Photo by Annette Babek

Chester Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    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

Browse Select Chester Vacation Homes

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (8)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is CA $265
CA $809 total
includes taxes & fees
Aug 28 - Aug 29
Thames River Retreat · CT College+Casinos+USCGA

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

10.0 out of 10, Exceptional, (97)
"We loved our time at White Gate. Very peaceful!"
The price is CA $1,491
CA $2,689 total
includes taxes & fees
Sep 11 - Sep 12
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Direct waterfront vacation rental, family friendly, pets allowed

10.0 out of 10, Exceptional, (71)
"This was our third time renting and we had an excellent stay yet again. We are booked up for next year already!"
Direct waterfront vacation rental, family friendly, pets allowed

Spectacular home with an amazing river view

9.6 out of 10, Exceptional, (73)
"Beautiful house for our family trip. Nice location and view. "
Spectacular home with an amazing river view

Charming beach home, complete with pool & cozy guest house!

9.8 out of 10, Exceptional, (31)
"It was very comfortable and cozy, a very great place to spend with your loved ones, very spacious and had everything we needed to enjoy our stay."
Charming beach home, complete with pool & cozy guest house!

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
9.0 out of 10, Wonderful, (2)
"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)."
The price is CA $261
CA $633 total
includes taxes & fees
Aug 27 - Aug 28
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

4.8 out of 10, (3)
"Overall, my girlfriends and I had a good stay at this accommodation. Transparently, there were some hiccups in communication between the property manager and I in the week leading up to our trip that were not clearly stated in the home's description prior to us booking our stay, however, I felt that they were able to address my concerns and came up with solutions that felt satisfactory to my group and I. The property manager was overall understanding and receptive to my feedback through our...
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Charming 2-bedroom house in marvelous Montville with WiFi, AC

9.0 out of 10, Wonderful, (2)
"Perfect!"
Charming 2-bedroom house in marvelous Montville with WiFi, AC

Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

10.0 out of 10, Exceptional, (40)
"Very clean well kept property near beach - host very welcoming and receptive. Enjoyed our stay!"
Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

Historic Coastal Home • Marsh Views • Pet-Friendly

10.0 out of 10, Exceptional, (1)
"We had a wonderful weekend here!The host was very accommodating with check-in and check-out times. The house was beautiful, spotless and full of character. Lots of space for two families. The yard was really nice and much bigger than it seemed it the photos. We had a really great stay. "
Historic Coastal Home • Marsh Views • Pet-Friendly

Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

9.6 out of 10, Exceptional, (47)
"We loved being next door to Ocean Beach."
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

Waterfront Estate Home - Beach and Shared Pool - East

9.8 out of 10, Exceptional, (43)
"Perfect home for a big family gathering!"
Waterfront Estate Home - Beach and Shared Pool - East

The Beach Nest-Lux Cottage Steps to the Beach

9.8 out of 10, Exceptional, (6)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
The Beach Nest-Lux Cottage Steps to the Beach

Your Nest Near The Beach

10.0 out of 10, Exceptional, (13)
"Came back home to the beach and couldn't be happier staying here. Perfect little cottage. Super easy walk to the beach. Perfect location. Quiet. Owners were super responsive for anything and even left us a postcard and a treat upon arrival. Easy check in and out. Has a Keurig for your morning coffee. Wifi is great. I worked all week with not 1 problem or flicker. Bring your own board games if that's your thing. Bring your own spices if you're staying longer than a few days and want to cook....
Your Nest Near The Beach

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

9.6 out of 10, Exceptional, (133)
"Very much enjoyed our trip! "
The price is CA $577
CA $1,015 total
includes taxes & fees
Aug 25 - Aug 26
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Guilford home -self check in, off-street parking

9.2 out of 10, Wonderful, (9)
"Nice house, manageable distance from beaches and restaurants "
Guilford home -self check in, off-street parking

Private Apartment in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"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! "
The price is CA $182
CA $572 total
includes taxes & fees
Sep 9 - Sep 10
Private Apartment in Berlin

Beach community with private beaches

10.0 out of 10, Exceptional, (12)
"We had a wonderful week staying here with my family. It was family friendly, clear, had everything we needed and was a 10 min walk from beach!"
Beach community with private beaches

You and your Family deserve a break. Relax and enjoy lake front living

10.0 out of 10, Exceptional, (50)
"Every thing was great, nice property. Highly recommend."
You and your Family deserve a break. Relax and enjoy lake front living
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