Chester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Chester vacation rentals

Property grounds

Apartment in Chester Center

The little Chestnut. A charming historic apartment in Downtown Chester
10.0 out of 10, Exceptional, (6 reviews)
"A lovely little place! Everything we needed, in a great location."
United States
Michael S.
The price is ￥25,008
￥56,083 total
includes taxes & fees
Jan 28 - Jan 29
The little Chestnut. A charming historic apartment in Downtown Chester
Exterior

Mobile Home in East Lyme

Cozy Lakefront Tiny House
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is ￥13,504
￥31,931 total
includes taxes & fees
Feb 3 - Feb 4
Cozy Lakefront Tiny House
1 bedroom, free WiFi, bed sheets

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.
The price is ￥13,338
￥32,049 total
includes taxes & fees
Jan 29 - Jan 30
Lakefront Boho Tiny House
View from property

Cabin in East Haddam

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (106 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is ￥16,826
￥26,451 total
includes taxes & fees
Jan 28 - Jan 29
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Living area

Cottage in Oakdale,

The Tiny Cottage at Clem & Clyde's
10.0 out of 10, Exceptional, (3 reviews)
"We were looking for a place to stay while in town for a volleyball tournament. This space worked out perfectly. We will be back! Next time hopefully we’ll have time to enjoy the farm. Thank you!"
United States
Rebecca N.
The price is ￥13,199
￥18,267 total
includes taxes & fees
Jan 29 - Jan 30
The Tiny Cottage at Clem & Clyde's
On the beach

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
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
The price is ￥13,899
￥32,471 total
includes taxes & fees
Jan 28 - Jan 29
The Stern at Soundview · Beach+Ocean+Sunrise
Beach nearby, sun loungers, beach towels

Cottage in East Lyme

Beach Cottage, private beach and pass
10.0 out of 10, Exceptional, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is ￥26,258
￥61,666 total
includes taxes & fees
Jan 29 - Jan 30
Beach Cottage, private beach and pass
Smart TV, books

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
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 ￥15,491
￥64,629 total
includes taxes & fees
Jan 28 - Jan 29
Rogers Lake House (87) · CT College+Beach+USCGA
Dining

Vacation Home in Montville

Thames River Cottage · Near Casinos - USCGA
10.0 out of 10, Exceptional, (2 reviews)
"A lovely quick overnight."
United States
Bonnie H.
The price is ￥14,894
￥45,563 total
includes taxes & fees
Jan 29 - Jan 30
Thames River Cottage · Near Casinos - USCGA
Smart TV, fireplace, books

Vacation Home in Waterford

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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 ￥17,479
￥59,187 total
includes taxes & fees
Feb 4 - Feb 5
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Exterior

Villa in Norwich

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
9.8 out of 10, Exceptional, (16 reviews)
"Great property, beautiful grounds and appointed as described! Owners were great to work with and flexible. "
United States
Bill M.
The price is ￥18,154
￥39,247 total
includes taxes & fees
Jan 29 - Jan 30
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
1 bedroom, WiFi, bed sheets

Apartment in New London

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
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.
The price is ￥13,585
￥18,710 total
includes taxes & fees
Jan 28 - Jan 29
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
1 bedroom, desk, iron/ironing board, travel crib

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ￥13,739
￥29,361 total
includes taxes & fees
Jan 28 - Jan 29
1-bedroom cottage with Grove Beach 🏖️ access.
Interior

Vacation Home in Salem

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
The price is ￥17,083
￥58,425 total
includes taxes & fees
Jan 29 - Jan 30
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Outdoor dining

Villa in Norwich

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
9.8 out of 10, Exceptional, (47 reviews)
"Small place good for an individual or couple clean and as described."
United States
Anonymous traveler
The price is ￥19,883
￥39,692 total
includes taxes & fees
Jan 29 - Jan 30
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
Indoor pool, a heated pool

Villa in Norwich

Cozy Couples Getaway with Golf Course View & Spa
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
The price is ￥16,252
￥34,898 total
includes taxes & fees
Jan 28 - Jan 29
Cozy Couples Getaway with Golf Course View & Spa
Beach nearby

Vacation Home in New London

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
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 ￥16,672
￥38,060 total
includes taxes & fees
Feb 23 - Feb 24
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Exterior

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is ￥17,753
￥44,498 total
includes taxes & fees
Jan 28 - Jan 29
All New 1BR with tons of Charm
Fridge, microwave, oven, stovetop

Apartment in Wallingford Center

All New Studio apartment in center of town
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is ￥17,753
￥44,498 total
includes taxes & fees
Jan 28 - Jan 29
All New Studio apartment in center of town
Terrace/patio

Apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
10.0 out of 10, Exceptional, (1 review)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is ￥18,756
￥49,164 total
includes taxes & fees
Jan 28 - Jan 29
Soothing 2-bedroom lower-level apartment in Berlin
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

Hampton Inn Norwich

Hampton Inn Norwich

10/10 Excellent
"Staff was great. Clean facilities. "
Ralph 1-night trip
Posted 2 days ago
Hampton Inn Norwich

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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?

WATERFRONT VIEWS @ OCEAN BEACH GATE: 6 QUEEN 1 SOFA BED: This vacation home rental near Chester is located by the ocean and has an outdoor pool, a furnished patio, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.