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Chester Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Chester holiday rentals

Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (97)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is HK$788
HK$1,264 total
includes taxes & fees
15 Jan - 16 Jan
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$592
HK$1,505 total
includes taxes & fees
4 Jan - 5 Jan
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$646
HK$1,427 total
includes taxes & fees
10 Jan - 11 Jan
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
The Tiny Cottage at Clem & Clyde's

The Tiny Cottage at Clem & Clyde's

The Tiny Cottage at Clem & Clyde's
2.0 star property
Oakdale,
10.0 out of 10, Exceptional, (2)
"Cottage was perfect! The fresh eggs given to us by the host made for an awesome breakfast! The host was great! My 2 energetic boys loved every animal. The host made sure to take my boys through every fence/gate there was to get my boys front and center with the animals. This isn’t just about money him seeing my boys smile and run around with the animals definitely made his day! Left about an hour ago and my boys already asked 17 times when we are going back! "
United States
jeff
The price is HK$740
HK$1,006 total
includes taxes & fees
4 Jan - 5 Jan
The Tiny Cottage at Clem & Clyde's
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
Westbrook
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$728
HK$3,440 total
includes taxes & fees
5 Jan - 6 Jan
Beachside Bliss w/ Game Room, Gym & Golf Green
Exterior
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (16)
"Great property, beautiful grounds and appointed as described! Owners were great to work with and flexible. "
United States
Bill M.
The price is HK$916
HK$1,972 total
includes taxes & fees
6 Jan - 7 Jan
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (5)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is HK$672
HK$3,135 total
includes taxes & fees
4 Jan - 5 Jan
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

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

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
New London
8.0 out of 10, Very good, (17)
"Easy access. We loved our short stay. I would return again. "
United States
Suzanne M.
The price is HK$526
HK$1,557 total
includes taxes & fees
11 Jan - 12 Jan
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
East Lyme
9.0 out of 10, Wonderful, (4)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is HK$913
HK$2,827 total
includes taxes & fees
9 Jan - 10 Jan
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (7)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$895
HK$2,244 total
includes taxes & fees
4 Jan - 5 Jan
All New 1BR with tons of Charm
Exterior
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

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

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (54)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is HK$3,504
HK$6,342 total
includes taxes & fees
4 Jan - 5 Jan
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Property grounds
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

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

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Norwich
10.0 out of 10, Exceptional, (40)
"Great place to crash for a night when in town"
United States
Brendan H.
The price is HK$1,226
HK$2,473 total
includes taxes & fees
4 Jan - 5 Jan
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Beach nearby
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
10.0 out of 10, Exceptional, (6)
"Place is nice would stay again "
United States
nic
The price is HK$793
HK$2,884 total
includes taxes & fees
6 Jan - 7 Jan
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Exterior
Cozy Lakefront Tiny House

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
The price is HK$694
HK$1,633 total
includes taxes & fees
5 Jan - 6 Jan
Cozy Lakefront Tiny House
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is HK$773
HK$2,861 total
includes taxes & fees
5 Jan - 6 Jan
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Property grounds
Charming 3-bedroom ranch 1 minute from Mohegan Sun.

Charming 3-bedroom ranch 1 minute from Mohegan Sun.

Charming 3-bedroom ranch 1 minute from Mohegan Sun.
2.0 star property
Montville
10.0 out of 10, Exceptional, (15)
"Great place! Super clean and easy check in. Plenty of parking."
United States
Daniel W.
The price is HK$2,336
HK$3,963 total
includes taxes & fees
13 Jan - 14 Jan
Charming 3-bedroom ranch 1 minute from Mohegan Sun.
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4)
"Every thing was amazing "
United States
Annaliaa C.
The price is HK$685
HK$1,623 total
includes taxes & fees
5 Jan - 6 Jan
Lakefront Boho Tiny House
1 bedroom, WiFi, bed sheets
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
New London
10.0 out of 10, Exceptional, (7)
"We had a good experience staying with host, William. Going in and out of our unit was easy with the codes provided. The croissants provided for breakfast were large and delicious. We would stay there again."
United States
Ronald H.
The price is HK$685
HK$944 total
includes taxes & fees
4 Jan - 5 Jan
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$895
HK$2,244 total
includes taxes & fees
4 Jan - 5 Jan
Once the old Schools house now a newly furnished Apartment
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

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

10/10 Excellent
"Amazing comfortable stay, beds were very comfortable, spacious rooms for family. Friendly service and great breakfast! Will definitely stay here again next time! 4 minutes away from Mohegan sun."
Jilline 1-night trip
Posted 15 hours ago
Hyatt Place Uncasville - Casino Area

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!

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?

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA: This holiday home rental outside of Chester is located next to a golf course, and offers a garden, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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?

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 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.