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Chesterfield Holiday Apartments

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50 rentals in Chesterfield.
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Affordable Spacious Vacation Home on Lake Spofford, holiday rental in Chesterfield

Affordable Spacious Vacation Home on Lake Spofford

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Main House - Relax and enjoy the scenery, go and swim, fish or start your boat, holiday 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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Classic New England Farm House, holiday 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, holiday 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, holiday 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, holiday 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…, holiday rental in Chesterfield

Serenity Cottage in Southern Vermont…

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont!  Come Explore!, holiday rental in Chesterfield

Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont! Come Explore!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vacation Log Home In Southern Vermont, holiday rental in Chesterfield

Vacation Log Home In Southern Vermont

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, holiday 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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Camp Peace & Plenty North - a contemporary cabin in the woods w/ majestic views!, holiday 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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Magical Lakefront Home on Forest Lake, holiday 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, holiday 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!, holiday 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, holiday 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, holiday 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, holiday 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, holiday 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, holiday rental in Chesterfield

Vermont Log Cabin available for weekend and weekly

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lake Raponda Lakefront - 4 Seasons of fun, holiday rental in Chesterfield

Lake Raponda Lakefront - 4 Seasons of fun

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Mountain View Retreat - Close to all year round activities, holiday rental in Chesterfield

Mountain View Retreat - Close to all year round activities

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mt. Snow/Lake Raponda, holiday rental in Chesterfield

Mt. Snow/Lake Raponda

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Lake Side Getaway, Quiet, and Peaceful, holiday 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, holiday 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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Bright three-level home w/water views, jetted tub, firepit, and more!, holiday rental in Chesterfield

Bright three-level home w/water views, jetted tub, firepit, and more!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake house getaway on pristine Spofford Lake, New Hampshire, holiday rental in Chesterfield

Lake house getaway on pristine Spofford Lake, New Hampshire

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

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

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 Chesterfield

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 Chesterfield

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 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, holiday rental in Chesterfield

Adorable Studio apartment in Brattleboro

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

Church sanctuary

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet-Friendly Escape w/ Deck, 8 Miles to Mount Snow, holiday rental in Chesterfield

Pet-Friendly Escape w/ Deck, 8 Miles to Mount Snow

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Casual lux near Hermitage Club & Four Columns Inn, holiday 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!, holiday 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, holiday rental in Chesterfield

Mountain Side

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Robin's Nest' Cottage w/ Hot Tub - Near Lake, holiday rental in Chesterfield

Robin's Nest' Cottage w/ Hot Tub - Near Lake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Jacksonville Cabin w/ Wraparound Deck & Views, holiday 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, holiday rental in Chesterfield

Hilltop Home with Great Views

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Fairbrothers Getaway, holiday 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!, holiday rental in Chesterfield

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 Chesterfield

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 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!, holiday rental in Chesterfield

'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 Chesterfield

Jabulani Luxury Rural Stay

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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