Winchester Vacation Rentals, Houses & More


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Areas near Winchester

1 / 21

Beautiful Lake Side Getaway, Quiet, and Peaceful

  • 2
  • 6
  • Min stay varies

$100

Details

Great rentals within 20 miles that match your search

1 / 16

Pet-friendly private, peaceful, pond-front home

  • 2
  • 4
  • 7 nights min

$120

Details

1 / 16

Church sanctuary

  • 3
  • 6
  • 2 nights min

$260

Details

1 / 26

Steps to the sandy beach

  • 3
  • 6
  • Min stay varies

$160

Details

1 / 20

Romantic Vermont Vacation Cabin with View

  • 2
  • 6
  • 2 nights min

$135

Details

1 / 32

Stone 'n Sky Lodge on an Ancient Stone Landscape

  • 4
  • 14
  • 2 nights min

$285

Details

1 / 28

Elegant Mountainside Country Estate

  • 6
  • 12
  • 2 nights min

$275

Details

1 / 10

Foster West Farmhouse- Alyson's Orchard

  • 4
  • 8
  • 2 nights min

$900

Details

1 / 24

Stunning Luxury Estate on 140 Acres - with Hot Tub and A/C

  • 5
  • 10
  • 2 nights min

$701

Details

1 / 12

Historical Farm House

  • 1
  • 2
  • 2 nights min

$46

Details

1 / 15

3 BDR Farmhouse on Tranquil 105 acre Organic Farm

  • 3
  • 8
  • 3 nights min

$264

Details

1 / 5

Adorable Studio apartment in Brattleboro

  • 2
  • 1 night min

$135

Details

1 / 40

Beautiful House overlooking Spofford Lake

  • 4
  • 10
  • Min stay varies

$150

Details

1 / 13

Rochambeau Lodge ~ Alyson's Orchard

  • 8
  • 18
  • 2 nights min

$1001

Details

1 / 11

The Sugarhouse on the Scott Farm

  • 1
  • 2
  • 1 night min

$176

Details

1 / 18

Hideaway in the southwest New Hampshire Woods

  • 5
  • 10
  • 3 nights min

$290

Details

1 / 5

Foster Farmhouse East Wing - Alyson's Orchard

  • 3
  • 8
  • 2 nights min

$600

Details

1 / 12

Classic New England Farm House

  • 1
  • 2
  • 2 nights min

$46

Details

1 / 7

PARADISE on EARTH! - Historic 4BR Farmhouse

  • 4
  • 8
  • 3 nights min

$285

Details

1 / 23

Pet and family friendly home on a private hilltop.

  • 2
  • 8
  • 1 night min

$201

Details

1 / 24

Lakefront Cottage

  • 2
  • 7
  • 7 nights min

$157

Details

1 / 5

Vermont Log Cabin available for weekend and weekly

  • 2
  • 5
  • 2 nights min

$110

Details

1 / 18

Penthouse at Brandt House B&B

  • 1
  • 4
  • 2 nights min

$249

Details

1 / 15

Enchanting Rockwood Pond Home with Hot Tub!

  • 3
  • 10
  • Min stay varies

$196

Details

1 / 22

Enchanting Rockwood Pond Home with Hot Tub!

  • 3
  • 9
  • Min stay varies

$201

Details

1 / 24

Mt. Snow/Stratton Area One of a kind private compound on 100 beautiful acres

  • 7
  • 16
  • Min stay varies

$750

Details

1 / 13

Cozy Cabin at the base of Mt Monadnock

  • 3
  • 6
  • 2 nights min

$226

Details

1 / 11

Stunning Forest Lake Home with Hot Tub!

  • 4
  • 9
  • Min stay varies

$201

Details

1 / 15

Stunning Forest Lake Home with Hot Tub open all Yr

  • 4
  • 10
  • Min stay varies

$196

Details

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