Hotels in Winchester

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Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9

Where to stay in Winchester?

37-inch LCD TV with cable channels, TV

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1,012 reviews)
Wake up to free breakfast at this university-adjacent hotel with room service and helpful staff. The Commonwealth restaurant serves lunch and dinner, while a bar and deli offer casual options. Explore nearby Mullins Center and UMass Fine Arts Center with ease.
The price is $143
$161 total
includes taxes & fees
Aug 9 - Aug 10
Hotel UMass
Reception

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, (1,004 reviews)
This hotel puts you close to Yankee Candle Village and Mount Sugarloaf State Reservation. Enjoy clean rooms with free WiFi and parking, plus attentive 24-hour staff to assist throughout your stay. UMass Amherst is just a short drive away.
The price is $99
$110 total
includes taxes & fees
Jul 30 - Jul 31
Red Roof Inn PLUS+ South Deerfield – Amherst
Exterior

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1,016 reviews)
Set in Hadley, this comfortable hotel offers free breakfast, WiFi, and parking just 5 minutes from UMass Amherst. Take a morning dip in the indoor pool or visit the fitness center. Popular attractions like Autobahn and Cinemark At Hampshire Mall are conveniently nearby.
The price is $148
$166 total
includes taxes & fees
Aug 20 - Aug 21
Comfort Inn & Suites Hadley - Amherst
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, (1,004 reviews)
Escape to this welcoming hotel in Keene, where you'll find an indoor pool and fitness center near local shops and eateries. Despite its commercial location, guests enjoy a quiet atmosphere, free breakfast, and helpful staff to enhance your stay.
The price is $129
$140 total
includes taxes & fees
Jul 26 - Jul 27
Keene Elm City Hotel, an Ascend Collection Hotel
Front of property - evening/night

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (837 reviews)
Experience charm at this colonial hotel steps from Amherst College. Enjoy American cuisine at 30Boltwood restaurant, unwind at the bar/lounge, or relax on the rooftop terrace. Free WiFi and parking near Emily Dickinson Museum and local transit.
The price is $179
$199 total
includes taxes & fees
Aug 3 - Aug 4
Inn on Boltwood
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
9.0 out of 10, Wonderful, (1,011 reviews)
Discover a peaceful retreat with Swedish spa services and a welcoming bar. Near Wachusett Mountain Ski Area, this countryside haven offers in-room refrigerators and convenient access to scenic Dunn State Park. Guests rave about the restaurant and attentive staff.
The price is $170
$190 total
includes taxes & fees
Jul 26 - Jul 27
The Colonial Hotel
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,000 reviews)
Quiet rooms welcome travelers to this restful retreat near the Ashuelot River and Thorne Sagendorph Art Gallery. The restaurant and bar provide delicious meals, while fellow guests rave about the free breakfast and helpful staff.
The price is $139
$151 total
includes taxes & fees
Jul 26 - Jul 27
Best Western Plus Keene Hotel
Front of property

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (211 reviews)
Enjoy mountain adventures from this secluded retreat with free WiFi and parking. Kayak, bike, or snowshoe directly from the property. Helpful staff ensure a memorable stay near Shattuck Brook Wildlife Management Area.
The price is $192
$223 total
includes taxes & fees
Jul 27 - Jul 28
Vikings Villages Resort
Studio Suite, Multiple Beds | Desk, laptop workspace, WiFi (free), bed sheets

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (193 reviews)
Discover West Hatfield from this welcoming motel with 24-hour reception and complimentary WiFi. Explore nearby Pioneer Valley Indoor Karting or Connecticut River Greenway State Park, then return to hassle-free accommodations with free parking.
The price is $110
$122 total
includes taxes & fees
Jul 26 - Jul 27
River Valley Inn
Deluxe Room, 1 Queen Bed, Valley View | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.0 out of 10, Wonderful, (36 reviews)
The price is $135
$151 total
includes taxes & fees
Jul 26 - Jul 27
Windmill Motel Restaurant
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (941 reviews)
The price is $171
$188 total
includes taxes & fees
Jul 26 - Jul 27
Latchis Hotel
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (1,001 reviews)
Immerse yourself in Brattleboro charm at this welcoming hotel with complimentary breakfast and parking. Unwind in the hot tub, energize at the fitness center, or grab a coffee at the café while exploring nearby attractions like Brattleboro Bowl.
The price is $121
$133 total
includes taxes & fees
Aug 11 - Aug 12
Hampton Inn Brattleboro
Lobby

Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.4 out of 10, (26 reviews)
Unwind at this Brattleboro motel offering massage treatments, American cuisine at India Masala House, and 2 indoor pools. Rooms include refrigerators and microwaves, with free WiFi and parking. Just minutes from Brattleboro Bowl and local attractions.
The price is $77
$84 total
includes taxes & fees
Aug 2 - Aug 3
Colonial Motel
Property amenity

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (751 reviews)
Conveniently located near UMass Amherst, this hotel offers a refreshing indoor pool and American cuisine at The Cafe. Enjoy amenities like a 24-hour fitness center, bar, and complimentary WiFi while staying close to Autobahn and Cinemark attractions.
The price is $161
$180 total
includes taxes & fees
Aug 16 - Aug 17
Courtyard by Marriott Hadley Amherst
Exterior

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,001 reviews)
The price is $138
$151 total
includes taxes & fees
Jul 26 - Jul 27
The Putney Inn
Exterior

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (378 reviews)
Nestled in Bernardston with nearby hiking trails, kayaking, and mountain biking opportunities, this welcoming inn offers free WiFi and parking. Close to Cushman Library and Powers Institute Museum, guests consistently praise the helpful staff and clean rooms.
The price is $180
$202 total
includes taxes & fees
Jul 27 - Jul 28
The Inn At Crumpin Fox
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (837 reviews)
Warm Brattleboro accommodations with complimentary breakfast, WiFi, and parking just minutes from United States Navy Seabee Bridge. Energize at the fitness center after exploring nearby attractions. Fellow travelers consistently praise the exceptionally helpful staff.
The price is $124
$136 total
includes taxes & fees
Aug 23 - Aug 24
Comfort Inn & Suites Brattleboro I-91
Lobby

Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (792 reviews)
Minutes from University of Massachusetts, this welcoming hotel offers free breakfast, WiFi, and parking. Guests can unwind in the indoor pool or fitness center after exploring nearby Autobahn and Cinemark. Travelers praise the helpful staff and spotless rooms.
The price is $163
$182 total
includes taxes & fees
Aug 17 - Aug 18
Homewood Suites by Hilton Hadley Amherst
Deluxe Room, 1 King Bed | Hypo-allergenic bedding available, iron/ironing board, WiFi (free)

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
10.0 out of 10, Exceptional, (139 reviews)
Set in a historic building, this B&B offers a complimentary full breakfast each morning and free WiFi. Explore nearby hiking trails or take a short drive to Puffers Pond South Beach. Convenient free parking makes day trips easy.
The price is $194
$217 total
includes taxes & fees
Aug 18 - Aug 19
Black Walnut 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, (1,004 reviews)
The price is $93
$101 total
includes taxes & fees
Jul 28 - Jul 29
Days Inn by Wyndham Keene NH
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.
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Top landmarks in Winchester

New England Sweetwater Farm & Distillery

New England Sweetwater Farm & Distillery is in the heart of Winchester, so why not stop by during your stay.
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Learn more about Winchester

Winchester is well-known for its attractions such as Pisgah State Park and New England Sweetwater Farm & Distillery. The city has something for everyone including sights like Conant Public Library and Loring Field within a scenic setting.

See all hotels in Winchester
A snow-covered town with a river running through it, surrounded by mountains and trees.

Check out reviews of Winchester hotels guests love

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"I loved everything about this hotel! They recently underwent a remodel so everything is brand new and beautiful. The breakfast was amazing. It is the first time that I see plant based patties in the breakfast for those of us that can’t have meat. the front desk personnel were always very informative and unhurried. I would absolutely love to come back here. The surroundings are amazing as well. Downtown Brattleboro is cute."
Mildred 1-night trip
Posted 18 hours ago
Hampton Inn Brattleboro

Frequently asked questions

What hotels do travelers like in Winchester?
Guests like Windmill Motel Restaurant.
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.