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

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 AED 551
AED 1,354 total
includes taxes & fees
12 Feb - 13 Feb
Charming 2-bedroom house with WiFi, AC in lovely Waterford

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 AED 477
AED 1,188 total
includes taxes & fees
12 Feb - 13 Feb
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

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 AED 444
AED 1,205 total
includes taxes & fees
12 Feb - 13 Feb
Thames River Cottage · Near Casinos - USCGA

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 AED 430
AED 1,030 total
includes taxes & fees
17 Feb - 18 Feb
Cozy, comfy,quiet &close to casinos

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)
"Needed an inexpensive place to stay for a trade show event. This was 20 minutes from Mohegan and perfect for me and an employee. "
United States
Hippy P.
The price is AED 271
AED 768 total
includes taxes & fees
23 Feb - 24 Feb
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

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 AED 422
AED 1,809 total
includes taxes & fees
22 Feb - 23 Feb
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

#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 AED 536
AED 1,215 total
includes taxes & fees
22 Feb - 23 Feb
#24 *Serenity* A Lakefront Cottage Retreat

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 AED 676
AED 1,736 total
includes taxes & fees
3 Mar - 4 Mar
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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 AED 353
AED 1,015 total
includes taxes & fees
12 Feb - 13 Feb
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 AED 542
AED 792 total
includes taxes & fees
17 Feb - 18 Feb
Cozy Guest Suite in Historic Home

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 AED 422
AED 820 total
includes taxes & fees
24 Feb - 25 Feb
Family Stays: Middletown, CT

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 AED 610
AED 1,995 total
includes taxes & fees
17 Feb - 18 Feb
Beachside Bliss w/ Game Room, Gym & Golf Green

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 AED 643
AED 1,845 total
includes taxes & fees
12 Feb - 13 Feb
Winner's Getaway - 2mi to Mohegan Sun

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 AED 638
AED 1,647 total
includes taxes & fees
12 Feb - 13 Feb
Shantok Queen suites walk to Mohegan casino/Wi-Fi

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
8.8 out of 10, Excellent, (3 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 AED 698
AED 1,567 total
includes taxes & fees
12 Feb - 13 Feb
Entire Vacation Home in Waterford Connecticut

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is AED 661
AED 1,326 total
includes taxes & fees
12 Feb - 13 Feb
Stylish Modern Stay Steps from the Ocean

Charming Lakeview, 3 Bedroom home in Colchester

Charming Lakeview, 3 Bedroom home in Colchester
Colchester
10.0 out of 10, Exceptional, (1 review)
"Property was perfect for our Christmas break - very clean and tidy, had everything needed. Beds are comfortable and rooms feel spacious. Check-in was a breeze. Water pressure is a little low in the shower but the owners are aware of the issue. You can't go wrong with staying here!"
United States
Meagan P.
The price is AED 694
AED 1,375 total
includes taxes & fees
13 Feb - 14 Feb
Charming Lakeview, 3 Bedroom home in Colchester

Luxury, New, Quiet - King Beds, 5 minutes to Mohegan Sun

Luxury, New, Quiet - King Beds, 5 minutes to Mohegan Sun
Montville
9.8 out of 10, Exceptional, (7 reviews)
"Very clean and comfortable "
United States
Kathleen A.
The price is AED 798
AED 1,793 total
includes taxes & fees
12 Feb - 13 Feb
Luxury, New, Quiet - King Beds, 5 minutes to Mohegan Sun

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 AED 856
AED 1,975 total
includes taxes & fees
12 Feb - 13 Feb
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is AED 731
AED 1,671 total
includes taxes & fees
2 Mar - 3 Mar
#29 - Modern 5 Bedroom/2 Bath
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

Explore a world of travel with Expedia