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Our top choices for Winchester hotels

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,011 reviews)
"LOVED THE HOTEL AND LOVED THE AREA."
United States
Derrick Michael
November 6th, 2025
$144 nightly
The price is $161
Apr 19 - Apr 20
Total with taxes and fees
The Colonial Hotel

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1,022 reviews)
"Parking was easy, property felt safe and clean. Breakfast was free, but very ordinary."
United States
Richard
13 days ago
$127 nightly
The price is $141
May 5 - May 6
Total with taxes and fees
Comfort Inn & Suites Hadley - Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,008 reviews)
"Clean room, nice staff, lots of parking."
United States
Ben
3 days ago
$98 nightly
The price is $110
Apr 20 - Apr 21
Total with taxes and fees
Red Roof Inn PLUS+ South Deerfield – Amherst

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1,013 reviews)
"The hotel was very clean. Staff was lovely very helpful with questions."
United States
Sheila
3 days ago
$118 nightly
The price is $132
May 10 - May 11
Total with taxes and fees
Hotel UMass

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (182 reviews)
"Great home base for day trips."
United States
Jen
9 days ago
$247 nightly
The price is $270
Apr 19 - Apr 20
Total with taxes and fees
Vikings Villages Resort

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (174 reviews)
"The breakfast made. The house was cozy. Served by Joan was great."
United States
Paul
November 18th, 2025
$169 nightly
The price is $179
May 3 - May 4
Total with taxes and fees
Centennial House

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (961 reviews)
"Keisha the overnight hotel desk and information employee was THE BEST!"
United States
Michael
2 days ago
$105 nightly
The price is $115
Apr 28 - Apr 29
Total with taxes and fees
Hampton Inn Brattleboro

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)
"The room was clean and breakfast was very good."
United States
Sandra
3 days ago
$144 nightly
The price is $156
Apr 19 - Apr 20
Total with taxes and fees
Best Western Plus Keene Hotel

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1,002 reviews)
"Awesome and clean and quiet love the staff."
United States
Jeremiah
1 day ago
Colonial Motel And Spa

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,001 reviews)
"Staff were lovely. Parking was plentiful."
United States
Lilly
16 days ago
$94 nightly
The price is $103
Apr 19 - Apr 20
Total with taxes and fees
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, (793 reviews)
"Staff was friendly and pool was nice."
United States
Joshua
December 1st, 2025
$147 nightly
The price is $161
May 10 - May 11
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91

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)
"The room was very clean. The staff was very nice."
United States
Sandra
3 days ago
$135 nightly
The price is $146
Apr 19 - Apr 20
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (79 reviews)
"The staff was very pleasant. We were pleased with our stay."
United States
Annette
November 21st, 2025
$152 nightly
The price is $170
Apr 22 - Apr 23
Total with taxes and fees
TownePlace Suites by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (714 reviews)
"The staff were extremely helpful for our stay. The hotel is good."
United States
Rudolph
9 days ago
$143 nightly
The price is $160
Apr 20 - Apr 21
Total with taxes and fees
Courtyard by Marriott Hadley Amherst

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, (1,002 reviews)
"The beds were super comfortable. The breakfast bar had a large variety of food."
United States
Danielle
3 days ago
$169 nightly
The price is $186
Apr 19 - Apr 20
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (789 reviews)
"Beautiful historic property perfectly situated. From the friendly staff."
United States
Tigerron
5 days ago
$195 nightly
The price is $217
May 3 - May 4
Total with taxes and fees
Inn on Boltwood

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (358 reviews)
"The gentleman at the counter was very friendly."
United States
Loren
January 26th, 2026
$204 nightly
The price is $228
Apr 19 - Apr 20
Total with taxes and fees
The Inn At Crumpin Fox

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (863 reviews)
"You love retro vintage history quiet. A movie theatre in the hotel."
United States
Heather
17 days ago
$126 nightly
The price is $138
Apr 22 - Apr 23
Total with taxes and fees
Latchis Hotel

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,001 reviews)
"The rrooms were clean, shower was great."
United States
laurel
17 days ago
$81 nightly
The price is $89
Apr 20 - Apr 21
Total with taxes and fees
The Covered Bridge Inn

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,000 reviews)
"The room was great. The staff was wonderful."
United States
Wendy
November 2nd, 2025
$189 nightly
The price is $205
Apr 24 - Apr 25
Total with taxes and fees
Courtyard by Marriott Keene Downtown
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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 downtown 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

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Winchester is ideal for outdoor enthusiasts, offering activities like hiking, skiing, and exploring beautiful forests and parks.
  • Scenic Beauty: Enjoy stunning landscapes that provide a perfect backdrop for romantic getaways and family outings.
  • Charming Downtown: Stroll through the welcoming downtown area, filled with friendly locals and quaint shops.
  • Recreational Activities: Visit the dropzone waterpark and partake in various entertainment options for a fun-filled experience.
  • Cozy Accommodations: Choose from a range of inviting hotels and bed & breakfasts for a comfortable stay.

Find great hotels near Winchester

Winchester, New Hampshire, offers a charming selection of accommodations, including cozy hotels and inviting bed & breakfasts. Whether you're seeking a pet-friendly getaway, a base for adventure, or business travel amenities, the area has something to meet your needs. Explore the best hotels in Winchester and enjoy a memorable stay surrounded by beautiful landscapes and warm hospitality.

  • Best Western Plus Keene Hotel: This 3-star hotel, rated 8.4 out of 10, is a family-friendly and pet-friendly haven just 11 miles from Winchester. Best Western Plus Keene Hotel caters to a diverse range of travelers, including families and business guests. Amenities for children, such as free cribs, make it an ideal choice for families. The hotel also welcomes pets, with specific policies that accommodate dogs and service animals. Guests can enjoy the comfort of well-appointed rooms and the convenience of being close to local attractions, making it a versatile option for any visitor.
  • Colonial Motel And Spa: Located 12 miles from Winchester, this 3-star motel is perfect for those seeking adventure and relaxation. With a focus on family and spa experiences, Colonial Motel And Spa offers a range of exciting activities, including snow tubing, skiing, and mountain biking nearby. The full-service spa and pool provide opportunities for relaxation, with amenities such as a sauna and adult supervision required for the pool. Family-friendly features like a first aid kit and window guards ensure that children are safe and entertained, making this a great option for families looking for both adventure and relaxation.
  • The Covered Bridge Inn: This budget-friendly hotel, also located 12 miles from Winchester, is an excellent choice for adventure seekers. The Covered Bridge Inn offers access to a variety of outdoor activities, such as hiking, snowboarding, and rafting nearby. Ideal for travelers who wish to explore the great outdoors without breaking the bank, this inn provides a cozy and affordable lodging option. With a focus on adventure, guests can immerse themselves in the beautiful landscapes and thrilling sports that the area has to offer.

Where to stay in and around Winchester

Winchester, New Hampshire, offers a delightful blend of outdoor adventures and scenic beauty for visitors. Stroll through the charming downtown area, where friendly locals create a welcoming atmosphere. Explore the serene landscapes perfect for a romantic getaway or family-friendly activities. For those looking to venture further, nearby attractions provide opportunities for adventure in secluded settings. Whether you're seeking relaxation or excitement, Winchester promises an unforgettable travel experience.

  • Brattleboro: Located approximately 10 miles from Winchester, Brattleboro is a vibrant city that draws visitors year-round, with peak travel occurring from July to September. Known for its stunning natural beauty, Brattleboro is a haven for outdoor enthusiasts seeking skiing adventures and sports experiences. The surrounding landscape features picturesque lakes, majestic mountains, and the scenic expanse of a national state park, making it an ideal spot for nature lovers. In addition to winter sports, the city offers a charming downtown area filled with local shops, cafés, and art galleries, providing a perfect blend of outdoor adventure and cultural exploration.
  • Keene: Just 12 miles from Winchester, Keene is a delightful city that offers an excellent mix of outdoor activities and beautiful scenery. With visitor numbers peaking in July, August, and October, this area is a popular destination for those seeking adventure. The nearby ski fields and resorts cater to winter sports enthusiasts, while the serene lakes and the presence of a modern college university create a lively atmosphere. Outdoor festivals and community events often take place here, inviting visitors to immerse themselves in local culture and enjoy the stunning landscapes that surround the city.
  • Richmond: Situated within the area of Winchester, Richmond is a quaint village that attracts a moderate number of travelers, especially during the peak seasons of February and June to July. Known for its outdoor activities, Richmond is an excellent base for skiing and adventure sports. The local landscape features inviting lakes and the historic town hall, alongside access to a national state park that showcases the region's natural beauty. The village's close-knit community and charming ambiance make it a perfect spot for those looking to relax and enjoy the great outdoors.

Things to do near Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and romantic getaways, offering scenic views and recreational activities. Visitors can enjoy skiing at local slopes, explore educational attractions, and unwind at the dropzone waterpark. There are also various entertainment options and event venues, making it a great destination for a fun-filled vacation.

Shopping

In Winchester, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, visit the Keene Shopping Center about 15 miles away, where you'll find a variety of retail stores, restaurants, and a vibrant shopping atmosphere.

Recreation

At Crumpin-Fox Golf Club, indulge in luxury while enjoying a round of golf amidst scenic views and top-notch facilities, located 10 miles from Winchester. Similarly, the Brattleboro Country Club offers a lavish golfing experience, just 12 miles away, perfect for unwinding and connecting with nature.

Adventure

Winchester offers thrilling outdoor adventures at Pisgah State Park, where you can hike scenic trails, bike through lush forests, and discover hidden waterfalls. For a unique experience, try kayaking on Lake Monomonac, enjoying the tranquil waters and beautiful views of the surrounding nature.

Nightlife

Winchester offers a cozy nightlife with charming bars like the Winchester Tavern for casual drinks and local brews. If you're in the mood for live music, check out the local venues featuring talented bands that create a lively atmosphere perfect for dancing and socializing.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are March and December to January, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Tuesday. The most expensive day to stay in Winchester is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package deal.

Find the best attractions near Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and romantic getaways, offering stunning scenery and a variety of attractions. Visitors can explore beautiful forests, nature reserves, and parks that cater to those seeking adventure and eco-friendly experiences. Whether you're hiking, picnicking, or simply enjoying the natural beauty, Winchester has something for everyone looking to connect with nature.

  • Brattleboro Common: This charming urban park, located 11 miles from Winchester, offers a perfect blend of family-friendly spaces and vibrant city life. Enjoy leisurely strolls, community events, and lush greenery, making it an ideal spot for relaxation and recreation.
  • Spofford Lake: Just 10 miles away, Spofford Lake is a picturesque destination for outdoor enthusiasts. With its serene beaches and stunning scenery, it's perfect for romantic picnics, swimming, and kayaking, making it a tranquil retreat for all visitors.
  • New England Center for Circus Arts: Located 11 miles from Winchester, this unique arts center celebrates circus culture through performances and workshops. Experience innovative acts and immerse yourself in the vibrant world of circus arts, a true cultural gem.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly SunnyAverageSlightly Low
February25.2°F (-3.8°C)Light RainMostly SunnySlightly LowAverage
March32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
April45.0°F (7.2°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageSlightly High
June64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
July71.2°F (21.8°C)Light RainMostly SunnySlightly HighAverage
August69.3°F (20.7°C)Light RainMostly SunnyAverageAverage
September61.9°F (16.6°C)Light RainMostly SunnySlightly HighSlightly High
October50.5°F (10.3°C)Light RainMostly SunnyAverageSlightly High
November38.7°F (3.7°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Winchester

When visiting Winchester, New Hampshire, you have several airport options to consider. BOSton Logan International Airport (BOS) is approximately 75 miles away, with nearby hotels like Encore Boston Harbor, InterContinental Boston, and Boston Harbor Hotel, all within 3 miles of the airport. Hartford's Bradley International Airport (BDL) is about 60 miles from Winchester, offering accommodations such as DoubleTree by Hilton, Simsbury 1820 House, and Marriott Hartford Downtown. Lastly, Providence's T.F. Green Airport (PVD) is around 87 miles away, with options like Omni Providence Hotel, Hotel Providence, and Renaissance Providence Downtown Hotel, all situated approximately 7 miles from the airport.

Frequently asked questions

What is the best area to stay in Winchester?
The best area to stay in Winchester is near Main Street, particularly around its intersection with Richmond Road (Route 119) and Ashuelot Street.

This central area provides convenient access to local businesses and the town's main attractions. You'll find Winchesters's Town Common here, a pleasant green space, and the town's historic architecture. This location is ideal for independent travelers and couples who appreciate being within walking distance of local shops and eateries.

For those looking for a more secluded experience with direct access to nature, the areas surrounding Pisgah State Park, just west of the town center, offer a quieter alternative. While fewer lodging options are directly within the park, nearby accommodations provide easy access to hiking trails, fishing, and kayaking opportunities.
When is the best time to go to Winchester?
The best time to visit Winchester, New Hampshire, is during the shoulder seasons of late spring (May to early June) and early autumn (September to October).

These periods offer pleasant weather conditions, fewer crowds, and a variety of outdoor activities. Late spring brings blooming foliage and comfortable temperatures, ideal for hiking and exploring the natural beauty of the region. Early autumn showcases stunning fall foliage, making it a picturesque time for scenic drives and enjoying local harvest festivals.

For travelers who enjoy outdoor recreation and prefer comfortable temperatures without the peak summer crowds, these shoulder seasons provide an excellent balance.
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?
With Expedia, you earn OneKeyCash™* on eligible Winchester hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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 $89 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.

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