Photo by Donny Campos

Winchester Hotels

Most hotels are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Tonight
May 4 - May 5
Tomorrow
May 5 - May 6
Next weekend
May 10 - May 12

Filter by

Popular filters
Popular filters
Total price
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

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
7.4 out of 10, Good, (871)
"Had a nice stay. Nice and quiet, bed was comfortable and shower had great pressure. The furniture was outdated, but everything was clean and functioned well. Near stores and restaurants and the main roads. The breakfast was a bit lacking, but the coffee was good. "
The price is €88
includes taxes & fees
19 May - 20 May
Days Inn by Wyndham Keene NH
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, (895)
"Cleanest hotel bathroom I've ever seen. Good food. Friendly staff. "
The price is €135
includes taxes & fees
6 May - 7 May
Courtyard by Marriott Keene Downtown
Best Western Plus Keene Hotel
Interior entrance
Best Western Plus Keene Hotel
3.0 star property
8.2 out of 10, Very good, (1003)
"breakfast area was the best equipped of any I have ever stayed at!"
The price is €140
includes taxes & fees
6 May - 7 May
Best Western Plus Keene Hotel
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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, (718)
"Great stay, great staff! "
The price is €127
includes taxes & fees
19 May - 20 May
Holiday Inn Express Keene, an IHG Hotel
Hampton Inn & Suites Keene
Reception
Hampton Inn & Suites Keene
2.5 star property
9.0 out of 10, Wonderful, (160)
"The room was comfortable and clean. Breakfast was great "
The price is €123
includes taxes & fees
20 May - 21 May
Hampton Inn & Suites Keene
Econo Lodge Brattleboro
View from room
Econo Lodge Brattleboro
2.0 star property
5.8 out of 10, (485)
"Clean quiet and affordable place with a friendly staff. Small critique: put a small shelf in the shower for shampoo/soap etc. "
The price is €116
includes taxes & fees
6 May - 7 May
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, (223)
"This was our second year staying at this property and will return. The property and rooms are outdated but always very clean and the staff is very friendly and accommodating. Parking is easy and we feel safe. "
The price is €177
includes taxes & fees
19 May - 20 May
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, (120)
"The hosts were wonderfully helpful!"
The price is €148
includes taxes & fees
6 May - 7 May
The Carriage Barn Inn
Latchis Hotel
Interior
Latchis Hotel
2.5 star property
8.4 out of 10, Very good, (559)
"Fun place to stay "
The price is €112
includes taxes & fees
6 May - 7 May
Latchis Hotel
Centennial House
Exterior detail
Centennial House
3.5 star property
9.4 out of 10, Exceptional, (126)
"Loved our stay"
The price is €195
includes taxes & fees
7 May - 8 May
Centennial House
The One Cat B&B
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (65)
"This is an awesome B&B! Pat and Conrad are great hosts and they live on site so they are available if you need anything. The room was clean and very spacious. There was comfortable seating in addition to the bed. The room had it's own Keurig machine and it's own AC/heat system. Breakfast the next morning was delicious. Several food and drink options to consider. Also, Conrad bakes his own bread. I had the maple oat bread which was so good. This was my first time in Brattleboro. I will definitely...
The price is €169
includes taxes & fees
4 Jun - 5 Jun
The One Cat B&B
Lakefront Orange Vacation Rental - Pet Friendly!
Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (6)
"Crystal was an exceptional hostess! "
Lakefront Orange Vacation Rental - Pet Friendly!
Enjoy your stay in an antique home in an antique toy museum!
Interior
Enjoy your stay in an antique home in an antique toy museum!
9.2 out of 10, Wonderful, (7)
"A unique enjoyable experience "
The price is €498
includes taxes & fees
6 May - 7 May
Enjoy your stay in an antique home in an antique toy museum!
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, (128)
"Rented the Castle for a Mom's get-a-way weekend to celebrate my 40th with 8 friends. The house and the property were fantastic and we had a wonderful stay. There was plenty of space so we could have our own rooms and sleep in. The kitchen was very well equipped and we enjoyed cooking together and exploring the castle and grounds - there's a great easy 45 min hike around the lake. Highly recommend bringing tiaras to wear in the hot tub while sipping mulled wine on a lovely fall day. Definitely...
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries
1 bedroom, iron/ironing board, WiFi, bed sheets
Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries
10.0 out of 10, Exceptional, (33)
"We spent two nights here while exploring Keene and Brattleboro. The place was clean we also had a nice afternoon at the brewery!"
Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Fridge, microwave, stovetop, coffee/tea maker
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (22)
"This property is fairytale cute, so welcoming and relaxing. We had a beautiful stay in Vermont thanks to this location. And there were surprise puppies on site!!!!! Honestly this was the kind of trip that gives you confidence in vacation rentals. Clean, wonderfully decorated, off the beaten path a truly relaxing stay! Go outside at night!!!! We dont have stars like that in the city."
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Spectacular Mountain views with all the amentities nearby
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, (38)
"The vrbo was as-described and the hosts exceptionally personable and friendly. Exemplary!"
Spectacular Mountain views with all the amentities nearby
Downtown Hot Tub Escape
Property grounds
Downtown Hot Tub Escape
9.4 out of 10, Exceptional, (3)
"Wonderfully located not to far from plenty of great restaurants and really well kept home that accomadated 9 adults for the night perfectly. Clear instructions for all the amenities in the home made it easy and fun."
The price is €315
includes taxes & fees
7 May - 8 May
Downtown Hot Tub Escape
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior
Cozy Updated Log Cabin with Mountain Views close to Monadnock
9.6 out of 10, Exceptional, (18)
"We absolutely loved the privacy and seclusion of the property. Everything was clean and tidy, minus some trash that was left around the firepit, presumably from a previous guest, that we cleaned up. The kitchen was well stocked with cooking tools and the bathroom was just big enough. Guests should take note though that the shower was definitely a tight fit for my 6'1" husband and the furniture was also a struggle for him. One of the beds was only about 4 inches off the ground and the seating was...
The price is €265
includes taxes & fees
6 May - 7 May
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Charming Waterfront Log Cabin
Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (23)
"My husband and I stayed for 2 nights at this lovely log cabin on the pond. Although the weather did not cooperate outdoors, we had all the comforts of home indoors. The cabin was warm and toasty and the view out to the pond did not disappoint-fog rising on the water in the morning, steady rain throughout the day and then clearing at night with a moon reflected on the water. The cabin is stocked with games and the tv/streaming easy to navigate. If you want peace and quiet this is the cabin to...
Charming Waterfront Log Cabin
Don't see what you're looking for?
See all available properties in Winchester
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.

More cheap stays in Winchester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT
The price is €90 per night from Jun 5 to Jun 6
€90
per night
5 Jun - 6 Jun
8.2/10 Very Good! (1,003 reviews)

Winchester hotels information

Number of reviews
4,935
Accommodation
379 hotels
Lowest Price
€88
Highest Price
€498

Frequently asked questions

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 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, Birch Point and Rhododendron State Park. Additionally, you might want to add Ashuelot River 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.

Recent Reviews in Winchester
Expedia verified reviews

The Putney Inn

The Putney Inn

5/5 Excellent
"The place is not new but the owners have done a good job sprucing up everything. My room was clean, the heat/AC worked, the window opened, lots of outlets and lamps, extra tp in the bathroom. Free strong wifi. Minimal but adequate breakfast. I would definitely stay there again."
A verified traveller stayed at The Putney Inn
Posted 4 days ago
The Putney Inn