Book Holiday Homes in Winchester

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Featured Holiday Homes in Winchester

River House

River House

2 out of 5
Brookline
Located in Newfane, this vacation home is on the waterfront, within a 15-minute drive of West River and The Putney School.
River House
Charming Waterfront Log Cabin

Charming Waterfront Log Cabin

Fitzwilliam
Located in Fitzwilliam, this vacation home is on the waterfront, within a 5-minute drive of Fitzwilliam Library and Fitzwilliam Town Hall.
Charming Waterfront Log Cabin
Green River Cottage-A Woodland Retreat

Green River Cottage-A Woodland Retreat

Guilford
When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.
Green River Cottage-A Woodland Retreat
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Hilltop Home with Great Views

Hilltop Home with Great Views

Putney
With a stay at this vacation home in Putney, you'll be within a 5-minute drive of Harlow's and Next Stage Arts.
Hilltop Home with Great Views
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Newfane
With a stay at this vacation home in Newfane, you'll be within a 15-minute drive of West River and Townshend State Park.
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington
Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.
Beautiful Custom Built Timber Frame Home, Sleeps 11
Inviting mountain view home with game room, balcony & W/D

Inviting mountain view home with game room, balcony & W/D

West Dover
Located in West Dover, this vacation home is in the mountains, a 2-minute drive from Green Mountain National Forest and 7 minutes from North Branch Deerfield ...
Inviting mountain view home with game room, balcony & W/D
Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres

Royalston
Located in Royalston, this vacation home is a 4-minute drive from Royalston Falls and 6 minutes from Doane's Falls.
Historic Home w/ Modern Updates on < 4 Acres
Shelburne Falls #1 Rated STR.  Blue on South. Style design with comfort..

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Buckland
With a stay at this vacation home, you'll be centrally located in Shelburne Falls, just a 3-minute walk from Deerfield River and 9 minutes by foot from Lamson ...
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
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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.

Winchester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winchester vacation homes are the perfect way for you to wing it.

Holiday houses in Winchester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winchester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winchester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winchester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winchester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winchester Holiday Homes essential information

Accommodation
104 Holiday Homes
Lowest Price
AU$163
Highest Price
AU$250
Popular accommodation
River House, Charming Waterfront Log Cabin, Green River Cottage-A Woodland Retreat, Hilltop Home with Great Views, Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck, Beautiful Custom Built Timber Frame Home, Sleeps 11, Inviting mountain view home with game room, balcony & W/D, Historic Home w/ Modern Updates on < 4 Acres, Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Top trending hotels in Winchester

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
The price is AU$250 per night from 24 Dec to 25 Dec
AU$250
includes taxes & fees
24 Dec - 25 Dec
Located in Gardner, The Colonial Hotel is a 2-minute drive from Dunn State Park and 6 minutes from Mount Wachusett Community College.
The Colonial Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 1 Jan to 2 Jan
AU$172
includes taxes & fees
1 Jan - 2 Jan 2025
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 ...
Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 12 Jan to 13 Jan
AU$163
includes taxes & fees
12 Jan - 13 Jan 2025
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Hampton Inn Brattleboro
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The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$201 per night from 6 Jan to 7 Jan
AU$201
includes taxes & fees
6 Jan - 7 Jan 2025
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.
The Covered Bridge Inn
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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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^Subject to availability and chosen travel dates.