Find hotels in Winchester, CT from Rp1.439.946

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Check prices for these dates

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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Our top choices for Winchester hotels

Couples treatment room(s), steam room, body treatments, aromatherapy
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection
5.0 star property
Washington
9.2 out of 10, Wonderful, (55)
"Incredible place - will definitely return. "
United States
Andrew
The price is Rp14.862.172
Rp17.862.688 total
includes taxes & fees
26 Dec - 27 Dec
Mayflower Inn & Spa, Auberge Collection
Property grounds
Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (102)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
The price is Rp2.347.100
Rp2.605.281 total
includes taxes & fees
27 Dec - 28 Dec
Truman Gillet House Bed & Breakfast
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Cornwall Inn and Lodge

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (155)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is Rp3.547.474
Rp4.079.595 total
includes taxes & fees
26 Dec - 27 Dec
Cornwall Inn and Lodge
Lobby sitting area
The Litchfield Inn

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.0 out of 10, Wonderful, (963)
"A delightful stay from beginning to end - clean, bright, beautiful in a lovely are of the state. "
United States
Lori
The price is Rp4.870.568
Rp5.601.187 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Litchfield Inn
Lunch and dinner served
Delamar West Hartford

Delamar West Hartford

Delamar West Hartford
4.0 star property
West Hartford
9.8 out of 10, Exceptional, (1000)
"Clean room, great staff and overall warm atmosphere."
United States
Gavrosh
The price is Rp4.901.804
Rp5.888.880 total
includes taxes & fees
4 Jan - 5 Jan 2026
Delamar West Hartford
Front of property
Gedney Farm

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (133)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is Rp3.109.740
Rp3.411.384 total
includes taxes & fees
4 Jan - 5 Jan 2026
Gedney Farm
The Parlor Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds
9 Academy

9 Academy

9 Academy
4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
"Nice room. "
South Korea
JeongHoon
The price is Rp8.277.719
Rp9.519.376 total
includes taxes & fees
8 Jan - 9 Jan 2026
9 Academy
Reception
Elm Motel

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123)
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is Rp1.492.085
Rp1.666.609 total
includes taxes & fees
23 Jan - 24 Jan 2026
Elm Motel
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished
The Old Inn On The Green

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is Rp5.113.325
Rp6.170.358 total
includes taxes & fees
29 Dec - 30 Dec
The Old Inn On The Green
Front of property
Hitching Post Country Motel

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (81)
"Basic accommodation that was clean and easy."
United States
Elizabeth
The price is Rp2.179.450
Rp2.506.368 total
includes taxes & fees
27 Dec - 28 Dec
Hitching Post Country Motel
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is Rp1.760.325
Rp2.024.374 total
includes taxes & fees
26 Dec - 27 Dec
Locust Tree Bed and Breakfast LLC
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (41)
"The place is lovely, room is cozy, and the bed is comfy"
United States
Mark
The price is Rp2.719.494
Rp3.037.675 total
includes taxes & fees
30 Dec - 31 Dec
Wilder House Berkshires
Terrace/patio
The Abner Hotel

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.2 out of 10, Wonderful, (46)
"Spacious room and friendly staff "
United States
Frank
The price is Rp3.643.035
Rp4.189.574 total
includes taxes & fees
19 Jan - 20 Jan 2026
The Abner Hotel
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi
The White Hart

The White Hart

The White Hart
4.0 star property
Salisbury
9.6 out of 10, Exceptional, (143)
"Great charming place, friendly, helpful staff"
United States
David
The price is Rp4.832.008
Rp5.556.759 total
includes taxes & fees
4 Jan - 5 Jan 2026
The White Hart
Library
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (165)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is Rp2.755.328
Rp3.168.627 total
includes taxes & fees
8 Jan - 9 Jan 2026
Blackberry River Inn
Lobby
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1000)
"Amazing stay"
United States
Marquise
The price is Rp2.323.294
Rp2.671.788 total
includes taxes & fees
1 Jan - 2 Jan 2026
DoubleTree by Hilton Hotel Bristol, Connecticut
Desk, free cots/infant beds, rollaway beds, free WiFi
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1000)
"Clean comfortable room,great parking and local shopping "
United States
Julie
The price is Rp1.583.853
Rp1.821.431 total
includes taxes & fees
28 Dec - 29 Dec
Days Inn by Wyndham Torrington
Front of property
Simsbury 1820 House

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1000)
"Very nice room, pleasant and helpful staff"
United States
Concetta
The price is Rp2.665.635
Rp3.354.677 total
includes taxes & fees
29 Dec - 30 Dec
Simsbury 1820 House
Exterior
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (171)
"Breakfast was easy and good options. "
United States
jessica
The price is Rp2.045.330
Rp2.352.130 total
includes taxes & fees
1 Jan - 2 Jan 2026
Home2 Suites by Hilton Bristol
Exterior
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1000)
"Professional very clean and good breakfast "
United States
Piotr
The price is Rp2.048.348
Rp2.355.600 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Inn & Suites Hartford/Farmington
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.
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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.
See properties

Northwestern Connecticut Community College

Explore the campus of Northwestern Connecticut Community College during your stay in Winchester.
See properties

Top Winchester Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"So convenient for early departures, great rooms and friendly staff."
Mark 1-night trip
Posted 6 days ago
Sheraton Hartford Hotel at Bradley Airport
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Staff was very friendly, grounds are impeccable. Food was great, room was very nice. Absolutely amazing experience "
Kent Allen 4-night trip
Posted 2 months ago
Mayflower Inn & Spa, Auberge Collection

More cheap stays in Winchester

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
The price is Rp1.252.178 per night from 29 Dec to 30 Dec
Rp1.252.178
Rp1.439.946 total
29 Dec - 30 Dec
includes taxes & fees
7.8/10 Good! (1,005 reviews)

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 traveller data. Two other choices for your stay in the area are Extended Stay America Suites Hartford Farmington and Avon Old Farms Hotel. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What are some hotels with pools in Winchester?
Avon Old Farms Hotel: Features a sauna, a seasonal outdoor pool and buffet. Hampton Inn & Suites Hartford/Farmington and Homewood Suites by Hilton Hartford-Farmington are two additional hotels with an on-site pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester will definitely find plenty to explore and enjoy. In Winchester, there are 17 hotels and other accommodation options to choose from. Find out more about Winchester.
What should I see while I'm in Winchester?
Favourite 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 itinerary are Winchester Historical Society and Platt Hill State Park. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the seasonal weather in Winchester?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 15 cm of snowfall.