Search Vacation Homes in Chester

  • 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

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 reviews)
"Place is nice would stay again "
United States
nic
The price is ¥17,075
¥58,261 total
includes taxes & fees
Jan 29 - Jan 30
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

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 reviews)
"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 ¥15,504
¥64,088 total
includes taxes & fees
Jan 29 - Jan 30
Rogers Lake House (87) · CT College+Beach+USCGA

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 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is ¥17,469
¥58,711 total
includes taxes & fees
Feb 4 - Feb 5
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA
Montville
10.0 out of 10, Exceptional, (2 reviews)
"A lovely quick overnight."
United States
Bonnie H.
The price is ¥14,914
¥45,247 total
includes taxes & fees
Jan 29 - Jan 30
Thames River Cottage · Near Casinos - USCGA

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 review)
"The home was very clean and welcoming."
United States
Michelle M.
The price is ¥22,881
¥56,249 total
includes taxes & fees
Jan 29 - Jan 30
Charming 2-bedroom house with WiFi, AC in lovely Waterford

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 reviews)
"Very cute house with nice extra touches like 2 bottles of water and new toothpaste (perfect because we forgot ours!). "
United States
Christie P.
The price is ¥16,474
¥37,608 total
includes taxes & fees
Feb 23 - Feb 24
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Montville
10.0 out of 10, Exceptional, (5 reviews)
"The property was perfect for our trip. Wonderful stay and amazing contact with the hosttess. "
United States
Redebaron 7.
The price is ¥19,830
¥49,194 total
includes taxes & fees
Jan 29 - Jan 30
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 reviews)
"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 ¥18,256
¥55,799 total
includes taxes & fees
Jan 29 - Jan 30
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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, (2 reviews)
"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 ¥19,380
¥60,605 total
includes taxes & fees
Feb 1 - Feb 2
Shantok Queen suites walk to Mohegan casino/Wi-Fi

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (20 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is ¥18,305
¥35,084 total
includes taxes & fees
Feb 9 - Feb 10
Family Stays: Middletown, CT

Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.6 out of 10, Exceptional, (48 reviews)
"Great place to stay. I have nothing bad to say about the place."
United States
Jose M.
The price is ¥19,830
¥45,075 total
includes taxes & fees
Feb 17 - Feb 18
Cozy, comfy,quiet &close to casinos

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"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 ¥13,576
¥38,951 total
includes taxes & fees
Jan 29 - Jan 30
#24 *Serenity* A Lakefront Cottage Retreat

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 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ¥17,542
¥43,970 total
includes taxes & fees
Jan 29 - Jan 30
Once the old Schools house now a newly furnished Apartment

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is ¥15,407
¥44,946 total
includes taxes & fees
Feb 1 - Feb 2
Private Apartment in Berlin

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is ¥22,515
¥32,757 total
includes taxes & fees
Feb 10 - Feb 11
Cozy Guest Suite in Historic Home

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ¥20,135
¥76,125 total
includes taxes & fees
Feb 4 - Feb 5
Beachside Bliss w/ Game Room, Gym & Golf Green

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Clinton
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is ¥18,396
¥76,413 total
includes taxes & fees
Feb 10 - Feb 11
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

Winner's Getaway - 2mi to Mohegan Sun

Winner's Getaway - 2mi to Mohegan Sun
Westside Norwich
10.0 out of 10, Exceptional, (12 reviews)
"Close to casino, would recommend"
United States
Joe M.
The price is ¥29,135
¥82,471 total
includes taxes & fees
Feb 1 - Feb 2
Winner's Getaway - 2mi to Mohegan Sun

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
9.0 out of 10, Wonderful, (2 reviews)
"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 ¥28,983
¥64,754 total
includes taxes & fees
Jan 29 - Jan 30
Entire Vacation Home in Waterford Connecticut

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful home on the water. Home was very clean and well furnished. Would stay again/recommend."
United States
Christopher O.
The price is ¥31,625
¥91,744 total
includes taxes & fees
Jan 29 - Jan 30
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
146
Accommodation
364 Vacation Homes
Lowest Price
¥32,757
Highest Price
¥91,744

Explore a world of travel with Expedia