Winchester Vacation Rentals
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Vacation Rentals in Winchester
FaLL Western Mass Getaway-Airhockey-Firepit
Colrain MA
$576 nightly
The price is $644 total per night
$644 total
Dec 9 - Dec 10
Total with taxes and fees
Located in Colrain, this vacation home is within a 5-minute drive of Arthur A. Smith Covered Bridge and G. William Pitt House and Collection.
Hot Tub
Kitchen
Beautiful Custom Built Timber Frame Home, Sleeps 11
Wilmington VT
Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.
Hot Tub
Kitchen
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Shelburne Falls MA
With a stay at this vacation home in Shelburne Falls, you'll be a 1-minute walk from Deerfield River and 7 minutes by foot from Arms Cemetery.
Kitchen
Washer
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Townshend VT
Located in Townshend, this vacation home is in the mountains, within a 15-minute drive of West River and Newfane Town Hall.
Kitchen
Washer
Lovely 2nd Floor Apartment
Greenfield MA
$193 nightly
The price is $216 total per night
$216 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Located in Greenfield, this vacation home is within a 5-minute drive of Fresenius Medical Care at Franklin Medical Center and Energy Park.
Kitchen
Air conditioning
Lakefront 3BR Log Cabin w/ Dock and Fire Pit
Rindge NH
With a stay at this vacation home in Rindge, you'll be on the waterfront, just a 1-minute walk from Contoocook Lake and 11 minutes by foot from Jowder's Cove Beach.
Kitchen
Washer
Beautiful, private log cabin with huge, relaxing screened porch
Townshend VT
When you stay at this vacation home in Townshend, you'll be in the mountains and 12 minutes by car from West River.
Kitchen
Washer
Charming Waterfront Log Cabin
Fitzwilliam NH
Located in Fitzwilliam, this vacation home is on the waterfront, within a 5-minute drive of Fitzwilliam Library and Fitzwilliam Town Hall.
Kitchen
Free WiFi
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Whitingham VT
Located in Jacksonville, this vacation home is on a lake, a 2-minute drive from Honora Winery and 6 minutes from Jacksonville Pond.
Kitchen
Washer
Beautiful Lakefront home - perfect getaway for every season!
Ashburnham MA
Located in Ashburnham, this vacation home is on the waterfront, within a 5-minute drive of Lower Naukeag Lake and Millers River.
Hot Tub
Kitchen
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.
Winchester Vacation Rentals essential information
Accommodation | 110 Vacation Rentals |
|---|---|
Lowest Price | $216 |
Highest Price | $644 |
Popular accommodation | FaLL Western Mass Getaway-Airhockey-Firepit, Beautiful Custom Built Timber Frame Home, Sleeps 11, Stylish new 2 bedroom property in enchanting Shelburne Falls Village., Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC, Lovely 2nd Floor Apartment, Lakefront 3BR Log Cabin w/ Dock and Fire Pit, Beautiful, private log cabin with huge, relaxing screened porch, Charming Waterfront Log Cabin, Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking, Beautiful Lakefront home - perfect getaway for every season! , Nestled on the edge of the woods near Mount Monadnock, Inviting mountain view home with game room, balcony & W/D |