Photo by Donny Campos

Winchester Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 21 - Jul 22
Tomorrow
Jul 22 - Jul 23
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Winchester hotels

The Maguire House Bed & Breakfast
Property grounds

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 P15,728
P15,728 total
includes taxes & fees
Jul 30 - Jul 31
The Maguire House Bed & Breakfast
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1005)
"Very good hotel "
The Colonial Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Free daily on-the-go breakfast

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (407)
"Clean, comfortable, easy check in/check out. Beautiful location, staff was friendly and efficient. "
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 "
Monadnock Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (152)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is P11,492
P12,469 total
includes taxes & fees
Jul 22 - Jul 23
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, (1004)
"Hotel itself clean and nice but surrounding area has homeless people, or seems a little sketchy, which made us a little nervous walking around town "
The price is P9,666
P10,487 total
includes taxes & fees
Jul 27 - Jul 28
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, (725)
"Friendly, helpful staff. Old hotel in good condition. "
The price is P8,579
P9,308 total
includes taxes & fees
Aug 17 - Aug 18
Fairfield Inn & Suites by Marriott Keene Downtown
The Burrell House
Exterior

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (131)
"Beautiful Inn!! Very happy customer ! I’ll be back !"
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)
"Nice hotel "
The price is P7,664
P8,315 total
includes taxes & fees
Jul 23 - Jul 24
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (316)
"Keene NH Hampton was probaly the nicest Hampton I ever stayed at. Clean & friendly "
The price is P8,457
P9,176 total
includes taxes & fees
Jul 27 - Jul 28
Hampton Inn & Suites Keene
Keene Elm City Hotel, Ascend Hotel Collection
Indoor pool

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very Good, (860)
"Good place to stop "
The price is P6,383
P6,925 total
includes taxes & fees
Jul 27 - Jul 28
Keene Elm City Hotel, Ascend Hotel Collection
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout drapes, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1005)
"Great stay"
The price is P5,737
P6,225 total
includes taxes & fees
Aug 10 - Aug 11
Days Inn by Wyndham Keene NH
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (156)
"Great breakfast, friendly staff"
The price is P9,951
P10,518 total
includes taxes & fees
Jul 23 - Jul 24
Centennial House
Inn at Valley Farms
Library

Inn at Valley Farms

2.0 star property
10.0 out of 10, Exceptional, (9)
"Wonderful location and property"
The price is P11,978
P12,996 total
includes taxes & fees
Jul 27 - Jul 28
Inn at Valley Farms
The Inn At Crumpin Fox
Front of property

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (305)
"Very nice and very responsive staff"
The price is P10,809
P12,074 total
includes taxes & fees
Aug 13 - Aug 14
The Inn At Crumpin Fox
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (103)
"Great stay"
The price is P17,223
P18,687 total
includes taxes & fees
Jul 28 - Jul 29
Chesterfield Inn
Hampton Inn & Suites Greenfield
Down comforters, desk, blackout drapes, soundproofing

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (819)
"Great property and staff!"
The price is P9,577
P10,697 total
includes taxes & fees
Jul 27 - Jul 28
Hampton Inn & Suites Greenfield
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1010)
"Certainly convenient, right off 91."
The Putney Inn
Latchis Hotel
Hiking

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (760)
"Great location, amazing history and architecture."
The price is P7,978
P8,777 total
includes taxes & fees
Jul 23 - Jul 24
Latchis Hotel
The One Cat B&B
Exterior

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is P12,868
P14,155 total
includes taxes & fees
Jul 28 - Jul 29
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Top Winchester Hotel Reviews

Latchis Hotel

Latchis Hotel

10/10 Excellent
"We have stayed at The Latchis a few times now and it is always a nice place to stay, from the friendly helpful staff to the clean room and amenities. The room we stayed in this time was one we have previously stayed in and it was recently updated with new furniture and it was nice. The location is convenient and very walkable to stores and restaurants in the downtown area. We will definitely be returning to stay at The Latchis again. "
Luke A. 1-night trip
Posted 2 days ago
Latchis Hotel

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 traveler data. Other good options for your stay in 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, most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.

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 two additional hotels with an onsite pool. View all hotels with pools in Winchester.

What is the best hotel near Hartness State Airport (VSF)?

The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.

What is staying in Winchester like?

Visitors to Winchester are sure to enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 6 hotels and other accommodations to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

Natural beauty is on display at Richmond Wildlife Manangement Area, Rhododendron State Park, and Ashuelot River. A couple of additional sights to add to your agenda are Winchester Speedpark and Pisgah State Park. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.