Holiday Homes in Winchester
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46 rentals in Winchester.
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Stay at a Craft Brewery
1 bedroom
1 bathroom
Sleeps 2
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Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries
1 bedroom
1 bathroom
Sleeps 3
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Magical Lakefront Home on Forest Lake
2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Lake Side Getaway, Quiet, and Peaceful
2 bedrooms
1 bathroom
Sleeps 6
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Stunning Forest Lake Home with Hot Tub open all Yr
4 bedrooms
2 bathrooms
Sleeps 10
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Stunning Forest Lake Home with Hot Tub!
4 bedrooms
2 bathrooms
Sleeps 9
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Large modern house with huge open great room and four large bedrooms with baths
4 bedrooms
4 bathrooms
Sleeps 12
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Serenity Cottage in Southern Vermont…
2 bedrooms
2 bathrooms
Sleeps 4
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Secluded Vacation Home with direct lake frontage on Contoocook Lake in NH
4 bedrooms
2 bathrooms
Sleeps 8
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Sprawling, secluded gourmand's large cottage at base of Mt Monadnock
5 bedrooms
3 bathrooms
Sleeps 12
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Sweet Spot in a Region that Shines in Every Season
3 bedrooms
2 bathrooms
Sleeps 8
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Beautiful lakefront log home nestled in the pines
3 bedrooms
3 bathrooms
Sleeps 8
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Laurel Lake Cottage in New Hampshire
2 bedrooms
1 bathroom
Sleeps 5
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Secluded Architect designed House - Monadnock Region - Great Escape
3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful House overlooking Spofford Lake
4 bedrooms
2 bathrooms
Sleeps 10
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Pet And Family Friendly Hilltop House In Putney Vermont
0 bedrooms
1 bathroom
Sleeps 8
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Quiet Vermont Home Close To Everything
2 bedrooms
2 bathrooms
Sleeps 6
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Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
4 bedrooms
1 bathroom
Sleeps 12
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Vermont Log Cabin available for weekend and weekly
2 bedrooms
1 bathroom
Sleeps 5
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Lakefront all-season beauty and fun!
2 bedrooms
1 bathroom
Sleeps 6
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Spring Escape, Get away in the falls❤️
5 bedrooms
2 bathrooms
Sleeps 10
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Spacious Lakeside Waterfront Summer Cottage
3 bedrooms
1 bathroom
Sleeps 6
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Stone 'n Sky Lodge on an Ancient Stone Landscape
4 bedrooms
3 bathrooms
Sleeps 14
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The Fishing Cottage, A Sweetwater Stay
2 bedrooms
1 bathroom
Sleeps 5
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Main House - Relax and enjoy the scenery, go and swim, fish or start your boat
3 bedrooms
2 bathrooms
Sleeps 7
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Affordable Spacious Vacation Home on Lake Spofford
3 bedrooms
3 bathrooms
Sleeps 7
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Lake house getaway on pristine Spofford Lake, New Hampshire
2 bedrooms
2 bathrooms
Sleeps 8
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Penthouse - Steps to the Sandy Beach & clear water
3 bedrooms
2 bathrooms
Sleeps 6
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PARADISE on EARTH! - Historic 4BR Farmhouse
4 bedrooms
2 bathrooms
Sleeps 8
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Classic New England Farm House
1 bedroom
1 bathroom
Sleeps 2
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Steps to the sandy beach
3 bedrooms
2 bathrooms
Sleeps 6
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A Healing Forest Space in the Heart of New England
0 bedrooms
1 bathroom
Sleeps 4
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Marlboro, Vermont Ski House - discount offered
5 bedrooms
4 bathrooms
Sleeps 10
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Victorian Lakefront Cottage With Spectacular Sunrise View Of Water
4 bedrooms
1 bathroom
Sleeps 8
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Adorable Studio apartment in Brattleboro
0 bedrooms
1 bathroom
Sleeps 2
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Cobb Hill Estate - 6 brs sleeps 15 on 750 acres!
6 bedrooms
4 bathrooms
Sleeps 15
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Church sanctuary
3 bedrooms
2 bathrooms
Sleeps 6
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Historical Farm House
1 bedroom
1 bathroom
Sleeps 2
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Colonial Keene House on 7 Acres w/ Pool!
9 bedrooms
7 bathrooms
Sleeps 18
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Serene Shelburne Studio Cabin w/Spring-Fed Pool!
0 bedrooms
1 bathroom
Sleeps 6
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Hilltop Home with Great Views
2 bedrooms
3 bathrooms
Sleeps 6
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NEW! Grand Estate w/ Courtyard - 2 Mi to Downtown!
8 bedrooms
9 bathrooms
Sleeps 15
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Tentrr - Hillside Camp in Southern Vermont
1 bedroom
1 bathroom
Sleeps 4
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Timeless Red Sox Retreat w/ Scenic Mountain Views!
4 bedrooms
4 bathrooms
Sleeps 10
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'Red Sweetheart Barn Studio' w/ Mtn & River Views!
0 bedrooms
1 bathroom
Sleeps 2
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Jabulani Luxury Rural Stay
3 bedrooms
3 bathrooms
Sleeps 8
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Frequently Asked Questions about Winchester
- Yes, here are some popular holiday rentals in Winchester that have a pool:
- Beautiful Lake Side Getaway, Quiet, and Peaceful
- Stunning Forest Lake Home with Hot Tub open all Yr
- Stunning Forest Lake Home with Hot Tub!
- Yes, here are some popular holiday rentals in Winchester that have internet access:
- Beautiful Lake Side Getaway, Quiet, and Peaceful
- Stunning Forest Lake Home with Hot Tub open all Yr
- Stunning Forest Lake Home with Hot Tub!
- The best pet friendly rentals in Winchester are:
- Stunning Forest Lake Home with Hot Tub open all Yr
- Stunning Forest Lake Home with Hot Tub!
- Stay at a Craft Brewery
- Some of the most popular kid friendly rentals in Winchester are:
- Stunning Forest Lake Home with Hot Tub open all Yr
- Stunning Forest Lake Home with Hot Tub!
- Magical Lakefront Home on Forest Lake