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Holiday Rentals in Winchester

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46 rentals in Winchester.
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Stay at a Craft Brewery, holiday rental in Winchester

Stay at a Craft Brewery

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, holiday rental in Winchester

Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Magical Lakefront Home on Forest Lake, holiday rental in Winchester

Magical Lakefront Home on Forest Lake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Lake Side Getaway, Quiet, and Peaceful, holiday rental in Winchester

Beautiful Lake Side Getaway, Quiet, and Peaceful

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning Forest Lake Home with Hot Tub open all Yr, holiday rental in Winchester

Stunning Forest Lake Home with Hot Tub open all Yr

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Forest Lake Home with Hot Tub!, holiday rental in Winchester

Stunning Forest Lake Home with Hot Tub!

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Large modern house with huge open great room and four large bedrooms with baths, holiday rental in Winchester

Large modern house with huge open great room and four large bedrooms with baths

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Serenity Cottage in Southern Vermont…, holiday rental in Winchester

Serenity Cottage in Southern Vermont…

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Secluded Vacation Home with direct lake frontage  on Contoocook Lake in NH, holiday rental in Winchester

Secluded Vacation Home with direct lake frontage on Contoocook Lake in NH

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, holiday rental in Winchester

Sprawling, secluded gourmand's large cottage at base of Mt Monadnock

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Sweet Spot in a Region that Shines in Every Season, holiday rental in Winchester

Sweet Spot in a Region that Shines in Every Season

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful lakefront log home nestled in the pines, holiday rental in Winchester

Beautiful lakefront log home nestled in the pines

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Laurel Lake Cottage in New Hampshire, holiday rental in Winchester

Laurel Lake Cottage in New Hampshire

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Secluded Architect designed House - Monadnock Region - Great Escape, holiday rental in Winchester

Secluded Architect designed House - Monadnock Region - Great Escape

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful House overlooking Spofford Lake, holiday rental in Winchester

Beautiful House overlooking Spofford Lake

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Pet And Family Friendly Hilltop House In Putney Vermont, holiday rental in Winchester

Pet And Family Friendly Hilltop House In Putney Vermont

0 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Quiet Vermont Home Close To Everything, holiday rental in Winchester

Quiet Vermont Home Close To Everything

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Winchester

Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford

4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Vermont Log Cabin available for weekend and weekly, holiday rental in Winchester

Vermont Log Cabin available for weekend and weekly

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakefront all-season beauty and fun!, holiday rental in Winchester

Lakefront all-season beauty and fun!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spring Escape, Get away in the falls❤️, holiday rental in Winchester

Spring Escape, Get away in the falls❤️

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Lakeside Waterfront Summer Cottage, holiday rental in Winchester

Spacious Lakeside Waterfront Summer Cottage

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stone 'n Sky Lodge on an Ancient Stone Landscape, holiday rental in Winchester

Stone 'n Sky Lodge on an Ancient Stone Landscape

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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The Fishing Cottage, A Sweetwater Stay, holiday rental in Winchester

The Fishing Cottage, A Sweetwater Stay

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Main House - Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Winchester

Main House - Relax and enjoy the scenery, go and swim, fish or start your boat

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Affordable Spacious Vacation Home on Lake Spofford, holiday rental in Winchester

Affordable Spacious Vacation Home on Lake Spofford

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Lake house getaway on pristine Spofford Lake, New Hampshire, holiday rental in Winchester

Lake house getaway on pristine Spofford Lake, New Hampshire

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Penthouse - Steps to the Sandy Beach & clear water, holiday rental in Winchester

Penthouse - Steps to the Sandy Beach & clear water

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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PARADISE on EARTH! - Historic 4BR Farmhouse, holiday rental in Winchester

PARADISE on EARTH! - Historic 4BR Farmhouse

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Classic New England Farm House, holiday rental in Winchester

Classic New England Farm House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Steps to the sandy beach, holiday rental in Winchester

Steps to the sandy beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Healing Forest Space in the Heart of New England, holiday rental in Winchester

A Healing Forest Space in the Heart of New England

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Marlboro, Vermont Ski House - discount offered, holiday rental in Winchester

Marlboro, Vermont Ski House - discount offered

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Winchester

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Adorable Studio apartment in Brattleboro, holiday rental in Winchester

Adorable Studio apartment in Brattleboro

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cobb Hill Estate - 6 brs sleeps 15 on 750 acres!, holiday rental in Winchester

Cobb Hill Estate - 6 brs sleeps 15 on 750 acres!

6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Church sanctuary, holiday rental in Winchester

Church sanctuary

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historical Farm House, holiday rental in Winchester

Historical Farm House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Colonial Keene House on 7 Acres w/ Pool!, holiday rental in Winchester

Colonial Keene House on 7 Acres w/ Pool!

9 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Serene Shelburne Studio Cabin w/Spring-Fed Pool!, holiday rental in Winchester

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hilltop Home with Great Views, holiday rental in Winchester

Hilltop Home with Great Views

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Grand Estate w/ Courtyard - 2 Mi to Downtown!, holiday rental in Winchester

NEW! Grand Estate w/ Courtyard - 2 Mi to Downtown!

8 bedrooms
9 bathrooms
Sleeps 15
Match: Sleeps
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Tentrr - Hillside Camp in Southern Vermont, holiday rental in Winchester

Tentrr - Hillside Camp in Southern Vermont

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Timeless Red Sox Retreat w/ Scenic Mountain Views!, holiday rental in Winchester

Timeless Red Sox Retreat w/ Scenic Mountain Views!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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'Red Sweetheart Barn Studio' w/ Mtn & River Views!, holiday rental in Winchester

'Red Sweetheart Barn Studio' w/ Mtn & River Views!

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Jabulani Luxury Rural Stay, holiday rental in Winchester

Jabulani Luxury Rural Stay

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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