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Chester Holiday Rentals

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Holiday Rentals in Chester

Postcard Cabins Machimoodus

2.0 star property
9.4 out of 10, Exceptional, (46)
"Great stay"
The price is NZ$355
includes taxes & fees
12 Aug - 13 Aug
Postcard Cabins Machimoodus

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 NZ$543
includes taxes & fees
12 Aug - 13 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 NZ$360
includes taxes & fees
12 Aug - 13 Aug
The Stern at Soundview · Beach+Ocean+Sunrise

Regency Inn and Suites - Non Smoking King

8.0 out of 10, Very good, (3)
"Desk clerk was wonderful. Made sure my stay was everything that I needed."
The price is NZ$202
includes taxes & fees
12 Aug - 13 Aug
Regency Inn and Suites - Non Smoking King

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 NZ$873
includes taxes & fees
12 Aug - 13 Aug
Thames River Retreat · CT College+Casinos+USCGA

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 NZ$223
includes taxes & fees
12 Aug - 13 Aug
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

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 NZ$881
includes taxes & fees
8 Sept - 9 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 NZ$1,052
includes taxes & fees
24 Aug - 25 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

Shoreline Oasis

8.8 out of 10, Excellent, (5)
"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 NZ$438
includes taxes & fees
12 Aug - 13 Aug
Shoreline Oasis

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (28)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is NZ$418
includes taxes & fees
12 Aug - 13 Aug
1-bedroom cottage with Grove Beach 🏖️ access.

Rustic Lakeside Cabin at White Gate Farm

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

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
8.8 out of 10, Excellent, (3)
"I love everything about this property. Excellent response from host. Excellent cleanliness of place. OVERALL TOP EXPERIENCE. 1000 PERCENT will be back."
The price is NZ$317
includes taxes & fees
26 Aug - 27 Aug
Freeboard at Soundview · Beach+Ocean+Sunrise

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

2.0 star property
9.2 out of 10, Wonderful, (10)
"Beautiful location, very comfortable for our small family."
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

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

10.0 out of 10, Exceptional, (137)
"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

Regency Inn and Suites - Handicapped Non Smoking Double Bed

The price is NZ$202
includes taxes & fees
12 Aug - 13 Aug
Regency Inn and Suites - Handicapped Non Smoking Double Bed

The Anchor at Soundview · Beach+Ocean+Sunrise

2.0 star property
8.0 out of 10, Very good, (1)
"Great stay. Clean, all amenities provided, located short walk from beach. I wouldn’t call it an apartment or studio, though. It’s the size of a bedroom and includes only a bed, dresser, fridge and microwave. Not even a chair. Description made me expect a bit more but if you know the size going in, it’s a marvelous place to stay. "
The price is NZ$326
includes taxes & fees
19 Aug - 20 Aug
The Anchor at Soundview · Beach+Ocean+Sunrise

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (92)
"It was a very nice stay. Sound of the ocean was calming. We would go back. "
Waterfront House with picture-perfect views from all 3 levels.

Queen, exclusive Bath, Free Wi-Fi, Self check in

8.0 out of 10, Very good, (1)
"This is a solid stay for a night or two, but it is very bare minimum - like a hostel. If you're looking for something besides a hostel experience I suggest looking elsewhere. Location is good, but you do hear the highway from the room. Owner is nice, but the walk-through of the place is unnecessary. Everything is straightforward. "
The price is NZ$202
includes taxes & fees
12 Aug - 13 Aug
Queen, exclusive Bath, Free Wi-Fi, Self check in

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is NZ$322
includes taxes & fees
12 Aug - 13 Aug
The Mast at Soundview · Beach+Ocean+Sunrise

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

8.0 out of 10, Very good, (10)
"loved the property!"
The price is NZ$497
includes taxes & fees
15 Aug - 16 Aug
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
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?

Regency Inn and Suites - RS Handicapped Non Smoking Double Bed Hearing: This holiday home rental outside of Chester is equipped with an indoor pool, air conditioning and cable TV to help you feel comfortable during your stay. Kitchen amenities such as a fridge and a microwave can make your holiday run smoothly.

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.