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

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chester vacation rentals

A cabin with a dining table set for two, a bicycle, and a small porch area.

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, (213 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is ￥20,023
￥30,278 total
includes taxes & fees
Nov 30 - Dec 1
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A large, white, multi-story building with a prominent tower and a flag on top.

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 traveler
The price is ￥20,180
￥35,899 total
includes taxes & fees
Nov 3 - Nov 4
Walk To Goodspeed Opera House!
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥25,634
￥43,960 total
includes taxes & fees
Nov 10 - Nov 11
1-bedroom cottage with Grove Beach 🏖️ access.
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

4. 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, (30 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is ￥31,926
￥55,990 total
includes taxes & fees
Oct 31 - Nov 1
The gardners Cottage 1 mile from long Island Sound - pet friendly
A beach with waves, a clear sky, and a sandy shore.

5. 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 ￥28,649
￥69,852 total
includes taxes & fees
Nov 2 - Nov 3
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

6. 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, (40 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 ￥20,352
￥42,179 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

7. 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 ￥45,438
￥88,304 total
includes taxes & fees
Nov 2 - Nov 3
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

8. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
Adorable Cottage, 5 min walk to water & town
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (3 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥32,280
￥92,696 total
includes taxes & fees
Nov 10 - Nov 11
Beachside Bliss w/ Game Room, Gym & Golf Green
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

10. 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)
"Cute little house with excellent amenities. Perfect for our cousins getaway!"
United States
Karol T.
The price is ￥33,132
￥72,338 total
includes taxes & fees
Nov 3 - Nov 4
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

11. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
The price is ￥35,590
￥86,043 total
includes taxes & fees
Oct 31 - Nov 1
Adorable Cottage with Cottage porch, walk to water & town
A modern kitchen with a central island, bar stools, and pendant lighting.

12. 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, (35 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 ￥102,551
￥173,311 total
includes taxes & fees
Oct 31 - Nov 1
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A modern living room with a large TV, white cabinetry, and a view of the outdoors.

13. 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 ￥97,265
￥210,343 total
includes taxes & fees
Nov 12 - Nov 13
Charming beach home, complete with pool & cozy guest house!
A modern living room with a leather sofa, a dining table with chairs, a kitchen area with white cabinets, and a chandelier.

14. #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 ￥30,197
￥74,169 total
includes taxes & fees
Nov 2 - Nov 3
#29 - Modern 5 Bedroom/2 Bath
A beach with a house in the background, a clear sky, and a calm sea.

15. 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 ￥24,849
￥57,252 total
includes taxes & fees
Nov 6 - Nov 7
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A beach with waves, a clear sky, and a sandy shore.

16. 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 ￥20,594
￥52,539 total
includes taxes & fees
Nov 2 - Nov 3
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A hotel reception area with a receptionist, a guest, and a child.

17. Cozy 2 Full Beds|Free Parking & Wifi

Cozy 2 Full Beds|Free Parking & Wifi
Niantic
10.0 out of 10, Exceptional, (55 reviews)
"Close to local spots, good value for what you get."
United States
Anonymous traveler
The price is ￥12,714
￥14,621 total
includes taxes & fees
Nov 4 - Nov 5
Cozy 2 Full Beds|Free Parking & Wifi
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

18. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is ￥41,178
￥58,359 total
includes taxes & fees
Nov 17 - Nov 18
Westbrook Getaway-Near Beaches, Train & Shoreline
A rocky shoreline with a beach and ocean in the background.

19. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.4 out of 10, Very good, (6 reviews)
"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."
United States
Janine
The price is ￥21,249
￥42,194 total
includes taxes & fees
Nov 2 - Nov 3
The Stern at Soundview · Beach+Ocean+Sunrise
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

20. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is ￥16,093
￥40,390 total
includes taxes & fees
Nov 1 - Nov 2
2BR Apartment Near Wesleyan 102
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

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

10/10 Excellent
"Great breakfast! Comfortable and clean rooms."
Silvia 1-night trip
Posted 1 hour ago
Hyatt Place Uncasville - Casino Area

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?

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.