Photo by Annette Babek

Chester Holiday Rentals

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Holiday Rentals in Chester

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

10.0 out of 10, Exceptional, (31)
"The perfect place to relax and get ready for a night out after an amazing day at the spa. Wish we had more time to enjoy the fireplace and rhe balcony. Nice open space wirh plenty of room and very well equipped, comfortable. We loved it!"
The price is AU$558
includes taxes & fees
13 Jan - 14 Jan
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises

10.0 out of 10, Exceptional, (11)
"This was a lovely place to stay after a day at the spa. Super clean, updated, easy check in. The only thing we didnt like was the foam mattress on the bed. You would sink into a hole, making it hard to move. But nothing that would make me not stay here again. 5/5 would recommend "
The price is AU$394
includes taxes & fees
14 Jan - 15 Jan
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (23)
"We loved our trip. The cottage is beautifully done and the views incredible. We appreciated the hospitality extended by our host (and Nico the dog!) and enjoyed exploring the nearby woodland. Our kids are already asking if we can go back and visit again. "
Private Guest House w/ Deck + Spectacular Views!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

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

9.6 out of 10, Exceptional, (4)
"The host was very nice when I had an issue with communication! Cute little villa!"
The price is AU$464
includes taxes & fees
13 Jan - 14 Jan
Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

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

7.2 out of 10, Good, (7)
"Stayed here for a weekend at Mystic with my parents who are older. Lots of steps from the street so bear in mind. Claude was very kind when I called him with questions and the water and fruit on the kitchen table was a nice touch. Neighborhood is a bit loud from front bedroom but beds were oh so cozy and again, CLEAN CLEAN CLEAN!"
The price is AU$456
includes taxes & fees
13 Jan - 14 Jan
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

70 Year old cottage on 2.8 acres, stunning views and sunsets

8.4 out of 10, Very good, (6)
"We all liove the various Connecticut shore towns, and Ild Lyme was delightful. We revisited some favorite spots, and discovered a few new ones. The vintage appliances were particularly nice to find, and looking at old photos, we realized that the original cottage was really 100 years old!"
70 Year old cottage on 2.8 acres, stunning views and sunsets

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (106)
"Lovely rental; very easy to work with property manager. Clean, close to ocean - would rent again"
The price is AU$822
includes taxes & fees
15 Jan - 16 Jan
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

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

10.0 out of 10, Exceptional, (128)
"Although I went went it is cold the view and location were excellant. I can definately see taking advantage of this place during the summer. The host was responsive and available. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

10.0 out of 10, Exceptional, (33)
"Spacious, full stocked, amenity filled home with enough room for family members to gather and/or spread out.The game room is perfect for all ages with a variety of choices for your competitive play. Grocery/liquor store and Gillette Castle State Park are minutes away.Beautiful area. "
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

10.0 out of 10, Exceptional, (43)
"Condo was great!"
The price is AU$488
includes taxes & fees
13 Jan - 14 Jan
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (20)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is AU$312
includes taxes & fees
15 Jan - 16 Jan
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (89)
"House is beautiful and the view even better. On the waters edge and very quiet grandkids were occupied and very happy "
Waterfront Cottage in Branford

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (106)
"Ideal venue for peace, quiet and unplugged introspection."
Rustic Lakeside Cabin at White Gate Farm

Waterfront Home with a View

9.6 out of 10, Exceptional, (101)
"Beautiful property…definitely would stay again. It is a nice, quiet, serene spot on the water. "
Waterfront Home with a View

Beach House

9.8 out of 10, Exceptional, (50)
"Wonderful location. Cozy space we had a wonderful time"
Beach House

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Waterfront! Charming 4BR Cottage on the Niantic River!

9.6 out of 10, Exceptional, (59)
"We loved the antique house filled with family treasures. We spent many peaceful hours by the firepit looking over the river. The location is great, close to restaurants and stores. Amy is a wonderful host, checking in with us to make sure everything was okay. Thank you Amy. "
Waterfront! Charming 4BR Cottage on the Niantic River!

Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

9.8 out of 10, Exceptional, (44)
"Amazing property and relaxing weekend! 😄 Host was accommodating and responded promptly. Disappointed with accuracy of listing regarding the spa tub and picture/listing of canoe. Planned a canoe day and was unable due to no canoe on property. Dog loved the yard and enjoyed her stay too! "
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

Spacious Oceanview Villa (Sleeps 22)

10.0 out of 10, Exceptional, (33)
"Great house, beds were very comfortable, house was exteremely well-equipped, area was lovely."
Spacious Oceanview Villa (Sleeps 22)
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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Other types of properties in Chester you may be interested in

Mohegan Sun

4.5 star property
9.2 out of 10, Wonderful, (1705)
"Excellent"
The price is AU$354
includes taxes & fees
12 Jan - 13 Jan
Mohegan Sun

Hyatt Place Uncasville - Casino Area

3.0 star property
9.2 out of 10, Wonderful, (2283)
"NO VENDING MACHINES...ONLY SODA WAS DR PEPPER 😳"
The price is AU$178
includes taxes & fees
27 Jan - 28 Jan
Hyatt Place Uncasville - Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 star property
8.8 out of 10, Excellent, (1617)
"C"
The price is AU$139
includes taxes & fees
15 Jan - 16 Jan
Microtel Inn & Suites by Wyndham Uncasville Casino Area
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.

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?

Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River: This holiday home rental outside of Chester is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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.

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. While here, Cockaponset State Forest 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.