Chester Vacation Rentals

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Our top choices for Chester vacation rentals

9.6 out of 10, Exceptional, (99 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
$149 nightly
The price is $171
Jan 13 - Jan 14
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Cottage was perfect! The fresh eggs given to us by the host made for an awesome breakfast! The host was great! My 2 energetic boys loved every animal. The host made sure to take my boys through every fence/gate there was to get my boys front and center with the animals. This isn’t just about money him seeing my boys smile and run around with the animals definitely made his day! Left about an hour ago and my boys already asked 17 times when we are going back! "
United States
jeff
$115 nightly
The price is $129
Jan 15 - Jan 16
Total with taxes and fees
The Tiny Cottage at Clem & Clyde's
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$171 nightly
The price is $193
Jan 19 - Jan 20
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

Vacation Home in Berlin

Private Apartment in Berlin
2.0 star property
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.
$224 nightly
The price is $254
Jan 13 - Jan 14
Total with taxes and fees
Private Apartment in Berlin
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
$157 nightly
The price is $178
Jan 12 - Jan 13
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

Mobile Home in East Lyme

Lakefront Boho Tiny House
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
$186 nightly
The price is $210
Jan 12 - Jan 13
Total with taxes and fees
Lakefront Boho Tiny House
8.0 out of 10, Very Good, (1 review)
"Wonderful stay. Very quiet, spacious, comfy bed, nice soft sheets. Surprisingly private. Great location right across from clubhouse, and very close to Inn. Only disappointment was not being able to use the fireplace. Also if more than one night, may need to ask for more towels. Only 3 provided. "
United States
Julie
$211 nightly
The price is $227
Jan 12 - Jan 13
Total with taxes and fees
Cozy Couples Getaway with Golf Course View & Spa
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
$321 nightly
The price is $362
Jan 12 - Jan 13
Total with taxes and fees
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Vacation Home in Montville

Cozy, comfy,quiet &close to casinos
9.6 out of 10, Exceptional, (47 reviews)
"Great place to stay. I have nothing bad to say about the place."
United States
Jose M.
$222 nightly
The price is $251
Jan 12 - Jan 13
Total with taxes and fees
Cozy, comfy,quiet &close to casinos
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.
$356 nightly
The price is $403
Jan 12 - Jan 13
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA

Mobile Home in East Lyme

Cozy Lakefront Tiny House
10.0 out of 10, Exceptional, (2 reviews)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
$187 nightly
The price is $212
Jan 12 - Jan 13
Total with taxes and fees
Cozy Lakefront Tiny House
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.
$325 nightly
The price is $367
Jan 15 - Jan 16
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
10.0 out of 10, Exceptional, (7 reviews)
"We had a good experience staying with host, William. Going in and out of our unit was easy with the codes provided. The croissants provided for breakfast were large and delicious. We would stay there again."
United States
Ronald H.
$108 nightly
The price is $121
Jan 12 - Jan 13
Total with taxes and fees
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
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.
$177 nightly
The price is $201
Jan 26 - Jan 27
Total with taxes and fees
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
10.0 out of 10, Exceptional, (2 reviews)
"A lovely quick overnight."
United States
Bonnie H.
$246 nightly
The price is $278
Jan 19 - Jan 20
Total with taxes and fees
Thames River Cottage · Near Casinos - USCGA
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
$304 nightly
The price is $343
Jan 12 - Jan 13
Total with taxes and fees
Shantok Queen suites walk to Mohegan casino/Wi-Fi
2.0 star property
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.
$308 nightly
The price is $348
Jan 12 - Jan 13
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
$326 nightly
The price is $369
Jan 12 - Jan 13
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Waterford
10.0 out of 10, Exceptional, (14 reviews)
"Cottage was perfect. Immaculate, well equipped, beautifully decorated. It had everything we needed! My family and I loved our stay here and will definitely be back."
United States
Nina B.
$271 nightly
The price is $308
Jan 12 - Jan 13
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
9.6 out of 10, Exceptional, (8 reviews)
"Super quick trip to get over to Mohegan for a basketball game."
United States
Brooke
$273 nightly
The price is $309
Jan 12 - Jan 13
Total with taxes and fees
Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
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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Top Chester Hotel Reviews

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Chester?

Yes, we offer vacation rentals close to well known sights in Chester, or you can go with a more secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theaters while you're in the area.

What are some of the best vacation rentals in Chester?

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA: This vacation home rental near Chester is located next to a golf course and offers a garden, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Chester?

Expedia has 3 vacation rentals for your stay in Chester.

What’s there to see and do in Chester?

Cultural attractions include Norma Terris Theater, whereas Connecticut River is a spot to enjoy nature. While here, Connecticut Valley Railroad State Park Trail and Chester Creek Marina are other places worth a visit.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip or a small group gathering.