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Winchester Hotels from S$128

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Check prices for these dates

Tonight
16 May - 17 May
Tomorrow
17 May - 18 May
This weekend
16 May - 18 May
Next weekend
23 May - 25 May

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Top 10 trending Winchester hotels

The Maguire House Bed & Breakfast
Building design

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
The price is S$357
includes taxes & fees
22 May - 23 May
The Maguire House Bed & Breakfast
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1011)
"Clean, roomy, great bar and restaurant on the premises "
The price is S$232
includes taxes & fees
18 May - 19 May
The Colonial Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Front of property

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (399)
"Nice hotel"
The price is S$252
includes taxes & fees
26 May - 27 May
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"Hi it’s a beautiful inn and very comfortable "
The price is S$247
includes taxes & fees
18 May - 19 May
Monadnock Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (146)
"This is a great place to stay. Host, Joe, was very friendly and helpful. The room was clean and cozy , and nicely furnished. Common areas were very comfortable and welcoming. We will definitely come back! "
The price is S$277
includes taxes & fees
19 May - 20 May
The Carriage Barn Inn
Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1003)
"Great check in experience and clean, comfortable rooms. "
The price is S$227
includes taxes & fees
2 Jun - 3 Jun
Courtyard by Marriott Keene Downtown
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (707)
"Perfect spot, right in the middle of everything. Staff was great and rooms were, spacious, clean and quiet."
The price is S$205
includes taxes & fees
1 Jun - 2 Jun
Fairfield Inn & Suites by Marriott Keene Downtown
The Burrell House
Exterior

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (126)
"It’s a beautiful property and walking distance to everywhere. "
The price is S$192
includes taxes & fees
18 May - 19 May
The Burrell House
Best Western Plus Keene Hotel
Exterior

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1001)
"Great hotel with a wonderful restaurant in the hotel!"
The price is S$186
includes taxes & fees
1 Jun - 2 Jun
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (297)
"Was a very nice hotel. We had a really nice stay."
The price is S$208
includes taxes & fees
1 Jun - 2 Jun
Hampton Inn & Suites Keene
Keene Elm City Hotel, Ascend Hotel Collection
In-room safe, desk, iron/ironing board, free cots/infant beds

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (826)
"You can never go wrong choosing a Holiday Inn Express. This one in Keene, NH was conveniently located, clean, and has plenty of parking. They offer a hot buffet breakfast which is very nice. The staff were all very professional and helpful especially Dylan the night manager. My only disappointment was the gym was closed for renovations. "
The price is S$130
includes taxes & fees
18 May - 19 May
Keene Elm City Hotel, Ascend Hotel Collection
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, (1002)
"Convenient to places to eat in shopping, easy to find. Friendly staff, easy check in. Decent shape of the building and clean in the rooms. "
The price is S$128
includes taxes & fees
19 May - 20 May
Days Inn by Wyndham Keene NH
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (152)
"This historic property is very nice. Beds are comfortable. The hosts are very welcoming and communication was very good. Breakfast was outstanding! I highly recommend this property and hope to return for another visit someday. "
The price is S$265
includes taxes & fees
1 Jun - 2 Jun
Centennial House
Inn at Valley Farms
Library

Inn at Valley Farms

2.0 star property
10.0 out of 10, Exceptional, (5)
"Wonderful location and property"
The price is S$229
includes taxes & fees
2 Jun - 3 Jun
Inn at Valley Farms
The Inn At Crumpin Fox
Terrace/patio

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (285)
"We enjoyed our stay very much."
The price is S$325
includes taxes & fees
18 May - 19 May
The Inn At Crumpin Fox
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (101)
"Charming place with friendly staff and owners."
The price is S$424
includes taxes & fees
20 May - 21 May
Chesterfield Inn
Hampton Inn & Suites Greenfield
Down duvets, desk, blackout curtains, soundproofing

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (796)
"Love the hotel good service friendly staff "
The price is S$214
includes taxes & fees
1 Jun - 2 Jun
Hampton Inn & Suites Greenfield
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1006)
"Quaint little Inn with spacious rooms and comfy beds. Just perfect and the guy at the front desk was super friendly and helpful! Would stay again if in the area "
The price is S$148
includes taxes & fees
18 May - 19 May
The Putney Inn
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (735)
"Our stay at the Latchis was wonderful! Super cool to be staying in an old art deco building, and we even took advantage of the movie theater a couple of times. Extremely conveniently located in the center of downtown, just a stone’s throw away from the Amtrak station. "
The price is S$250
includes taxes & fees
19 May - 20 May
Latchis Hotel
The One Cat B&B
Exterior detail

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Such nice innkeepers! And a bespoke breakfast to boot. I hope I'm back in Brattleboro soon so I can spend another night at the One Cat B&B. Next time I hope to meet the cat."
The price is S$321
includes taxes & fees
19 May - 20 May
The One Cat B&B
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.
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Learn more about Winchester

Get away to relaxing Winchester! Enjoy the lake views, forests and more.

See all hotels in Winchester
Photo by Donny Campos
Open Photo by Donny Campos

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 Best Western Plus Keene Hotel. See all available top hotels, or 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: Features a sauna, an indoor pool and free self parking. Colonial Motel And Spa and Best Western Plus Keene Hotel 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 Loring Field, Birch Point and Rhododendron State Park. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Pisgah State Park. 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.