Find hotels in Winchester, NH from CA $121

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Apr 23 - Apr 24
Tomorrow
Apr 24 - Apr 25
This weekend
Apr 24 - Apr 26
Next weekend
May 1 - May 3

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (963 reviews)
"I wish I could have stayed longer. Very nice hotel "
United States
Rosa
The price is CA $168
CA $185 total
includes taxes & fees
Apr 29 - Apr 30
Hampton Inn Brattleboro
Exterior

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,001 reviews)
"Great Stay!"
United States
Nicholas
The price is CA $115
CA $126 total
includes taxes & fees
Apr 28 - Apr 29
The Putney Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (30 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is CA $175
CA $190 total
includes taxes & fees
May 18 - May 19
Four Columns Inn
Breakfast area

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,000 reviews)
"Clean room, quiet, good price "
United States
Derek
The price is CA $108
CA $119 total
includes taxes & fees
Apr 27 - Apr 28
The Covered Bridge Inn
Front of property

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 CA $155
CA $240 total
includes taxes & fees
Apr 24 - Apr 25
Blooming Inn
In-room safe, desk, blackout drapes, iron/ironing board

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,001 reviews)
"It is an economy, hotel, and had all the basics covered. It was clean, and the beds were comfortable."
Canada
Julie
The price is CA $138
CA $150 total
includes taxes & fees
Apr 28 - Apr 29
Days Inn by Wyndham Keene NH
Lobby

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, (1,000 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 CA $185
CA $200 total
includes taxes & fees
Apr 26 - Apr 27
Keene Elm City Hotel, an Ascend Collection Hotel
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (352 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is CA $215
CA $237 total
includes taxes & fees
May 13 - May 14
Colonel Williams Inn
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,000 reviews)
"Great staff, great food, clean, friendly"
United States
Thomas
The price is CA $195
CA $218 total
includes taxes & fees
Apr 29 - Apr 30
The Colonial Hotel
Exterior

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 CA $206
CA $230 total
includes taxes & fees
May 4 - May 5
The Burrell House
Front of property

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (182 reviews)
"Great place and very clean!!"
United States
Emil
The price is CA $276
CA $322 total
includes taxes & fees
Apr 28 - Apr 29
Vikings Villages Resort
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (868 reviews)
"Room was clean. Staff was very friendly "
United States
Deanna
The price is CA $149
CA $164 total
includes taxes & fees
Apr 30 - May 1
Latchis Hotel
Restaurant

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 CA $197
CA $214 total
includes taxes & fees
Apr 26 - Apr 27
Best Western Plus Keene Hotel
Free daily continental breakfast

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 CA $218
CA $236 total
includes taxes & fees
Apr 30 - May 1
The Carriage Barn Inn
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (794 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is CA $162
CA $179 total
includes taxes & fees
Apr 28 - Apr 29
Comfort Inn & Suites Brattleboro I-91
Lobby sitting area

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (17 reviews)
"Warm hospitality, very nice breakfast"
United States
Christopher
The price is CA $212
CA $230 total
includes taxes & fees
Apr 27 - Apr 28
Inn at Valley Farms
Exterior

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 CA $266
CA $293 total
includes taxes & fees
Apr 24 - Apr 25
The Inn At Quail Run
Front of property

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 CA $140
CA $154 total
includes taxes & fees
Apr 27 - Apr 28
Black Mountain Inn
BBQ/picnic area

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.2 out of 10, Wonderful, (460 reviews)
"Clean and quiet accommodations. Good take out breakfast. Smooth, automated check in and out. Will definitely come again..."
United States
Milan
The price is CA $196
CA $227 total
includes taxes & fees
Apr 28 - Apr 29
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Front of property

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 CA $328
CA $361 total
includes taxes & fees
Apr 29 - Apr 30
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Winchester attractions

Winchester Speedpark

You can take time to visit Winchester Speedpark during your travels to Winchester. While you're in the area, stroll along the lakeside.
See properties

Cass Pond

Commune with nature and explore the great outdoors at Cass Pond during your travels in Richmond.
See properties

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 downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester
Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

Recent Reviews in Winchester

Four Columns Inn

Four Columns Inn

10/10 Excellent
"All good"
Robert 1-night trip
Posted 12 hours ago
Four Columns Inn

More cheap stays in Winchester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
The price is CA $115 per night from Apr 28 to Apr 29
CA $115
CA $126 total
Apr 28 - Apr 29
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)

Hotels in Winchester with star rating

Frequently asked questions

When is the best time to go to Winchester?
The best time to visit Winchester, New Hampshire, is during the autumn months, particularly from late September to late October, for the spectacular fall foliage.

This period offers clear, crisp weather and the vibrant colours of the changing leaves, making it ideal for outdoor activities like hiking, scenic drives, and exploring the local countryside. The area surrounding Winchester is known for its natural beauty, with various trails and viewpoints to experience the seasonal display.

Couples looking for a romantic getaway will find this time particularly appealing. The picturesque landscapes provide a beautiful backdrop for leisurely drives through the New Hampshire countryside or cosy evenings by a fireplace. Many local inns and B&Bs offer special packages during the fall.

Families will also enjoy visiting in autumn. The cooler temperatures are superb for outdoor adventures without the summer heat, and there are often local harvest festivals or apple-picking opportunities in the wider region.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How can I save on a Winchester hotel booking with Expedia?
Members always get our best prices. Find our best Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from CA $121 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia