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Our top choices for Chester vacation homes

1. 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 ¥30,441
¥84,020 total
includes taxes & fees
Nov 10 - Nov 11
Beachside Bliss w/ Game Room, Gym & Golf Green

2. 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 ¥33,254
¥69,437 total
includes taxes & fees
Nov 8 - Nov 9
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

3. 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 ¥47,072
¥87,019 total
includes taxes & fees
Nov 16 - Nov 17
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

4. NEW private studio 1.1 miles to beach in East Lyme

NEW private studio 1.1 miles to beach in East Lyme
East Lyme
The price is ¥17,102
¥21,567 total
includes taxes & fees
Nov 9 - Nov 10
NEW private studio 1.1 miles to beach in East Lyme

5. 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 ¥108,883
¥207,036 total
includes taxes & fees
Nov 12 - Nov 13
Charming beach home, complete with pool & cozy guest house!

6. The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (8 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is ¥16,848
¥52,988 total
includes taxes & fees
Dec 2 - Dec 3
The Bay Cottage · Rocky Neck Park, Beach & Niantic

7. 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 ¥114,804
¥180,955 total
includes taxes & fees
Nov 6 - Nov 7
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

8. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is ¥23,774
¥42,793 total
includes taxes & fees
Nov 16 - Nov 17
Family Stays: Middletown, CT

9. 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 ¥23,385
¥62,407 total
includes taxes & fees
Nov 17 - Nov 18
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

10. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.4 out of 10, Exceptional, (93 reviews)
"This is a great location, walking distance to the green and other sites. It also worked well for our girls trip of 4 women."
United States
Liz H.
The price is ¥47,505
¥97,227 total
includes taxes & fees
Nov 9 - Nov 10
Historic New England home ,Reunions Beach pass

11. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ¥20,902
¥47,156 total
includes taxes & fees
Nov 12 - Nov 13
Once the old Schools house now a newly furnished Apartment

12. Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is ¥25,510
¥71,617 total
includes taxes & fees
Nov 9 - Nov 10
Cozy basement apartment with private bathroom, kitchen and entrance.

13. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (75 reviews)
"All aspects of our stay were excellent!"
United States
Lori G.
The price is ¥14,109
¥36,970 total
includes taxes & fees
Nov 11 - Nov 12
Cozy, comfy,quiet &close to casinos

14. Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
New London
8.0 out of 10, Very good, (31 reviews)
"Good location, great price, communication always great with the host. Accommodations were clean, decorative and comfortable. Heat and air, family friendly, and neat. Will return and recommend to friends and family!"
United States
Alicia W.
The price is ¥13,824
¥36,120 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

15. Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA
Montville
10.0 out of 10, Exceptional, (4 reviews)
"A lovely quick overnight."
United States
Bonnie H.
The price is ¥21,791
¥50,976 total
includes taxes & fees
Nov 9 - Nov 10
Thames River Cottage · Near Casinos - USCGA

16. Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (13 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is ¥24,039
¥65,816 total
includes taxes & fees
Nov 9 - Nov 10
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

17. Lakeside Bliss

Lakeside Bliss
East Lyme
9.6 out of 10, Exceptional, (32 reviews)
"Lovely house - excellently equipped and fun decor. The owner was gracious and flexible and the location is beautiful. "
United States
Brenda M.
The price is ¥56,863
¥79,605 total
includes taxes & fees
Dec 5 - Dec 6
Lakeside Bliss

18. Coastal retreat, short walk to downtown!

Coastal retreat, short walk to downtown!
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"Check-in was very easy, kitchen was well stocked with basics, lots of towels and toiletries. Perfect space and location for our family weekend. Great host recommendations for places to visit as well!"
United States
Hannah R.
The price is ¥46,438
¥67,272 total
includes taxes & fees
Nov 30 - Dec 1
Coastal retreat, short walk to downtown!

19. Winner's Getaway - 2mi to Mohegan Sun

Winner's Getaway - 2mi to Mohegan Sun
Westside Norwich
10.0 out of 10, Exceptional, (14 reviews)
"Excellent on all points!"
United States
DAVID C.
The price is ¥32,303
¥84,654 total
includes taxes & fees
Nov 8 - Nov 9
Winner's Getaway - 2mi to Mohegan Sun

20. Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
9.8 out of 10, Exceptional, (27 reviews)
"Our host was amazing from the first day we booked through checkout. The property was so much fun and the views were incredible. No complaints!"
United States
Kristine E.
The price is ¥46,728
¥108,470 total
includes taxes & fees
Nov 9 - Nov 10
Thames River Retreat · CT College+Casinos+USCGA
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.

Learn more about Chester

Charming galleries and local shops line Main Street, where you'll find handcrafted jewelry and Connecticut River Valley artwork. Catch a performance at the Goodspeed Opera House in East Haddam or kayak Chester Creek when summer temperatures rise.

A calm lake surrounded by vibrant autumn foliage.

Top reviews in Chester

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