A calm river with boats, wooden docks, and buildings along the shore.

Chester Vacation Rentals

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Our top choices for Chester vacation rentals

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (202 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is CA $180
CA $272 total
includes taxes & fees
Nov 16 - Nov 17
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveller
The price is CA $199
CA $344 total
includes taxes & fees
Nov 9 - Nov 10
Walk To Goodspeed Opera House!

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (62 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $147
CA $296 total
includes taxes & fees
Oct 21 - Oct 22
1-bedroom cottage with Grove Beach 🏖️ access.

4. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (39 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is CA $177
CA $376 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

5. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (29 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is CA $223
CA $426 total
includes taxes & fees
Oct 28 - Oct 29
The gardners Cottage 1 mile from long Island Sound - pet friendly

6. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Great spot Very clean"
United States
Dorothy W.
The price is CA $260
CA $638 total
includes taxes & fees
Oct 19 - Oct 20
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

7. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (15 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is CA $284
CA $642 total
includes taxes & fees
Oct 18 - Oct 19
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

8. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is CA $409
CA $796 total
includes taxes & fees
Oct 21 - Oct 22
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

9. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is CA $262
CA $807 total
includes taxes & fees
Oct 21 - Oct 22
Beachside Bliss w/ Game Room, Gym & Golf Green

10. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (34 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is CA $919
CA $1,553 total
includes taxes & fees
Oct 29 - Oct 30
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

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

Charming beach home, complete with pool & cozy guest house!
Clinton
9.8 out of 10, Exceptional, (56 reviews)
"Beautiful, open and clean. Perfect for a family stay!"
United States
Juliana A.
The price is CA $954
CA $1,995 total
includes taxes & fees
Nov 12 - Nov 13
Charming beach home, complete with pool & cozy guest house!

12. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is CA $212
CA $503 total
includes taxes & fees
Oct 20 - Oct 21
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

13. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is CA $341
CA $487 total
includes taxes & fees
Oct 20 - Oct 21
Westbrook Getaway-Near Beaches, Train & Shoreline

14. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (64 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is CA $159
CA $385 total
includes taxes & fees
Oct 29 - Oct 30
Insta-worthy Couples Retreat: Perfect for romantic getaway!

15. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is CA $185
CA $458 total
includes taxes & fees
Oct 19 - Oct 20
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

16. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
The price is CA $389
CA $827 total
includes taxes & fees
Nov 2 - Nov 3
#29 - Modern 5 Bedroom/2 Bath

17. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
9.6 out of 10, Exceptional, (4 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is CA $155
CA $421 total
includes taxes & fees
Oct 19 - Oct 20
2BR Apartment Near Wesleyan 301

18. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (13 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is CA $147
CA $197 total
includes taxes & fees
Oct 19 - Oct 20
The Tiny Cottage & Mini Farm

19. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (5 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is CA $186
CA $394 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Lakefront Tiny House
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental near Chester is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 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, Chester Creek Marina and Connecticut Valley Railroad State Park Trail 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.