Winhall, Vermont

Vacation Rentals in Winhall, Vermont

Discover 73 vacation rental properties in Winhall. From 1 to 16 bedrooms. Average $534/night. 100% have pools.

73 verified listings Book securely on VRBO Prices updated March 2026

73 properties available

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

1 bed 1 bath
PoolA/CWiFiBalcony
$194/night
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Beautiful Chalet For All Seasons

Beautiful Chalet For All Seasons

4 beds 1 bath
PoolA/CWiFiBalcony
$171/night
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Cozy Stratton Hideaway

Cozy Stratton Hideaway

2 beds 1 bath
PoolA/CWiFiBalcony
$124/night
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Less the 1 mile to Bromley!

Less the 1 mile to Bromley!

3 beds 2 baths
PoolA/CWiFiBalcony
$175/night
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By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

3 beds 2 baths
PoolA/CWiFiBalcony
$236/night
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Townhouse with winter shuttle access, grill, forests/pond view, fireplace, deck

Townhouse with winter shuttle access, grill, forests/pond view, fireplace, deck

3 beds 3 baths
PoolA/CWiFiBalcony
$229/night
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BOGO Sale, Golf, Hiking, pool table, pac man, 4bedrooms with private baths.

BOGO Sale, Golf, Hiking, pool table, pac man, 4bedrooms with private baths.

4 beds 4 baths
PoolA/CWiFiBalcony
$286/night
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2-story dog-friendly mountain home with wood fireplace, balcony, deck, & grill

2-story dog-friendly mountain home with wood fireplace, balcony, deck, & grill

4 beds 2 baths
PoolA/CWiFiBalcony
$281/night
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Charming dog-friendly condo with balcony, full kitchen, & washer/dryer

Charming dog-friendly condo with balcony, full kitchen, & washer/dryer

2 beds 1 bath
PoolA/CWiFiBalcony
$99/night
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This cabin is a 2 bedroom(s), 1.5 bathrooms, located in Winhall, VT.

This cabin is a 2 bedroom(s), 1.5 bathrooms, located in Winhall, VT.

2 beds 1 bath
PoolA/CWiFiBalcony
$264/night
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The Mushroom House of Manchester Vermont

The Mushroom House of Manchester Vermont

3 beds 2 baths
PoolA/CWiFiBalcony
$276/night
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Comfortable condo near access road of Stratton Mountain Resort with fireplace

Comfortable condo near access road of Stratton Mountain Resort with fireplace

3 beds 3 baths
PoolA/CWiFiBalcony
$278/night
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Cozy Manchester Getaway with Amazing Views!!!

Cozy Manchester Getaway with Amazing Views!!!

4 beds 2 baths
PoolA/CWiFiBalcony
$395/night
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Beautiful Manchester VT Mountain Retreat w/Hot Tub

Beautiful Manchester VT Mountain Retreat w/Hot Tub

5 beds 3 baths
PoolA/CWiFiBalcony
$356/night
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The Burrow

The Burrow

2 beds 1 bath
PoolA/CWiFiBalcony
$396/night
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Mountain view chalet near Manchester/Stratton

Mountain view chalet near Manchester/Stratton

3 beds 1 bath
PoolA/CWiFiBalcony
$180/night
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Spacious Chalet W/ Endless Entertainment THE BARN

Spacious Chalet W/ Endless Entertainment THE BARN

6 beds 4 baths
PoolA/CWiFiBalcony
$1,016/night
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Log Cabin Escape Close to Skiing & Shops

Log Cabin Escape Close to Skiing & Shops

3 beds 2 baths
PoolA/CWiFiBalcony
$537/night
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Charming home with mountain-view, sauna, hot tub, pool table, & washer/dryer

Charming home with mountain-view, sauna, hot tub, pool table, & washer/dryer

5 beds 4 baths
PoolA/CWiFiBalcony
$229/night
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Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

3 beds 3 baths
PoolA/CWiFiBalcony
$199/night
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Stratton Loft with Pool

Stratton Loft with Pool

4 beds 2 baths
PoolA/CWiFiBalcony
$218/night
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Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

3 beds 2 baths
PoolA/CWiFiBalcony
$552/night
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Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

6 beds 3 baths
PoolA/CWiFiBalcony
$673/night
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Mid-Century Modern Chalet in Stratton Mountain - 2 min from slopes

Mid-Century Modern Chalet in Stratton Mountain - 2 min from slopes

4 beds 2 baths
PoolA/CWiFiBalcony
$677/night
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Ski Condo right down the road from Stratton Mountain

Ski Condo right down the road from Stratton Mountain

3 beds 1 bath
PoolA/CWiFiBalcony
$401/night
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Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

7 beds 4 baths
PoolA/CWiFiBalcony
$834/night
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Shuttle / walk to village & lifts! Mountainside!

Shuttle / walk to village & lifts! Mountainside!

4 beds 2 baths
PoolA/CWiFiBalcony
$331/night
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Spacious + Private Ski Lodge on 20+ Acres - 10 min to Stratton, 5 min to Bromley

Spacious + Private Ski Lodge on 20+ Acres - 10 min to Stratton, 5 min to Bromley

5 beds 4 baths
PoolA/CWiFiBalcony
$690/night
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Ski Chalet on private 35 acre property with hot tub + stratton vip parking pass

Ski Chalet on private 35 acre property with hot tub + stratton vip parking pass

4 beds 3 baths
PoolA/CWiFiBalcony
$768/night
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3 Level 2900 Sq. Ft. House: 6 Bedrooms, 4.5 Baths, & 2 Fireplaces

3 Level 2900 Sq. Ft. House: 6 Bedrooms, 4.5 Baths, & 2 Fireplaces

6 beds 4 baths
PoolA/CWiFiBalcony
$603/night
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Charming dog-friendly home on 4+ acres with mountain/valley views & firepit

Charming dog-friendly home on 4+ acres with mountain/valley views & firepit

4 beds 3 baths
PoolA/CWiFiBalcony
$170/night
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Stratton home with spectacular mountain view and hot tub! kitchen updated 2024

Stratton home with spectacular mountain view and hot tub! kitchen updated 2024

5 beds 3 baths
PoolA/CWiFiBalcony
$552/night
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*Hilltop Hideaway* Hot Tub in Iconic Chalet

*Hilltop Hideaway* Hot Tub in Iconic Chalet

3 beds 3 baths
PoolA/CWiFiBalcony
$373/night
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Charming retreat close to skiing with firepit, W/D, & fireplace - dog friendly

Charming retreat close to skiing with firepit, W/D, & fireplace - dog friendly

5 beds 3 baths
PoolA/CWiFiBalcony
$177/night
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2024 Seasonal Summer Rental

2024 Seasonal Summer Rental

3 beds 3 baths
PoolA/CWiFiBalcony
$502/night
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Dog-friendly home with hot tub, game room, fireplace, & ski lodge parking

Dog-friendly home with hot tub, game room, fireplace, & ski lodge parking

7 beds 7 baths
PoolA/CWiFiBalcony
$631/night
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Green Mountain Manor - Ski and Summer Chalet

Green Mountain Manor - Ski and Summer Chalet

7 beds 5 baths
PoolA/CWiFiBalcony
$2,015/night
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Stratton Trailside Condo

Stratton Trailside Condo

3 beds 3 baths
PoolA/CWiFiBalcony
$828/night
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Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt

Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt

3 beds 4 baths
PoolA/CWiFiBalcony
$535/night
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Secluded dog-friendly mountain home near Stratton w/ firepit, deck, & fireplace

Secluded dog-friendly mountain home near Stratton w/ firepit, deck, & fireplace

3 beds 2 baths
PoolA/CWiFiBalcony
$239/night
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Green Mountain National Forest Ski Chalet

Green Mountain National Forest Ski Chalet

5 beds 3 baths
PoolA/CWiFiBalcony
$500/night
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Winterland Chalet Stratton Mountain LONG TERM RENTAL ONLY December 1- March 31.

Winterland Chalet Stratton Mountain LONG TERM RENTAL ONLY December 1- March 31.

4 beds 4 baths
PoolA/CWiFiBalcony
$899/night
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Cozy abode with a deck, grill, wood stove, full kitchen, W/D, and partial AC

Cozy abode with a deck, grill, wood stove, full kitchen, W/D, and partial AC

3 beds 2 baths
PoolA/CWiFiBalcony
$155/night
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Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

5 beds 3 baths
PoolA/CWiFiBalcony
$278/night
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Stratton Mountain Home

Stratton Mountain Home

4 beds 3 baths
PoolA/CWiFiBalcony
$523/night
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Mountain Retreat Getaway 5 Min to Swimming Pond

Mountain Retreat Getaway 5 Min to Swimming Pond

3 beds 1 bath
PoolA/CWiFiBalcony
$410/night
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5 miles to Stratton! Family-friendly with game room and deck!

5 miles to Stratton! Family-friendly with game room and deck!

3 beds 2 baths
PoolA/CWiFiBalcony
$502/night
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Room for the whole family!

Room for the whole family!

4 beds 3 baths
PoolA/CWiFiBalcony
$371/night
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Showing 48 of 73 properties

More destinations in Vermont

Ludlow (398) Killington (396) Stowe (286) Wilmington (219) Warren (200) Dover (172) Stratton (133) Manchester (78) Quechee (78) West Dover (72) Burlington (66) Jay (61) Colchester (60) Cambridge (50) Waitsfield (50) Peru (45) Mendon (44) Woodstock (40) Castleton (39) Manchester Center (37)