Windsor County Vacation Rentals

Icon
Icon
Icon
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Icon

Vermont Cottage On Lake Amherst & Sanctuary ~ Pet Friendly ~ Fire Pit ~ Fire place ~ Between Okemo & Killington Areas ~ Route 100

6 Bedrooms
4 Bathrooms
3 Guides
4.98IconIconIconIconIcon
90 reviews
$800 - $900 / night (excl. fees & taxes)
Icon
Icon
Icon
Vermont Cottage Amherst Lake & Sanctuary
Icon

LakeAmherstRentals~Good Woods Cottage~Okemo Killington~Dog Friendly~Hot Tub~Fire Pit~

4 Bedrooms
3 Bathrooms
3 Guides
5IconIconIconIconIcon
55 reviews
$650 / night (excl. fees & taxes)
Icon
Icon
Killington Grandview House
Icon

Contemporary Spacious 7br/6.5 bath home near Killington VT

7 Bedrooms
6½ Bathrooms
3 Guides
4.86IconIconIconIconIcon
7 reviews
$1100 / night (excl. fees & taxes)
Icon
Icon
Icon
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Icon

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

6 Bedrooms
2 Bathrooms
3 Guides
5IconIconIconIconIcon
107 reviews
$550 / night (excl. fees & taxes)
Icon
Icon
Icon
The Crooked House
Icon

3BR 2.5BA mountain house w/ sauna near Killington

3 Bedrooms
2½ Bathrooms
3 Guides
5IconIconIconIconIcon
100 reviews
$225 - $500 / night (excl. fees & taxes)
Icon
Icon
Icon
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
Icon

Nirvana Sanctuary House~Fire Place~Okemo Killington 2 BR 3BA

2 Bedrooms
3 Bathrooms
3 Guides
5IconIconIconIconIcon
31 reviews
$425 / night (excl. fees & taxes)
Icon
Icon
Icon
Cool Haven~Cute Cottage in Plymouth, Vermont.
Icon

1 BR Cottage Fireplace~Lake Views~Hot Tub~Dog Freindly~Private

1 Bedroom
2 Bathrooms
3 Guides
5IconIconIconIconIcon
34 reviews
$350 / night (excl. fees & taxes)
Icon
Icon
Icon
Forty Winks Cottage In Vermont
Icon

3 BR~3BA~DogFriendly~FirePlace~HotTub~FirePit~Charming~Cozy~Unique~Vintage~Okemo~Killington

3 Bedrooms
3 Bathrooms
3 Guides
4.98IconIconIconIconIcon
52 reviews
$600 / night (excl. fees & taxes)
Icon
Icon
Icon
2 Bdrm, Lower Level, Okemo, 25 Acre Mtn Playground
Icon

25 Acre Mountain Playground, Close to Okemo, 2 Bedroom

2 Bedrooms
1 Bathroom
3 Guides
5IconIconIconIconIcon
27 reviews
$250 - $300 / night (excl. fees & taxes)
Icon
Icon
Icon
2 Bdrm, Upper Level, Okemo, 25 Acre Mtn Playground
Icon

Close to Okemo, 25 Acre Mountain Playground, 2 Bedroom

2 Bedrooms
1 Bathroom
3 Guides
5IconIconIconIconIcon
13 reviews
$250 - $300 / night (excl. fees & taxes)
Icon
Icon
Kilbourne Lodge︙3BR/2BA+Pets+Fireplace+Boot Dryer
Icon

Kilbourne Lodge︙3BR/2BA+Pets+Fireplace+Boot Dryer

3 Bedrooms
2 Bathrooms
3 Guides
4.91IconIconIconIconIcon
33 reviews
$165 - $980 / night (excl. fees & taxes)
Icon
Icon
Trailside Chalet
Icon

Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

5 Bedrooms
2 Bathrooms
3 Guides
4.9IconIconIconIconIcon
59 reviews
$250 - $2100 / night (excl. fees & taxes)
Icon
Icon
Icon
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Icon

Twinkle Cottage~HotTub~FirePit~Dogs~Volley Ball~Croquet~

1 Bedroom
2 Bathrooms
3 Guides
$350 / night (excl. fees & taxes)
Icon
Icon
Killington VT Condo - Mountain Green
Icon

Walk to Snowshed - Remote Work Hub - Hot Tub/Pool

1 Bedroom
1 Bathroom
3 Guides
$137 - $858 / night (excl. fees & taxes)
Icon
Icon
Mount Holly Lake & Ski Hideaway
Icon

Mount Holly Lake & Ski Hideaway

4 Bedrooms
2 Bathrooms
3 Guides
5IconIconIconIconIcon
37 reviews
$299 / night (excl. fees & taxes)
Icon
Icon
Updated Home in Heart of Rutland, Near Slopes
Icon

Updated Home in Heart of Rutland, Near Slopes

4 Bedrooms
3 Bathrooms
3 Guides
4.64IconIconIconIconIcon
14 reviews
$205 - $499 / night (excl. fees & taxes)
Icon
Icon
Heavenly Killington luxury home on Killington Road
Icon

Heavenly Killington luxury home on Killington Road

7 Bedrooms
4 Bathrooms
3 Guides
5IconIconIconIconIcon
83 reviews
$600 - $2975 / night (excl. fees & taxes)
Icon
Icon
Clocktower Chalet
Icon

*January 50% Discount* Walk to Okemo Lodge & Lifts. Private Home with Hot Tub

4 Bedrooms
2 Bathrooms
3 Guides
5IconIconIconIconIcon
31 reviews
$275 - $1500 / night (excl. fees & taxes)
Icon
Icon
Mountain View Manor
Icon

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

6 Bedrooms
5 Bathrooms
3 Guides
$670 - $2122 / night (excl. fees & taxes)
Icon
Icon
Hillside Haven
Icon

Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo

5 Bedrooms
3 Bathrooms
3 Guides
$300 - $1545 / night (excl. fees & taxes)
    1 – 20 Rentals