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Winchester Rentals

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Price range

Per night

$10 - $500

Winchester Rentals

24 Houses

Beautiful Lake Side Getaway, Quiet, and Peaceful

Winchester apartment

2 bedrooms / 1 bathroom / sleeps 6

“Relaxing vacation” We vacationed here for the first two weeks of July. Bill and Sandy were fabulous hosts. They were attentive to our needs and generous with their time taking us out in their boat to view the fireworks. The space is decorated taste

Price per night from

$100

1 / 21

Stay at a Craft Brewery

Winchester apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$101

1 / 17

Stunning Forest Lake Home with Hot Tub open all Yr

Winchester house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 18 minutes

Price per night from

$196

1 / 15

Great rentals within 20 miles that match your search

PARADISE on EARTH! - Historic 4BR Farmhouse

West Halifax house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$285

1 / 7

Stone 'n Sky Lodge on an Ancient Stone Landscape

New Salem house

4 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 56 minutes

Price per night from

$285

1 / 32

NEW! Beautiful Log House 3.5 Mi. to Spofford Lake!

Westmoreland house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 53 minutes

Price per night from

$140

1 / 28

Colonial Keene House on 7 Acres w/ Pool!

Keene house

9 bedrooms / 7 bathrooms / sleeps 18

Responds fast! avg. 10 minutes

Price per night from

$476

1 / 30

Classic New England Farm House

Chesterfield b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 53 minutes

Price per night from

$45

1 / 12

Adorable Studio apartment in Brattleboro

Brattleboro apartment

/ 1 bathroom / sleeps 2

Price per night from

$136

1 / 5

Vermont Log Cabin available for weekend and weekly

Guilford log cabin

2 bedrooms / 1 bathroom / sleeps 5

“Hidden Gem” My boyfriend and I had the pleasure of staying at this beautiful cabin a couple of weeks ago and honestly, I can't say enough good things about it! For starters, it is gorgeous both inside and out and much bigger than we had anticipated.

Price per night from

$111

1 / 5

Romantic Vermont Vacation Cabin with View

Newfane cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 53 minutes

Price per night from

$150

1 / 24

Church sanctuary

West Dummerston house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$260

1 / 16

Historic Lakefront Spofford Cottage

Spofford house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$370

1 / 7

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

Shelburne Falls studio

Studio / 1 bathroom / sleeps 6

Responds fast! avg. 10 minutes

Price per night from

$166

1 / 26

3 BDR Farmhouse on Tranquil 105 acre Organic Farm

Walpole house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$264

1 / 15

Penthouse at Brandt House B&B

Greenfield b and b

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$250

1 / 18

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

West Halifax house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$600

1 / 39

Historical Farm House

Chesterfield b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 53 minutes

Price per night from

$45

1 / 12

Cobb Hill Estate - 6 brs sleeps 15 on 750 acres!

Harrisville villa

6 bedrooms / 4 bathrooms / sleeps 15

Responds fast! avg. 1 hour 23 minutes

Price per night from

$551

1 / 24

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

Newfane house

7 bedrooms / 6 bathrooms / sleeps 20

Price per night from

$751

1 / 22

Beautiful House overlooking Spofford Lake

Spofford house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$161

1 / 40

Enchanting Rockwood Pond Home with Hot Tub!

Fitzwilliam house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 18 minutes

Price per night from

$195

1 / 15

Affordable Spacious Vacation Home on Lake Spofford

Chesterfield house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$161

1 / 40

Steps to the sandy beach

Spofford house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$131

1 / 26
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