Title: Chester Vacation Rentals from $171: Search Short-Term Rentals | Expedia.com

[Chester Travel Guide](https://expedia.com/Chester.dx183058)[Hotels in Chester](https://expedia.com/Chester-Hotels.d183058.Travel-Guide-Hotels)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d183058.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d183058.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/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

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=183058&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/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 three months

[May 22 - May 24](https://www.expedia.com/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)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=183058&startDate=2026-06-19&endDate=2026-06-21&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 rentals

![View from property](https://images.trvl-media.com/lodging/111000000/110240000/110235400/110235311/b135be5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/111000000/110240000/110235400/110235311/544f5445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/111000000/110240000/110235400/110235311/ca76e60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, bed sheets](https://images.trvl-media.com/lodging/111000000/110240000/110235400/110235311/342b45b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

East Haddam

9.6/10

Exceptional

(120 reviews)

"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "

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

Aliah

$149 nightly

$171 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/East-Haddam-Hotels-Postcard-Cabins-Machimoodus.h110235311.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)

![Interior](https://images.trvl-media.com/lodging/91000000/90770000/90765600/90765591/a7ea2ff2.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)

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

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

New London

8.0/10

Very Good

(17 reviews)

"Needed an inexpensive place to stay for a trade show event. This was 20 minutes from Mohegan and perfect for me and an employee. "

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

Hippy P.

$179 nightly

$203 total

Mar 3 - Mar 4

Total with taxes and fees

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

![Living area](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/07929bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/98cb4c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/b8b9f031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/f4b0f948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Tiny Cottage at Clem & Clyde's

[](https://www.expedia.com/Montville-Hotels-The-Tiny-Cottage-At-Clem-Clydes.h122919838.Hotel-Information)

Oakdale,

10/10

Exceptional

(6 reviews)

"Cottage was perfect! The fresh eggs given to us by the host made for an awesome breakfast! The host was great! My 2 energetic boys loved every animal. The host made sure to take my boys through every fence/gate there was to get my boys front and center with the animals. This isn’t just about money him seeing my boys smile and run around with the animals definitely made his day! Left about an hour ago and my boys already asked 17 times when we are going back! "

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

jeff

$115 nightly

$129 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Montville-Hotels-The-Tiny-Cottage-At-Clem-Clydes.h122919838.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/2ca462c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/77ded06a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/29b6a8ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/30204b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Stern at Soundview · Beach+Ocean+Sunrise

[](https://www.expedia.com/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information)

Old Lyme

10/10

Exceptional

(3 reviews)

"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "

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

Lylian

$189 nightly

$212 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.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)

![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)

![Interior](https://images.trvl-media.com/lodging/83000000/82960000/82951600/82951570/ff886fbb.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)

### Winner's Getaway - 2mi to Mohegan Sun

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

Westside Norwich

10/10

Exceptional

(12 reviews)

"Close to casino, would recommend"

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

Joe M.

$457 nightly

$478 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/105000000/104330000/104323600/104323511/bbfdc6ba.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)

![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)

### Cozy, comfy,quiet &close to casinos

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

Montville

9.6/10

Exceptional

(48 reviews)

"Very nice place to stay clean and quiet and close to the casino where I ended up losing 5000"

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

John c.

$250 nightly

$283 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Montville-Hotels-Cozy.h104323511.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)

![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)

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

![Dining](https://images.trvl-media.com/lodging/115000000/114410000/114400800/114400746/20f06711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

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

Montville

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.

$286 nightly

$324 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Spa](https://images.trvl-media.com/lodging/120000000/119510000/119503800/119503715/62fdad7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Spa](https://images.trvl-media.com/lodging/120000000/119510000/119503800/119503715/6b12f074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119510000/119503800/119503715/f1848242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119510000/119503800/119503715/c74214af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun

[](https://www.expedia.com/Norwich-Hotels-Luxe-Condo-In-Norwich-Less-Than-3-Minutes-From-Mohegan-Sun.h119503715.Hotel-Information)

Norwich

9.6/10

Exceptional

(9 reviews)

"We had a lovely stay at Cindy’s Villa. Close to the pool, and just great amenities. We would stay again"

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

Elisabeth W.

$191 nightly

$216 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Norwich-Hotels-Luxe-Condo-In-Norwich-Less-Than-3-Minutes-From-Mohegan-Sun.h119503715.Hotel-Information)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/65f83363.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/92000000/91720000/91713800/91713725/034a5b48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/b3ddf07f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91720000/91713800/91713725/w750h486x0y3-ef058f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

[](https://www.expedia.com/Higganum-Hotels-Cozy-Comforts-Country-Living-At-Its-Finest-Just-10-Min-To-Downtown-Middletown.h91713725.Hotel-Information)

Haddam

10/10

Exceptional

(28 reviews)

"Fantastic experience from beginning to end! Loved every minute of my stay! "

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

Jody U.

$226 nightly

$256 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Higganum-Hotels-Cozy-Comforts-Country-Living-At-Its-Finest-Just-10-Min-To-Downtown-Middletown.h91713725.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)

![Dining](https://images.trvl-media.com/lodging/107000000/106390000/106381400/106381352/cc3d5620.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)

![3 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106390000/106381400/106381352/a001054f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Entire Vacation Home in Waterford Connecticut

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

Waterford

8.8/10

Excellent

(3 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.

$377 nightly

$427 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/d84925d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/deffdcef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/a991ed0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/62b9e13d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The gardners Cottage 1 mile from long Island Sound - pet friendly

[](https://www.expedia.com/Clinton-Hotels-The-Gardners-Cottage-1-Mile-From-Long-Island-Sound-Pet-Friendly.h88510197.Hotel-Information)

Clinton

10/10

Exceptional

(21 reviews)

"Enjoyed our stay - Highly recommend!"

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

Mary S.

$231 nightly

$261 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Clinton-Hotels-The-Gardners-Cottage-1-Mile-From-Long-Island-Sound-Pet-Friendly.h88510197.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111590000/111580300/111580292/0f4ff70e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111590000/111580300/111580292/b7591d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111590000/111580300/111580292/9eb51e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111590000/111580300/111580292/7a8ef60f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Lakefront Tiny House

[](https://www.expedia.com/East-Lyme-Hotels-Cozy-Lakefront-Tiny-House.h111580292.Hotel-Information)

East Lyme

10/10

Exceptional

(3 reviews)

"It was a peaceful and quant "

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

Patricia M.

$233 nightly

$264 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/East-Lyme-Hotels-Cozy-Lakefront-Tiny-House.h111580292.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/97000000/96500000/96499800/96499733/ca43bb7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96500000/96499800/96499733/8e982e3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96500000/96499800/96499733/1c1b3c17.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/97000000/96500000/96499800/96499733/5905d816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Thames River Cottage · Near Casinos - USCGA

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

Montville

10/10

Exceptional

(2 reviews)

"A lovely quick overnight."

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

Bonnie H.

$266 nightly

$298 total

Mar 3 - Mar 4

Total with taxes and fees

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

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/947697cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/9ddc24ce.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/bec199ec.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/106000000/105310000/105302000/105301933/0298db95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rogers Lake House (87) · CT College+Beach+USCGA

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

Old Lyme

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.

$420 nightly

$472 total

Mar 3 - Mar 4

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/66000000/65400000/65396400/65396309/1fef5fbb.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)

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

### Once the old Schools house now a newly furnished Apartment

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

Wallingford Center

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.

$284 nightly

$302 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/2db3f072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/02f647fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/0888acaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/646c7316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All New 1BR with tons of Charm

[](https://www.expedia.com/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information)

Wallingford Center

9.8/10

Exceptional

(8 reviews)

"Charming, unique, and very comfortable. Would surely stay again. "

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

David S.

$284 nightly

$302 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.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/e689a456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/95b993b0.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)

### LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

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

Clinton

10/10

Exceptional

(4 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.

$435 nightly

$492 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100700000/100695600/100695579/w1018h683x3y0-fb2af3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100700000/100695600/100695579/w952h683x36y0-498afb43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100700000/100695600/100695579/w868h683x78y0-fc345448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100700000/100695600/100695579/w920h683x52y0-2ef64a29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

[](https://www.expedia.com/Norwich-Hotels-Cozy-Villa-Spa-Retreat-Near-Mohegan.h100695579.Hotel-Information)

Norwich

10/10

Exceptional

(43 reviews)

"Great location"

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

Jeff F.

$207 nightly

$234 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Norwich-Hotels-Cozy-Villa-Spa-Retreat-Near-Mohegan.h100695579.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/dad41f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/ac508f02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/4b86b544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/eacee686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All New Studio apartment in center of town

[](https://www.expedia.com/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.Hotel-Information)

Wallingford Center

10/10

Exceptional

(2 reviews)

"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."

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

Nadine C.

$297 nightly

$318 total

Mar 7 - Mar 8

Total with taxes and fees

[](https://www.expedia.com/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.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)

![Dining](https://images.trvl-media.com/lodging/115000000/114190000/114187500/114187476/87e567b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom house with WiFi, AC in lovely Waterford

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

Waterford

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.

$326 nightly

$369 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Waterford-Hotels-Charming-2-Bedroom-House-With-WiFi.h114187476.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.com/Hotel-Search?startDate=2026-03-14&endDate=2026-03-15&regionId=183058&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CABIN)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VILLA)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CONDO)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America&regionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=HOUSE_BOAT)

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## Top Chester Hotel Reviews

![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

"Spotless room great staff"

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

![Clarion Inn](https://images.trvl-media.com/lodging/1000000/10000/7600/7519/36377da0_y.jpg)

### Clarion Inn

10/10 Excellent

"Excellent "

[](https://expedia.com/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information)

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

### Mohegan Sun

10/10 Excellent

"Great experience!"

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

![Sleep Inn & Suites Niantic North](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/cf19af3a_y.jpg)

### Sleep Inn & Suites Niantic North

10/10 Excellent

"Staff were super friendly, Room was great. Breakfast was yummy and the pool was warm! Handled a horrible snow storm very well!"

[](https://expedia.com/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information)

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

### Hampton Inn Norwich

10/10 Excellent

"The Hot Tub was amazing after a long day at work on Saturday. Clean and great temp!"

[](https://expedia.com/Norwich-Hotels-Hampton-Inn-Norwich.h18258245.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

"Very clean room. Staff was excellent. Very welcoming. Would and will stay there again, no question. "

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

![Hampton Inn & Suites Rocky Hill - Hartford South](https://images.trvl-media.com/lodging/24000000/23520000/23512500/23512415/5b8179ec_y.jpg)

### Hampton Inn & Suites Rocky Hill - Hartford South

10/10 Excellent

"Great hotel! Very clean, amazing breakfast, Carrie was very attentive at the front desk. Nearby the highway and other stores."

[](https://expedia.com/Hartford-Hotels-Hampton-Inn-Suites-Rocky-Hill-Hartford-South.h23512415.Hotel-Information)

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg)

### Water's Edge Resort & Spa

10/10 Excellent

"Everything was wonderful Very nice staff Room was very clean Bed was comfy View was wonderful "

[](https://expedia.com/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.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

"The room was very clean. Would stay again"

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

## Find out more about Chester

**Everything you need to know about Chester vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chester vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $171 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chester rentals**

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
- All accommodation types in Chester

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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Chester ](https://expedia.com/Chester-Private-Vacation-Homes.d183058-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Chester ](https://expedia.com/Chester-Cottages.d183058-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Chester ](https://expedia.com/Chester-Apartments.d183058-aaApartments.Travel-Guide-Accommodation)
- [Motels in Chester ](https://expedia.com/Chester-Motels.d183058-aaMotels.Travel-Guide-Accommodation)
- [Condo Rentals in Chester ](https://expedia.com/Chester-Condos.d183058-aaCondos.Travel-Guide-Accommodation)
- [Villas in Chester ](https://expedia.com/Chester-Villas.d183058-aaVillas.Travel-Guide-Accommodation)
- [B&B in Chester ](https://expedia.com/Chester-Bed-And-Breakfast.d183058-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Resorts in Chester ](https://expedia.com/Chester-Resorts.d183058-aaResorts.Travel-Guide-Accommodation)
- [Cabin Rentals in Chester ](https://expedia.com/Chester-Cabins.d183058-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Chester ](https://expedia.com/Chester-Agritourism.d183058-aaAgritourism.Travel-Guide-Accommodation)
- [Inns in Chester ](https://expedia.com/Chester-Inns.d183058-aaInns.Travel-Guide-Accommodation)
- [Houseboats in Chester ](https://expedia.com/Chester-Houseboats.d183058-aaHouseboats.Travel-Guide-Accommodation)
- [Aparthotels in Chester ](https://expedia.com/Chester-Apart-Hotels.d183058-aaApartHotels.Travel-Guide-Accommodation)
- [RV Parks in Chester ](https://expedia.com/Chester-RV-Parks.d183058-aaRVParks.Travel-Guide-Accommodation)
- [Guest Houses in Chester ](https://expedia.com/Chester-Guest-Houses.d183058-aaGuestHouses.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chester?

### What are some of the best vacation rentals in Chester?

### How many vacation rentals are there in Chester?

### What’s there to see and do in Chester?

### What’s a vacation rental in Chester like?

### Expedia's Latest Trends

Hotels

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- [Mystic Hotels](https://expedia.com/Mystic-Hotels.d9007.Travel-Guide-Hotels)
- [Wallingford Hotels](https://expedia.com/Wallingford-Hotels.d7533.Travel-Guide-Hotels)
- [New Haven Hotels](https://expedia.com/New-Haven-Hotels.d180036.Travel-Guide-Hotels)
- [Fairfield Hotels](https://expedia.com/Fairfield-Hotels.d8066.Travel-Guide-Hotels)
- [Stamford Hotels](https://expedia.com/Stamford-Hotels.d602523.Travel-Guide-Hotels)
- [West Hartford Hotels](https://expedia.com/West-Hartford-Hotels.d7700.Travel-Guide-Hotels)
- [Shelton Hotels](https://expedia.com/Shelton-Hotels.d9795.Travel-Guide-Hotels)
- [Greenwich Hotels](https://expedia.com/Greenwich-Hotels.d8045.Travel-Guide-Hotels)
- [Waterbury Hotels](https://expedia.com/Waterbury-Hotels.d10425.Travel-Guide-Hotels)

Flights

- [Flights to New Haven](https://expedia.com/Cheap-Flights-To-New-Haven.d180036.Travel-Guide-Flights)
- [Flights from Hartford](https://expedia.com/lp/flights/180005/flights-from-hartford)
- [Flights to Hartford](https://expedia.com/Cheap-Flights-To-Hartford.d180005.Travel-Guide-Flights)

Cars

- [Car rentals in New Haven](https://expedia.com/Car-Rentals-In-New-Haven.d180036.Car-Rental-Guide)
- [Car rentals in Stamford](https://expedia.com/Car-Rentals-In-Stamford.d602523.Car-Rental-Guide)
- [Car rentals in Bridgeport](https://expedia.com/Car-Rentals-In-Bridgeport.d525.Car-Rental-Guide)
- [Car rentals in Hartford](https://expedia.com/Car-Rentals-In-Hartford.d180005.Car-Rental-Guide)
- [Car rentals in Danbury](https://expedia.com/Car-Rentals-In-Danbury.d6046722.Car-Rental-Guide)
- [Car rentals in Waterbury](https://expedia.com/Car-Rentals-In-Waterbury.d10425.Car-Rental-Guide)

Activities

- [Things to do in Hartford](https://expedia.com/Things-To-Do-In-Hartford.d180005.Travel-Guide-Activities)

General

- [Visit Hartford](https://expedia.com/Hartford.dx180005)
- [Visit Stamford](https://expedia.com/Stamford.dx602523)
- [Visit New Haven](https://expedia.com/New-Haven.dx180036)

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