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
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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Classic New England Farm House
1 bedroom
1 bathroom
Sleeps 2
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Penthouse - Steps to the Sandy Beach & clear water
3 bedrooms
2 bathrooms
Sleeps 6
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Historical Farm House
1 bedroom
1 bathroom
Sleeps 2
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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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Vacation Log Home In Southern Vermont
3 bedrooms
2 bathrooms
Sleeps 9
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Camp Peace & Plenty North - a contemporary cabin in the woods w/ majestic views!
3 bedrooms
3 bathrooms
Sleeps 10
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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 House overlooking Spofford Lake
4 bedrooms
2 bathrooms
Sleeps 10
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Ski, Snowboard, Hike, or just Relax at our Spacious Home for Family and Friends!
5 bedrooms
3 bathrooms
Sleeps 12
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Waterfront Lake Raponda Vacation Paradise
3 bedrooms
2 bathrooms
Sleeps 6
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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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Mountain View Retreat - Close to all year round activities
4 bedrooms
2 bathrooms
Sleeps 6
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Lake Raponda Lakefront - 4 Seasons of fun
3 bedrooms
2 bathrooms
Sleeps 10
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Beautiful Lake Side Getaway, Quiet, and Peaceful
2 bedrooms
1 bathroom
Sleeps 6
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Vermont Log Cabin w/ Amazing Views, Close to Mount Snow
2 bedrooms
1 bathroom
Sleeps 6
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Lake house getaway on pristine Spofford Lake, New Hampshire
2 bedrooms
2 bathrooms
Sleeps 8
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3 BDR Farmhouse on Tranquil 105 acre Farm
3 bedrooms
2 bathrooms
Sleeps 8
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Stay at a Craft Brewery
1 bedroom
1 bathroom
Sleeps 2
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Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more
4 bedrooms
2 bathrooms
Sleeps 5
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PARADISE on EARTH! - Historic 4BR Farmhouse
4 bedrooms
2 bathrooms
Sleeps 8
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Stunning Forest Lake Home with Hot Tub open all Yr
4 bedrooms
2 bathrooms
Sleeps 10
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Steps to the sandy beach
3 bedrooms
2 bathrooms
Sleeps 6
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Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3 bedrooms
2 bathrooms
Sleeps 8
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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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Church sanctuary
3 bedrooms
2 bathrooms
Sleeps 6
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Stunning Forest Lake Home with Hot Tub!
4 bedrooms
2 bathrooms
Sleeps 9
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Casual lux near Hermitage Club & Four Columns Inn
4 bedrooms
6 bathrooms
Sleeps 8
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Rustic East Dover Home w/ Deck - Near Mount Snow!
2 bedrooms
2 bathrooms
Sleeps 8
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Mountain Side
3 bedrooms
2 bathrooms
Sleeps 12
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Colonial Keene House on 7 Acres w/ Pool!
9 bedrooms
7 bathrooms
Sleeps 18
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Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more
4 bedrooms
2 bathrooms
Sleeps 5
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Jacksonville Cabin w/ Wraparound Deck & Views
3 bedrooms
2 bathrooms
Sleeps 8
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Hilltop Home with Great Views
2 bedrooms
3 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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Tentrr Signature Site - Fairbrothers Getaway
1 bedroom
1 bathroom
Sleeps 4
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NEW! Grand Estate w/ Courtyard - 2 Mi to Downtown!
8 bedrooms
9 bathrooms
Sleeps 15
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Marlboro, Vermont Ski House - discount offered
5 bedrooms
4 bathrooms
Sleeps 10
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Tentrr - Hillside Camp in Southern Vermont
1 bedroom
1 bathroom
Sleeps 4
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Mt. Snow/Lake Raponda
3 bedrooms
2 bathrooms
Sleeps 6
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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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Spectacular 7-Bedroom Family Home w/Deck Views/Free WiFi/Near Skiing - Dogs OK!
7 bedrooms
5 bathrooms
Sleeps 13
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