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Chesterfield Vacation Rentals

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50 rentals in Chesterfield.
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Main House - Relax and enjoy the scenery, go and swim, fish or start your boat, vacation rental in Chesterfield

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, vacation rental in Chesterfield

Affordable Spacious Vacation Home on Lake Spofford

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Classic New England Farm House, vacation rental in Chesterfield

Classic New England Farm House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Penthouse - Steps to the Sandy Beach & clear water, vacation rental in Chesterfield

Penthouse - Steps to the Sandy Beach & clear water

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historical Farm House, vacation rental in Chesterfield

Historical Farm House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Large modern house with huge open great room and four large bedrooms with baths, vacation rental in Chesterfield

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…, vacation rental in Chesterfield

Serenity Cottage in Southern Vermont…

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Vacation Log Home In Southern Vermont, vacation rental in Chesterfield

Vacation Log Home In Southern Vermont

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Camp Peace & Plenty North - a contemporary cabin in the woods w/ majestic views!, vacation rental in Chesterfield

Camp Peace & Plenty North - a contemporary cabin in the woods w/ majestic views!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, vacation rental in Chesterfield

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, vacation rental in Chesterfield

Magical Lakefront Home on Forest Lake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful House overlooking Spofford Lake, vacation rental in Chesterfield

Beautiful House overlooking Spofford Lake

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Ski, Snowboard, Hike, or just Relax at our Spacious Home for Family and Friends!, vacation rental in Chesterfield

Ski, Snowboard, Hike, or just Relax at our Spacious Home for Family and Friends!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Lake Raponda Vacation Paradise, vacation rental in Chesterfield

Waterfront Lake Raponda Vacation Paradise

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet And Family Friendly Hilltop House In Putney Vermont, vacation rental in Chesterfield

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, vacation rental in Chesterfield

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, vacation rental in Chesterfield

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, vacation rental in Chesterfield

Vermont Log Cabin available for weekend and weekly

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Mountain View Retreat - Close to all year round activities, vacation rental in Chesterfield

Mountain View Retreat - Close to all year round activities

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake Raponda Lakefront - 4 Seasons of fun, vacation rental in Chesterfield

Lake Raponda Lakefront - 4 Seasons of fun

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Lake Side Getaway, Quiet, and Peaceful, vacation rental in Chesterfield

Beautiful Lake Side Getaway, Quiet, and Peaceful

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vermont Log Cabin w/ Amazing Views, Close to Mount Snow, vacation rental in Chesterfield

Vermont Log Cabin w/ Amazing Views, Close to Mount Snow

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake house getaway on pristine Spofford Lake, New Hampshire, vacation rental in Chesterfield

Lake house getaway on pristine Spofford Lake, New Hampshire

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 BDR Farmhouse on Tranquil 105 acre Farm, vacation rental in Chesterfield

3 BDR Farmhouse on Tranquil 105 acre Farm

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stay at a Craft Brewery, vacation rental in Chesterfield

Stay at a Craft Brewery

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more, vacation rental in Chesterfield

Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more

4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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PARADISE on EARTH! - Historic 4BR Farmhouse, vacation rental in Chesterfield

PARADISE on EARTH! - Historic 4BR Farmhouse

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Forest Lake Home with Hot Tub open all Yr, vacation rental in Chesterfield

Stunning Forest Lake Home with Hot Tub open all Yr

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Steps to the sandy beach, vacation rental in Chesterfield

Steps to the sandy beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Wilmington Cabin, 8 Mi. to Mt Snow!, vacation rental in Chesterfield

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, vacation rental in Chesterfield

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, vacation rental in Chesterfield

Adorable Studio apartment in Brattleboro

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Church sanctuary, vacation rental in Chesterfield

Church sanctuary

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Forest Lake Home with Hot Tub!, vacation rental in Chesterfield

Stunning Forest Lake Home with Hot Tub!

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Casual lux near Hermitage Club & Four Columns Inn, vacation rental in Chesterfield

Casual lux near Hermitage Club & Four Columns Inn

4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Rustic East Dover Home w/ Deck - Near Mount Snow!, vacation rental in Chesterfield

Rustic East Dover Home w/ Deck - Near Mount Snow!

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mountain Side, vacation rental in Chesterfield

Mountain Side

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Colonial Keene House on 7 Acres w/ Pool!, vacation rental in Chesterfield

Colonial Keene House on 7 Acres w/ Pool!

9 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more, vacation rental in Chesterfield

Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more

4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Jacksonville Cabin w/ Wraparound Deck & Views, vacation rental in Chesterfield

Jacksonville Cabin w/ Wraparound Deck & Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hilltop Home with Great Views, vacation rental in Chesterfield

Hilltop Home with Great Views

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

A Healing Forest Space in the Heart of New England

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Fairbrothers Getaway, vacation rental in Chesterfield

Tentrr Signature Site - Fairbrothers Getaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Grand Estate w/ Courtyard - 2 Mi to Downtown!, vacation rental in Chesterfield

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

8 bedrooms
9 bathrooms
Sleeps 15
Match: Sleeps
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Marlboro, Vermont Ski House - discount offered, vacation rental in Chesterfield

Marlboro, Vermont Ski House - discount offered

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr - Hillside Camp in Southern Vermont, vacation rental in Chesterfield

Tentrr - Hillside Camp in Southern Vermont

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Mt. Snow/Lake Raponda, vacation rental in Chesterfield

Mt. Snow/Lake Raponda

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Timeless Red Sox Retreat w/ Scenic Mountain Views!, vacation rental in Chesterfield

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!, vacation rental in Chesterfield

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

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Spectacular 7-Bedroom Family Home w/Deck Views/Free WiFi/Near Skiing - Dogs OK!, vacation rental in Chesterfield

Spectacular 7-Bedroom Family Home w/Deck Views/Free WiFi/Near Skiing - Dogs OK!

7 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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