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Our top choices for Winchester hotels

Premium bedding, down comforters, 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, (783)
Located near Sunnybrook State Park with free breakfast, WiFi, and parking. This hotel offers a fitness center with hiking and skiing trails nearby. Guests praise the helpful staff while Hotchkiss-Fyler House Museum is just minutes away.
"Very pleasant check-in experience. Spacious room, comfortable beds, clean, easy parking."
United States
Laurel
The price is ₩146,828
₩168,852 total
includes taxes & fees
Jan 6 - Jan 7
Americas Best Value Inn Torrington CT
Desk, free cribs/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, (1002)
Near both Hotchkiss-Fyler House Museum and Warner Theater, this motel provides free breakfast, WiFi, and parking. Guests appreciate the clean rooms and attentive staff. Enjoy the fitness center or venture out for nearby downhill skiing adventures.
"Clean comfortable room,great parking and local shopping "
United States
Julie
The price is ₩135,072
₩155,333 total
includes taxes & fees
Feb 1 - Feb 2
Days Inn by Wyndham Torrington
Reception
Elm Motel

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123)
Located in Westfield, this motel offers free WiFi and parking with round-the-clock front desk assistance. Enjoy easy access to nearby attractions like Holcomb Park and Elm Street Plaza, just a short drive from Bradley International Airport.
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is ₩128,571
₩143,609 total
includes taxes & fees
Jan 23 - Jan 24
Elm Motel
Exterior
Simsbury Inn

Simsbury Inn

Simsbury Inn
3.5 star property
Simsbury Center
9.2 out of 10, Wonderful, (282)
Surrounded by New England charm, this Weatogue hotel offers 3 restaurants serving local cuisine, plus an indoor pool and health club. Enjoy free breakfast and parking while exploring nearby Rosedale Farms & Vineyards and Stratton Brook State Park.
"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 ₩416,053
₩509,917 total
includes taxes & fees
Jan 9 - Jan 10
Simsbury Inn
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)
Tucked into Cornwall Bridge, this country motel provides free WiFi and parking for nature enthusiasts. Explore nearby Housatonic Meadows State Park or try snowboarding, then return to comfort with 24-hour front desk service.
"Basic accommodation that was clean and easy."
United States
Elizabeth
The price is ₩187,801
₩215,971 total
includes taxes & fees
Jan 2 - Jan 3
Hitching Post Country Motel
Front of property
Simsbury 1820 House

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1004)
Immerse yourself in the historic charm of this restored inn, offering a peaceful atmosphere with an indoor pool and fitness center. Enjoy free breakfast, then explore nearby attractions or rent bikes to discover the area's vineyards and performing arts venues.
"Friendly, welcoming, and helpful staff. The room was beautiful and clean. The bar and restaurant were cozy; drinks and food delicious. "
United States
Christina
The price is ₩228,901
₩288,070 total
includes taxes & fees
Jan 6 - Jan 7
Simsbury 1820 House
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)
Located in the heart of Cornwall Bridge, this inviting lodge offers a seasonal outdoor pool and complimentary continental breakfast. Explore nearby Kent Falls State Park or hike the Appalachian Trail, just 30 minutes away.
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is ₩305,682
₩351,534 total
includes taxes & fees
Jan 2 - Jan 3
Cornwall Inn and Lodge
Deluxe Studio, Multiple Beds, Non Smoking | 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, (1002)
This quiet retreat offers complimentary WiFi and on-the-go breakfast daily. Located near Batterson Park Pond and Hill-Stead Museum, with helpful staff praised by guests. Only 13 minutes from Hartford Union Station for convenient travel connections.
"Room was clean, staff were nice."
United States
Stephen
The price is ₩107,526
₩123,650 total
includes taxes & fees
Jan 8 - Jan 9
Extended Stay America Suites Hartford Farmington
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, (917)
Experience tranquility at this Plainville hotel with an indoor swimming pool and 24-hour gym. Enjoy free breakfast, WiFi, and parking while being close to Crescent Lake and Relic Brewing Company. The exceptionally helpful staff ensures a peaceful, comfortable stay.
"The room was very clean, and the check-in staff was very courteous."
United States
Kristin
The price is ₩145,619
₩167,462 total
includes taxes & fees
Jan 8 - Jan 9
Fairfield Inn & Suites by Marriott Plainville
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, (178)
This modern hotel offers a 24-hour fitness center and spacious suites with refrigerators and microwaves. Enjoy the terrace, grab a drink at the bar, or visit the coffee shop. Pine Lake Park and Casey Field are located nearby with free parking for guests.
"Place is immaculate and staff super friendly and helpful "
United States
Yarah
The price is ₩181,393
₩208,602 total
includes taxes & fees
Jan 8 - Jan 9
Home2 Suites by Hilton Bristol
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)
Enjoy American cuisine by candlelight at the fine dining restaurant of this historic inn. A terrace and garden enhance the countryside charm, while the seasonal pool offers refreshing relaxation near Questing and New Marlborough Town Library.
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is ₩439,087
₩529,856 total
includes taxes & fees
Jan 4 - Jan 5
The Old Inn On The Green
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (274)
Set on the greens in Lakeville, this inn provides a tranquil retreat with spa services, deep-tissue massages, and fitness options. Guests can enjoy meals at the restaurant, drinks at the bar, and easy access to local museums and tea rooms.
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is ₩257,837
₩296,513 total
includes taxes & fees
Jan 3 - Jan 4
Interlaken Inn & Resort
Front of property
Gedney Farm

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (133)
Embrace country charm at this Great Barrington hotel with a garden terrace and full-service restaurant. Unwind at the bar after exploring nearby Questing trails, then enjoy free breakfast before heading to New Marlborough Town Library.
"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 ₩267,037
₩292,939 total
includes taxes & fees
Jan 4 - Jan 5
Gedney Farm
The Parlor Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds
9 Academy

9 Academy

9 Academy
4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
This charming 4-star retreat offers complimentary self-parking and WiFi in a serene setting. Explore nearby Mount Frissell and Scoville Memorial Library, or enjoy seasonal outdoor adventures like snowboarding and canoeing.
"Nice room. "
South Korea
JeongHoon
The price is ₩710,817
₩817,440 total
includes taxes & fees
Jan 12 - Jan 13
9 Academy
Interior
PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (178)
Discover this welcoming hotel in Terryville with free WiFi and parking. Nearby Witch's Dungeon Classic Movie Museum offers quirky entertainment, while Rockwell Park provides outdoor adventures. The 24-hour front desk ensures seamless service.
"Good basic room, squeeky beds and the bathroom faucets doesnt turn off. Good value though for $103.50"
United States
David
The price is ₩115,570
₩132,905 total
includes taxes & fees
Feb 1 - Feb 2
PLYMOUTH MOTOR LODGE
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, (144)
Set in Salisbury near Mount Frissell, this historic hotel welcomes you with free breakfast and WiFi. After exploring nearby Hanging Rock Park, relax in the garden or enjoy a drink at the bar while savoring the terrace views.
"Amazing stay. Incredible staff, attention to detail. Beyond expectations "
United States
Jeanette
The price is ₩367,222
₩422,305 total
includes taxes & fees
Jan 7 - Jan 8
The White Hart
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)
Discover cozy comfort at this Granby B&B offering complimentary full breakfast, WiFi, and parking. Nearby hiking trails provide outdoor adventure while McLean Game Refuge and Old New-Gate Prison & Copper Mine offer fascinating day trips. Bradley International Airport is just 14 minutes away.
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
The price is ₩201,548
₩223,718 total
includes taxes & fees
Jan 7 - Jan 8
Truman Gillet House Bed & Breakfast
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, (1001)
Stylish rooms await at this wellness-focused hotel with an upscale restaurant and bar. Relax with rejuvenating treatments at the full-service spa after exploring Blue Back Square. Free WiFi and parking complement the 24-hour fitness center.
"Clean room, great staff and overall warm atmosphere."
United States
Gavrosh
The price is ₩447,581
₩536,320 total
includes taxes & fees
Feb 1 - Feb 2
Delamar West Hartford
BBQ/picnic area
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, (1001)
Retreat to this quiet hotel featuring a refreshing indoor pool and fitness center. Located just 15 minutes from Connecticut Convention Center, enjoy free breakfast, WiFi and parking while exploring local attractions like Hill-Stead Museum.
"Everything from reservation to check-in. Room cleanliness and dining room selections were excellent."
United States
Ken
The price is ₩170,682
₩196,284 total
includes taxes & fees
Jan 4 - Jan 5
Homewood Suites by Hilton Hartford-Farmington
Staircase
The Farmington Inn & Suites

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1002)
Wake to fresh breakfast at Victoria's Cafe before exploring nearby Miss Porter's School and Hill-Stead Museum. The helpful staff ensures comfort in clean rooms, while the health club offers post-sightseeing relaxation, all just 30 minutes from Bradley Airport.
"Love the inn"
United States
Donna
The price is ₩142,523
₩188,736 total
includes taxes & fees
Jan 7 - Jan 8
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

Walk around the campus at Northwestern Connecticut Community College as part of your travels around Winchester.
See properties

Top Winchester Hotel Reviews

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"The hotel is amazing but room services is not good if u want to dinner in the room not good food just snacks But other than that it’s amazing place "
vera alice 1-night trip
Posted 2 days 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 ₩107,526 per night from Jan 8 to Jan 9
₩107,526
₩123,650 total
Jan 8 - Jan 9
includes taxes & fees
7.8/10 Good! (1,001 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 traveler data. Other good choices for your visit to the area are The Farmington Inn & Suites and Extended Stay America Suites Hartford Farmington. 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! 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?
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 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 17 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 Laurel Lanes. A couple of additional sights to add to your agenda are The Marina at Highland Lake and Winchester Historical Society. 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.