The second floor of the house was perfect for a great getaway. The technology worked perfectly. The bottom floor looked barren and dreary. The house was fairly clean and the appliances were modern."
Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

10.0 out of 10, Exceptional, (49)
"It was wonderful very cozy I would definitely stay again it was absolutely amazing we had a mishap with another stay somewhere near and this company was able to get us in same day and take care of all of our needs five star definitely recommend!!!"
The price is AU$398
includes taxes & fees
10 Dec - 11 Dec
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD

10.0 out of 10, Exceptional, (102)
"It’s a fun little cottage and Julie is a wonderful host!"
Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD
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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Other types of properties in Gloucester you may be interested in

Beauport Hotel Gloucester

3.5 star property
9.6 out of 10, Exceptional, (789)
"Was a wonderful hotel. Everyone so nice & it is so attractive. We had a room on the ocean & it was gorgeous. Only minor complaint was the gym was too small. The food was EXCELLENT!! "
The price is AU$334
includes taxes & fees
24 Nov - 25 Nov
Beauport Hotel Gloucester

The Hotel at Cape Ann Marina

3.5 star property
8.4 out of 10, Very good, (661)
"I liked staying at a marina and I liked the little deck, pool, food, staff, parking. I think an updated remodel is in order. Thank you"
The price is AU$216
includes taxes & fees
2 Dec - 3 Dec
The Hotel at Cape Ann Marina

Castle Manor Inn

2.5 star property
8.4 out of 10, Very good, (947)
"Chef Dan and Kamden made our morning breakfast buffet experience even more enjoyable! Food was delicious and we loved how hospitable they were. John greeted us upon arrival and made some great recommendations about restaurants and touring Gloucester. We stayed in the Inn in room Sunnyside up on third floor which had such a comfortable bed! There is some traffic noise so bring air plugs. The view from this Inn is soothing and cozy. The Crane Estate in Ipswich and the Hammond castle are a must...
The price is AU$275
includes taxes & fees
24 Nov - 25 Nov
Castle Manor 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.
Beautiful view of the beach with palm trees

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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.

How many holiday rentals are there in Gloucester?

Expedia has 152 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.