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Holiday Rentals in Chester

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Holiday Rentals in Chester

Our top choices for Chester holiday rentals

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (50)
"Great stay"
The price is €181
includes taxes & fees
21 Aug - 22 Aug
Postcard Cabins Machimoodus

Regency Inn and Suites - RS Handicapped Non Smoking Double Bed Hearing

6.0 out of 10, (5)
"The listing states a 1 bedroom, don’t be confused thinking there is a room with a door and then another room, as it’s just a single room with a bed. There was one gentleman that was very blunt and rude with his words. I unfortunately dealt with him prior to my visit, via phone, and once I got there. However, I had interaction with two others and the experience with them was very pleasant! Breakfast staff was extremely welcoming and friendly! (They check your paper for breakfast- be sure to bring...
The price is €107
includes taxes & fees
21 Aug - 22 Aug
Regency Inn and Suites - RS Handicapped Non Smoking Double Bed Hearing

Charming houseboat in pleasant New London with AC, WiFi

9.8 out of 10, Exceptional, (7)
"Very nice people. Boat was roomy and well stocked but dirty. Toilet pump was broken and made loud noises all night. We were not informed this was an issue til checkout. Some other small issues "
The price is €283
includes taxes & fees
23 Aug - 24 Aug
Charming houseboat in pleasant New London with AC, WiFi

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is €174
includes taxes & fees
2 Sept - 3 Sept
The Stern at Soundview · Beach+Ocean+Sunrise

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (6)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is €556
includes taxes & fees
21 Aug - 22 Aug
Thames River Retreat · CT College+Casinos+USCGA

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (10)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is €353
includes taxes & fees
21 Aug - 22 Aug
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

6.0 out of 10, (4)
"Really convenient location breakfast was good. Rooms were clean."
The price is €107
includes taxes & fees
21 Aug - 22 Aug
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

Regency Inn and Suites - Non Smoking Double Bed with Kitchen

10.0 out of 10, Exceptional, (1)
The price is €147
includes taxes & fees
21 Aug - 22 Aug
Regency Inn and Suites - Non Smoking Double Bed with Kitchen

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is €228
includes taxes & fees
26 Aug - 27 Aug
Shoreline Oasis

Regency Inn and Suites - Handicapped Non Smoking Double Bed

The price is €107
includes taxes & fees
21 Aug - 22 Aug
Regency Inn and Suites - Handicapped Non Smoking Double Bed

Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

9.8 out of 10, Exceptional, (9)
"William was very thorough with our check in and a pleasure to deal with"
The price is €118
includes taxes & fees
21 Aug - 22 Aug
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (113)
"Just amazing!"
Rustic Lakeside Cabin at White Gate Farm

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (29)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is €208
includes taxes & fees
1 Sept - 2 Sept
1-bedroom cottage with Grove Beach 🏖️ access.

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (96)
"We loved our time at White Gate. Very peaceful!"
The price is €1,703
includes taxes & fees
11 Sept - 12 Sept
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.0 out of 10, Wonderful, (4)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
The price is €166
includes taxes & fees
26 Aug - 27 Aug
Freeboard at Soundview · Beach+Ocean+Sunrise

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is €421
includes taxes & fees
15 Sept - 16 Sept
adorable ranch in beach community

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (40)
"My wife and I loved our weekend stay at this cabin!"
The price is €581
includes taxes & fees
26 Aug - 27 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (139)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun

2.0 star property
10.0 out of 10, Exceptional, (17)
"I’ve stayed here twice and both visits were great. I would definitely recommend this property to anyone looking for a cozy and luxurious space."
The price is €392
includes taxes & fees
24 Aug - 25 Aug
Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
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 Chester Hotel Reviews

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theatres while you're in the area.

What are some of the best holiday rentals that Chester has to offer?

Thames River Retreat · CT College+Casinos+USCGA: This holiday home rental outside of Chester is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Chester?

Expedia has 3 holiday rentals for your stay in Chester.

What’s there to see and do in Chester?

Connecticut River and Connecticut Valley Railroad State Park Trail are a couple of scenic spots to enjoy the outdoors, whereas Norma Terris Theater is one of the cultural attractions. Chester Creek Marina and Gillette Castle State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.