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Top Holiday Rentals in Gloucester

Charming Downtown Gloucester Retreat. Walk to Restaurants, Museums, Waterfront
10.0 out of 10, Exceptional, (1)
"Our family enjoyed the two floors and large rooms. It was very convenient to walk to the main street and harbor."
Charming Downtown Gloucester Retreat. Walk to Restaurants, Museums, Waterfront
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
10.0 out of 10, Exceptional, (171)
"We really enjoyed our 2 night stay. The house is beautiful and very clean. Easy walking distance from the beach and only a short drive to Gloucester, Rockport, Halibut State Park and Crane Beach. Very quiet location."
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Beautiful, Cozy Ultra Convenient Salem Home
10.0 out of 10, Exceptional, (5)
"Nice private and quiet location with plenty of sleeping spaces and locations to be together. Short distance to down town and the commuter train."
The price is £252
per night
6 May - 7 May
Beautiful, Cozy Ultra Convenient Salem Home
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The Warlock House: Speak Spells, Wave Wands, Ride Brooms - 5min Walk to Salem, Big TV, WiFi, Parking
10.0 out of 10, Exceptional, (22)
"Loved the house and it was convenient to everything we wanted to see in Salem. The decor was amazing and you can definitely tell there was attention to every detail. Clean and quiet. Would definitely recommend and would stay there again. "
The price is £633
per night
8 May - 9 May
The Warlock House: Speak Spells, Wave Wands, Ride Brooms - 5min Walk to Salem, Big TV, WiFi, Parking
Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD
10.0 out of 10, Exceptional, (80)
"This property was just what we were look for Very clean, comfy beds,great shower. Hope to return this summer for a longer stay."
The price is £381
per night
7 May - 8 May
Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
10.0 out of 10, Exceptional, (28)
"We had such a great time staying in Rachel's space. The building is located right in a lovely area of Marblehead, and the space itself was just what we were looking for. It was small but well laid out, with everything we needed for a great weekend. The best part was Rachel's communication. The check-in was effortless. She was incredibly responsive to questions and very helpful in her responses. She sets an extremely high bar for future rentals like this."
The price is £196
per night
7 May - 8 May
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
10.0 out of 10, Exceptional, (150)
"MUCH better than expected. Cutest little home!!! Highly recommend to stay here :)"
The price is £181
per night
13 May - 14 May
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Walk to the ocean, very private. Secluded, woodsy location.
10.0 out of 10, Exceptional, (3)
"Clean and cozy studio. Was working in the area for a few days and was a relaxing place to come back to in the evening."
Walk to the ocean, very private. Secluded, woodsy location.
The Great Escape on Hampton Beach. Beach directly across the street.
10.0 out of 10, Exceptional, (36)
"Had a great time. The room was perfect. Scott was attentive and gave great recommendations for food and activities. Would definitely return. Only drawback was lack of a stove/oven but it did not affect us for such a short stay"
The Great Escape on Hampton Beach. Beach directly across the street.
Lovely 3-Bedroom in Historic Downtown Ipswich
10.0 out of 10, Exceptional, (5)
"Nice location in the center of everywhere I needed to be. Clean and enough space for my needs. Everything was functional and had no issues whatsoever."
The price is £267
per night
2 Jun - 3 Jun
Lovely 3-Bedroom in Historic Downtown Ipswich
Leslie's Retreat: Spacious home ideally located to everything
10.0 out of 10, Exceptional, (199)
"Room for all. Close to downtown."
Leslie's Retreat: Spacious home ideally located to everything
Upscale waterfront condo short walk to North Beach
10.0 out of 10, Exceptional, (25)
"Lovely place to stay, had everything you could need to be comfortable. Complete with friendly dog next door. Hosts very helpful and friendly."
Upscale waterfront condo short walk to North Beach
Cozy and Sweet home , peaceful and quite, close to boston, salem, revere
10.0 out of 10, Exceptional, (1)
"This place was quiet, charming and clean Owner was very friendly and helpful with recommendations on how to get to where we wanted to go."
The price is £139
per night
31 May - 1 Jun
Cozy and Sweet home , peaceful and quite, close to boston, salem, revere
Dog-friendly home with a partial river view & deck - steps from park & beach
10.0 out of 10, Exceptional, (1)
"We were looking for a house to rent week to week as we hunt for a house to purchase and this was the perfect fit for us!"
Dog-friendly home with a partial river view & deck - steps from park & beach
Salem Vacation Rental: 1 Mi to Downtown!
10.0 out of 10, Exceptional, (2)
Salem Vacation Rental: 1 Mi to Downtown!
The Salty Dog | Pet Friendly | Private Yard
9.8 out of 10, Exceptional, (14)
"We were very comfortable and had everything we needed. Walks on the beach, lobster and beach pizza! I couldnt connect to the house rules so if i neglected anything i apologize."
The price is £323
per night
20 May - 21 May
The Salty Dog | Pet Friendly | Private Yard
Beach Life Bliss - steps to the beach
9.6 out of 10, Exceptional, (9)
"We stayed for a quick trip to Mass. and wanted something nearby lots of good areas. We hadn’t stayed in Gloucester before but LOVED it, and it was easy to get to Salem and Rockport! The host was friendly and helpful and responded to us quickly! The house was very clean and perfect for our trip. We loved the charm and all the furniture was comfortable. We are already talking about wanting to go back!"
The price is £298
per night
15 May - 16 May
Beach Life Bliss - steps to the beach
Beautiful Ocean Front Condo in Hampton Beach, NH
9.6 out of 10, Exceptional, (4)
"Very clean and comfortable "
The price is £133
per night
8 May - 9 May
Beautiful Ocean Front Condo in Hampton Beach, NH
House near down town Salem
9.6 out of 10, Exceptional, (20)
"Clean, easy parking, easy entry. Quaint diner to walk to on corner of the street. A good spot to lay your head after exploring Salem."
The price is £306
per night
9 May - 10 May
House near down town Salem
Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.
9.6 out of 10, Exceptional, (48)
"My boyfriend and I stayed here for a long weekend and it was amazing. Sandra and Joe are very responsive and willing to make your stay great."
Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.
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See all available properties in Gloucester
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.

Gloucester Holiday Rental Travel Info

Number of holiday rentals
25
Popular accommodation
Gloucester private holiday homes
Known landmarks
Good Harbour Beach, Wingaersheek Beach and Hammond Castle
International airport
Boston, MA (BOS-Logan Intl.)

Other types of properties in Gloucester you may be interested in

Beauport Hotel Gloucester
3.5 star property
9.6 out of 10, Exceptional, (709)
"Wonderful experience would stay again "
The price is £204
per night
5 May - 6 May
Beauport Hotel Gloucester
Ocean House Hotel at Bass Rocks
4.0 star property
9.0 out of 10, Wonderful, (614)
"We loved the friendliness and welcoming cheer exhibited by the front desk and dining staff. Would visit again for sure! "
The price is £142
per night
14 May - 15 May
Ocean House Hotel at Bass Rocks
The Hotel at Cape Ann Marina
3.5 star property
8.2 out of 10, Very good, (509)
"The staff are very professional, kind, pleasant, and a wealth of knowledge navigating Gloucester. This was our first time here at Cape Ann Marina Hotel and we enjoyed every minute of our stay. From having drinks with Bartender Megan to meeting new friends during the tasty continental breakfast. We will be back if we ever drive through Gloucester again! "
The price is £143
per night
5 May - 6 May
The Hotel at Cape Ann Marina
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.

Everything you need to know about Gloucester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gloucester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gloucester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gloucester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gloucester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gloucester holiday rentals we have selected for you start as low as £133 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gloucester rentals

At Expedia, we put the best Gloucester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gloucester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gloucester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gloucester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Beach Life Bliss - steps to the beach: This highly rated holiday home rental in Gloucester is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Gloucester?

Expedia has 151 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.

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