Windham County, VT, USA Vacation rentals • comparison for Airbnb, Vrbo and Booking prices

United States Massachusetts Pittsfield vacation rental compare prices direct by owner 2297482

Hidden Oasis in the Mountains by Evergreen Home

5.0 (152)

5 Bedrooms • 10 Guests

$745 avg/night

United States Massachusetts New Marlborough vacation rental compare prices direct by owner 24109993

Ski Rental: Hot tub, Sauna, Game Room, Fireplaces!

5.0 (34)

5 Bedrooms • 14 Guests

$1,434 avg/night

United States Massachusetts Cheshire vacation rental compare prices direct by owner 26549912

Berkshires Lakefront Retreat by Evergreen Home

5.0 (64)

4 Bedrooms • 8 Guests

$883 avg/night

United States Vermont Stratton vacation rental compare prices direct by owner 25022299

Catey Rose Retreat|Movie Theatre-Hot Tub-Fireplace

5.0 (29)

7 Bedrooms • 16 Guests

$3,607 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 9676490

5 Stars w/ Hot Tub, Sunny Patio, Game Room, Views!

5.0 (24)

4 Bedrooms • 14 Guests

$1,063 avg/night

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United States Massachusetts Great Barrington vacation rental compare prices direct by owner 25055050

Renovated Private Guest House by Evergreen Home

5.0 (27)

2 Bedrooms • 5 Guests

$160 avg/night

United States Vermont Ludlow vacation rental compare prices direct by owner 1910499

Okemo Mountain Lodge 1BR - Ski In / Ski Out

5 Bedrooms • 12 Guests

$2,105 avg/night

United States Vermont Ludlow vacation rental compare prices direct by owner 33035408

Sleek 2BR Kettlebrook Condo with Fireplace, Ski-in

5.0 (22)

2 Bedrooms • 6 Guests

$1,051 avg/night

United States Vermont Killington vacation rental compare prices direct by owner 9437837

Stunning Log home with outdoor hot tub Ridgetop

5.0 (11)

4 Bedrooms • 8 Guests

$1,318 avg/night

United States Vermont Ludlow vacation rental compare prices direct by owner 32356408

3-BR Winterplace Ski-In/Out Okemo Condo w/ Loft

5.0 (16)

3 Bedrooms • 10 Guests

$1,616 avg/night

United States Massachusetts Lenox vacation rental compare prices direct by owner 11500496

Sophisticated Lenox Retreat by Evergreen Home

4.9 (66)

4 Bedrooms • 8 Guests

$684 avg/night

United States Vermont Killington vacation rental compare prices direct by owner 33504935

Wobbly Cabin: Cozy Ski Home Close To Everything!

4.9 (36)

2 Bedrooms • 6 Guests

$369 avg/night

United States Vermont Killington vacation rental compare prices direct by owner 37710493

93 Glazebrook Rd - E2: 2BR/1.5BA Condo. Fireplace.

4.9 (18)

2 Bedrooms • 6 Guests

$502 avg/night

United States Vermont Killington vacation rental compare prices direct by owner 1986531

The Mountain Suite at Killington: NEW Luxury Condo! Sleeps 10.Close to Mtn 112/3

4.9 (17)

2 Bedrooms • 10 Guests

$859 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 2823058

Winter Lake Views, Close to Butternut!

4.9 (32)

4 Bedrooms • 8 Guests

$763 avg/night

United States Vermont Jamaica vacation rental compare prices direct by owner 26592908

The Post Haus: one-of-a-kind modern VT experience

4.9 (126)

2 Bedrooms • 4 Guests

$632 avg/night

United States New York Ghent vacation rental compare prices direct by owner 27827009

Grand Estate w/ Mountain Views by Evergreen Home

4.9 (60)

7 Bedrooms • 12 Guests

$971 avg/night

United States Vermont Killington vacation rental compare prices direct by owner 33026513

Renovated 4 bedroom w/sauna, jacuzzi tub, sportsB7

4.9 (9)

4 Bedrooms • 10 Guests

$1,400 avg/night

United States Vermont Killington vacation rental compare prices direct by owner 33585280

Snow Place Like Whiffletree: 3BR/2BA Condo

4.9 (14)

3 Bedrooms • 6 Guests

$817 avg/night

United States New York Fort Ann vacation rental compare prices direct by owner 13059948

Lakefront Lookout-Hot tub-Fireplace-Dock-Game Room

4.9 (45)

4 Bedrooms • 14 Guests

$1,200 avg/night

United States Vermont Wilmington vacation rental compare prices direct by owner 26573016

Stylish Chimney Hill Home - Close to Mt. Snow!

4.9 (27)

3 Bedrooms • 6 Guests

$634 avg/night

United States Vermont Ludlow vacation rental compare prices direct by owner 33114260

Trailside Mountain View 4-BR Okemo Haven

4.9 (25)

4 Bedrooms • 8 Guests

$1,463 avg/night

United States Vermont Killington vacation rental compare prices direct by owner 10201125

Renovated Trail Creek #50 3BR/2BA Loft w/ AC.

4.9 (58)

3 Bedrooms • 6 Guests

$819 avg/night

United States Vermont Ludlow vacation rental compare prices direct by owner 27137788

On Shuttle - 3BR Brookhaven Condo

4.9 (13)

3 Bedrooms • 8 Guests

$837 avg/night

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