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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (201 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is ￥21,372
￥31,860 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥21,372
￥37,480 total
includes taxes & fees
Oct 27 - Oct 28
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
9.6 out of 10, Exceptional, (61 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥16,385
￥33,068 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥19,789
￥40,686 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥24,934
￥47,395 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥23,870
￥54,490 total
includes taxes & fees
Nov 3 - Nov 4
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

7. 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 ￥26,216
￥74,657 total
includes taxes & fees
Oct 15 - Oct 16
Adorable Cottage, 5 min walk to water & town
A beach with a house in the background, a clear sky, and a calm sea.

8. 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 ￥24,934
￥57,606 total
includes taxes & fees
Oct 20 - Oct 21
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A stone pier leading to a beach with houses in the background.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (62 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 ￥17,810
￥43,097 total
includes taxes & fees
Oct 19 - Oct 20
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

10. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (12 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 ￥16,385
￥22,010 total
includes taxes & fees
Oct 13 - Oct 14
The Tiny Cottage & Mini Farm
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

11. 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 ￥31,662
￥71,319 total
includes taxes & fees
Oct 12 - Oct 13
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A rocky shoreline with a beach and ocean in the background.

12. 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 ￥18,565
￥38,876 total
includes taxes & fees
Oct 12 - Oct 13
The Anchor at Soundview · Beach+Ocean+Sunrise
A cozy room with a bed, a dining table set with bowls and spoons, and a view of a lake and trees.

13. 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 ￥19,852
￥42,761 total
includes taxes & fees
Nov 3 - Nov 4
Lakefront Boho Tiny House
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

14. 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 ￥21,768
￥45,282 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Lakefront Tiny House
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

15. 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 ￥45,593
￥89,081 total
includes taxes & fees
Oct 21 - Oct 22
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A modern living room with a sofa, a dining table, and a massage chair.

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 ￥28,907
￥72,662 total
includes taxes & fees
Oct 12 - Oct 13
#29 - Modern 5 Bedroom/2 Bath
A spacious living room with a wooden dining table, gray sofa, and a large window.

17. 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 ￥36,744
￥98,338 total
includes taxes & fees
Nov 3 - Nov 4
Beachside Bliss w/ Game Room, Gym & Golf Green
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

18. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is ￥24,728
￥53,925 total
includes taxes & fees
Oct 12 - Oct 13
#24 Serenity A Lakefront Cottage Retreat
Veterans Park, near the house

19. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (33 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is ￥21,372
￥40,528 total
includes taxes & fees
Oct 14 - Oct 15
Family Stays: Middletown, CT
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, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is ￥22,084
￥48,147 total
includes taxes & fees
Oct 12 - Oct 13
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

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

8/10 Good
"Front desk staff helpful. First room had a bug coming out of the A/C unit, but the second room was fine. No refrigerator in room. First floor walls in hallways and some doors had paint scraped off by laundry carts. Hallway carpets were dingy. Very limited breakfast selection."
Peggy 2-night trip
Posted 8 hours ago
Microtel Inn & Suites by Wyndham 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.