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Chester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Rentals in Chester

Postcard Cabins Machimoodus
Standard Cabin, 1 Queen Bed | Exterior

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (70)
"Great stay"
The price is ￥20,655
￥29,735 total
includes taxes & fees
Oct 1 - Oct 2
Postcard Cabins Machimoodus
The Stern at Soundview · Beach+Ocean+Sunrise
On the beach

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 ￥8,427
￥25,440 total
includes taxes & fees
Oct 1 - Oct 2
The Stern at Soundview · Beach+Ocean+Sunrise
Charming houseboat in pleasant New London with AC, WiFi
Interior

Charming houseboat in pleasant New London with AC, WiFi

9.6 out of 10, Exceptional, (12)
"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 ￥22,290
￥48,072 total
includes taxes & fees
Oct 31 - Nov 1
Charming houseboat in pleasant New London with AC, WiFi
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath
1 bedroom, WiFi, bed sheets

Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

10.0 out of 10, Exceptional, (6)
"Didn’t know what to expect in new London. The host William is by far a class act. The hospitality upon first entry was remarkable. Spotless clean everything. Never saw whiter sheets! I will defiantly return and enjoy the complimentary breakfast!"
The price is ￥13,077
￥18,011 total
includes taxes & fees
Oct 1 - Oct 2
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath
Rustic Lakeside Cabin at White Gate Farm
Interior

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (120)
"Beautiful cabin on the lake. Will definitely stay again. Easy check-in easy check out. You wont regret staying here!"
Rustic Lakeside Cabin at White Gate Farm
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

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

10.0 out of 10, Exceptional, (13)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is ￥26,005
￥44,766 total
includes taxes & fees
Oct 1 - Oct 2
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Outdoor pool

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

10.0 out of 10, Exceptional, (103)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
1 bedroom, WiFi, bed sheets

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

9.6 out of 10, Exceptional, (12)
"William was very thorough with our check in and a pleasure to deal with"
The price is ￥13,077
￥18,011 total
includes taxes & fees
Oct 1 - Oct 2
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
Shoreline Oasis
Exterior

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 ￥26,599
￥39,022 total
includes taxes & fees
Oct 5 - Oct 6
Shoreline Oasis
Freeboard at Soundview · Beach+Ocean+Sunrise
On the beach

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.2 out of 10, Wonderful, (5)
"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 ￥7,660
￥24,563 total
includes taxes & fees
Oct 13 - Oct 14
Freeboard at Soundview · Beach+Ocean+Sunrise
The Mast at Soundview · Beach+Ocean+Sunrise
On the beach

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 ￥8,619
￥25,660 total
includes taxes & fees
Oct 28 - Oct 29
The Mast at Soundview · Beach+Ocean+Sunrise
Thames River Retreat · CT College+Casinos+USCGA
Property grounds

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (15)
"Clean"
The price is ￥35,128
￥94,624 total
includes taxes & fees
Oct 28 - Oct 29
Thames River Retreat · CT College+Casinos+USCGA
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Exterior

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

10.0 out of 10, Exceptional, (47)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is ￥53,496
￥103,426 total
includes taxes & fees
Oct 6 - Oct 7
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Casino Getaway! 2M from Mohegan 8M from Foxwoods
Terrace/patio

Casino Getaway! 2M from Mohegan 8M from Foxwoods

6.0 out of 10, (1)
"Elliot was available and courteous reservation and check in easy. Upon arrival 1st floor bathroom sink was not draining well, 2nd floor bathroom tub does not drain well hot and cold water are reversed sink water is also reversed. Missing sheet rock in dining room. All walls have either nails popping or water damage. We only slept at the residence one evening. I manage multiple high end properties on Nantucket and maintaining them year round. First impression is Most important to insure future...
The price is ￥19,135
￥38,935 total
includes taxes & fees
Oct 27 - Oct 28
Casino Getaway! 2M from Mohegan 8M from Foxwoods
Spacious Oceanview Villa (Sleeps 22)
Pool

Spacious Oceanview Villa (Sleeps 22)

10.0 out of 10, Exceptional, (43)
"Perfect for a larger group"
The price is ￥74,003
￥143,726 total
includes taxes & fees
Oct 1 - Oct 2
Spacious Oceanview Villa (Sleeps 22)
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Beach nearby

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

7.8 out of 10, Good, (12)
"loved the property!"
The price is ￥22,468
￥46,248 total
includes taxes & fees
Oct 6 - Oct 7
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Outdoor dining

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

2.0 star property
10.0 out of 10, Exceptional, (9)
"This listing was perfect for our stay. Close to the water, beautifully styled, and plenty of items to cook and clean.Thanks so much, Erin!"
The price is ￥29,898
￥58,002 total
includes taxes & fees
Oct 21 - Oct 22
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Cozy Coastal Cottage New London
Fridge, microwave, oven, stovetop

Cozy Coastal Cottage New London

9.4 out of 10, Exceptional, (9)
"It was the perfect little place for a night away from the kids. "
The price is ￥31,206
￥68,857 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Coastal Cottage New London
The Bridge at Soundview · Beach+OceanView+Sunrise
On the beach

The Bridge at Soundview · Beach+OceanView+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (1)
"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."
The price is ￥21,193
￥75,625 total
includes taxes & fees
Oct 1 - Oct 2
The Bridge at Soundview · Beach+OceanView+Sunrise
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Property grounds

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

10.0 out of 10, Exceptional, (38)
"Great place to crash for a night when in town"
The price is ￥23,405
￥47,349 total
includes taxes & fees
Oct 1 - Oct 2
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
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

Hampton Inn Norwich

Hampton Inn Norwich

10/10 Excellent
"easy parking, clean room and excellent staff"
Thomas 1-night trip
Posted 16 hours ago
Hampton Inn Norwich

Find out more about Chester

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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Frequently asked questions

Are there vacation rentals in Chester?

Yes, we offer vacation rentals close to well known sights in Chester, or you can go with a more secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theaters while you're in the area.

What are some of the best vacation rentals in Chester?

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food: This vacation home rental near Chester is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in Chester?

Cultural attractions include Norma Terris Theater, whereas Connecticut River is a spot to enjoy nature. While here, Connecticut Valley Railroad State Park Trail and Chester Creek Marina are other places worth a visit.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip or a small group gathering.