Search Vacation Homes in Chester

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chester vacation homes

10.0 out of 10, Exceptional, (5)
"Place is nice would stay again "
United States
nic
The price is ¥14,257
¥55,710 total
includes taxes & fees
Dec 15 - Dec 16
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
10.0 out of 10, Exceptional, (4)
"Communication was excellent. "
United States
Katy C.
The price is ¥13,454
¥62,738 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Rogers Lake House (87) · CT College+Beach+USCGA
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 ¥14,659
¥56,171 total
includes taxes & fees
Dec 18 - Dec 19
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
10.0 out of 10, Exceptional, (1)
"The home was very clean and welcoming."
United States
Michelle M.
The price is ¥23,324
¥57,337 total
includes taxes & fees
Dec 21 - Dec 22
Charming 2-bedroom house with WiFi, AC in lovely Waterford
10.0 out of 10, Exceptional, (2)
"A lovely quick overnight."
United States
Bonnie H.
The price is ¥12,825
¥43,561 total
includes taxes & fees
Dec 17 - Dec 18
Thames River Cottage · Near Casinos - USCGA
2.0 star property
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 ¥18,234
¥56,764 total
includes taxes & fees
Dec 15 - Dec 16
The Bay Cottage · Rocky Neck Park, Beach & Niantic
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 traveler
The price is ¥13,692
¥54,510 total
includes taxes & fees
Dec 14 - Dec 15
Shantok Queen suites walk to Mohegan casino/Wi-Fi
8.0 out of 10, Very Good, (16)
"Easy access. We loved our short stay. I would return again. "
United States
Suzanne M.
The price is ¥9,096
¥29,485 total
includes taxes & fees
Dec 17 - Dec 18
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is ¥18,541
¥45,629 total
includes taxes & fees
Dec 14 - Dec 15
#24 *Serenity* A Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (3)
"Vincent was amazing to work with! We decided to change the dates and he was very patient and helpful while we got it updated with VRBO. The home is in a peaceful neighborhood with beautiful trees and active squirrels (my daughter’s favorite part). The location was convenient for our needs. We all enjoyed the game tables and the convenience of the washer and dryer. We even tried out the projector one night to watch a couple of episodes of Gilmore Girls – so fun! Vincent checked in once we arrived...
United States
Erin S.
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins
2.0 star property
9.0 out of 10, Wonderful, (2)
"Located so perfectly close to everything we wanted to do on vacation. The house was so clean and comfortable. Communication with the owner was A++. The neighbors were even so friendly and waving/smiling. It felt as if we were home. If we come back to that area again we hope this place will be available. "
United States
Jennifer A.
The price is ¥29,543
¥66,316 total
includes taxes & fees
Dec 21 - Dec 22
Entire Vacation Home in Waterford Connecticut

Vacation Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (18)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
The price is ¥18,659
¥35,296 total
includes taxes & fees
Dec 16 - Dec 17
Family Stays: Middletown, CT

Vacation Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is ¥18,230
¥49,244 total
includes taxes & fees
Dec 14 - Dec 15
Private Apartment in Berlin
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 ¥17,918
¥45,224 total
includes taxes & fees
Dec 15 - Dec 16
Once the old Schools house now a newly furnished Apartment

Vacation Home in Westside Norwich

Cozy and Private 3BR/2BA Near Casinos
9.6 out of 10, Exceptional, (5)
"4 adults plus one dog stayed here and it was wonderful. Clean quiet home."
United States
Susan P.
The price is ¥18,697
¥64,505 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Cozy and Private 3BR/2BA Near Casinos
2.0 star property
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 ¥22,109
¥78,908 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westside Norwich

Winner's Getaway - 2mi to Mohegan Sun
10.0 out of 10, Exceptional, (12)
"Close to casino, would recommend"
United States
Joe M.
The price is ¥23,808
¥73,966 total
includes taxes & fees
Dec 14 - Dec 15
Winner's Getaway - 2mi to Mohegan Sun

Vacation Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is ¥22,998
¥33,147 total
includes taxes & fees
Dec 15 - Dec 16
Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (4)
"Great house, super comfortable beds and great hospitality."
United States
Michele G.
The price is ¥20,255
¥50,248 total
includes taxes & fees
Dec 16 - Dec 17
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
10.0 out of 10, Exceptional, (17)
"We stayed at the Thames River House after our wedding with friends and it was the perfect spot. The home was beautiful, very clean, and had everything we needed for a relaxing and memorable stay. Couldn’t have asked for a better experience!"
United States
Brandon W.
The price is ¥33,065
¥94,938 total
includes taxes & fees
Dec 17 - Dec 18
Thames River Retreat · CT College+Casinos+USCGA
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

Find out more about Chester

Chester Vacation Homes information

Number of reviews
133
Accommodation
364 Vacation Homes
Lowest Price
¥29,485
Highest Price
¥94,938