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Cheap Winchester Hotels

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
$160 nightly
The price is $179 total per night
$179 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
26.28 mi from city center
Located in Gardner, The Colonial Hotel is a 2-minute drive from Dunn State Park and 6 minutes from Mount Wachusett Community College.
Pool
Hot Tub
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
$90 nightly
The price is $99 total per night
$99 total
Dec 20 - Dec 21
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.6 mi from city center
With a stay at The Covered Bridge Inn in Brattleboro, you'll be within a 10-minute walk of Brattleboro Bowl and United States Navy Seabee Bridge.
Parking included
Free WiFi
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
$188 nightly
The price is $210 total per night
$210 total
Dec 25 - Dec 26
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.71 mi from city center
With a stay at Hampton Inn & Suites Greenfield in Greenfield, you'll be within a 5-minute drive of Old Greenfield Village and Greenfield Community College.
Breakfast included
Pet friendly
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
$147 nightly
The price is $161 total per night
$161 total
Dec 26 - Dec 27
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.82 mi from city center
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Pool
Hot Tub
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
$118 nightly
The price is $128 total per night
$128 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
11.36 mi from city center
With a stay at Keene Elm City Hotel, an Ascend Collection Hotel in Keene, you'll be within a 5-minute drive of Cheshire Children's Museum and Historic Main Street.
Pool
Breakfast included
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
$112 nightly
The price is $123 total per night
$123 total
Dec 22 - Dec 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.76 mi from city center
When you stay at Comfort Inn & Suites Brattleboro I-91 in Brattleboro, you'll be near ski lifts, within a 10-minute walk of Connecticut River and United States Navy Seabee Bridge.
Pool
Breakfast included
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
$94 nightly
The price is $103 total per night
$103 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.86 mi from city center
With a stay at The Putney Inn in Putney, you'll be a 4-minute walk from Connecticut River and 8 minutes by foot from Yellow Barn.
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
$126 nightly
The price is $139 total per night
$139 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
10.35 mi from city center
When you stay at Latchis Hotel in Brattleboro, you'll be near ski lifts, just steps from Latchis Theatre and 5 minutes by foot from The Stone Church.
Pet friendly
Parking included
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
$165 nightly
The price is $179 total per night
$179 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.31 mi from city center
With a stay at Hampton Inn & Suites Keene in Keene, you'll be within a 5-minute drive of Ashuelot River and Cheshire Children's Museum.
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
$129 nightly
The price is $140 total per night
$140 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.18 mi from city center
Located in Keene, Best Western Plus Keene Hotel is in the suburbs, within a 5-minute drive of Cheshire Children's Museum and Keene State College.
Pool
Breakfast included
The Inn At Crumpin Fox

The Inn At Crumpin Fox

2.5 out of 5
71 Northfield Rd Bernardston MA
$141 nightly
The price is $158 total per night
$158 total
Dec 20 - Dec 21
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
10.67 mi from city center
Located in Bernardston, The Inn At Crumpin Fox is within a 10-minute drive of Northfield Mount Hermon School and Connecticut River.
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St Brattleboro VT
$52 nightly
The price is $57 total per night
$57 total
Dec 25 - Dec 26
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
10.26 mi from city center
With a stay at Econo Lodge Brattleboro in Brattleboro, you'll be near ski lifts, just a 3-minute walk from Vermont Marketplace and 7 minutes by foot from Brattleboro Memorial Hospital.
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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.

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Winchester hotels essential information

Accommodation
438 hotels
Lowest Price
$57
Highest Price
$210
Popular hotels
The Colonial Hotel, The Covered Bridge Inn, Hampton Inn & Suites Greenfield, Hampton Inn Brattleboro, Keene Elm City Hotel, an Ascend Collection Hotel, Comfort Inn & Suites Brattleboro I-91, The Putney Inn, Latchis Hotel, Hampton Inn & Suites Keene, Best Western Plus Keene Hotel, The Inn At Crumpin Fox, Econo Lodge Brattleboro

Most Recent Winchester Hotel Reviews

The Putney Inn

The Putney Inn

5 out of 5
Posted 9 hours ago
CheapTickets Verified Review
"Very quit, clea, and comfortable. "
A verified traveler stayed at The Putney Inn
The Putney Inn