Photo by Donny Campos

Hotels in Winchester

Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices

Check prices for these dates

This weekend
Next weekend

Where to stay in Winchester?

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (156)
The price is ¥22,191
¥23,456 total
includes taxes & fees
Jul 28 - Jul 29
Centennial House

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (761)
The price is ¥18,815
¥20,696 total
includes taxes & fees
Jul 24 - Jul 25
Latchis Hotel

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
The price is ¥27,905
¥30,696 total
includes taxes & fees
Jul 30 - Jul 31
The One Cat B&B

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1005)
Days Inn by Wyndham Keene NH

Econo Lodge Brattleboro

2.0 star property
5.6 out of 10, (535)
The price is ¥11,213
¥12,336 total
includes taxes & fees
Aug 21 - Aug 22
Econo Lodge Brattleboro

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (316)
The price is ¥21,911
¥23,774 total
includes taxes & fees
Jul 27 - Jul 28
Hampton Inn & Suites Keene

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very Good, (1004)
The price is ¥19,644
¥21,314 total
includes taxes & fees
Jul 27 - Jul 28
Best Western Plus Keene Hotel

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (305)
The price is ¥25,067
¥28,000 total
includes taxes & fees
Aug 6 - Aug 7
The Inn At Crumpin Fox

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (48)
The price is ¥38,889
¥42,777 total
includes taxes & fees
Jul 28 - Jul 29
Inn on Putney Road

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very Good, (860)
The price is ¥16,450
¥17,849 total
includes taxes & fees
Aug 5 - Aug 6
Keene Elm City Hotel, Ascend Hotel Collection

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (580)
The price is ¥22,305
¥24,201 total
includes taxes & fees
Jul 28 - Jul 29
Riverside Hotel, Ascend Hotel Collection

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1010)
The Covered Bridge Inn

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (445)
The price is ¥17,593
¥19,352 total
includes taxes & fees
Jul 31 - Aug 1
Black Mountain Inn

Vikings Villages Resort

2.0 star property
10.0 out of 10, Exceptional, (110)
The price is ¥28,795
¥33,584 total
includes taxes & fees
Aug 6 - Aug 7
Vikings Villages Resort

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (103)
The price is ¥44,147
¥47,900 total
includes taxes & fees
Jul 24 - Jul 25
Chesterfield Inn

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
The price is ¥29,456
¥31,960 total
includes taxes & fees
Jul 27 - Jul 28
The Carriage Barn Inn

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1006)
The price is ¥14,381
¥15,820 total
includes taxes & fees
Jul 24 - Jul 25
Colonial Motel And Spa

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (659)
The price is ¥20,081
¥22,089 total
includes taxes & fees
Jul 27 - Jul 28
Comfort Inn & Suites Brattleboro I-91

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very Good, (852)
The price is ¥18,567
¥20,424 total
includes taxes & fees
Aug 10 - Aug 11
Hampton Inn Brattleboro

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (999)
The price is ¥24,922
¥27,414 total
includes taxes & fees
Jul 27 - Jul 28
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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.

Top landmarks in Winchester

Learn more about Winchester

Winchester is well-known for its attractions such as Winchester Speedpark and Pisgah State Park. The city has something for everyone including sights like Richmond Wildlife Manangement Area and Rhododendron State Park within a scenic setting.

The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.
Photo by Donny Campos
Open Photo by Donny Campos

Check out reviews of Winchester hotels guests love

Frequently asked questions

What hotels do travelers like in Winchester?
Guests like Beautiful lake side get away, quiet, and peaceful..
Can I book refundable hotels in Winchester?
If you need the flexibility to change your travel plans to Winchester, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Winchester be like during my vacation?
July and August are typically the warmest months in Winchester when the average temp is 67°F. January and February are the coldest months when the average temperature is 28°F. October and July are the months with the most rain.
Why should I book my Winchester hotel through Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.