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
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chester vacation rentals

View from property

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, (186 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is AED 529
AED 924 total
includes taxes & fees
5 Oct - 6 Oct
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Exterior

2. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (42 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
The price is AED 500
AED 874 total
includes taxes & fees
24 Sep - 25 Sep
Walk To Goodspeed Opera House!
1 bedroom, desk, iron/ironing board, travel crib

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 407
AED 794 total
includes taxes & fees
6 Sep - 7 Sep
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, fireplace, books, music library

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, (36 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is AED 481
AED 969 total
includes taxes & fees
22 Sep - 23 Sep
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Coffee/tea maker, fridge, microwave, oven

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, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is AED 661
AED 1,209 total
includes taxes & fees
8 Sep - 9 Sep
The gardners Cottage 1 mile from long Island Sound - pet friendly
Interior

6. 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 AED 672
AED 1,812 total
includes taxes & fees
9 Sep - 10 Sep
Adorable Cottage, 5 min walk to water & town
Sun loungers, beach towels

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, (1 review)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is AED 579
AED 1,329 total
includes taxes & fees
8 Sep - 9 Sep
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Beach nearby

8. 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 563
AED 1,338 total
includes taxes & fees
7 Sep - 8 Sep
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Smart TV

9. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is AED 413
AED 549 total
includes taxes & fees
7 Sep - 8 Sep
The Tiny Cottage & Mini Farm
Dining

10. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
The price is AED 731
AED 2,297 total
includes taxes & fees
29 Sep - 30 Sep
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
1 bedroom, WiFi (free), bed sheets

11. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (9 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is AED 493
AED 1,037 total
includes taxes & fees
29 Sep - 30 Sep
Lakefront Boho Tiny House
Smart TV, fireplace, books, offices

12. 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, (12 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is AED 753
AED 1,676 total
includes taxes & fees
9 Sep - 10 Sep
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Beach

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is AED 731
AED 2,142 total
includes taxes & fees
8 Sep - 9 Sep
Beachside Bliss w/ Game Room, Gym & Golf Green
Exterior

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 AED 570
AED 1,132 total
includes taxes & fees
7 Sep - 8 Sep
Cozy Lakefront Tiny House
Beach nearby

15. The Mast at Soundview · Beach+Ocean+Sunrise

The Mast at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This is a good option if you're looking for somewhere spotlessly clean and convenient to lay your head at night while you hit the beach during the day. The beach is steps away and lovely."
United States
Alison H.
The price is AED 507
AED 1,004 total
includes taxes & fees
7 Sep - 8 Sep
The Mast at Soundview · Beach+Ocean+Sunrise
Beach nearby

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 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 AED 477
AED 1,077 total
includes taxes & fees
6 Oct - 7 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Beach nearby

17. Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"Very peaceful community. Great accommodations!"
United States
Joseph O.
The price is AED 559
AED 1,067 total
includes taxes & fees
7 Sep - 8 Sep
Keel at Soundview · Beach+OceanView+Sunrise
Coffee/tea maker, fridge, microwave, oven

18. 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 AED 459
AED 1,160 total
includes taxes & fees
8 Sep - 9 Sep
2BR Apartment Near Wesleyan 301
Exterior

19. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (65 reviews)
"It was great ocation for a weekend get away with friends to Mohegan Sun"
United States
Teresa M.
The price is AED 400
AED 960 total
includes taxes & fees
8 Sep - 9 Sep
Cozy, comfy,quiet &close to casinos
Interior

20. Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
9.8 out of 10, Exceptional, (12 reviews)
"Place is nice would stay again "
United States
nic
The price is AED 488
AED 1,509 total
includes taxes & fees
9 Sep - 10 Sep
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
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

Holiday Inn New London - Mystic Area by IHG

Holiday Inn New London - Mystic Area by IHG

8/10 Good
"The room was great but for the price was disappointed that it didn’t come with breakfast"
Anna 2-night trip
Posted 1 hour ago
Holiday Inn New London - Mystic Area by IHG

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, Connecticut Valley Railroad State Park Trail and Chester Creek Marina 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.