Search Winchester hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Winchester

Interior
The Colonial Hotel

The Colonial Hotel

3.0 star property
Gardner
8.8 out of 10, Excellent, (1001)
"Great hotel, fantastic restaurant, wonderful place!"
United States
Kate
Travelling with partner
The Colonial Hotel
Front of property
The Inn At Crumpin Fox

The Inn At Crumpin Fox

2.5 star property
Bernardston
9.2 out of 10, Wonderful, (342)
"Stayed twice with you now great staff nice rooms convenient location."
United States
Sergio
Travelling for leisure
The price is AU$220
includes taxes & fees
8 Dec - 9 Dec
The Inn At Crumpin Fox
Exterior detail
The Covered Bridge Inn

The Covered Bridge Inn

2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"The room was relatively clean and the bed pretty comfortable"
United States
Marilyn
Travelling with partner
The price is AU$131
includes taxes & fees
8 Dec - 9 Dec
The Covered Bridge Inn
Free daily on-the-go breakfast
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1000)
"the hotel is really quiet and clean!"
United States
Brandi
Travelling for leisure
The price is AU$252
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very good, (1000)
"very nice and restaurant was awesome"
United States
Dawn
Travelling for leisure
The price is AU$227
includes taxes & fees
8 Dec - 9 Dec
Best Western Plus Keene Hotel
Double Room
Gardner Inn

Gardner Inn

2.0 star property
Gardner
5.6 out of 10, (17)
"But the check in staff was nice and the large pictures of trees in the room my son really liked."
United States
Amber
Travelling with small children
The price is AU$150
includes taxes & fees
4 Jan - 5 Jan 2026
Gardner Inn
Reception
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

2.5 star property
Brattleboro
6.0 out of 10, (736)
"The good thing is bedding was clean"
United States
Julia
Travelling for leisure
The price is AU$118
includes taxes & fees
10 Dec - 11 Dec
Travelodge by Wyndham Brattleboro VT
Breakfast area
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
Peterborough
9.4 out of 10, Exceptional, (433)
"Clean, nice bed and bedding, good shower, easy to sleep in."
United States
morgan
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Sun deck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (628)
"I love this hotel and would definitely give it 5 stars"
United States
Kayla
The price is AU$249
includes taxes & fees
5 Jan - 6 Jan 2026
Riverside Hotel, an Ascend Collection Hotel
In-room safe, desk, blackout curtains, 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, (1001)
"Very clean - comfortable bed"
United States
christine
Travelling for leisure
The price is AU$157
includes taxes & fees
31 Dec - 1 Jan 2026
Days Inn by Wyndham Keene NH
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
8.6 out of 10, Excellent, (737)
"The bed was the best i have stayed in awhile."
United States
Daron
The price is AU$191
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn & Suites Brattleboro I-91
Front of property
Black Mountain Inn

Black Mountain Inn

2.0 star property
Brattleboro
7.4 out of 10, Good, (474)
"Very friendly and helpful staff, clean and quiet room."
United States
Paul
Travelling with family
The price is AU$169
includes taxes & fees
8 Dec - 9 Dec
Black Mountain Inn
Hiking
Latchis Hotel

Latchis Hotel

2.5 star property
Brattleboro
8.4 out of 10, Very good, (834)
"Retro rooms, vinyl record players, very comfortable beds!"
United States
Suzanne
Travelling for leisure
The price is AU$205
includes taxes & fees
17 Dec - 18 Dec
Latchis Hotel
Free breakfast
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 star property
Brattleboro
8.2 out of 10, Very good, (924)
"Pool and hot tub area was just renovated and looked great and worked great."
United States
Lisa
Travelling with friends
The price is AU$237
includes taxes & fees
13 Dec - 14 Dec
Hampton Inn Brattleboro
Exterior
Colonial Motel And Spa

Colonial Motel And Spa

3.0 star property
Brattleboro
6.8 out of 10, (1001)
"The room I was given was quite impressive in size."
United States
Linda
Travelling for business
The price is AU$199
includes taxes & fees
8 Dec - 9 Dec
Colonial Motel And Spa
Room, 2 Queen Beds, Non Smoking
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 star property
Greenfield
8.6 out of 10, Excellent, (877)
"Nice room with a comfortable bed."
United States
Andrea
Travelling for leisure
The price is AU$308
includes taxes & fees
13 Dec - 14 Dec
Hampton Inn & Suites Greenfield
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
Keene
8.8 out of 10, Excellent, (755)
"Great location in downtown Keene with lovely shops and restaurants."
United States
Julie
Travelling with family
The price is AU$294
includes taxes & fees
13 Dec - 14 Dec
Fairfield Inn & Suites by Marriott Keene Downtown
Reception
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
Keene
8.8 out of 10, Excellent, (352)
"The room was well appointed and very clean."
United States
MaryBeth
Travelling with family
The price is AU$241
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Keene
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (13)
"Great staff, fabulous rooms - spacious and loved the fireplace!"
United States
Caroline
Travelling solo
Four Columns Inn
Exterior
The Putney Inn

The Putney Inn

2.5 star property
Putney
8.4 out of 10, Very good, (1001)
"Quaint little Inn with spacious rooms and comfy beds"
United States
Tomy
Travelling solo
The Putney Inn
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

Winchester Speedpark thrills with professionally designed motocross tracks featuring challenging jumps and turns. Experience heart-pounding night races or watch competitors tackle the New England racing circuit.
See properties

New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskies while learning about the distillation process in a warm space adorned with reclaimed wood.
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 city centre 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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"The customer service at this hotel is consistently exceptional. Every staff member is friendly, professional, and welcoming, creating an atmosphere that feels truly comfortable. The property is impeccably clean, and the breakfast offerings are always enjoyable. I have had an excellent experience during each of my visits, and I highly recommend this hotel to others"
qader 2-night trip
Posted 7 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

More cheap accommodation in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is AU$157 per night from 31 Dec to 1 Jan
AU$157
31 Dec - 1 Jan 2026
includes taxes & fees
7/10 Good! (1,005 reviews)

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 Hampton Inn & Suites Greenfield and Hampton Inn Brattleboro. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Beautiful Custom Built Timber Frame Home, Sleeps 11: This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. 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: Features a sauna, an indoor pool and free self parking. Hampton Inn Brattleboro and Comfort Inn & Suites Brattleboro I-91 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 Birch Point, Ashuelot River and Cass Pond. A couple of additional sights to add to your itinerary are Pisgah State Park and New England Sweetwater Farm & Distillery. 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