Chesterfield Vacation Rentals, Houses & More


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Areas near Chesterfield

1 / 12

Classic New England Farm House

  • 1
  • 2
  • 2 nights min

$46

Details

Great rentals within 20 miles that match your search

1 / 22

Amazing Architectural Post-And-Beam Masterpiece Mt. Snow

  • 5
  • 9
  • 2 nights min

$465

Details

1 / 21

New Lakefront Cedar Log Home

  • 3
  • 12
  • 2 nights min

$450

Details

1 / 15

Stunning Forest Lake Home with Hot Tub open all Yr

  • 4
  • 10
  • Min stay varies

$196

Details

1 / 24

Sleek 4BR West Dover House w/Private Sauna!

  • 4
  • 8
  • Min stay varies

$350

Details

1 / 23

Lakeside Year Round Totally Renovated Home

  • 5
  • 10
  • 2 nights min

$600

Details

1 / 22

Contemporary Log Home - Little Creek Cabin

  • 3
  • 10
  • 2 nights min

$396

Details

1 / 22

Enchanting Rockwood Pond Home with Hot Tub!

  • 3
  • 9
  • Min stay varies

$201

Details

1 / 24

Gorgeous Estate with Swimming Pool Overlooking the Mountains

  • 6
  • 12
  • Min stay varies

$701

Details

1 / 15

Enchanting Rockwood Pond Home with Hot Tub!

  • 3
  • 10
  • Min stay varies

$196

Details

1 / 5

Adorable Studio apartment in Brattleboro

  • 2
  • 1 night min

$135

Details

1 / 11

Stunning Forest Lake Home with Hot Tub!

  • 4
  • 9
  • Min stay varies

$201

Details

1 / 16

Pet-friendly private, peaceful, pond-front home

  • 2
  • 4
  • 7 nights min

$120

Details

1 / 25

New! Luxurious 4BR Grafton Home on Charming Farm!

  • 4
  • 8
  • Min stay varies

$250

Details

1 / 31

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

  • 3
  • 10
  • Min stay varies

$87

Details

1 / 13

Rochambeau Lodge ~ Alyson's Orchard

  • 8
  • 18
  • 2 nights min

$1001

Details

1 / 26

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

  • 4
  • 12
  • Min stay varies

$200

Details

1 / 11

The Sugarhouse on the Scott Farm

  • 1
  • 2
  • 1 night min

$176

Details

1 / 24

Amazing House near Mt. Snow with Hot Tub. Sleeps 11

  • 4
  • 11
  • Min stay varies

$351

Details

1 / 38

James Gandolfini Stayed Here! Rustic 5BR Mount Snow Farmhouse on 120 Private

  • 5
  • 10
  • 2 nights min

$401

Details

1 / 10

Foster West Farmhouse- Alyson's Orchard

  • 4
  • 8
  • 2 nights min

$900

Details

1 / 18

Hideaway in the southwest New Hampshire Woods

  • 5
  • 10
  • 3 nights min

$290

Details

1 / 20

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

  • 4
  • 4
  • 3 nights min

$135

Details

1 / 7

PARADISE on EARTH! - Historic 4BR Farmhouse

  • 4
  • 8
  • 3 nights min

$285

Details

1 / 12

All-Season Gem Mount Snow Stratton Lake Whitingham

  • 3
  • 6
  • 1 night min

$150

Details

1 / 26

Steps to the sandy beach

  • 3
  • 6
  • Min stay varies

Inquire for Rates

Details

1 / 9

Lovely Mt Snow Condo

  • 2
  • 7
  • 1 night min

$226

Details

1 / 13

Log Cabin With Views

  • 4
  • 10
  • Min stay varies

$201

Details

1 / 23

Pet and family friendly home on a private hilltop.

  • 2
  • 8
  • 1 night min

$201

Details

1 / 28

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

  • 4
  • 16
  • Min stay varies

$129

Details

1 / 15

3 BDR Farmhouse on Tranquil 105 acre Organic Farm

  • 3
  • 8
  • 3 nights min

$264

Details

1 / 5

Foster Farmhouse East Wing - Alyson's Orchard

  • 3
  • 8
  • 2 nights min

$600

Details

1 / 5

Vermont Log Home splender

  • 4
  • 8
  • 1 night min

$226

Details

1 / 21

Beautiful Lake Side Getaway, Quiet, and Peaceful

  • 2
  • 6
  • Min stay varies

$100

Details

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

$1501

Details

1 / 20

Romantic Vermont Vacation Cabin with View

  • 2
  • 6
  • 2 nights min

$135

Details

1 / 12

Historical Farm House

  • 1
  • 2
  • 2 nights min

$46

Details

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