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, (28)
"The only ‘concern’ we had was that the heated pool wasn’t heated. Ice cold. Also, one other minor issue was that there were no coffee creamers supplied to the unit. Other than that, the stay was pretty good and room ess quiet and comfortable. "
The price is AU$532
includes taxes & fees
24 Nov - 25 Nov
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

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!

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$432
includes taxes & fees
25 Nov - 26 Nov
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

10.0 out of 10, Exceptional, (102)
"We really enjoyed our stay. Beds, linens, towels all super comfortable. Kitchen bright and useful. Bathrooms spotless. 2 minute walk to cute beach. Tons of stuff to do in the area. Great, private backyard well appointed with portable fire pit, grill, furniture. Lots of kid games and books and puzzles in house. Need functional carbon monoxide detector. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Spacious Oceanview Villa (Sleeps 22)

10.0 out of 10, Exceptional, (29)
"The house was perfect for a large group! We used it for our wedding party and the house was awesome. Had everything we could have needed. Katie was an awesome host and is very responsive! Would 1000% recommend!!!"
The price is AU$1,560
includes taxes & fees
25 Nov - 26 Nov
Spacious Oceanview Villa (Sleeps 22)

Historical New England coastal holiday home-2 min. from Ocean Beach

10.0 out of 10, Exceptional, (33)
"The host was incredibly kind and accommodating. We particularly enjoyed the beach pass, as we drove ~3 min to the beautiful water in the morning. The amenities were absolutely gorgeous and beyond functional. Plenty of bathrooms, showers, sinks, sitting areas, etc. for our party. We had a wonderful stay!"
Historical New England coastal holiday home-2 min. from Ocean Beach

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

10.0 out of 10, Exceptional, (43)
"Condo was great!"
The price is AU$473
includes taxes & fees
24 Nov - 25 Nov
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

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

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

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

9.4 out of 10, Exceptional, (3)
"The host was very nice when I had an issue with communication! Cute little villa!"
The price is AU$443
includes taxes & fees
24 Nov - 25 Nov
Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Beach House

9.8 out of 10, Exceptional, (47)
"It's Christmas all year and we loved it! So so cozy. From my elderly mom to my toddler everyone was happy. Kids lived the playground and we loved how easy and comfortable the house was. Joe also left us delicious cookies from a local bakery. Thank you Joe!!! "
Beach House

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

10.0 out of 10, Exceptional, (84)
"This was such a central location for my East coast family to meet up. Perfect lodging for folks coming from lots of different areas and spatial needs. We had a lovely time going to the farm stand and made a beautiful meal from the produce we picked up. Thanks for an amazing stay! "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

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

9.8 out of 10, Exceptional, (43)
"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

Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

10.0 out of 10, Exceptional, (19)
"Lovely house. Perfect for a family getaway for children and adults. Nice number of sleeping options. Three full bathrooms a big plus. Great communal areas and a wonderful backyard. Short walk to the beach. Great time of year to enjoy being on the beach without all the crowds and summer heat. "
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

Shalom Cottage with private beach rights.

9.0 out of 10, Wonderful, (17)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AU$276
includes taxes & fees
3 Dec - 4 Dec
Shalom Cottage with private beach rights.

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

9.8 out of 10, Exceptional, (25)
"We spent the weekend at the shore to celebrater my wife's 70th Birthday. The accommodations were fabulous and everyone enjoyed the home, the view and the location. Thank you to our host Laura."
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

"Salt 'n' Lyme" - Walk to everything !

9.4 out of 10, Exceptional, (29)
"Nice place in quiet neighborhood with great owner. "
"Salt 'n' Lyme" - Walk to everything !

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!
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, (1670)
"Mohegan Sun, great getaway adventure"
The price is AU$355
includes taxes & fees
25 Nov - 26 Nov
Mohegan Sun

Hyatt Place Uncasville - Casino Area

3.0 star property
9.2 out of 10, Wonderful, (2217)
"Great location. Clean. Quiet. Friendly. "
The price is AU$186
includes taxes & fees
3 Dec - 4 Dec
Hyatt Place Uncasville - Casino Area

Motel 6 New Haven - Branford, CT

2.0 star property
6.6 out of 10, (1007)
"Thanks "
The price is AU$124
includes taxes & fees
23 Dec - 24 Dec
Motel 6 New Haven - Branford, CT
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Chester?

Expedia has 4 holiday rentals for your stay in Chester.

What’s there to see and do in Chester?

Cockaponset State Forest and Connecticut River are a couple of scenic spots to enjoy the outdoors, whereas Norma Terris Theater is one of the cultural attractions. 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.