Winchester Hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Filter by

Guest rating
Guest rating
Star rating

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, (783)
Located near Sunnybrook State Park with free breakfast, WiFi, and parking. This hotel offers a fitness centre 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 €100
includes taxes & fees
4 Jan - 5 Jan
Americas Best Value Inn Torrington CT
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, (1002)
Near both Hotchkiss-Fyler House Museum and Warner Theatre, this motel provides free breakfast, WiFi, and parking. Guests appreciate the clean rooms and attentive staff. Enjoy the fitness centre or venture out for nearby downhill skiing adventures.
"Clean comfortable room,great parking and local shopping "
United States
Julie
The price is €92
includes taxes & fees
1 Feb - 2 Feb
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
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 €302
includes taxes & fees
2 Jan - 3 Jan
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 €127
includes taxes & fees
2 Jan - 3 Jan
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 centre. 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 €170
includes taxes & fees
4 Jan - 5 Jan
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 €207
includes taxes & fees
2 Jan - 3 Jan
Cornwall Inn and Lodge
Deluxe Studio, Multiple Beds, Non Smoking
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, (1001)
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 €73
includes taxes & fees
4 Jan - 5 Jan
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 €99
includes taxes & fees
8 Jan - 9 Jan
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 centre 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 €127
includes taxes & fees
11 Jan - 12 Jan
Home2 Suites by Hilton Bristol
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed
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 €313
includes taxes & fees
4 Jan - 5 Jan
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 €175
includes taxes & fees
2 Jan - 3 Jan
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 €173
includes taxes & fees
4 Jan - 5 Jan
Gedney Farm
The Parlor Suite
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 €483
includes taxes & fees
5 Jan - 6 Jan
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 Film 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 €783
includes taxes & fees
5 Jan - 6 Jan
PLYMOUTH MOTOR LODGE
John Harney Suite
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 savouring the terrace views.
"Amazing stay. Incredible staff, attention to detail. Beyond expectations "
United States
Jeanette
The price is €249
includes taxes & fees
4 Jan - 5 Jan
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 cosy 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 €132
includes taxes & fees
2 Jan - 3 Jan
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 centre.
"Clean room, great staff and overall warm atmosphere."
United States
Gavrosh
The price is €317
includes taxes & fees
1 Feb - 2 Feb
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 centre. Located just 15 minutes from Connecticut Convention Centre, 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 €116
includes taxes & fees
4 Jan - 5 Jan
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, (1001)
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 €112
includes taxes & fees
2 Jan - 3 Jan
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Simsbury Inn

Simsbury Inn

10/10 Excellent
"Staff is amazing. Samantha was so very helpful at check in. The room was soooo neat and clean. The hotel itself is so nice. And breakfast was great. Even with the bad weather they were amazing "
Hector 2-night trip
Posted 2 days ago
Simsbury Inn

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 €73 per night from 4 Jan to 5 Jan
€73
4 Jan - 5 Jan
includes taxes & fees
7.8/10 Good! (1,000 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 The Farmington Inn & Suites and Extended Stay America Suites Hartford Farmington. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This holiday home rental outside of Winchester offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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, 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 Laurel Lanes. A couple of additional sights to add to your itinerary are The Marina at Highland Lake and Winchester Historical Society. 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.

Explore a world of travel with Expedia