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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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, (221 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is AED 466
AED 705 total
includes taxes & fees
7 Dec - 8 Dec
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 AED 474
AED 808 total
includes taxes & fees
1 Dec - 2 Dec
Walk To Goodspeed Opera House!
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

3. 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, (31 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is AED 744
AED 1,253 total
includes taxes & fees
9 Nov - 10 Nov
The gardners Cottage 1 mile from long Island Sound - pet friendly
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

4. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
The price is AED 485
AED 832 total
includes taxes & fees
10 Nov - 11 Nov
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.

5. 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 AED 459
AED 928 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
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 AED 396
AED 1,051 total
includes taxes & fees
9 Nov - 10 Nov
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

7. 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 AED 895
AED 2,034 total
includes taxes & fees
9 Nov - 10 Nov
Adorable Cottage with Cottage porch, walk to water & town
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

8. 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 AED 944
AED 1,886 total
includes taxes & fees
9 Nov - 10 Nov
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

9. 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 AED 1,091
AED 2,017 total
includes taxes & fees
16 Nov - 17 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

10. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is AED 1,117
AED 1,482 total
includes taxes & fees
1 Dec - 2 Dec
Westbrook Getaway-Near Beaches, Train & Shoreline
A beach with a house in the background, a clear sky, and a calm sea.

11. 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 AED 545
AED 1,052 total
includes taxes & fees
15 Nov - 16 Nov
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home! We very much enjoyed our stay and hope to be back again!"
United States
Morgan M.
The price is AED 862
AED 2,200 total
includes taxes & fees
1 Dec - 2 Dec
Beachside Bliss w/ Game Room, Gym & Golf Green
A modern living room with a leather sofa, a dining table with chairs, a kitchen area with white cabinets, and a chandelier.

13. #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 AED 764
AED 1,730 total
includes taxes & fees
23 Nov - 24 Nov
#29 - Modern 5 Bedroom/2 Bath
A lakeside deck with a table and chairs, a dock extending into the water, and a view of the lake surrounded by trees.

14. Romantic Getaway at The Lake!

Romantic Getaway at The Lake!
East Haddam
The price is AED 562
AED 859 total
includes taxes & fees
1 Dec - 2 Dec
Romantic Getaway at The Lake!
A vehicle's dashboard with a steering wheel, multiple gauges, and a radio.

15. Sunny 1 Queen Bed Smk Free Parking

Sunny 1 Queen Bed Smk Free Parking
Niantic
10.0 out of 10, Exceptional, (45 reviews)
"More roomy than other budget motels around here."
United States
Anonymous traveler
The price is AED 285
AED 328 total
includes taxes & fees
9 Nov - 10 Nov
Sunny 1 Queen Bed Smk Free Parking
A pond with rocks and a dog in the background.

16. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (14 reviews)
"Love love love this place. A very unique setting on a little farm and the cabin was great. Everything ya need. A gorgeous setting. Tom, the owner is great. Will. Be. Back."
United States
Paul
The price is AED 496
AED 614 total
includes taxes & fees
3 Dec - 4 Dec
The Tiny Cottage & Mini Farm
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

17. 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.
Cozy Lakefront Tiny House
A cozy room with a bed, a dining table set with bowls and spoons, and a view of a lake and trees.

18. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (12 reviews)
"This place was amazing! Tiny house was spotless with everything you need for a home away from home. Being right on the lake was so relaxing and peaceful. If you’re looking for a quiet couples weekend away, run to book this house!"
United States
Linda M.
The price is AED 412
AED 909 total
includes taxes & fees
9 Nov - 10 Nov
Lakefront Boho Tiny House
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 AED 500
AED 952 total
includes taxes & fees
11 Nov - 12 Nov
The Stern at Soundview · Beach+Ocean+Sunrise
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

20. 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 AED 403
AED 1,004 total
includes taxes & fees
10 Nov - 11 Nov
2BR Apartment Near Wesleyan 301
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

8/10 Good
"Pros: Clean! Excellent staff (shout out to Kiana!) Breakfast included Shuttle to Moheghan Sun Hot water Good shower nozzle options Close and simple drive to Moheghan Cons: Hard/very firm beds A bit expensive, overpriced Basic room and amenities Scarce parking late at night (concert at Moheghan) Grab bar in shower right where one stands so it makes it very narrow Water escaped the curtain, going all over the floor Overall, I would recommend this hotel. Pros outweigh. We like the Hampton Inn!"
Malene 1-night trip
Posted 5 hours ago
Hampton Inn Norwich

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.