Compare Cheap Hotels in Winchester

Name: Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Address: Fitzwilliam

Secret Bargains - Save an extra 10% or more on select hotels

Cheap Winchester Hotels

The Colonial Hotel

625 Betty Spring Road, Gardner, MA

$156

includes taxes & fees

$140 per night

Dec 23 - Dec 24

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

Colonial Motel And Spa

889 Putney Rd, Brattleboro, VT

$108

includes taxes & fees

$98 per night

Jan 1 - Jan 2, 2025

Free Cancellation

Reserve now, pay when you stay

11.51 mi from city center

A stay at Colonial Motel And Spa places you in the heart of Brattleboro, steps from Brattleboro Bowl and 11 minutes by foot from New England Center for Circus Arts.

Pool

Hot Tub

Hampton Inn Brattleboro

1378 Putney Road, Brattleboro, VT

$102

includes taxes & fees

$93 per night

Jan 12 - Jan 13, 2025

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

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT

$141

includes taxes & fees

$128 per night

Dec 30 - Dec 31

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.

Breakfast included

Parking included

Courtyard by Marriott Keene Downtown

75 Railroad St, Keene, NH

$128

includes taxes & fees

$118 per night

Jan 12 - Jan 13, 2025

Free Cancellation

Reserve now, pay when you stay

12.25 mi from city center

A stay at Courtyard by Marriott Keene Downtown places you in the heart of Keene, steps from Historic Main Street and 3 minutes by foot from Colonial Theatre.

Pool

Pet friendly

The Putney Inn

57 Putney Landing Rd, Putney, VT

$102

includes taxes & fees

$93 per night

Jan 16 - Jan 17, 2025

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.

Breakfast included

Pet friendly

Days Inn by Wyndham Keene NH

3 Ash Brook Road, Keene, NH

$91

includes taxes & fees

$84 per night

Jan 16 - Jan 17, 2025

Free Cancellation

Reserve now, pay when you stay

11.1 mi from city center

Located in Keene, Days Inn by Wyndham Keene NH is in a shopping district, within a 5-minute drive of Cheshire Children's Museum and Historical Society of Cheshire County.

Breakfast included

Pet friendly

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road, Brattleboro, VT

$104

includes taxes & fees

$95 per night

Dec 23 - Dec 24

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

Latchis Hotel

50 Main Street, Brattleboro, VT

$124

includes taxes & fees

$113 per night

Dec 19 - Dec 20

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 Greenfield

184 Shelburne Rd, Greenfield, MA

$151

includes taxes & fees

$135 per night

Dec 29 - Dec 30

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.

Pool

Breakfast included

Hampton Inn & Suites Keene

126 Key Rd, Keene, NH

$137

includes taxes & fees

$127 per night

Jan 5 - Jan 6, 2025

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.

Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!

15.21 mi from city center

Located in Fitzwilliam, this castle is on the waterfront, within a 10-minute drive of Hyde Park and Monument Park.

Pool

Hot Tub

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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	400 hotels
Lowest Price	$91
Highest Price	$156
Popular hotels	The Colonial Hotel, Colonial Motel And Spa, Hampton Inn Brattleboro, The Covered Bridge Inn, Courtyard by Marriott Keene Downtown, The Putney Inn, Days Inn by Wyndham Keene NH, Comfort Inn & Suites Brattleboro I-91, Latchis Hotel, Hampton Inn & Suites Greenfield, Hampton Inn & Suites Keene, Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!