Hotels in Winchester

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Where to stay in Winchester?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Winchester on Hotels.com. These Winchester hotels consistently deliver on quality, location and traveler experience. Last updated on September 18, 2026.

43-inch LCD TV with digital channels, streaming services

1. Blackberry River Inn

Norfolk

CNY1,006

CNY1,157 total

includes taxes & fees

Sep 20 - Sep 21

Desk, cribs (free), rollaway beds (surcharge), WiFi (free)

2. Days Inn by Wyndham Torrington

Torrington

CNY587

CNY675 total

includes taxes & fees

Oct 18 - Oct 19

Premium bedding, down comforters, Select Comfort beds, in-room safe

3. Americas Best Value Inn Torrington CT

Torrington

CNY740

CNY851 total

includes taxes & fees

Oct 20 - Oct 21

Luxury Suite, 1 King Bed, Balcony, Garden View | Living area

4. Manor House Inn

Norfolk

CNY2,206

CNY2,449 total

includes taxes & fees

Sep 21 - Sep 22

5. Locust Tree Bed and Breakfast LLC

East Canaan

CNY704

CNY810 total

includes taxes & fees

Sep 20 - Sep 21

6. Simsbury 1820 House

Simsbury Center

CNY1,267

CNY1,573 total

includes taxes & fees

Sep 21 - Sep 22

Hypo-allergenic bedding available, blackout drapes, iron/ironing board

7. Truman Gillet House Bed & Breakfast

Granby

CNY939

CNY1,042 total

includes taxes & fees

Sep 20 - Sep 21

King Cabin Room | Premium bedding, down comforters, pillowtop beds, minibar

8. The Litchfield Inn

Litchfield

CNY1,895

CNY2,179 total

includes taxes & fees

Sep 30 - Oct 1

9. Residence Inn by Marriott Hartford Avon

Avon

CNY963

CNY1,108 total

includes taxes & fees

Sep 27 - Sep 28

10. Gedney Farm

Great Barrington

CNY1,539

CNY1,688 total

includes taxes & fees

Sep 20 - Sep 21

Suite (Chamber) | In-room safe, WiFi (free)

11. The Abner Hotel

Litchfield Historic District

CNY2,082

CNY2,394 total

includes taxes & fees

Sep 30 - Oct 1

12. Avon Old Farms Hotel

Avon

CNY1,292

CNY1,632 total

includes taxes & fees

Oct 8 - Oct 9

Penthouse (Penthouse Suite) | Premium bedding, in-room safe, desk, soundproofing

13. Interlaken Inn & Resort

Lakeville

CNY1,282

CNY1,474 total

includes taxes & fees

Oct 18 - Oct 19

Deluxe Room, 1 King Bed | Hypo-allergenic bedding available, down comforters, in-room safe, desk

14. The Farmington Inn & Suites

Farmington

CNY1,133

CNY1,419 total

includes taxes & fees

Sep 20 - Sep 21

Desk, iron/ironing board, WiFi (free), bed sheets

15. Extended Stay America Suites Hartford Farmington

Farmington

CNY737

CNY848 total

includes taxes & fees

Sep 20 - Sep 21

16. Simsbury Inn

Simsbury Center

CNY1,906

CNY2,339 total

includes taxes & fees

Sep 29 - Sep 30

Room (5) | Iron/ironing board (on request), WiFi (free)

17. The Millerton Inn

Millerton

CNY1,684

CNY1,905 total

includes taxes & fees

Sep 20 - Sep 21

18. Wilder House Berkshires

Sheffield

CNY1,293

CNY1,444 total

includes taxes & fees

Sep 27 - Sep 28

19. Cornwall Inn and Lodge

Cornwall Bridge

CNY1,419

CNY1,632 total

includes taxes & fees

Sep 21 - Sep 22

20. Hitching Post Country Motel

Cornwall Bridge

CNY872

CNY1,002 total

includes taxes & fees

Sep 20 - Sep 21

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Go beyond your typical stay in Winchester

Pet friendly

Pool

Family friendly

Hot tub

Cottage

Top landmarks in Winchester

Highland Lake

Highland Lake is 2.6 mi (4.3 km) from central Winchester, why not stop by during your stay.

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Northwestern Connecticut Community College

If you'd like to get a taste of Winchester student life, check out Northwestern Connecticut Community College, in the heart of the town.

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The Marina at Highland Lake

Imagine strolling along The Marina at Highland Lake for some great waterfront pics. It's located 1.8 mi (2.9 km) from central Winchester.

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Winchester Historical Society

8.0/10 (1 review)

You might want to get your camera out and head to Winchester Historical Society— just one of the landmarks located 1.9 mi (3.1 km) from central Winchester.

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Platt Hill State Park

Platt Hill State Park is 2.4 mi (3.8 km) from central Winchester, why not stop by during your stay.

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American Mural Project

The center of Winchester is home to cultural attractions like American Mural Project, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Northwestern Connecticut Community College, Highland Lake, and The Village.

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Tatro Pond

Tatro Pond is 2.5 mi (4.1 km) from central Winchester, why not stop by during your stay.

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Northwestern Connecticut Community College Library

Northwestern Connecticut Community College Library is worth a visit when in central Winchester.

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Check out reviews of Winchester hotels guests love

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent

"Very clean hotel"

Days Inn by Wyndham Torrington

10/10 Excellent

"Very clean room. I was surprised. Had shampoo and body wash supplied. No tube of lotion by sink so couldn’t TCB. Oh well. For price, would definitely stay there again."

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent

"Good location. Shuttle offered to wedding. Good venue for after party."

The Litchfield Inn

10/10 Excellent

"second time staying here! wonderful place"

Home2 Suites by Hilton Bristol

10/10 Excellent

"Great stay. We will be back!"

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent

"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."

Delamar West Hartford

10/10 Excellent

"Lovely, comfortable and clean room! Staff upon check-in (8pm) was helpful and friendly."

Frequently asked questions

How much does a hotel room cost in Winchester?

You can discover great hotels in Winchester from CNY675 with properties to suit all budgets and needs. If you're looking for an affordable hotel in Winchester that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.

How can I find deals and earn rewards at Winchester hotels?

Discover great deals on Winchester hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. And make sure to check out our last-minute deals on Winchester hotels.

Can I book Winchester hotels with free cancellation?

To book a refundable Winchester hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some popular hotels in central Winchester?

If you're looking for hotels in central Winchester, check out Rock Hall Luxe Lodging. Travelers love Rock Hall Luxe Lodging for its location, as well as the outdoor pool, hot tub and outdoor tennis court this bed & breakfast offers.

What hotels do travelers recommend in Winchester?

Guests like Days Inn by Wyndham Torrington and Americas Best Value Inn Torrington CT.

Can I book refundable accommodations in Winchester?

If you want the flexibility to change your plans to Winchester, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Winchester if I want a vacation rental instead of a hotel?

If you're looking for a good alternative to a hotel, browse our selection of 11 vacation homes. In addition, you can choose from 5 apartments.

What will the weather in Winchester be like during my vacation?

July and August are typically the warmest months in Winchester when the average temp is 67°F. January and February are the coldest months when the average temperature is 30°F. July and October are the months with the most rain.

Why should I book my Winchester hotel with Hotels.com?

There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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