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Chester Holiday Rentals

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Check prices for these dates

Tonight
8 Aug - 9 Aug
Tomorrow
9 Aug - 10 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Holiday Rentals in Chester

Postcard Cabins Machimoodus
Escape to a serene forest retreat with a cozy fire pit and comfortable Adirondack chairs.

Postcard Cabins Machimoodus

2.0 star property
9.4 out of 10, Exceptional, (45)
"Great stay"
The price is HK$1,170
HK$1,661 total
includes taxes & fees
19 Aug - 20 Aug
Postcard Cabins Machimoodus
Regency Inn and Suites - RS Handicapped Non Smoking Double Bed Hearing
Welcome to our hotel lobby, featuring a high ceiling, polished reception desk, and a glass display case showcasing breakfast items.

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

5.4 out of 10, (3)
"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 HK$686
HK$946 total
includes taxes & fees
10 Aug - 11 Aug
Regency Inn and Suites - RS Handicapped Non Smoking Double Bed Hearing
Charming houseboat in pleasant New London with AC, WiFi
Cozy space with a kitchenette, flat-screen TV, and cushioned seating area.

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 HK$1,177
HK$2,539 total
includes taxes & fees
10 Aug - 11 Aug
Charming houseboat in pleasant New London with AC, WiFi
The Stern at Soundview · Beach+Ocean+Sunrise
Enjoy a serene beach experience with access to the ocean and a sailboat visible in the distance.

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 HK$738
HK$1,703 total
includes taxes & fees
27 Aug - 28 Aug
The Stern at Soundview · Beach+Ocean+Sunrise
Regency Inn and Suites - Non Smoking King
Enjoy cooking in this well-equipped kitchen with a long counter, refrigerator, and coffee machine.

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 HK$686
HK$946 total
includes taxes & fees
12 Aug - 13 Aug
Regency Inn and Suites - Non Smoking King
Thames River Retreat · CT College+Casinos+USCGA
Relax on the deck with a sofa and chair, taking in the serene views of the lake and surrounding hills.

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 HK$1,776
HK$4,931 total
includes taxes & fees
17 Aug - 18 Aug
Thames River Retreat · CT College+Casinos+USCGA
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
Simple, functional bedroom with a single bed, bedside tables, and a window with a view.

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

9.8 out of 10, Exceptional, (8)
"William was very thorough with our check in and a pleasure to deal with"
The price is HK$769
HK$1,042 total
includes taxes & fees
10 Aug - 11 Aug
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
adorable ranch in beach community
Walk along the beach on a paved path, bordered by grass and rocky shoreline, with the ocean stretching out to the horizon.

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 HK$2,010
HK$4,120 total
includes taxes & fees
8 Sept - 9 Sept
adorable ranch in beach community
The Anchor at Soundview · Beach+Ocean+Sunrise
Enjoy a serene beach experience with access to the ocean and a picturesque sailboat in the distance.

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 HK$597
HK$1,526 total
includes taxes & fees
19 Aug - 20 Aug
The Anchor at Soundview · Beach+Ocean+Sunrise
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Surrounded by lush greenery, this cabin features a cozy porch with seating and a stone pathway leading to the entrance.

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

10.0 out of 10, Exceptional, (39)
"My wife and I loved our weekend stay at this cabin!"
The price is HK$2,944
HK$5,297 total
includes taxes & fees
24 Aug - 25 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Shoreline Oasis
Stroll up to this charming colonial-style house, featuring a welcoming front porch with a bench and a beautiful garden.

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 HK$1,405
HK$2,046 total
includes taxes & fees
11 Aug - 12 Aug
Shoreline Oasis
1-bedroom cottage with Grove Beach 🏖️ access.
Relax in comfort with a sofa, throw blanket, and natural light pouring in through the large window.

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 HK$1,095
HK$2,076 total
includes taxes & fees
12 Aug - 13 Aug
1-bedroom cottage with Grove Beach 🏖️ access.
Rustic Lakeside Cabin at White Gate Farm
Enjoy a serene lake view from the comfort of this cabin, featuring a large window, wicker chair, and cozy reading nook.

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (112)
"Just amazing!"
Rustic Lakeside Cabin at White Gate Farm
Freeboard at Soundview · Beach+Ocean+Sunrise
Enjoy a serene beach experience with access to the ocean and a picturesque palm tree.

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 HK$567
HK$1,483 total
includes taxes & fees
26 Aug - 27 Aug
Freeboard at Soundview · Beach+Ocean+Sunrise
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Enjoy a refreshing dip in the pool surrounded by a deck and basketball hoop.

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

10.0 out of 10, Exceptional, (136)
"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
Enjoy a well-equipped kitchen with a long counter, perfect for preparing meals and snacks.

Regency Inn and Suites - Handicapped Non Smoking Double Bed

The price is HK$686
HK$946 total
includes taxes & fees
10 Aug - 11 Aug
Regency Inn and Suites - Handicapped Non Smoking Double Bed
Queen, exclusive Bath, Free Wi-Fi, Self check in
1 bedroom, WiFi, bed sheets

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 HK$683
HK$942 total
includes taxes & fees
10 Aug - 11 Aug
Queen, exclusive Bath, Free Wi-Fi, Self check in
Waterfront House with picture-perfect views from all 3 levels.
Enjoy a serene sea view from the large window, accompanied by comfortable seating and a small table.

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.
The Mast at Soundview · Beach+Ocean+Sunrise
Enjoy a serene beach experience with a calm ocean and a sailboat on the horizon.

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.0 out of 10, Wonderful, (2)
"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 HK$718
HK$1,672 total
includes taxes & fees
3 Sept - 4 Sept
The Mast at Soundview · Beach+Ocean+Sunrise
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Enjoy a serene beach experience with access to the shore.

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 HK$1,109
HK$2,322 total
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"We only stayed one night, but the area looked beautiful and tranquil."
Alicia 1-night trip
Posted 5 hours ago
Saybrook Point Resort & Marina

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.