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Compare Winchester 2 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Our top choices for Winchester 2-star hotels

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1006)
"Would stay again"
$111 nightly
The price is $121
Sep 2 - Sep 3
Total with taxes and fees
Days Inn by Wyndham Keene NH

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
8.4 out of 10, Very Good, (889)
"Had a great time at this location"
$125 nightly
The price is $136
Sep 7 - Sep 8
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1004)
"Lovely night. Room and bath was clean. "
$71 nightly
The price is $78
Sep 2 - Sep 3
Total with taxes and fees
The Covered Bridge Inn

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very Good, (874)
"Super easy check in and nice room! "
$127 nightly
The price is $139
Sep 7 - Sep 8
Total with taxes and fees
Hampton Inn Brattleboro

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (778)
"Great stay!"
$126 nightly
The price is $139
Sep 7 - Sep 8
Total with taxes and fees
Latchis Hotel

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (680)
"Really good staff! "
$131 nightly
The price is $144
Sep 2 - Sep 3
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1008)
"Very enjoyable stay"
$106 nightly
The price is $117
Sep 2 - Sep 3
Total with taxes and fees
The Putney Inn

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (841)
"Great place with a walkable eating option"
$163 nightly
The price is $182
Sep 7 - Sep 8
Total with taxes and fees
Hampton Inn & Suites Greenfield

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
9.6 out of 10, Exceptional, (590)
"Great place!"
$152 nightly
The price is $165
Sep 2 - Sep 3
Total with taxes and fees
Riverside Hotel, an Ascend Collection Hotel

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (700)
"I was only there for a few hours sleep "
$71 nightly
The price is $78
Sep 14 - Sep 15
Total with taxes and fees
Travelodge by Wyndham Brattleboro VT

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (419)
"Highly recommend PEARL restaurant nearby! Always comfortable accommodations. "
$149 nightly
The price is $162
Sep 1 - Sep 2
Total with taxes and fees
Riverhouse by Weekender (Formerly Jack Daniels Inn)

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (316)
"Spacious rooms, tends to be very quiet, stayed several times"
$194 nightly
The price is $217
Sep 1 - Sep 2
Total with taxes and fees
The Inn At Crumpin Fox

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (330)
"Great hotel with friendly staff"
$182 nightly
The price is $198
Sep 2 - Sep 3
Total with taxes and fees
Hampton Inn & Suites Keene

Econo Lodge Brattleboro

2.0 star property
5.6 out of 10, (556)
"The good: convenient to grocery store next door. Linens were clean. The bad: room was dirty, had roaches, our feet were quickly filthy just from walking in the carpet, old liquid splashed on the walls and never cleaned. No housekeeping over three day stay."
$100 nightly
The price is $110
Sep 29 - Sep 30
Total with taxes and fees
Econo Lodge Brattleboro

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (459)
"The bed was super comfortable and the sheets were very soft and also comfortable. "
$145 nightly
The price is $160
Sep 1 - Sep 2
Total with taxes and fees
Black Mountain Inn

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1000)
"Good room, great breakfast options "
$169 nightly
The price is $186
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Vikings Villages Resort

2.0 star property
10.0 out of 10, Exceptional, (124)
"Hospitality was incredible!"
$225 nightly
The price is $245
Sep 7 - Sep 8
Total with taxes and fees
Vikings Villages Resort

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (735)
"We stayed in the loft room and it was great! Right downtown, free parking right out the back and the staff is super nice. I would definitely go back!"
$178 nightly
The price is $193
Sep 15 - Sep 16
Total with taxes and fees
Fairfield Inn & Suites by Marriott Keene Downtown

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (138)
"Beautiful room, beautiful house, fun area!"
$137 nightly
The price is $149
Sep 2 - Sep 3
Total with taxes and fees
The Burrell House

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (269)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
$176 nightly
The price is $191
Sep 2 - Sep 3
Total with taxes and fees
Monadnock Inn
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Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Winchester.
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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.

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.

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

Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Winchester Motel Guide

Planning a getaway with only a few bucks to spare? Expedia can help! With the inexpensive rates at the top motels in Winchester, New Hampshire you can put together the vacation of your dreams without spending every penny of your yearly travel budget.

These smaller places are ideal if you need a home base that lets you easily explore the local sights; many of the best motels in Winchester are located near major freeways and public transportation. Plus, when you book a cheap deal on a motel in Winchester, you’ll find quiet rooms, complimentary toiletries, and comfortable sleeping areas, so you can unwind after a long day.

No matter which motel you choose, don't forget to use the travel tools at Expedia to search for local discounts, compare rates on the hottest motels, and plan your next vacation. You won't believe how budget-friendly an amazing getaway can be.

Also, feel free to check out the motels near me page to find the cheapest deals on motels near your current location.

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Explore a world of travel with Expedia

Frequently asked questions

How much does it cost to stay in a 2-star hotel in Winchester?
Travelers can find great deals on Winchester 2-star hotels from $78 with Expedia – but remember that prices vary throughout the year. Factors like demand and location can affect hotel prices, and it's often more expensive to stay in Winchester hotels during weekends, holidays and high season. Try searching for 2-star Winchester hotels during midweek to track down the best deals.
What is the difference between a 2-star Winchester hotel and a 3-star hotel?
With all the home comforts travelers need, 2-star Winchester hotels make a great base for exploring. These hotels are designed for convenience, and usually have comfy rooms, daily housekeeping services, and a 24-hour front desk. Some also have their own restaurant. For travelers who want to take things up a gear, 3-star Winchester hotels might tick all the boxes. These mid-range hotels often have spacious rooms and extra amenities for a relaxing stay, such as a pool, gym, restaurant or bar.