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Chester Holiday Rentals

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Check prices for these dates

Tonight
14 Nov - 15 Nov
Tomorrow
15 Nov - 16 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in Chester

Property grounds
One private bedroom with work space and shared home with spa.

One private bedroom with work space and shared home with spa.

Rocky Hill
The price is HK$715
HK$1,067 total
includes taxes & fees
16 Nov - 17 Nov
One private bedroom with work space and shared home with spa.
Interior
Walk to Downtown-Pet Friendly, Private Deck & Fireplace

Walk to Downtown-Pet Friendly, Private Deck & Fireplace

Branford Center
The price is HK$1,069
HK$2,094 total
includes taxes & fees
16 Nov - 17 Nov
Walk to Downtown-Pet Friendly, Private Deck & Fireplace
Fridge, stovetop, coffee/tea maker, toaster
Charming New England Tiny Home in Cromwell, CT

Charming New England Tiny Home in Cromwell, CT

Cromwell
The price is HK$932
HK$1,706 total
includes taxes & fees
16 Nov - 17 Nov
Charming New England Tiny Home in Cromwell, CT
Interior
2-bedroom Oasis in Portland

2-bedroom Oasis in Portland

2.0 star property
Portland
The price is HK$1,225
HK$4,571 total
includes taxes & fees
18 Nov - 19 Nov
2-bedroom Oasis in Portland
Exterior
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, (80)
"Very nice cabins "
United States
Jairo
The price is HK$1,002
HK$1,510 total
includes taxes & fees
16 Nov - 17 Nov
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

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

Old Lyme
10.0 out of 10, Exceptional, (3)
"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$671
HK$3,129 total
includes taxes & fees
16 Nov - 17 Nov
Rogers Lake House (87) · CT College+Beach+USCGA
On the beach
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)
"Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. "
United States
Olivia C.
The price is HK$591
HK$1,510 total
includes taxes & fees
18 Nov - 19 Nov
The Stern at Soundview · Beach+Ocean+Sunrise
Beach nearby
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, (4)
"Place is nice would stay again "
United States
nic
The price is HK$711
HK$2,778 total
includes taxes & fees
16 Nov - 17 Nov
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Private kitchen
Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Waterford
10.0 out of 10, Exceptional, (1)
"The home was very clean and welcoming."
United States
Michelle M.
The price is HK$1,166
HK$2,865 total
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom house with WiFi, AC in lovely Waterford
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Lakefront Boho Tiny House

East Lyme
10.0 out of 10, Exceptional, (3)
"My husband has always wanted to try a tiny house. This place exceeded our expectations. Lovely house. Lovely lake. He was in heaven fishing and kayaking "
United States
Asha A.
The price is HK$923
HK$1,887 total
includes taxes & fees
9 Dec - 10 Dec
Lakefront Boho Tiny House
Exterior
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$675
HK$1,610 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Lakefront Tiny House
Smart TV, books
Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA

Montville
10.0 out of 10, Exceptional, (2)
"A lovely quick overnight."
United States
Bonnie H.
The price is HK$641
HK$2,177 total
includes taxes & fees
4 Dec - 5 Dec
Thames River Cottage · Near Casinos - USCGA
Exterior
Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Norwich
9.6 out of 10, Exceptional, (8)
"Villa Noir was a nice place. The upstairs neighbors thump around a bit, but it wasn't a stampede all night. The villa came with ear plugs which helped with the thumping and my snoring partner. Major bonus! It was a comfortable stay. Instead of a queen bed as advertised, there were two full beds, but it turns into a king pretty effortlessly. The temps were in the upper 20s outside in the night and I woke up to it being very cold. The thermostat must have reset in the night or perhaps it was...
United States
J H.
The price is HK$1,049
HK$2,191 total
includes taxes & fees
16 Nov - 17 Nov
Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
Smart TV
Shantok Queen suites walk to Mohegan casino/Wi-Fi

Shantok Queen suites walk to Mohegan casino/Wi-Fi

Montville
10.0 out of 10, Exceptional, (1)
"This was just a quick one night, Stay. As we were at the casino for a concert. The house was a great location clean, access was easy. Everything was as was stated on the website. I would definitely stay there again."
United States
Anonymous traveller
The price is HK$684
HK$2,724 total
includes taxes & fees
16 Nov - 17 Nov
Shantok Queen suites walk to Mohegan casino/Wi-Fi
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

Wallingford Center
9.0 out of 10, Wonderful, (13)
"The fact that it was listed with a hot tub and there wasn't one was very disappointing! Clean and cute. Location was convenient. Could use a better bed and pillows. It was a good place to stay,"
United States
Robert K.
The price is HK$715
HK$2,011 total
includes taxes & fees
16 Nov - 17 Nov
Once the old Schools house now a newly furnished Apartment
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

Norwich
10.0 out of 10, Exceptional, (39)
"Great place to crash for a night when in town"
United States
Brendan H.
The price is HK$1,224
HK$2,460 total
includes taxes & fees
16 Nov - 17 Nov
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is HK$699
HK$2,162 total
includes taxes & fees
17 Nov - 18 Nov
Soothing 2-bedroom lower-level apartment in Berlin
Property grounds
Cozy Couples Getaway with Golf Course View & Spa

Cozy Couples Getaway with Golf Course View & Spa

Norwich
8.0 out of 10, Very good, (1)
"Wonderful stay. Very quiet, spacious, comfy bed, nice soft sheets. Surprisingly private. Great location right across from clubhouse, and very close to Inn. Only disappointment was not being able to use the fireplace. Also if more than one night, may need to ask for more towels. Only 3 provided. "
United States
Julie
The price is HK$1,206
HK$2,291 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Couples Getaway with Golf Course View & Spa
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

Waterford
10.0 out of 10, Exceptional, (10)
"Open concept home beautiful with private yard space. It was perfect for our stay"
United States
Berlyne S.
The price is HK$731
HK$2,801 total
includes taxes & fees
17 Nov - 18 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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

Mohegan Sun

Mohegan Sun

10/10 Excellent
"I haven't been in a long period of time. Pleasant surprise..... Room was updated, comfortable. All staff were professional and helpful."
Elizabeth 1-night trip
Posted 2 days ago
Mohegan Sun

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:

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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?

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food: This holiday home rental outside of Chester is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.