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186 Houses

(3) Very Good 

20

Large, Lovely, Affordable Mountain Home

Vermont / Windham

Windham house

5 10 30 nights min

  • 5 bedrooms
  • sleeps 10
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“I rented a house for a weekend and received much more than a pla” I rented the Windham County House for a weekend to hold a retreat for first year students at Middlebury College who are still adjusting to college life. This house provided us with an
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Price per night from

$95

Price per night from

$95

37

Secluded, elegant home w/ furnished deck - close to skiing!

Vermont / Windham

Windham house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$127

Price per night from

$127

Great rentals within 20 miles that match your search

Distance approx 6.96 km from Windham Show on Map

16

Newly Remodeled Townhome

Vermont / Jamaica

Jamaica townhouse

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$571

Price per night from

$571

Distance approx 16.75 km from Windham

(14) Excellent 

18

A Vermont House for All Seasons

Vermont / Ludlow

Ludlow cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Ski
  • Child Friendly
“Perfect, just PERFECT” This house is just perfect for my group of 6. Everything is exactly as described. It's clean, warm & cozy, has everything that you need. Owner is very nice & thoughtful as well, you can find little notes throughout the house. Co
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Price per night from

$257

Responds fast!
avg. 2 hours 59 minutes

Price per night from

$257

Distance approx 15.84 km from Windham

(2) Excellent 

11

Ski-in/out Luxury 3 Bedroom & 3 Bathroom Okemo Penthouse Condo at Jackson Gore

Vermont / Ludlow

Ludlow apartment

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$1,479

Price per night from

$1,479

Distance approx 7.57 km from Windham

8

Blue Door Farm Cottage - SKI! Bromley 4mi., Magic 5mI., Stratton 12mi, Okemo..

Green Mountains / Peru

Peru house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$191

Responds fast!
avg. 56 minutes

Price per night from

$191

Distance approx 16.09 km from Windham

(2) Excellent 

20

Five Bedroom Secluded Ski House Located Two Miles From Downtown Manchester

Green Mountains / Manchester

Manchester house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$314

Price per night from

$314

Distance approx 15.72 km from Windham

(14) Excellent 

11

The Barn at Four Tooth Farm

Green Mountains / Manchester

Manchester house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden
“Felt like home” First class in every way. Beautiful view from the "wall of windows". We found ourselves drinking coffee by the fireplace admiring the view late into the morning rather than getting up and at it.Top notch kitchen if your are inclined t
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Price per night from

$300

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$300

Distance approx 16.42 km from Windham

20

Casual lux near Hermitage Club & Four Columns Inn

Vermont / South Newfane

South Newfane villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 10 mi
  • Ski
  • Ask about children

Price per night from

$1,720

Price per night from

$1,720

Distance approx 7.81 km from Windham

(1) Very Good 

10

Hugging Bear Inn - Tower Room

Vermont / Chester

Chester b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 19 mi
  • Child Friendly
  • Air conditioning

Price per night from

$136

Price per night from

$136

Distance approx 18.21 km from Windham

(2) Excellent 

21

3 Season Cabin - sleeping porch lake trails playground

Vermont / Mount Holly

Mount Holly log cabin

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$103

Price per night from

$103

Distance approx 14.25 km from Windham

16

Okemo Slopeside Rental located at the Main Base!

Vermont / Ludlow

Ludlow condo

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Ski
  • Child Friendly

Price per night from

$430

Price per night from

$430

Distance approx 11.17 km from Windham

22

Slopeside Townhome in Bromley Village

Green Mountains / Peru

Peru townhouse

4 11 2 nights min

  • 4 bedrooms
  • sleeps 11
  • 2 nights min
  • Child Friendly

Price per night from

$314

Price per night from

$314

Distance approx 8.71 km from Windham Show on Map

(6) Excellent 

18

Beautiful Vacation Home at Strattonwald at Stratton Mountain

Vermont / Stratton Mountain

Stratton Mountain house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$514

Responds fast!
avg. 3 hours 35 minutes

Price per night from

$514

Distance approx 13.59 km from Windham

16

South Face Village

Vermont / Ludlow

Ludlow condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$514

Price per night from

$514

Distance approx 14.12 km from Windham

9

Spotless newer ski home

Vermont / Cavendish

Cavendish house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$514

Price per night from

$514

Distance approx 16.89 km from Windham

(1) Excellent 

26

25 Acre Mtn Playground, 2 Bd, Great Ski Access, Close to Okemo, VAST trails

Vermont / Ludlow

Ludlow apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$229

Responds fast!
avg. 3 hours 36 minutes

Price per night from

$229

Distance approx 10.52 km from Windham

(2) Excellent 

12

2 Bedroom/2 Bath Condo

Vermont / Stratton Mountain

Stratton Mountain apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly

Price per night from

$344

Price per night from

$344

Distance approx 15.35 km from Windham

16

Fox Run -- Sleeps 10 - 12, Only 1 mile from Okemo Jackson Gore Base

Vermont / Ludlow

Ludlow townhouse

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$457

Price per night from

$457

Distance approx 18.27 km from Windham

24

Awesome! 6BR, Secluded Hot Tub, sleeps 12, WIFI!!

Vermont / Dover

Dover house

6 12 2 nights min

  • 6 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$486

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$486

Distance approx 6.96 km from Windham Show on Map

24

Jamaica Townhome w/ Pool - Mins to Stratton Mtn!

Vermont / Jamaica

Jamaica house

2 12 min stay varies

  • 2 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$337

Responds fast!
avg. 22 minutes

Price per night from

$337

Distance approx 7.81 km from Windham

11

Hugging Bear Inn - Bear's Den Room

Vermont / Chester

Chester b and b

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$159

Price per night from

$159

Distance approx 18.25 km from Windham

25

Luxury Lakefront Home near Okemo

Vermont / Ludlow

Ludlow house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Ski
  • Child Friendly

Price per night from

$740

Price per night from

$740

Distance approx 6.52 km from Windham

16

2016-17 Booking now for entire Ski Season $8000.00

Vermont / Londonderry

Londonderry chalet

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$400

Price per night from

$400

Distance approx 18.27 km from Windham

(1) Excellent 

15

3 BDR Farmhouse on Tranquil 105 acre Organic Farm

New Hampshire / Walpole

Walpole house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 8 mi
  • Child Friendly
  • Air conditioning

Price per night from

$302

Price per night from

$302

Distance approx 7.09 km from Windham Show on Map

24

Live & Breathe VT- Village Home, Yoga Studio, Ski!

Vermont / Jamaica

Jamaica house

4 9 3 nights min

  • 4 bedrooms
  • sleeps 9
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$286

Price per night from

$286

Distance approx 18.57 km from Windham

26

West Dover Home w/Hot Tub- Short Drive to Mt. Snow

Vermont / Dover

Dover house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$223

Responds fast!
avg. 22 minutes

Price per night from

$223

Distance approx 14.93 km from Windham

32

Private Home w/ Views - Near Manchester Golf & Ski

Green Mountains / Dorset

Dorset house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$543

Responds fast!
avg. 22 minutes

Price per night from

$543

Distance approx 13.61 km from Windham

16

Quiet Hillside 4 Bedroom Carriage House W/3 Baths

Vermont / Ludlow

Ludlow guest house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$343

Price per night from

$343

Distance approx 5.55 km from Windham

24

Chester House Just 12 Mins to Magic Mtn Ski Area!

Vermont / Chester

Chester house

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$155

Responds fast!
avg. 21 minutes

Price per night from

$155

Distance approx 18.21 km from Windham

20

Cabin in the Big Woods - sleeping porch lake trails playground

Vermont / Mount Holly

Mount Holly log cabin

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$92

Price per night from

$92

Distance approx 7.68 km from Windham

10

The 1843 Stone House - Chester, VT (3bdrm/ 2 ba)

Vermont / Chester

Chester house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly

Price per night from

$200

Price per night from

$200

Distance approx 11.86 km from Windham Show on Map

18

Vermont home located in the mountains between Mt. Snow & Stratton Mt

Vermont / Wardsboro

Wardsboro log cabin

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$343

Price per night from

$343

Distance approx 10.78 km from Windham

16

3 BR/Bth Townhouse/Condo Grt loc. Stratton Mtn. VT

Vermont / Stratton Mountain

Stratton Mountain apartment

3 8 90 nights min

  • 3 bedrooms
  • sleeps 8
  • 90 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$266

Price per night from

$266

Distance approx 11.52 km from Windham

(3) Excellent 

20

Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo

Vermont / Proctorsville

Proctorsville house

8 20 2 nights min

  • 8 bedrooms
  • sleeps 20
  • 2 nights min
  • Ski
  • Child Friendly
  • Private garden

Price per night from

$457

Price per night from

$457

Distance approx 19.18 km from Windham

30

West Dover Home w/Game Room-Pool & Fire Pit Access

Vermont / Dover

Dover house

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$326

Responds fast!
avg. 22 minutes

Price per night from

$326

Distance approx 7.29 km from Windham Show on Map

7

Beautiful 5 BR/5 BA Home 10 mins from Stratton

Vermont / Jamaica

Jamaica house

5 11 2 nights min

  • 5 bedrooms
  • sleeps 11
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$1,028

Price per night from

$1,028

Distance approx 9.49 km from Windham Show on Map

(9) Very Good 

10

Stratton 4 Bedroom Home

Vermont / Stratton Mountain

Stratton Mountain house

4 11 2 nights min

  • 4 bedrooms
  • sleeps 11
  • 2 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$400

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$400