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
22 Nov - 23 Nov
Tomorrow night
23 Nov - 24 Nov
This weekend
22 Nov - 24 Nov

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Winchester hotels

Latchis Hotel
Interior
Latchis Hotel
2.5 star property
8.4 out of 10, Very good, (678)
"Took Amtrak and decided to spend one night in town. Hotel conveniently located to station, local bus, and shops/restaurants. Easily walkable to anywhere you need to go, and movie theater next door had convenient timings. Clean room, comfortable bed, and so much space in the room. "
The price is €127
includes taxes & fees
1 Dec - 2 Dec
Latchis Hotel
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, (963)
"Great rooms and service love it my favorite place to stay in Keene "
The price is €78
includes taxes & fees
9 Dec - 10 Dec
Days Inn by Wyndham Keene NH
Best Western Plus Keene Hotel
Exterior
Best Western Plus Keene Hotel
3.0 star property
8.2 out of 10, Very good, (1002)
"Best breakfast. Balcony is too small you can’t even put a chair on it"
The price is €136
includes taxes & fees
3 Dec - 4 Dec
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Reception
Hampton Inn & Suites Keene
2.5 star property
8.8 out of 10, Excellent, (256)
"Great place!"
The price is €138
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Keene
Courtyard by Marriott Keene Downtown
Hypo-allergenic bedding, in-room safe, desk, laptop workspace
Courtyard by Marriott Keene Downtown
3.0 star property
8.8 out of 10, Excellent, (994)
"Well appointments room, very spacious and quiet. Fan I bathroom did not work "
The price is €121
includes taxes & fees
8 Dec - 9 Dec
Courtyard by Marriott Keene Downtown
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, (799)
"Nice clean room comfortable I would stay again when in the area. "
The price is €128
includes taxes & fees
9 Dec - 10 Dec
Holiday Inn Express Keene, an IHG Hotel
Econo Lodge Brattleboro
View from room
Econo Lodge Brattleboro
2.0 star property
5.6 out of 10, (515)
"It was fine. We just stopped in for the night after a concert"
The price is €84
includes taxes & fees
1 Dec - 2 Dec
Econo Lodge Brattleboro
The Inn At Crumpin Fox
Terrace/patio
The Inn At Crumpin Fox
2.5 star property
9.2 out of 10, Wonderful, (274)
"Near good dining…."
The price is €221
includes taxes & fees
25 Nov - 26 Nov
The Inn At Crumpin Fox
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 €186
includes taxes & fees
24 Nov - 25 Nov
The Carriage Barn Inn
Centennial House
Exterior detail
Centennial House
3.5 star property
9.6 out of 10, Exceptional, (145)
"Lovely bed & breakfast!!! We appreciate the hospitality and delicious breakfast. "
The price is €179
includes taxes & fees
30 Nov - 1 Dec
Centennial House
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 One Cat B&B
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
9.8 out of 10, Exceptional, (6)
"Our two night stay was great. Loved how close it was to the bike path and the fire pit in the back. Clare was very responsive!"
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
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
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, (142)
"Mother-of-bride: Since everyone attending my daughter's wedding in NH came from a different state I wanted a place where she and her bridesmaids could spend the night together before the wedding and have plenty of room to get ready on the big day. It was a generous and very awesome gift to be able to give our princess a castle for the night! TY Hunt Castle, you did not disappoint. Everyone was in awe of this spectacular home."
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Lakefront Orange Vacation Rental - Pet Friendly!
Outdoor dining
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (11)
"Great host communication, everything we needed, unexpected extras (like dog treats), and a beautiful view. Would gladly stay again!"
Lakefront Orange Vacation Rental - Pet Friendly!
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior
Cozy Updated Log Cabin with Mountain Views close to Monadnock
9.4 out of 10, Exceptional, (20)
"Very nice, clean, and great area. We enjoyed it very much!"
Cozy Updated Log Cabin with Mountain Views close to Monadnock
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
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 €357
includes taxes & fees
24 Nov - 25 Nov
Downtown Hot Tub Escape
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
Charming Waterfront Log Cabin
3 bedrooms, travel cot, free WiFi, bed sheets
Charming Waterfront Log Cabin
9.4 out of 10, Exceptional, (36)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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 The Covered Bridge Inn and Colonial Motel And Spa. 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 Pisgah State Park, Ashuelot River and Birch Point. Additionally, you might want to add Rhododendron 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.