Title: Chester Vacation Home Rentals from CA $292: Search Top Private Vacation Homes for Rent | Expedia.ca

[Hotels in Chester](https://expedia.ca/Chester-Hotels.d183058.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d183058.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d183058.Travel-Guide-Flights)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d183058.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d183058.Destination-Travel-Guides)

![Connecticut River Autumn Landscape with the view of landmark architectures on the woodland hill, a tranquil New England scenery](https://images.trvl-media.com/place/183058/c14a28ee-62e4-4e76-85a4-650e5a230000.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/183058/c14a28ee-62e4-4e76-85a4-650e5a230000.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester vacation homes

![Interior](https://images.trvl-media.com/lodging/83000000/82830000/82820400/82820354/26e77899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/83000000/82830000/82820400/82820354/a620bbe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82830000/82820400/82820354/292baab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82830000/82820400/82820354/19ce922b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Salem

[](https://www.expedia.ca/Salem-Hotels-Gardner-Lake-2-Queen1King2-BathLaundry-Private.h82820354.Hotel-Information)

10/10

Exceptional

(6 reviews)

"Place is nice would stay again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

nic

CA $152

CA $519 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Salem-Hotels-Gardner-Lake-2-Queen1King2-BathLaundry-Private.h82820354.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/87f067c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/423fe469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/8aa6190f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/01fcfbdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Lyme

[](https://www.expedia.ca/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

10/10

Exceptional

(5 reviews)

"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hemie J.

CA $138

CA $568 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/d4679987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/1c55c50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/9e705245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/544c1919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterford

[](https://www.expedia.ca/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information)

10/10

Exceptional

(11 reviews)

"We had a nice stay. Kitchen well stocked and house was clean and comfortable."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elaine A.

CA $156

CA $522 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/97000000/96500000/96499800/96499733/639c3b0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96500000/96499800/96499733/83b07e7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96500000/96499800/96499733/b97e6778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96500000/96499800/96499733/605d40ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Montville

[](https://www.expedia.ca/Montville-Hotels-Thames-River-Cottage.h96499733.Hotel-Information)

10/10

Exceptional

(2 reviews)

"A lovely quick overnight."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bonnie H.

CA $133

CA $402 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Montville-Hotels-Thames-River-Cottage.h96499733.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/115000000/114190000/114187500/114187476/c78f7795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114190000/114187500/114187476/66104531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114190000/114187500/114187476/ac410528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/115000000/114190000/114187500/114187476/8280e405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterford

[](https://www.expedia.ca/Waterford-Hotels-Charming-2-Bedroom-House-With-WiFi.h114187476.Hotel-Information)

10/10

Exceptional

(1 review)

"The home was very clean and welcoming."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle M.

CA $204

CA $500 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Waterford-Hotels-Charming-2-Bedroom-House-With-WiFi.h114187476.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/91000000/90770000/90765600/90765591/f675f793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90770000/90765600/90765591/340f2349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90770000/90765600/90765591/6b0c0082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90770000/90765600/90765591/51e593bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in New London

[](https://www.expedia.ca/New-London-Hotels-Cozy-2-Bedroom-Vacation-Home-Free-WiFi-Parking.h90765591.Hotel-Information)

8.0/10

Very good

(17 reviews)

"Very cute house with nice extra touches like 2 bottles of water and new toothpaste (perfect because we forgot ours!). "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christie P.

CA $147

CA $343 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/New-London-Hotels-Cozy-2-Bedroom-Vacation-Home-Free-WiFi-Parking.h90765591.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/115000000/114410000/114400800/114400746/c80e2ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114410000/114400800/114400746/627f1446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/115000000/114410000/114400800/114400746/25d234f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114410000/114400800/114400746/97bb15e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Montville

[](https://www.expedia.ca/Montville-Hotels-Cozy-3-Bedroom-House-Near-Mystic-And-Mohegan-Foxwood-Casinos.h114400746.Hotel-Information)

10/10

Exceptional

(5 reviews)

"The property was perfect for our trip. Wonderful stay and amazing contact with the hosttess. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Redebaron 7.

CA $177

CA $436 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Montville-Hotels-Cozy-3-Bedroom-House-Near-Mystic-And-Mohegan-Foxwood-Casinos.h114400746.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3f0d43b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/878d2c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/17c0663e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3a7a158a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Lyme

[](https://www.expedia.ca/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

9.0/10

Wonderful

(4 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah G.

CA $163

CA $495 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/113000000/112380000/112376100/112376012/14a45cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112380000/112376100/112376012/cb15d4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112380000/112376100/112376012/0ea47345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112380000/112376100/112376012/4164ab27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Montville

[](https://www.expedia.ca/Montville-Hotels-Shantok-Queen-Suites-Walk-To-Mohegan-CasinoWi-Fi.h112376012.Hotel-Information)

10/10

Exceptional

(2 reviews)

"This was just a quick one night, Stay. As we were at the casino for a concert. The house was a great location clean, access was easy. Everything was as was stated on the website. I would definitely stay there again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

CA $173

CA $537 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Montville-Hotels-Shantok-Queen-Suites-Walk-To-Mohegan-CasinoWi-Fi.h112376012.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/42181017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/ffcbfb18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/6924fd2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111110000/111107100/111107034/47595254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Family-Stays-In-Middletown.h111107034.Hotel-Information)

10/10

Exceptional

(20 reviews)

"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Harmony R.

CA $163

CA $314 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Middletown-Hotels-Family-Stays-In-Middletown.h111107034.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/105000000/104330000/104323600/104323511/116f18b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/105000000/104330000/104323600/104323511/2ecc6a8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104330000/104323600/104323511/856c96c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104330000/104323600/104323511/3b2d1c87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Montville

[](https://www.expedia.ca/Montville-Hotels-Cozy.h104323511.Hotel-Information)

9.6/10

Exceptional

(48 reviews)

"Great place to stay. I have nothing bad to say about the place."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jose M.

CA $177

CA $403 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Montville-Hotels-Cozy.h104323511.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/f4556137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/28ce53e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/c55a23f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90710000/90707200/90707157/d2e5a74a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

[](https://www.expedia.ca/Middletown-Hotels-24-Serenity-A-Lakefront-Cottage-Retreat.h90707157.Hotel-Information)

9.8/10

Exceptional

(21 reviews)

"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nichole N.

CA $101

CA $321 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Middletown-Hotels-24-Serenity-A-Lakefront-Cottage-Retreat.h90707157.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/50a4b3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/64f9f4d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/1fef5fbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/d8cf55dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wallingford Center

[](https://www.expedia.ca/Wallingford-Hotels-Once-The-Old-Schools-House-Now-A-Newly-Furnished-Apartment.h65396309.Hotel-Information)

9.0/10

Wonderful

(13 reviews)

"Excellent option for a short stay near the heart of it all in Wallingford."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeanette W.

CA $156

CA $395 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Wallingford-Hotels-Once-The-Old-Schools-House-Now-A-Newly-Furnished-Apartment.h65396309.Hotel-Information)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/da7468b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/601ebe37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/433534ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/108000000/107980000/107976300/107976290/f293483a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Berlin

[](https://www.expedia.ca/Berlin-Hotels-Private-Apartment-In-Berlin.h107976290.Hotel-Information)

9.2/10

Wonderful

(5 reviews)

"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daniel L.

CA $137

CA $405 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Berlin-Hotels-Private-Apartment-In-Berlin.h107976290.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/faf6d210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/96041570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/1b8a6cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119305500/119305470/eb680fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Cozy-Guest-Suite-In-Historic-Home.h119305470.Hotel-Information)

10/10

Exceptional

(1 review)

"Perfect for a single traveler. Clean, roomy, quaint room. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brooke

CA $201

CA $292 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Middletown-Hotels-Cozy-Guest-Suite-In-Historic-Home.h119305470.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/891accf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/55b895af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/021898ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/9036247c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westbrook

[](https://www.expedia.ca/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

10/10

Exceptional

(1 review)

"Perfect house for 6 guests. Loved that it was close to the beach."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shannon G.

CA $179

CA $677 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/eea5c652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a31fd902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a34caa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/e689a456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Clinton

[](https://www.expedia.ca/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elya D.

CA $164

CA $693 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/83000000/82960000/82951600/82951570/c079fb62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82960000/82951600/82951570/9a96c457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82960000/82951600/82951570/84135737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/83000000/82960000/82951600/82951570/e6487e36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westside Norwich

[](https://www.expedia.ca/Norwich-Hotels-Renovated-4BR-Close-To-Casinos.h82951570.Hotel-Information)

10/10

Exceptional

(12 reviews)

"Close to casino, would recommend"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joe M.

CA $208

CA $666 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Norwich-Hotels-Renovated-4BR-Close-To-Casinos.h82951570.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106390000/106381400/106381352/57ee2426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106390000/106381400/106381352/848d58eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106390000/106381400/106381352/be2c4e64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106390000/106381400/106381352/cc3d5620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterford

[](https://www.expedia.ca/Waterford-Hotels-Entire-Vacation-Home-In-Waterford-Connecticut.h106381352.Hotel-Information)

9.0/10

Wonderful

(2 reviews)

"Located so perfectly close to everything we wanted to do on vacation. The house was so clean and comfortable. Communication with the owner was A++. The neighbors were even so friendly and waving/smiling. It felt as if we were home. If we come back to that area again we hope this place will be available. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer A.

CA $258

CA $578 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Waterford-Hotels-Entire-Vacation-Home-In-Waterford-Connecticut.h106381352.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103050000/103041100/103041064/31af5648.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103050000/103041100/103041064/164317bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/104000000/103050000/103041100/103041064/3d136a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103050000/103041100/103041064/e6061ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterford

[](https://www.expedia.ca/Quaker-Hill-Hotels-Thames-River-Retreat-CT-CollegeCasinosUSCGA.h103041064.Hotel-Information)

10/10

Exceptional

(20 reviews)

"Beautiful home on the water. Home was very clean and well furnished. Would stay again/recommend."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christopher O.

CA $282

CA $815 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Quaker-Hill-Hotels-Thames-River-Retreat-CT-CollegeCasinosUSCGA.h103041064.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-11&endDate=2026-02-12&regionId=183058&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Villas

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Apartments

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=CONDO)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=CABIN)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=HOUSE_BOAT)

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## Top Chester Hotel Reviews

![Hampton Inn Norwich](https://images.trvl-media.com/lodging/19000000/18260000/18258300/18258245/d98f34e1_y.jpg)

### Hampton Inn Norwich

10/10 Excellent

"Staff was great. Clean facilities. "

[](https://expedia.ca/Norwich-Hotels-Hampton-Inn-Norwich.h18258245.Hotel-Information)

![Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area](https://images.trvl-media.com/lodging/1000000/810000/800500/800485/75539c58_y.jpg)

### Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

10/10 Excellent

"Clean, comfortable, room had everything needed, microwave, coffee, safe, blow dryer etc. The water pressure was great. Bathroom had a low light that was great as a nightlight. Sitting area was perfect for the guest who just wasn't ready to retire before everyone else and both tv's swiveled for better viewing. Continental breakfast was great with plenty to choose from. Didn't get to check them out but had a gym and pool as well. Valet was perfect for trip to Casino with hours until from 4PM TO 2AM. Stayed at other places nearby. This is by far the best."

[](https://expedia.ca/Montville-Hotels-Fairfield-By-Marriott-Inn-Suites-Uncasville-Groton-Area.h800485.Hotel-Information)

![Microtel Inn & Suites by Wyndham Uncasville Casino Area](https://images.trvl-media.com/lodging/1000000/810000/801800/801773/ed4520c7_y.jpg)

### Microtel Inn & Suites by Wyndham Uncasville Casino Area

10/10 Excellent

"Room very clean and quiet. Front desk AM shift person on 1/22 has a great personality. Very welcoming and friendly"

[](https://expedia.ca/Montville-Hotels-Microtel-Inn-Suites-By-Wyndham-Uncasville.h801773.Hotel-Information)

![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg)

### Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"I have stayed here a number of times, and each time the room has been spotless and smells fresh. The staff is very friendly and always offers to help in some way, whether it's to get the snow off my car or provide bottled water. I will be staying here again!"

[](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Hyatt Place Uncasville - Casino Area](https://images.trvl-media.com/lodging/3000000/2600000/2593900/2593874/46d6d7fc_y.jpg)

### Hyatt Place Uncasville - Casino Area

10/10 Excellent

"Staff was very courteous. "

[](https://expedia.ca/Montville-Hotels-Hyatt-Place-Mohegan-Sun.h2593874.Hotel-Information)

![Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy](https://images.trvl-media.com/lodging/111000000/110240000/110235400/110235311/400d8813_y.jpg)

### Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"i absolutely loved this place ! so cozy & a great place to just disconnect from the world . went during the winter time & the campfire worked wonderfully , as well as the heat/AC inside the cabin . the area was a little scary at night since there’s no streetlights but the comfort of this place made me feel very safe so no complaints here . & of course the staff was super helpful & had great hospitality (thank you Dominick !) & definitely somewhere i will be visiting again soon ! "

[](https://expedia.ca/East-Haddam-Hotels-Postcard-Cabins-Machimoodus.h110235311.Hotel-Information)

![Mohegan Sun](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/60dec0f3_y.jpg)

### Mohegan Sun

10/10 Excellent

"It was great, thanks!"

[](https://expedia.ca/Montville-Hotels-Mohegan-Sun.h894248.Hotel-Information)

![Motel 6 Niantic, CT - New London](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039681/0c062ad1_y.jpg)

### Motel 6 Niantic, CT - New London

10/10 Excellent

"The room was spotless the water was very hot which was great and the heat worked perfectly I was in the back which was very quiet slept like a baby !"

[](https://expedia.ca/Niantic-Hotels-Motel-6-Niantic.h1039681.Hotel-Information)

![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg)

### Motel 6 New Haven - Branford, CT

10/10 Excellent

"O"

[](https://expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.Hotel-Information)

## Find out more about Chester

## Chester Vacation Homes information

| Number of reviews | 145                |
| ----------------- | ------------------ |
| Accommodation     | 364 Vacation Homes |
| Lowest Price      | CA $292            |
| Highest Price     | CA $815            |

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