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Featured Holiday Homes in Winchester

Cozy Home Near Downtown, Shops, and Restaurants.

Cozy Home Near Downtown, Shops, and Restaurants.

2 out of 5
Keene
The price is AU$930 per night from 29 Apr to 30 Apr
AU$930
includes taxes & fees
29 Apr - 30 Apr
Located in Keene, this vacation home is within a 15-minute walk of Ashuelot River and Cheshire Children's Museum.
Cozy Home Near Downtown, Shops, and Restaurants.
The Jelly Mill-A River Retreat

The Jelly Mill-A River 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.
The Jelly Mill-A River Retreat
1810 Brook Side Mill/House / EV Level 2 Charging on Site

1810 Brook Side Mill/House / EV Level 2 Charging on Site

Shelburne Falls
Located in Shelburne Falls, this vacation home is in a rural location, within a 5-minute drive of Deerfield River and Bald Mountain Pottery.
1810 Brook Side Mill/House / EV Level 2 Charging on Site
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GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Located in Jacksonville, this vacation home is a 1-minute drive from Jacksonville Pond and 6 minutes from Harriman Reservoir.
GAMERS HAVEN, River Wine Inn!
 Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
The price is AU$540 per night from 2 May to 3 May
AU$540
includes taxes & fees
2 May - 3 May
Located in Putney, this vacation home is on a lake, within a 5-minute drive of Harlow's and Next Stage Arts.
Family Friendly Hilltop House In Putney Vermont
Bright three-level home with water views, jetted tub, firepit, and pool table

Bright three-level home with water views, jetted tub, firepit, and pool table

Jacksonville
Located in Jacksonville, this vacation home is on a lake, a 1-minute drive from Jacksonville Pond and 7 minutes from Honora Winery.
Bright three-level home with water views, jetted tub, firepit, and pool table
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
Located in Newfane, this vacation home is a 3-minute drive from Rock River Preserve and 6 minutes from West River.
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Greenfield
The price is AU$282 per night from 28 Apr to 29 Apr
AU$282
includes taxes & fees
28 Apr - 29 Apr
Located in Greenfield, this vacation home is within a 5-minute drive of Fresenius Medical Care at Franklin Medical Center and Energy Park.
Lovely 2nd Floor Apartment
Beautiful Lakefront home - perfect getaway for every season!

Beautiful Lakefront home - perfect getaway for every season!

Ashburnham
Located in Ashburnham, this vacation home is on the waterfront, within a 5-minute drive of Lower Naukeag Lake and Millers River.
Beautiful Lakefront home - perfect getaway for every season!
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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
117 Holiday Homes
Lowest Price
AU$160
Highest Price
AU$930
Popular accommodation
Cozy Home Near Downtown, Shops, and Restaurants., The Jelly Mill-A River Retreat, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, GAMERS HAVEN, River Wine Inn!, Family Friendly Hilltop House In Putney Vermont, Bright three-level home with water views, jetted tub, firepit, and pool table, Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck, Lovely 2nd Floor Apartment, Beautiful Lakefront home - perfect getaway for every season!

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$246 per night from 27 Apr to 28 Apr
AU$246
includes taxes & fees
27 Apr - 28 Apr
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
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$190 per night from 4 May to 5 May
AU$190
includes taxes & fees
4 May - 5 May
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Hampton Inn Brattleboro
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$170 per night from 12 May to 13 May
AU$170
includes taxes & fees
12 May - 13 May
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
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The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd, Putney, VT
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 30 Apr to 1 May
AU$160
includes taxes & fees
30 Apr - 1 May
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.
The Putney 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.