Located near Hotchkiss-Fyler House Museum and Warner Theater, this motel offers free WiFi and parking. Enjoy the on-site fitness center or venture to nearby downhill skiing. Clean rooms provide a comfortable base while the exceptionally helpful staff ensures a pleasant stay.
Unwind in this peaceful country retreat with a seasonal outdoor pool and complimentary gourmet breakfast. Located near Haystack Mountain State Park, the inn offers free WiFi and parking while helpful staff ensure a memorable stay in Norfolk's quiet surroundings.
This charming hotel offers free breakfast, WiFi, and parking while keeping you near outdoor adventures. Enjoy the fitness center after exploring nearby Sunnybrook State Park or hit local ski slopes in winter. The friendly staff ensures a comfortable stay.
Wake up to complimentary breakfast at this cozy B&B, then explore nearby trails by foot or on free rental bikes. Infinity Music Hall and Norfolk Historical Museum are close, while perks like free WiFi, parking, and a garden enhance your countryside retreat.
Wake up to a complimentary full breakfast at this cozy East Canaan B&B. Located near Land of Nod Vineyard and Winery, the inn offers free parking and daily housekeeping. Guests consistently praise the helpful staff for making stays memorable.
Savor free breakfast at this inviting 3-star hotel before exploring nearby Litchfield Town Green. Return for evening drinks at the bar while taking in views from the rooftop terrace. Free WiFi and parking make your Connecticut getaway seamless.
Discover historic charm at this B&B near McLean Game Refuge. Wake up to a daily full breakfast before exploring hiking trails. Free WiFi and parking add convenience while Old New-Gate Prison is just a short drive away.
Escape to this tranquil Litchfield hotel offering rejuvenating spa treatments from deep-tissue massages to hydrotherapy. Enjoy the seasonal pool, onsite restaurant, and bar while staying close to Litchfield Town Green and nature trails.
Wake up to a complimentary breakfast at this Bristol hotel before exploring nearby Pine Lake Park. Unwind in the hot tub after a workout in the 24-hour fitness center, or enjoy a drink at the bar. In-room refrigerators and microwaves add convenience to your stay.
Located in Farmington, this hotel offers free WiFi and parking, plus an indoor pool and hot tub for relaxation. Enjoy a complimentary breakfast before exploring nearby Hill-Stead Museum, or maintain your routine at the 24-hour fitness center.
Experience culinary delights at The Old Inn Fine Dining, featuring American cuisine for breakfast, lunch, and dinner. Cool off in the seasonal pool, then sip drinks at the bar. Nearby attractions Questing and New Marlborough Town Library await your exploration.
Immerse yourself in the rich history of this Simsbury B&B, where an indoor pool and fitness center await. Enjoy complimentary breakfast, WiFi, and bike rentals near Performing Arts Center, with 2 bars and a restaurant for evening relaxation.
Steps from White Memorial Conservation Center and Mount Tom State Park, this Litchfield Inn features a full-service spa for rejuvenating treatments. Enjoy complimentary breakfast, WiFi, and parking while the attentive staff ensures a memorable stay.
This extended-stay hotel offers a seasonal outdoor pool and tennis court just 15 minutes from Connecticut Convention Center. Explore nearby Farmington Valley Arts Center while enjoying spacious rooms with sofa beds and kitchenettes.
Escape to the Berkshires in this inviting Sheffield accommodation with complimentary WiFi and parking. Start your day with cooked-to-order weekend breakfast before exploring nearby Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary.
Escape to this serene Farmington hotel, just 15 minutes from Hartford Convention Center. Start your day with complimentary breakfast at Victoria's Café before exploring nearby Miss Porter's School. The health club, room service, and exceptionally helpful staff ensure a comfortable stay.
In Bristol, this hotel offers a tranquil atmosphere with an indoor pool for relaxation. Guests can enjoy American cuisine at The Willows restaurant or unwind at the bar. The 24-hour fitness center, free WiFi, and parking enhance your stay near Pine Lake Park.
This inviting hotel offers convenient perks including complimentary WiFi and parking. Located near Witch's Dungeon Classic Movie Museum and Rockwell Park, you'll enjoy comfortable accommodations with 24-hour front desk service for a hassle-free stay.
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.
You might want to get your camera out and head to Winchester Historical Society— just one of the landmarks located 1.9 mi (3.1 km) from central Winchester.
If you like quiet time surrounded by flowers and greenery, then make a stop at Rowley Fields in the heart of Winchester. Want to stretch your legs some more? Head to Walker Field, just a short walk away.
The center of Winchester is home to cultural attractions like American Mural Project, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Highland Lake, The Village, and Northwestern Connecticut Community College.
We had a wonderful getaway and loved staying at the Manor. The innkeepers were amazing, our room was gorgeous, comfortable and breakfast was delicious.
We came to see a local nursery and really enjoyed the hospitality, food, home comforts and EV charge-up. Wayne and Kim really know the area and are great guides. Plus the home is beautiful with a lovely yard to relax in.
I was impressed by the historic charm of the hotel. There is even a dedicated room detailing the history of the area, educational significance and courthouse beginnings. The court room restaurant and rooftop bar are definitely worth a visit. The rooms were spacious and clean. We will definitely be back.
Just a beautiful home with clean, comfortable rooms and an amazing Innkeeper.
Breakfasts are elegant and delicious. We stayed here in 2025 and returned in 2026 for Labor Day weekend. Will hopefully repeat in 2027.
Everything is great and there is an Asian theme. We especially like leaving our shoes at the entance and using provided slippers instead our shoes so as to not do not bring dirt into the premises.
From the moment I arrived I knew my stay would be peaceful and comfortable. This is not a corporate, antiseptic hotel that could sit anywhere, this is a home.
The welcome is appreciated after a long day.
We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches.
We were also able to park right outside our...
Beautiful warm yet modern design - ripe for Architectural Digest. Staff is friendly and helpful. Rooms are spacious and well-appointed. Morning breakfast is terrific. Cute town to navigate within steps of the hotel.
This location is exceptional and is beautifully decorated with original art, mostly watercolors.
Only negative was the loud and sleep disruptive hvac unit that cycled through cycles every few minutes.
Their service was impeccable, needed a few items and they delivered it within minutes to our room. They served a hot breakfast with plenty of choices, such a pleasant way to start our day. Plenty of towels at the pool, every moment was relaxing and stress free.
Can I book refundable accommodations in Winchester?
If you want the flexibility to change your plans to Winchester, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Winchester if I want a vacation rental instead of a hotel?
If you're looking for a good alternative to a hotel, browse our selection of 11 vacation homes. In addition, you can choose from 5 apartments.
What will the weather in Winchester be like during my vacation?
July and August are typically the warmest months in Winchester when the average temp is 67°F. January and February are the coldest months when the average temperature is 30°F. July and October are the months with the most rain.
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