Winchester hotels from RM351

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Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

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Our top choices for Winchester hotels

Premium bedding, down duvets, Select Comfort beds, in-room safe
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (781)
"Walls are thin but it was clean and safe with friendly staff."
United States
Daniel
The price is RM417
RM479 total
includes taxes & fees
21 Dec - 22 Dec
Americas Best Value Inn Torrington CT
Free WiFi, bed sheets
Hitching Post Country Motel

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (80)
"Basic accommodation that was clean and easy."
United States
Elizabeth
The price is RM531
RM611 total
includes taxes & fees
19 Dec - 20 Dec
Hitching Post Country Motel
Indoor spa tub
Simsbury Inn

Simsbury Inn

Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (280)
"The personnel was very helpful & accomodating, both at the front desk & upstairs restaurant. I appreciated that they set out two rooms as adjoining even before I asked. "
United States
Sara
The price is RM976
RM1,212 total
includes taxes & fees
28 Dec - 29 Dec
Simsbury Inn
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, (1004)
"Clean comfortable room,great parking and local shopping "
United States
Julie
The price is RM379
RM435 total
includes taxes & fees
21 Dec - 22 Dec
Days Inn by Wyndham Torrington
Reception
Simsbury 1820 House

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1002)
"Very nice room, pleasant and helpful staff"
United States
Concetta
The price is RM650
RM818 total
includes taxes & fees
28 Dec - 29 Dec
Simsbury 1820 House
Free daily continental breakfast
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 RM864
RM994 total
includes taxes & fees
19 Dec - 20 Dec
Cornwall Inn and Lodge
Terrace/patio
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, (166)
"Everything was incredible "
United States
isaiah
The price is RM498
RM573 total
includes taxes & fees
28 Dec - 29 Dec
Home2 Suites by Hilton Bristol
Lobby
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
2.5 star property
Plainville
8.6 out of 10, Excellent, (911)
"Great place stayed several times."
United States
Marlene D
The price is RM392
RM451 total
includes taxes & fees
22 Dec - 23 Dec
Fairfield Inn & Suites by Marriott Plainville
Breakfast, lunch, dinner served; American cuisine
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 RM1,246
RM1,504 total
includes taxes & fees
21 Dec - 22 Dec
The Old Inn On The Green
Front of property
Gedney Farm

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (132)
"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 RM758
RM831 total
includes taxes & fees
21 Dec - 22 Dec
Gedney Farm
Desk, iron/ironing board, free WiFi, bed sheets
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very good, (1000)
"Clean room with a good bed, good shower and an excellent TV "
United States
Lester
The price is RM305
RM351 total
includes taxes & fees
28 Dec - 29 Dec
Extended Stay America Suites Hartford Farmington
Interior
PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (178)
"Good basic room, squeeky beds and the bathroom faucets doesnt turn off. Good value though for $103.50"
United States
David
The price is RM327
RM376 total
includes taxes & fees
31 Dec - 1 Jan 2026
PLYMOUTH MOTOR LODGE
Terrace/patio
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, (1001)
"Amazing stay"
United States
Marquise
The price is RM566
RM651 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel Bristol, Connecticut
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (271)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is RM732
RM841 total
includes taxes & fees
21 Dec - 22 Dec
Interlaken Inn & Resort
Property entrance
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 RM572
RM635 total
includes taxes & fees
20 Dec - 21 Dec
Truman Gillet House Bed & Breakfast
Exterior
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington
3.0 star property
Farmington
8.4 out of 10, Very good, (1000)
"The young woman who greeted my daughter and I was very sweet and kind. The room was clean and the beds very comfortable. Would definitely stay here again!"
United States
Lisa
The price is RM465
RM535 total
includes taxes & fees
21 Dec - 22 Dec
Homewood Suites by Hilton Hartford-Farmington
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)
"very good coffee bar in the lobby; clean and quiet room. spacious bathroom; good hot water pressure in the shower"
United States
Janet
The price is RM1,193
RM1,433 total
includes taxes & fees
4 Jan - 5 Jan 2026
Delamar West Hartford
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 RM2,017
RM2,320 total
includes taxes & fees
22 Dec - 23 Dec
9 Academy
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 RM1,039
RM1,194 total
includes taxes & fees
21 Dec - 22 Dec
The White Hart
Staircase
The Farmington Inn & Suites

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1000)
"Staff was very friendly and helpful. Rooms are lovely, good breakfast, beds are so comfortable. Always happy to stay here."
United States
Erin
The price is RM404
RM536 total
includes taxes & fees
28 Dec - 29 Dec
The Farmington Inn & Suites
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

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"Staff was great, room was clean/bed was comfy. Good location lots to offer with food choices / stores. I would definitely stay again. Thank you. "
Cristal 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Bristol, Connecticut

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 RM305 per night from 28 Dec to 29 Dec
RM305
RM351 total
28 Dec - 29 Dec
includes taxes & fees
7.8/10 Good! (1,004 reviews)

Frequently asked questions

What's the best place for a stay in Winchester?
The Farmington Inn & Suites, located 20.6 mi (33.1 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 Sheraton Hartford Hotel at Bradley Airport. 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: Offers 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, The Marina at Highland Lake and Burr Pond State Park. 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.

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