Photo by Donny Campos

Winchester Hotels

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check Winchester hotel prices

Tonight
23 Dec - 24 Dec
Tomorrow night
24 Dec - 25 Dec
This weekend
27 Dec - 29 Dec
Next weekend
3 Jan - 5 Jan

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Winchester hotels

Days Inn by Wyndham Keene NH
In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (973)
"Quiet. "
The price is €100
includes taxes & fees
5 Jan - 6 Jan 2025
Days Inn by Wyndham Keene NH
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (267)
"Exceeded my expectations."
The price is €132
includes taxes & fees
5 Jan - 6 Jan 2025
Hampton Inn & Suites Keene
Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1001)
"Lovely staff"
The price is €160
includes taxes & fees
25 Dec - 26 Dec
Courtyard by Marriott Keene Downtown
Best Western Plus Keene Hotel
Exterior

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1000)
"Nice room"
The price is €134
includes taxes & fees
24 Dec - 25 Dec
Best Western Plus Keene Hotel
Holiday Inn Express Keene, an IHG Hotel
Indoor pool

Holiday Inn Express Keene, an IHG Hotel

2.5 star property
8.4 out of 10, Very good, (801)
"Great location and service! Continental breakfast was great! Friendly and pleasant staff and amenities!"
The price is €123
includes taxes & fees
16 Jan - 17 Jan 2025
Holiday Inn Express Keene, an IHG Hotel
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (685)
"had a nice stay, clean room. walkable to most of the downtown. "
The price is €131
includes taxes & fees
1 Jan - 2 Jan 2025
Latchis Hotel
The Inn At Crumpin Fox
Terrace/patio

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (277)
"We enjoyed our stay very much."
The price is €192
includes taxes & fees
3 Jan - 4 Jan 2025
The Inn At Crumpin Fox
Econo Lodge Brattleboro
View from room

Econo Lodge Brattleboro

2.0 star property
5.6 out of 10, (516)
"It was fine. We just stopped in for the night after a concert"
Econo Lodge Brattleboro
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (142)
"Lovely old BnB, easy to find, very convenient Very clean room Great continental breakfast Loved ease of walking to downtown, many stores and restaurants Informative and very friendly and helpful owner"
The price is €159
includes taxes & fees
31 Dec - 1 Jan 2025
The Carriage Barn Inn
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (147)
"Lovely bed & breakfast!!! We appreciate the hospitality and delicious breakfast. "
The price is €202
includes taxes & fees
26 Dec - 27 Dec
Centennial House
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

9.8 out of 10, Exceptional, (7)
"This cabin was so cute and cozy and inside it was all neat! I love the smell of cabins and I love the size of the cabin. It was cold when we got there but that little cabin heats up very well when you turn up the heat. The water takes a couple seconds to warm up, but that's so minimal because the water can get hot. You can adjust the water to stay warm. There's a fridge, a microwave, a TV, dishes, hooks for hanging clothes, trash bins, cleaning supplies, etc... Such a beautiful cabin. It had...
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
The One Cat B&B
Exterior detail

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (74)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is €211
includes taxes & fees
26 Dec - 27 Dec
The One Cat B&B
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Interior

Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!

10.0 out of 10, Exceptional, (144)
"I can unequivocally say we had a wonderful time from the moment we drove up until we were driving away. We had booked this as a surprise for our adult children (and their partners) to stay with us. They were absolutely wowed by the amazing castle, the amazing views and just how cool it was. The caretaker Mike was incredibly helpful and helped get us set up perfectly. We would 100% stay again - if we could find an opening :-) "
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

10.0 out of 10, Exceptional, (2)
"Besides it being a *bit* cold, our stay was great! Very close to Brattleboro and a bunch of other walkable towns. Great hiking areas. The yurt was so cute and had pretty much every cooking supply you could need. Will be back again in warmer weather! :)"
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop

Downtown Hot Tub Escape

9.4 out of 10, Exceptional, (9)
"Brought my parents and my Brother to this rental - It was a nice place."
The price is €358
includes taxes & fees
6 Jan - 7 Jan 2025
Downtown Hot Tub Escape
The Covey House Retreat with InfraRed Sauna
Outdoor dining

The Covey House Retreat with InfraRed Sauna

10.0 out of 10, Exceptional, (3)
"We had an amazing stay, your place is awesome!"
The Covey House Retreat with InfraRed Sauna
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC
Interior

Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC

2.0 star property
The price is €391
includes taxes & fees
6 Jan - 7 Jan 2025
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC
Spectacular Mountain views with all the amentities nearby
Smart TV

Spectacular Mountain views with all the amentities nearby

9.8 out of 10, Exceptional, (51)
"What a wonderful place to stay!! We were in town for my 50th high school reunion, hadn’t been back to the area in 35 years. Our accommodations enhanced a beautiful weekend, and the foliage was the cherry on top! Spacious, clean, tastefully furnished and decorated. Well equipped with every utensil, and kitchen appliance you could need! Comfy bed, great shower & good water pressure too! Secluded and quiet, but very convenient to Bernardston, Northfield and Greenfield as well as I-91. Highly...
Spectacular Mountain views with all the amentities nearby
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Lake

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

9.8 out of 10, Exceptional, (15)
"Very nice house and property! "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Property grounds

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.0 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

What's the best place to stay in Winchester?

The Colonial Hotel, located 26.3 mi (42.3 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Colonial Motel And Spa and Hampton Inn Brattleboro. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

Charming Waterfront Log Cabin: This holiday home rental outside of Winchester is located on the waterfront, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. See all vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What are some hotels with pools in Winchester?

The Colonial Hotel: Offers a sauna, an indoor pool and free self parking. Colonial Motel And Spa and Hampton Inn Brattleboro are a couple of other choices that offer an on-site pool. View all hotels with pools in Winchester.

What is staying in Winchester like?

Visitors to Winchester will definitely enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 6 hotels and other accommodation options to choose from. Find out more about Winchester.

What are the top places to visit in Winchester?

Natural beauty is on display at Ashuelot River, Birch Point and Rhododendron State Park. Additionally, you might want to add Pisgah State Park to your itinerary. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.