Chesterfield Vacation Rentals, Houses & More


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Areas near Chesterfield

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1 / 12

Classic New England Farm House

  • 1
  • 2
  • 2 nights min

$45

Details

1 / 12

Historical Farm House

  • 1
  • 2
  • 2 nights min

$45

Details

3
1 / 16

Affordable Spacious Vacation Home on Lake Spofford

  • 3
  • 7
  • Min stay varies

$125

Details

Great rentals within 30 miles that match your search

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1 / 40

Beautiful House overlooking Spofford Lake

  • 4
  • 10
  • Min stay varies

$150

Details

1 / 26

Steps to the sandy beach

  • 3
  • 6
  • Min stay varies

$160

Details

1 / 11

The Sugarhouse on the Scott Farm

  • 1
  • 2
  • 1 night min

$175

Details

2
1 / 5

Adorable Studio apartment in Brattleboro

  • 2
  • 1 night min

$135

Details

1 / 23

Pet and family friendly home on a private hilltop.

  • 2
  • 8
  • 1 night min

$200

Details

1 / 16

Church sanctuary

  • 3
  • 6
  • 2 nights min

$235

Details

1 / 15

Stunning Forest Lake Home with Hot Tub open all Yr

  • 4
  • 10
  • Min stay varies

$195

Details

1 / 11

Stunning Forest Lake Home with Hot Tub!

  • 4
  • 9
  • Min stay varies

$200

Details

4
1 / 21

Beautiful Lake Side Getaway, Quiet, and Peaceful

  • 2
  • 6
  • Min stay varies

$100

Details

1 / 16

Cabin set on 30 private acres with amazing view.

  • 2
  • 6
  • 7 nights min

$143

Details

1 / 13

Rochambeau Lodge ~ Alyson's Orchard

  • 8
  • 18
  • 2 nights min

$1000

Details

1 / 10

Foster West Farmhouse- Alyson's Orchard

  • 4
  • 8
  • 2 nights min

$900

Details

1
1 / 15

3 BDR Farmhouse on Tranquil 105 acre Organic Farm

  • 3
  • 8
  • 3 nights min

$264

Details

2
1 / 20

Romantic Vermont Vacation Cabin with View

  • 2
  • 6
  • 2 nights min

$155

Details

1 / 5

Foster Farmhouse East Wing - Alyson's Orchard

  • 3
  • 8
  • 2 nights min

$600

Details

1 / 18

Hideaway in the southwest New Hampshire Woods

  • 5
  • 10
  • 3 nights min

$290

Details

6
1 / 5

Vermont Log Cabin available for weekend and weekly

  • 2
  • 5
  • 2 nights min

$110

Details

1 / 20

Casual lux near Hermitage Club & Four Columns Inn

  • 4
  • 8
  • 7 nights min

$1500

Details

1 / 15

Enchanting Rockwood Pond Home with Hot Tub!

  • 3
  • 10
  • Min stay varies

$195

Details

1
1 / 7

PARADISE on EARTH! - Historic 4BR Farmhouse

  • 4
  • 8
  • 3 nights min

$285

Details

1 / 22

Enchanting Rockwood Pond Home with Hot Tub!

  • 3
  • 9
  • Min stay varies

$200

Details

7
1 / 25

Log Cabin, 4 BR / 2 Bath Minutes to Mount Snow!

  • 4
  • 12
  • Min stay varies

$199

Details

1 / 12

All-Season Gem Mount Snow Stratton Lake Whitingham

  • 3
  • 6
  • 1 night min

$149

Details

1 / 31

Charming lakefront cabin with a deck, porch & water views - close to skiing!

  • 3
  • 6
  • Min stay varies

$112

Details

1 / 30

NEW! 3BR East Dover House Surrounded by Nature!

  • 3
  • 8
  • Min stay varies

$215

Details

1 / 21

Mountain Side

  • 3
  • 12
  • 2 nights min

$500

Details

1 / 23

Lakeside Year Round Totally Renovated Home

  • 5
  • 10
  • 2 nights min

$600

Details

8
1 / 20

Lake Warren-Alstead-Walpole-Keene- Fall Foliage Rates

  • 4
  • 4
  • 3 nights min

$135

Details

1 / 24

New Listing! Cozy & Private 2BR Wilmington Cabin w/Wifi, Fireplace & Deck

  • 2
  • 6
  • Min stay varies

$155

Details

1 / 28

Elegant Mountainside Country Estate

  • 6
  • 12
  • 2 nights min

$200

Details

1
1 / 16

Pet-friendly private, peaceful, pond-front home

  • 2
  • 4
  • 7 nights min

$120

Details

1 / 5

Vermont Log Home splender

  • 4
  • 8
  • 1 night min

$225

Details

1 / 21

New Lakefront Cedar Log Home

  • 3
  • 12
  • 2 nights min

$450

Details

1 / 28

Classic alpine home with private hot tub, soaking tub, & prime location

  • 4
  • 16
  • Min stay varies

$143

Details

1 / 31

Classic, dog-friendly cabin in the woods w/ private deck

  • 3
  • 10
  • Min stay varies

$80

Details

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