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Check prices for these dates

Tonight
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sep - 6 Sep

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Our top choices for Winchester hotels

Hotel
Reserve now, pay later
Breakfast included
Pet friendly
Wifi Included
Front of property
Front of property
Luxury Suite, 1 King Bed, Balcony, Garden View | Living area
Interior detail

1. Manor House Inn

Manor House Inn
Norfolk
United States
Kevin
AED 1,124
AED 1,247 total
includes taxes & fees
31 Aug - 1 Sep
Manor House Inn
Premium bedding, down comforters, Select Comfort beds, in-room safe
Exterior
Fitness facility
Lobby

2. Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
Torrington
United States
Carol
AED 441
AED 507 total
includes taxes & fees
24 Aug - 25 Aug
Americas Best Value Inn Torrington CT
Library
43-inch LCD TV with digital channels, streaming services
Interior
Library

3. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
Cheryl
AED 649
AED 746 total
includes taxes & fees
24 Aug - 25 Aug
Blackberry River Inn
Desk, cribs (free), rollaway beds (surcharge), WiFi (free)
Exterior
Property amenity
Exterior

4. Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
Torrington
United States
Juan
AED 340
AED 391 total
includes taxes & fees
26 Aug - 27 Aug
Days Inn by Wyndham Torrington
Exterior
Aerial view
Exterior
1 bedroom, bed sheets

5. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Regina
AED 386
AED 444 total
includes taxes & fees
24 Aug - 25 Aug
Locust Tree Bed and Breakfast LLC
Garden
Standard Double Room, 1 Queen Bed | Desk, laptop workspace, WiFi (free), individually decorated
Living area
Executive House, Multiple Beds | Living area

6. Sunny Peace Homestay

Sunny Peace Homestay
Harwinton
United States
Dean
AED 479
AED 762 total
includes taxes & fees
24 Aug - 25 Aug
Sunny Peace Homestay
Exterior
Seasonal outdoor pool
Mews Garden Room | Terrace/patio
44-inch Smart TV with digital channels, Netflix, Hulu

7. Belden House & Mews

Belden House & Mews
Litchfield Historic District
United States
laura
AED 1,604
AED 1,992 total
includes taxes & fees
8 Sep - 9 Sep
Belden House & Mews
Restaurant
Terrace/patio
Rooftop terrace
Suite (Chamber) | In-room safe, WiFi (free)

8. The Abner Hotel

The Abner Hotel
Litchfield Historic District
United States
Eduardo
AED 514
AED 592 total
includes taxes & fees
17 Sep - 18 Sep
The Abner Hotel
Front of property
Exterior detail
Dinner served
Indoor wedding

9. Gedney Farm

Gedney Farm
Great Barrington
United States
Jane
AED 830
AED 911 total
includes taxes & fees
24 Aug - 25 Aug
Gedney Farm
Breakfast, lunch, dinner and brunch served
Interior
Thayer House, Room 201, 1 King bed, Jetted tub | Premium bedding, WiFi (free), individually decorated
Thayer House, Room 201, 1 King bed, Jetted tub | Living area | 32-inch TV with cable channels

10. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
AED 1,171
AED 1,413 total
includes taxes & fees
1 Sep - 2 Sep
The Old Inn On The Green
Library
King Cabin Room | Premium bedding, down comforters, pillowtop beds, minibar
Lobby sitting area
Garden view

11. The Litchfield Inn

The Litchfield Inn
Litchfield
United States
Sandra
AED 1,003
AED 1,154 total
includes taxes & fees
24 Aug - 25 Aug
The Litchfield Inn
WiFi (free), bed sheets
2 Double Beds | WiFi (free), bed sheets
Front of property
WiFi (free), bed sheets

12. Hitching Post Country Motel

Hitching Post Country Motel
Cornwall Bridge
United States
leo
AED 477
AED 549 total
includes taxes & fees
24 Aug - 25 Aug
Hitching Post Country Motel
Property entrance
Hypo-allergenic bedding available, blackout drapes, iron/ironing board
Interior
Interior

13. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
Granby
United States
Valerie
AED 514
AED 571 total
includes taxes & fees
1 Sep - 2 Sep
Truman Gillet House Bed & Breakfast
The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds
The Loft Suite | Terrace/patio
The Garden Suite | Private kitchen | Coffee/tea maker, stovetop, dishwasher, electric kettle
The Loft Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

14. 9 Academy

9 Academy
Salisbury
United States
Gina
AED 2,126
AED 2,445 total
includes taxes & fees
24 Aug - 25 Aug
9 Academy
Reception hall
Indoor pool, sun loungers
Front of property
Front of property

15. Simsbury Inn

Simsbury Inn
Simsbury Center
United States
Rachel
AED 878
AED 1,090 total
includes taxes & fees
16 Sep - 17 Sep
Simsbury Inn
John Harney Suite | Minibar, desk, iron/ironing board, WiFi (free)
Restaurant
Exterior
Outdoor dining

16. The White Hart

The White Hart
Salisbury
United States
William
AED 1,261
AED 1,450 total
includes taxes & fees
24 Aug - 25 Aug
The White Hart
Exterior
Exterior
Reception
Front of property

17. Simsbury 1820 House

Simsbury 1820 House
Simsbury Center
United States
Thomas
AED 621
AED 777 total
includes taxes & fees
24 Aug - 25 Aug
Simsbury 1820 House
BBQ/picnic area
Exterior
Restaurant
Seasonal outdoor pool, pool umbrellas, sun loungers

18. Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon
Avon
United States
Laura
AED 559
AED 642 total
includes taxes & fees
13 Sep - 14 Sep
Residence Inn by Marriott Hartford Avon
Interior detail
Interior detail
Interior detail
Wilder House Berkshires Room 1 | Premium bedding, blackout drapes, WiFi (free), individually decorated

19. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Jennifer
AED 722
AED 806 total
includes taxes & fees
1 Sep - 2 Sep
Wilder House Berkshires
Porch
Outdoor wedding area
Penthouse (Penthouse Suite) | Premium bedding, in-room safe, desk, soundproofing
Cottage, Lakeside | Terrace/patio

20. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
United States
Stacie
AED 790
AED 909 total
includes taxes & fees
22 Sep - 23 Sep
Interlaken Inn & Resort
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Stay near popular Winchester attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
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Platt Hill State Park

You can take time to visit Platt Hill State Park during your travels to Winchester.
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Northwestern Connecticut Community College

Walk around the campus at Northwestern Connecticut Community College as part of your travels around Winchester.
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The Marina at Highland Lake

Explore the waterfront in Winchester with a trip to The Marina at Highland Lake.
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Winchester Historical Society

8.0/10 (1 review)
You can spend an afternoon exploring the galleries in Winchester Historical Society during your trip to Winchester. Take in the live music in this relaxing area.
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Rowley Fields

Explore the great outdoors at Rowley Fields, a lovely green space in Winchester.
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Walker Field

Explore the great outdoors at Walker Field, a lovely green space in Winchester.
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Northwestern Connecticut Community College Library

After visiting Northwestern Connecticut Community College Library, make a plan to see the other sights and activities in Winchester.
See properties

Top Winchester Hotel Reviews

Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"The staff at Simsbury 1820 were the highlight of the stay. They were expecially friendly and very helpful. They had some suggestions of things to do that were interesting and area specific. Understandably but a bit disappointing was the inadquacy of the plumbing. It's a very old building but toilets could be updated."
Jill 3-night trip
Posted 4 hours ago
Simsbury 1820 House
The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"Breakfast until 11am was very helpful"
Svetlana 1-night trip
Posted 11 hours ago
The Farmington Inn & Suites
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

10/10 Excellent
"Ice machines didn't work"
cindy 1-night trip
Posted 1 day ago
Home2 Suites by Hilton Bristol
The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"From the first time stepping on the property we felt welcome. The staff was accommodating and invited us to enjoy the amenities while we waited for our room (we were early for check in). We took advantage and walked the property before heading off to explore the area. When we returned, we checked into our dog friendly room (after grabbing a freshly baked chocolate chip cookie). The room was clean and comfortable and our dog enjoyed it as well. The next morning we took advantage of the fitness center and pool and enjoyed a hot breakfast on property (made to order omelets were a hit). Overall I cannot say enough good things about the staff, accommodations and amenities. Highly recommend."
Phillip 1-night trip
Posted 1 day ago
The Litchfield Inn
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Beautiful property with lovely pool and spa area. The rooms are beautifully decorated. The staff are all friendly, welcoming, and very helpful. The grounds and gardens are well maintained. The hiking trail is highly recommended. My room in the main house was a bit noisy; the room above mine appeared to be a utility room that was active early in the morning. I could hear footsteps throughout the day. The dinner was overrated, but the breakfast and lunch were delicious."
Mary 3-night trip
Posted 2 days ago
Mayflower Inn & Spa, Auberge Collection
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

10/10 Excellent
"Comfortable bed, clean room, stayed overnight for concert in area. Breakfast consisted of yogurt, cereals, bread/bagel, juice, coffee. No coffee maker in room."
Juan 1-night trip
Posted 4 days ago
Days Inn by Wyndham Torrington

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
AED 317
AED 365 total
24 Aug - 25 Aug
includes taxes & fees
PLYMOUTH MOTOR LODGE
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

492 East Main St Torrington CT
AED 340
AED 391 total
26 Aug - 27 Aug
includes taxes & fees
7.4/10 Good! (1,004 reviews)
Days Inn by Wyndham Torrington
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
AED 364
AED 418 total
24 Aug - 25 Aug
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Extended Stay America Suites Hartford Farmington
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT
AED 441
AED 507 total
24 Aug - 25 Aug
includes taxes & fees
5.6/10 (809 reviews)
Americas Best Value Inn Torrington CT
Hitching Post Country Motel

Hitching Post Country Motel

45 Kent Rd S Cornwall Bridge CT
AED 477
AED 549 total
24 Aug - 25 Aug
includes taxes & fees
6.6/10 (108 reviews)
Hitching Post Country Motel
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

301 Colt Hwy Farmington CT
AED 509
AED 585 total
1 Sep - 2 Sep
includes taxes & fees
Hampton Inn & Suites Hartford/Farmington

Frequently asked questions

What's the best place for a stay in Winchester?
Sheraton Hartford Hotel at Bradley Airport, located 21.9 mi (35.2 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Homewood Suites by Hilton Hartford-Farmington and The Farmington Inn & Suites. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental in Winchester?
Lakefront Fall Foliage in New England Just 2 Hours From NYC: This vacation home rental outside of Winchester is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a private yard and a selection of games. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! You'll find that most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
To access more information about picking new dates or cancelling your trip to Winchester, head over to our customer service page.
What are some hotels with pools in Winchester?
Homewood Suites by Hilton Hartford-Farmington: Features a snack bar/deli, an indoor pool, and buffet. Avon Old Farms Hotel and Mayflower Inn & Spa, Auberge Collection are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester are sure to find plenty to explore and enjoy. In Winchester, there are 19 hotels and other accommodations to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Favorite places to visit include Highland Lake, Burr Pond State Park, and The Marina at Highland Lake. A couple of additional sights to add to your agenda are Platt Hill State Park and Laurel Lanes. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.