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

Chester Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chester holiday 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, (197 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is HK$1,059
HK$1,579 total
includes taxes & fees
2 Nov - 3 Nov
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 traveller
The price is HK$1,107
HK$1,920 total
includes taxes & fees
27 Oct - 28 Oct
Walk To Goodspeed Opera House!
A living room with a wooden dresser, a flat-screen TV, a dining table with chairs, and a kitchen area in the background.

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$939
HK$1,793 total
includes taxes & fees
27 Oct - 28 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
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.

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, (38 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 HK$981
HK$2,025 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

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 HK$1,236
HK$2,349 total
includes taxes & fees
8 Oct - 9 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
A beach with waves, a clear sky, and a sandy shore.

6. 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 HK$1,092
HK$2,597 total
includes taxes & fees
7 Oct - 8 Oct
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A beach with a house in the background, a clear sky, and a calm sea.

7. 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
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is HK$1,236
HK$2,832 total
includes taxes & fees
20 Oct - 21 Oct
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
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.
The price is HK$1,390
HK$3,812 total
includes taxes & fees
7 Oct - 8 Oct
Adorable Cottage, 5 min walk to water & town
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

9. 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, (14 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is HK$1,570
HK$3,535 total
includes taxes & fees
5 Oct - 6 Oct
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A stone pier leading to a beach with houses in the background.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (61 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 HK$890
HK$2,137 total
includes taxes & fees
14 Oct - 15 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
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 HK$1,624
HK$4,114 total
includes taxes & fees
5 Oct - 6 Oct
Adorable Cottage with Cottage porch, walk to water & town
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

12. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
The price is HK$812
HK$1,091 total
includes taxes & fees
6 Oct - 7 Oct
The Tiny Cottage & Mini Farm
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

13. 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 HK$2,260
HK$4,416 total
includes taxes & fees
12 Oct - 13 Oct
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

14. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (3 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 HK$1,038
HK$2,536 total
includes taxes & fees
5 Oct - 6 Oct
2BR Apartment Near Wesleyan 301
A cozy room with a bed, a dining table set with bowls and spoons, and a view of a lake and trees.

15. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is HK$1,036
HK$2,187 total
includes taxes & fees
6 Oct - 7 Oct
Lakefront Boho Tiny House
A beach with waves, a clear sky, and a sandy shore.

16. 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 HK$1,436
HK$3,503 total
includes taxes & fees
7 Oct - 8 Oct
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
A rocky shoreline with a beach and ocean in the background.

17. The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.8 out of 10, Excellent, (3 reviews)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
The price is HK$1,062
HK$2,105 total
includes taxes & fees
5 Oct - 6 Oct
The Anchor at Soundview · Beach+Ocean+Sunrise
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

18. 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 HK$1,200
HK$2,399 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Lakefront Tiny House
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

19. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
2BR Apartment Near Wesleyan 102
A modern living room with a sofa, a dining table, and a massage chair.

20. #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 HK$1,718
HK$3,969 total
includes taxes & fees
7 Oct - 8 Oct
#29 - Modern 5 Bedroom/2 Bath
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

Fairfield by Marriott Inn & Suites Wallingford New Haven

Fairfield by Marriott Inn & Suites Wallingford New Haven

10/10 Excellent
"The room was very clean, staff was helpful"
Carol 1-night trip
Posted less than an hour ago
Fairfield by Marriott Inn & Suites Wallingford New Haven

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 holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theatres while you're in the area.

What are some of the best holiday rentals that Chester has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Chester is located on the beach, and has a balcony, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Chester?

Expedia has 3 holiday 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 holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.