Title: Book the Best BOUTIQUE Hotels in Cheshire in 2025 | Expedia.ca

  

[Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d183057.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d183057.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d183057.Travel-Guide-Flights)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d183057.Destination-Travel-Guides)

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Photo by Tai Bui

# Find Boutique Hotels in Cheshire, CT from CA $203

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## Check availability on Cheshire Boutique Hotels

Tonight

[Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-24&endDate=2025-10-25&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-25&endDate=2025-10-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Cheshire Boutique Hotels

![Lobby](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/f224bafd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/f44c391a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/3fa625b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

Southbury

8.4/10

Very good

(1003)

"Great stay!!"

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

Geraldine

CA $159

CA $203 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.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=2025-11-07&endDate=2025-11-08&regionId=183057&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true)

## Top Cheshire Hotel Reviews

![Hyatt Place Milford / New Haven](//images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg)

### Hyatt Place Milford / New Haven

10/10 Excellent

"Rooms look old some of the furniture looks well used"

[](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information)

![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg)

### New Haven Hotel

10/10 Excellent

"Great location and the staff was warm and friendly. Stay here. "

[](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information)

## Frequently asked questions

### What's there to see and do in Cheshire?

> Enjoy the great selection of restaurants while you're in the area. Barker Character, Comic and Cartoon Museum, Cheshire Hollow Farm, and Mount Southington Ski Area are some of the local sights worth visiting. You might also like to explore more of the area and take in additional sights like Hubbard Park, Toyota Oakdale Theatre, and Palace Theatre while you're here.

### What kind of weather should I plan for when I travel to Cheshire?

> Understanding the weather in Cheshire will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Cheshire is 54 inches.

### What's the best way to get to my boutique hotel in Cheshire?

> You have a few options for traveling to and around Cheshire. The nearest major airport is Oxford, CT (OXC-Waterbury - Oxford), which is located 12 mi (19.3 km) from the heart of the city. If you'd like to explore around the area, you may want a rental car for your journey.

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