Winchester hotels from RM310

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (961 reviews)
"I wish I could have stayed longer. Very nice hotel "
United States
Rosa
The price is RM476
RM523 total
includes taxes & fees
28 Apr - 29 Apr
Hampton Inn Brattleboro

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,000 reviews)
"Great Stay!"
United States
Nicholas
The price is RM333
RM366 total
includes taxes & fees
19 Apr - 20 Apr
The Putney Inn

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (792 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is RM579
RM637 total
includes taxes & fees
21 Apr - 22 Apr
Comfort Inn & Suites Brattleboro I-91

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (28 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is RM516
RM562 total
includes taxes & fees
20 Apr - 21 Apr
Four Columns Inn

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,010 reviews)
"Great staff, great food, clean, friendly"
United States
Thomas
The price is RM569
RM636 total
includes taxes & fees
19 Apr - 20 Apr
The Colonial Hotel

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (171 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is RM599
RM650 total
includes taxes & fees
19 Apr - 20 Apr
The Carriage Barn Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,001 reviews)
"Clean room, quiet, good price "
United States
Derek
The price is RM282
RM310 total
includes taxes & fees
20 Apr - 21 Apr
The Covered Bridge Inn

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (72 reviews)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is RM771
RM848 total
includes taxes & fees
16 Apr - 17 Apr
The Inn At Quail Run

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (490 reviews)
"Pet friendly for $15 plus tax. The place noisy with heat turned on in the room "
United States
Angela
The price is RM428
RM471 total
includes taxes & fees
17 Apr - 18 Apr
Black Mountain Inn

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (863 reviews)
"Great location, great staff really cool old building with lots of character"
Canada
David
The price is RM527
RM580 total
includes taxes & fees
16 Apr - 17 Apr
Latchis Hotel

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (162 reviews)
"We had a wonderful stay at The Burrell House. The room was large, beautifully renovated with a well thought out design. It is a very short walk or drive to Main Street where there were a multitude of restaurants and shops. We truly enjoyed our stay and plan to book again soon. "
United States
Melissa
The price is RM592
RM660 total
includes taxes & fees
19 Apr - 20 Apr
The Burrell House

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (351 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is RM622
RM685 total
includes taxes & fees
26 Apr - 27 Apr
Colonel Williams Inn

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,001 reviews)
"Nice rooms"
United States
Kim
The price is RM569
RM618 total
includes taxes & fees
16 Apr - 17 Apr
Best Western Plus Keene Hotel

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is RM398
RM639 total
includes taxes & fees
16 Apr - 17 Apr
Blooming Inn

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (357 reviews)
"Perfect place for what we needed!"
United States
Cathleen
The price is RM727
RM812 total
includes taxes & fees
22 Apr - 23 Apr
The Inn At Crumpin Fox

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,001 reviews)
"Clean room, polite staff,kids enjoyed the indoor heated pool they also have a small gym and breakfast in the morning couldn't beat the price definitely a great place for the family dogs are also welcome!!"
United States
Sean
The price is RM534
RM579 total
includes taxes & fees
19 Apr - 20 Apr
Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (903 reviews)
"Good stay; great staff and nice clean rooms!"
United States
Peter
The price is RM687
RM768 total
includes taxes & fees
26 Apr - 27 Apr
Hampton Inn & Suites Greenfield

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is RM988
RM1,087 total
includes taxes & fees
18 Apr - 19 Apr
The One Cat B&B

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (770 reviews)
"Breakfast was great and location is perfect. Lots of good restaurants and bars to visit. Rooms are nice, but slightly dated, and the building is very cool."
United States
Keith
The price is RM727
RM789 total
includes taxes & fees
20 Apr - 21 Apr
Fairfield Inn & Suites by Marriott Keene Downtown

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (174 reviews)
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
The price is RM709
RM750 total
includes taxes & fees
3 May - 4 May
Centennial House
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winchester attractions

Learn more about Winchester

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic city centre district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

More cheap stays in Winchester

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.
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 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 7 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 Rhododendron State Park, Cass Pond and Royalston State Forest. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Winchester Speedpark. 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.

Explore a world of travel with Expedia