Windsor Area Vacation Rentals - Windsor Area, Vermont Vacation Rental Deals on Lake Rentals, Beach Houses, Condos, Cabins, Villas by VacaGuru.com!

$Ski-in\/out condo with fireplace, pool, hot tub, sauna & washer\/dryer$

Ski-in\/out condo with fireplace, pool, hot tub, sauna & washer\/dryer

2
3.0
6

Ludlow Vermont Condo From $130 per night (USD)

Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River

Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River

4
4.0
10

Rochester Vermont Private vacation home From $325 per night (USD)

Clean, Updated, & Well Appointed-Family & Dog Friendly Rental

Clean, Updated, & Well Appointed-Family & Dog Friendly Rental

2
3.0
6

Ludlow Vermont Apartment From $195 per night (USD)

Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity

Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity

2
1.0
4

Woodstock Vermont Private vacation home From $385 per night (USD)

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

2
2.0
6

Ludlow Vermont Apartment From $113 per night (USD)

IT'S FOLIAGE SEASON!

IT'S FOLIAGE SEASON!

1
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4

Woodstock Vermont Apartment From $135 per night (USD)

$Summer Specials! Fabulous Log Home, 6 BR\/4BA, Pool Table, Hot Tub on Okemo$

Summer Specials! Fabulous Log Home, 6 BR\/4BA, Pool Table, Hot Tub on Okemo

6
4.0
12

Ludlow Vermont Private vacation home From $325 per night (USD)

Reading Farms Estate

Reading Farms Estate

15
14.0
46

Reading Vermont Private vacation home From $3476 per night (USD)

Luxury 3BR Cabin 5 min Drive to Okemo and on Ski Shuttle Route

Luxury 3BR Cabin 5 min Drive to Okemo and on Ski Shuttle Route

3
2.0
6

Ludlow Vermont Private vacation home From $450 per night (USD)

Dog-friendly house near Okemo Mountain Resort, skiing, & heart of Ludlow Village

Dog-friendly house near Okemo Mountain Resort, skiing, & heart of Ludlow Village

3
3.0
8

Ludlow Vermont Private vacation home From $223 per night (USD)

Beautiful 3000 Square Foot Home

Beautiful 3000 Square Foot Home

5
3.0
10

Cavendish Vermont Cabin From $371 per night (USD)

$Dramatic Design & Landscape 3500 Sq Ft. Farmhouse W\/Jacuzzi&Swim Pond&CentralAC!$

Dramatic Design & Landscape 3500 Sq Ft. Farmhouse W\/Jacuzzi&Swim Pond&CentralAC!

7
4.0
28

Bridgewater Vermont Agritourism From $700 per night (USD)

Lake Rescue Chalet - 6-Bedroom Lake & Ski House with Hot Tub

Lake Rescue Chalet - 6-Bedroom Lake & Ski House with Hot Tub

6
2.0
12

Ludlow Vermont Chalet From $449 per night (USD)

Winterplace at Okemo Mountain

Winterplace at Okemo Mountain

2
2.0
9

Ludlow Vermont Condo From $210 per night (USD)

$Luxurious, Secluded, Ski Chalet, w\/ Country Decor & Hot Tub Near Okemo$

Luxurious, Secluded, Ski Chalet, w\/ Country Decor & Hot Tub Near Okemo

4
3.0
12

Ludlow Vermont Private vacation home From $303 per night (USD)

Quechee at its Finest!

Quechee at its Finest!

3
2.0
6

Hartford Vermont Private vacation home From $310 per night (USD)

Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!

1
1.0
3

Chester Vermont Bed & breakfast From $120 per night (USD)

King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

1
1.0
6

Chester Vermont Bed & breakfast From $70 per night (USD)

$Ludlow Home w\/ Hot Tub, Near Okemo Resort!$

Ludlow Home w\/ Hot Tub, Near Okemo Resort!

4
3.0
11

Ludlow Vermont Private vacation home From $374 per night (USD)

$Lake-view home with a private hot tub, fast WiFi, pool table, & washer\/dryer$

Lake-view home with a private hot tub, fast WiFi, pool table, & washer\/dryer

5
4.0
12

Ludlow Vermont Private vacation home From $190 per night (USD)

Bigfoot Chalet, SKI-Hike-Boat-Bike-Fish-RELAX!

Bigfoot Chalet, SKI-Hike-Boat-Bike-Fish-RELAX!

3
2.0
6

Ludlow Vermont Private vacation home From $160 per night (USD)

$Quiet Modern Luxury Home w\/ Memory Foam Beds, A\/C, FAST WiFi and Full Kitchen$

Quiet Modern Luxury Home w\/ Memory Foam Beds, A\/C, FAST WiFi and Full Kitchen

3
2.0
8

Bridgewater Vermont Private vacation home From $360 per night (USD)

Secluded 2600 sqft home 15 min from Okemo and Killington

Secluded 2600 sqft home 15 min from Okemo and Killington

3
4.0
8

Plymouth Vermont Chalet From $324 per night (USD)

Stunning Lakeside home - ideal family getaway or work from home spot

Stunning Lakeside home - ideal family getaway or work from home spot

3
3.0
8

Ludlow Vermont Private vacation home From $575 per night (USD)

$Comfortable home with jetted tub, patio, & W\/D- near skiing$

Comfortable home with jetted tub, patio, & W\/D- near skiing

3
2.0
8

Ludlow Vermont Private vacation home From $235 per night (USD)

Ski House on Lake Rescue, 3.5 Miles from Okemo

Ski House on Lake Rescue, 3.5 Miles from Okemo

4
3.0
8

Ludlow Vermont Private vacation home From $298 per night (USD)

$Great 4BR\/3BA for families in village w\/ easy shuttle access. Read our reviews!$

Great 4BR\/3BA for families in village w\/ easy shuttle access. Read our reviews!

4
3.0
12

Ludlow Vermont Condo From $305 per night (USD)

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

3
2.0
6

Ludlow Vermont Cabin From $168 per night (USD)

Exquisite two bedroom, 1.5 bath end unit town home near Lake Pinneo and the Quechee Club.

Exquisite two bedroom, 1.5 bath end unit town home near Lake Pinneo and the Quechee Club.

2
2.0
4

Hartford Vermont Condo From $195 per night (USD)

New Lakeside Cottage near Okemo and Killington

New Lakeside Cottage near Okemo and Killington

2
2.0
5

Plymouth Vermont Cottage From $247 per night (USD)

$Ski On, Ski off Okemo Trailside Appartment, Sleeps 6\/ $550per night,$

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6\/ $550per night,

3
1.0
6

Ludlow Vermont Chalet From $550 per night (USD)

Great Location, Large Hot Tub, Wet Bar, Pool Table, Gas FP

Great Location, Large Hot Tub, Wet Bar, Pool Table, Gas FP

5
4.0
16

Ludlow Vermont Private vacation home From $635 per night (USD)

$Custom Luxury Home w\/Hot Tub on Okemo Mtn\/Family\/Group Friendly\/Shuttle Bus$

Custom Luxury Home w\/Hot Tub on Okemo Mtn\/Family\/Group Friendly\/Shuttle Bus

6
5.0
14

Ludlow Vermont Private vacation home From $990 per night (USD)

Ludlow Vermont Ski House

Ludlow Vermont Ski House

4
3.0
8

Ludlow Vermont Private vacation home From $1000 per night (USD)

1794 Pioneer House - Renovated, No Cleaning Fee

1794 Pioneer House - Renovated, No Cleaning Fee

2
2.0
4

Springfield Vermont Private vacation home From $234 per night (USD)

$Sunlit VT Country Home w\/Hot Tub. Ideal location near Woodstock village$

Sunlit VT Country Home w\/Hot Tub. Ideal location near Woodstock village

3
2.0
6

Woodstock Vermont Private vacation home From $301 per night (USD)

Delightful Cozy Space in Woodstock Village

Delightful Cozy Space in Woodstock Village

1
1.0
4

Woodstock Vermont Apartment From $191 per night (USD)

Beautiful 6 Bedroom Home in Quechee Vermont

Beautiful 6 Bedroom Home in Quechee Vermont

6
3.0
14

Hartford Vermont Private vacation home From $721 per night (USD)

Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!

Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!

1
1.0
4

Hartland Vermont Cabin From $350 per night (USD)

Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34

Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34

10
5.0
34

Ludlow Vermont Private vacation home From $650 per night (USD)

$\The Crooked House\ w\/ sauna on private wooded lot near Woodstock, Killington$

\"The Crooked House\" w\/ sauna on private wooded lot near Woodstock, Killington

3
3.0
8

Stockbridge Vermont Private vacation home From $255 per night (USD)

Beautiful farmhouse minutes to Okemo. Spacious, hot tub. Weekend shuttle bus.

Beautiful farmhouse minutes to Okemo. Spacious, hot tub. Weekend shuttle bus.

4
3.0
10

Ludlow Vermont Agritourism From $350 per night (USD)

School Brick House is the perfect location for a vacation

School Brick House is the perfect location for a vacation

3
2.0
6

Rochester Vermont Private vacation home From $178 per night (USD)

Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!

Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!

2
1.0
6

Hartland Vermont Cabin From $450 per night (USD)

Okemo 6 Bedroom Chalet.

Okemo 6 Bedroom Chalet.

6
2.0
13

Ludlow Vermont Chalet From $431 per night (USD)

Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

2
1.0
8

Ludlow Vermont Private vacation home From $400 per night (USD)

Okemo Mountain Slopeside Vacation Condo

Okemo Mountain Slopeside Vacation Condo

2
2.0
6

Ludlow Vermont Condo From $219 per night (USD)

Romantic Guest House Hideaway

Romantic Guest House Hideaway

1
1.0
2

Woodstock Vermont Private vacation home From $199 per night (USD)

Flash sale! Come ski Okemo! Enjoy this newly renovated, cozy home!

Flash sale! Come ski Okemo! Enjoy this newly renovated, cozy home!

3
2.0
6

Ludlow Vermont Private vacation home From $198 per night (USD)

Renovated Cabin Overlooking Waterfall and Pond

Renovated Cabin Overlooking Waterfall and Pond

2
1.0
4

Barnard Vermont Cabin From $303 per night (USD)

Stay Safe! Stay strong!

Stay Safe! Stay strong!

3
2.0
6

Ludlow Vermont Private vacation home From $245 per night (USD)

Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!

Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!

1
1.0
4

Windsor Vermont Cabin From $395 per night (USD)

Cottage On Main

Cottage On Main

2
1.0
2

Cavendish Vermont Private vacation home From $195 per night (USD)

Bright, Downtown 4-BR Home 3-min to Okemo

Bright, Downtown 4-BR Home 3-min to Okemo

4
3.0
8

Ludlow Vermont Private vacation home From $411 per night (USD)

Centrally-Located 3-BR Home 4-min to Okemo

Centrally-Located 3-BR Home 4-min to Okemo

3
3.0
7

Ludlow Vermont Private vacation home From $333 per night (USD)

5-BR Luxury Mountain Estate 5-min to Okemo

5-BR Luxury Mountain Estate 5-min to Okemo

5
4.0
12

Ludlow Vermont Private vacation home From $671 per night (USD)

Beautiful Historic 4-Season Country Estate in Okemo Valley

Beautiful Historic 4-Season Country Estate in Okemo Valley

5
5.0
10

Cavendish Vermont Agritourism From $432 per night (USD)

Ski, hike, swim or relax with family & friends in this nature lovers delight!

Ski, hike, swim or relax with family & friends in this nature lovers delight!

5
3.0
10

Reading Vermont Private vacation home From $221 per night (USD)

$OKEMO SKI IN\/OUT and WALK TO Solitude Pool\/Hottubs, 43' North & coffee!$

OKEMO SKI IN\/OUT and WALK TO Solitude Pool\/Hottubs, 43' North & coffee!

2
3.0
8

Ludlow Vermont Condo From $650 per night (USD)

$Mountainside Condo w\/ Access to Pool + Ski Shuttle$

Mountainside Condo w\/ Access to Pool + Ski Shuttle

3
2.0
8

Ludlow Vermont Condo From $291 per night (USD)

$Secluded Cabin w\/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing$

Secluded Cabin w\/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

3
3.0
8

Andover Vermont Private vacation home From $238 per night (USD)

$Comfy Condo w\/ High-Speed WiFi, Shared Pool, Wood-Burning Fireplace, and Balcony$

Comfy Condo w\/ High-Speed WiFi, Shared Pool, Wood-Burning Fireplace, and Balcony

1
1.0
6

Ludlow Vermont Condo Click For Pricing

$Lux Family Retreat @ Okemo\/Bromley. Arcade Machine$

Lux Family Retreat @ Okemo\/Bromley. Arcade Machine

4
3.0
11

Weston Vermont Private vacation home From $398 per night (USD)

Okemo Mtn Retreat < 1 Mi to Jackson Gore Base!

Okemo Mtn Retreat < 1 Mi to Jackson Gore Base!

3
4.0
9

Ludlow Vermont Private vacation home From $693 per night (USD)

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

5
4.0
14

Ludlow Vermont Chalet From $450 per night (USD)

The Clubhouse -11 BR Downtown, 7 Bath on shuttle

The Clubhouse -11 BR Downtown, 7 Bath on shuttle

11
7.0
34

Ludlow Vermont Lodge From $724 per night (USD)

$Ronnoco Farm-Charming Brownsville\/West Windsor, VT cottage$

Ronnoco Farm-Charming Brownsville\/West Windsor, VT cottage

3
1.0
6

West Windsor Vermont Cottage Click For Pricing

The Red Bridge House. 360° of lake views.

The Red Bridge House. 360° of lake views.

3
2.0
9

Ludlow Vermont Private vacation home From $420 per night (USD)

$Killington Area Escape w\/ Deck & Private Hot Tub!$

Killington Area Escape w\/ Deck & Private Hot Tub!

3
2.0
10

Stockbridge Vermont Cabin From $346 per night (USD)

$Ski on\/Ski off. Right on Sachem Trail. Okemo Trailside. 4bed\/2bath Sleeps 10.$

Ski on\/Ski off. Right on Sachem Trail. Okemo Trailside. 4bed\/2bath Sleeps 10.

4
2.0
10

Ludlow Vermont Private vacation home From $1650 per night (USD)

Beautiful Vacation Home with Spectacular Views

Beautiful Vacation Home with Spectacular Views

2
3.0
4

Hartford Vermont Private vacation home From $275 per night (USD)

Killington Region - Sleeps 19!

Killington Region - Sleeps 19!

7
6.0
19

Plymouth Vermont Private vacation home From $867 per night (USD)

Between Killington and Okemo, Close to Farm & Wilderness Camp

Between Killington and Okemo, Close to Farm & Wilderness Camp

4
2.0
8

Plymouth Vermont Private vacation home From $248 per night (USD)

Rustic lakeview cabin with fireplace, deck- near skiing

Rustic lakeview cabin with fireplace, deck- near skiing

2
2.0
10

Ludlow Vermont Private vacation home From $277 per night (USD)

Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge

Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge

4
2.0
8

Woodstock Vermont Private vacation home From $857 per night (USD)

Log Cabin home with Mt Ascutney views and pool table

Log Cabin home with Mt Ascutney views and pool table

4
4.0
14

West Windsor Vermont Cabin From $363 per night (USD)

Killington, Left Side of Duplex ,Outside Hot Tub, Charming, Cozy, Clean

Killington, Left Side of Duplex ,Outside Hot Tub, Charming, Cozy, Clean

4
2.0
10

Killington, West Bridgewater Vermont Private vacation home From $450 per night (USD)

Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations.

Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations.

1
1.0
4

Hartford Vermont Apartment From $245 per night (USD)

Mountain Top Cabin With Incredible Okemo Views And Sunsets

Mountain Top Cabin With Incredible Okemo Views And Sunsets

4
2.0
10

Ludlow Vermont Cabin From $350 per night (USD)

149 Upper Crossroad Unit B

149 Upper Crossroad Unit B

3
2.0
8

Ludlow Vermont Private vacation home From $250 per night (USD)

Village House on Shuttle Route- Great Location!

Village House on Shuttle Route- Great Location!

3
3.0
9

Ludlow Vermont Private vacation home From $750 per night (USD)

Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!

Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!

4
2.0
8

Woodstock Vermont Agritourism From $363 per night (USD)

Dog Friendly Home in S. Woodstock

Dog Friendly Home in S. Woodstock

3
3.0
7

Woodstock Vermont Private vacation home From $360 per night (USD)

Secluded and Serene - GET AWAY FROM IT ALL! Barnard, VT

Secluded and Serene - GET AWAY FROM IT ALL! Barnard, VT

2
1.0
8

South Royalton Vermont Cabin From $151 per night (USD)

PRIVATE & AFFORDABLE charming custom ranch in South Woodstock ! AC and WIFI.

PRIVATE & AFFORDABLE charming custom ranch in South Woodstock ! AC and WIFI.

4
2.0
7

Woodstock Vermont Private vacation home From $421 per night (USD)

Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside

Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside

4
4.0
10

Ludlow Vermont Condo From $1698 per night (USD)

OKEMO VACATION HOUSE, HOT TUB, CENTRAL AIR 6 Bdrm (2 K, 3 Q, 1 bunk), sleeps 14

OKEMO VACATION HOUSE, HOT TUB, CENTRAL AIR 6 Bdrm (2 K, 3 Q, 1 bunk), sleeps 14

6
5.0
14

Ludlow Vermont Private vacation home From $685 per night (USD)

Four Bedroom on 5+ Acres Close to Club with 180º Views

Four Bedroom on 5+ Acres Close to Club with 180º Views

4
3.0
9

Hartford Vermont Private vacation home From $471 per night (USD)

$Remodeled condo with free WiFi & shared W\/D - ski bus pickup across street$

Remodeled condo with free WiFi & shared W\/D - ski bus pickup across street

1
2.0
4

Ludlow Vermont Apartment From $193 per night (USD)

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

2
1.0
4

Plymouth Vermont Private vacation home From $119 per night (USD)

Charming and Chic Vacation Rental

Charming and Chic Vacation Rental

1
2.0
4

Woodstock Vermont Apartment From $234 per night (USD)

$Ski House On The Lake - 5 minutes to Okemo\n$

Ski House On The Lake - 5 minutes to Okemo\n

3
3.0
8

ludlow Vermont Private vacation home From $575 per night (USD)

Vermont Country Home

Vermont Country Home

4
2.0
8

Andover Vermont Private vacation home Click For Pricing

Relaxation Paradise

Relaxation Paradise

3
1.0
6

Rochester Vermont Private vacation home From $174 per night (USD)

Farm House located 1 mile from Okemo's Jackson Gore base lodge!

Farm House located 1 mile from Okemo's Jackson Gore base lodge!

4
2.0
8

Ludlow Vermont Private vacation home From $650 per night (USD)

Family Ski & Summer house 1.5 miles to Okemo, Close to Lakes

Family Ski & Summer house 1.5 miles to Okemo, Close to Lakes

4
3.0
11

Ludlow Vermont Private vacation home From $337 per night (USD)

TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18

TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18

6
4.0
18

Ludlow Vermont Condo From $271 per night (USD)

Meadow View- 35 Acres outside your door

Meadow View- 35 Acres outside your door

1
1.0
4

West Windsor Vermont Private vacation home From $177 per night (USD)

The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!

The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!

2
1.0
4

Cavendish Vermont Cabin From $162 per night (USD)

$Lakefront Vacation House w\/ quiet, sandy beach\/boats -$

Lakefront Vacation House w\/ quiet, sandy beach\/boats -

4
2.0
10

Plymouth Vermont Private vacation home From $324 per night (USD)

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