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Holiday Rentals in Proctorsville

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51 rentals in Proctorsville.
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The Stoma Ranch Outdoor Hot tub, holiday rental in Proctorsville
The Stoma Ranch Outdoor Hot tub, holiday rental in Proctorsville
The Stoma Ranch Outdoor Hot tub, holiday rental in Proctorsville

The Stoma Ranch Outdoor Hot tub

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Chester Farmhouse on 100 Acres, 15 Min to Okemo!, holiday rental in Proctorsville
Chester Farmhouse on 100 Acres, 15 Min to Okemo!, holiday rental in Proctorsville
Chester Farmhouse on 100 Acres, 15 Min to Okemo!, holiday rental in Proctorsville

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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NEW LISTING! Charming & spacious, two-story townhome - close to Okemo!, holiday rental in Proctorsville
NEW LISTING! Charming & spacious, two-story townhome - close to Okemo!, holiday rental in Proctorsville
NEW LISTING! Charming & spacious, two-story townhome - close to Okemo!, holiday rental in Proctorsville

NEW LISTING! Charming & spacious, two-story townhome - close to Okemo!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain, holiday rental in Proctorsville
Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain, holiday rental in Proctorsville
Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain, holiday rental in Proctorsville

Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo, holiday rental in Proctorsville
Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo, holiday rental in Proctorsville
Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo, holiday rental in Proctorsville

Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo, holiday rental in Proctorsville
Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo, holiday rental in Proctorsville
Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo, holiday rental in Proctorsville

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Holiday Rental House
8 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Village Ski Apartment, holiday rental in Proctorsville
Village Ski Apartment, holiday rental in Proctorsville
Village Ski Apartment, holiday rental in Proctorsville

Village Ski Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Log cabin in the Smokeshire Valley area of Chester., holiday rental in Proctorsville
Log cabin in the Smokeshire Valley area of Chester., holiday rental in Proctorsville
Log cabin in the Smokeshire Valley area of Chester., holiday rental in Proctorsville

Log cabin in the Smokeshire Valley area of Chester.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK, holiday rental in Proctorsville
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK, holiday rental in Proctorsville
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK, holiday rental in Proctorsville

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Traveling with kids? Check this secluded & updated 3-bedroom home close to Okemo, holiday rental in Proctorsville
Traveling with kids? Check this secluded & updated 3-bedroom home close to Okemo, holiday rental in Proctorsville
Traveling with kids? Check this secluded & updated 3-bedroom home close to Okemo, holiday rental in Proctorsville

Traveling with kids? Check this secluded & updated 3-bedroom home close to Okemo

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Save time - get the best Proctorsville rentals sent straight to your email!

Charming & Affordable Home with Spectacular Mtn Views!!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious chalet, 6 mins to Okemo, 4 bed, 4 bath,, holiday rental in Proctorsville
Spacious chalet, 6 mins to Okemo, 4 bed, 4 bath,, holiday rental in Proctorsville
Spacious chalet, 6 mins to Okemo, 4 bed, 4 bath,, holiday rental in Proctorsville

Spacious chalet, 6 mins to Okemo, 4 bed, 4 bath,

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Resort Home with Pool * 'The Castle Hill' Spa & Tennis

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Okemo Ski House,1 mile to Okemo Mt, on Shuttle Route, Walking Distance to town, holiday rental in Proctorsville
Okemo Ski House,1 mile to Okemo Mt, on Shuttle Route, Walking Distance to town, holiday rental in Proctorsville
Okemo Ski House,1 mile to Okemo Mt, on Shuttle Route, Walking Distance to town, holiday rental in Proctorsville

Okemo Ski House,1 mile to Okemo Mt, on Shuttle Route, Walking Distance to town

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Family & dog friendly house w/ deck & game room. Minutes to town, Okemo & lakes, holiday rental in Proctorsville
Family & dog friendly house w/ deck & game room. Minutes to town, Okemo & lakes, holiday rental in Proctorsville
Family & dog friendly house w/ deck & game room. Minutes to town, Okemo & lakes, holiday rental in Proctorsville

Family & dog friendly house w/ deck & game room. Minutes to town, Okemo & lakes

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
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Private Ludlow Village Home - 2 Miles from Okemo Base W/Access To Okemo Shuttle, holiday rental in Proctorsville
Private Ludlow Village Home - 2 Miles from Okemo Base W/Access To Okemo Shuttle, holiday rental in Proctorsville
Private Ludlow Village Home - 2 Miles from Okemo Base W/Access To Okemo Shuttle, holiday rental in Proctorsville

Private Ludlow Village Home - 2 Miles from Okemo Base W/Access To Okemo Shuttle

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Bright, open home w/ wrap-around deck & mountain views - 2 miles to skiing!, holiday rental in Proctorsville
Bright, open home w/ wrap-around deck & mountain views - 2 miles to skiing!, holiday rental in Proctorsville
Bright, open home w/ wrap-around deck & mountain views - 2 miles to skiing!, holiday rental in Proctorsville

Bright, open home w/ wrap-around deck & mountain views - 2 miles to skiing!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Skiing or Getting Away from it All? This House is what you need., holiday rental in Proctorsville
Skiing or Getting Away from it All? This House is what you need., holiday rental in Proctorsville
Skiing or Getting Away from it All? This House is what you need., holiday rental in Proctorsville

Skiing or Getting Away from it All? This House is what you need.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Charming condo with WiFi, pool access, & private washer/dryer - close to skiing, holiday rental in Proctorsville
Charming condo with WiFi, pool access, & private washer/dryer - close to skiing, holiday rental in Proctorsville
Charming condo with WiFi, pool access, & private washer/dryer - close to skiing, holiday rental in Proctorsville

Charming condo with WiFi, pool access, & private washer/dryer - close to skiing

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Last min summer deals still available 3000 sq ft Sanitized home Hot tub / Okemo, holiday rental in Proctorsville
Last min summer deals still available 3000 sq ft Sanitized home Hot tub / Okemo, holiday rental in Proctorsville
Last min summer deals still available 3000 sq ft Sanitized home Hot tub / Okemo, holiday rental in Proctorsville

Last min summer deals still available 3000 sq ft Sanitized home Hot tub / Okemo

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort, holiday rental in Proctorsville
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort, holiday rental in Proctorsville
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort, holiday rental in Proctorsville

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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OKEMO Mountain-Incredible view of the slopes!, holiday rental in Proctorsville
OKEMO Mountain-Incredible view of the slopes!, holiday rental in Proctorsville
OKEMO Mountain-Incredible view of the slopes!, holiday rental in Proctorsville

OKEMO Mountain-Incredible view of the slopes!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
More info
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Oma Kieferts  Kottage, holiday rental in Proctorsville
Oma Kieferts  Kottage, holiday rental in Proctorsville
Oma Kieferts  Kottage, holiday rental in Proctorsville

Oma Kieferts Kottage

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Affordable Single Family 1+ Mile to Mountain on shuttle to Okemo, holiday rental in Proctorsville
Affordable Single Family 1+ Mile to Mountain on shuttle to Okemo, holiday rental in Proctorsville
Affordable Single Family 1+ Mile to Mountain on shuttle to Okemo, holiday rental in Proctorsville

Affordable Single Family 1+ Mile to Mountain on shuttle to Okemo

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
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Charming Farmhouse with great views of Okemo., holiday rental in Proctorsville
Charming Farmhouse with great views of Okemo., holiday rental in Proctorsville
Charming Farmhouse with great views of Okemo., holiday rental in Proctorsville

Charming Farmhouse with great views of Okemo.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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VT Retreat - TV + Hot Tub + Pool Table, holiday rental in Proctorsville
VT Retreat - TV + Hot Tub + Pool Table, holiday rental in Proctorsville
VT Retreat - TV + Hot Tub + Pool Table, holiday rental in Proctorsville

VT Retreat - TV + Hot Tub + Pool Table

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Family-friendly home w/ game room, firepit & great location near skiing & town!, holiday rental in Proctorsville
Family-friendly home w/ game room, firepit & great location near skiing & town!, holiday rental in Proctorsville
Family-friendly home w/ game room, firepit & great location near skiing & town!, holiday rental in Proctorsville

Family-friendly home w/ game room, firepit & great location near skiing & town!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Okemo Mountain Family Fun House with a private tube, holiday rental in Proctorsville
Okemo Mountain Family Fun House with a private tube, holiday rental in Proctorsville
Okemo Mountain Family Fun House with a private tube, holiday rental in Proctorsville

Okemo Mountain Family Fun House with a private tube

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
More info
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Ludlow Village Home with Pool Table - Walk to Restaurants, holiday rental in Proctorsville
Ludlow Village Home with Pool Table - Walk to Restaurants, holiday rental in Proctorsville
Ludlow Village Home with Pool Table - Walk to Restaurants, holiday rental in Proctorsville

Ludlow Village Home with Pool Table - Walk to Restaurants

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Renovated condo, walk to dining, on bus route to ski slopes, holiday rental in Proctorsville
Renovated condo, walk to dining, on bus route to ski slopes, holiday rental in Proctorsville
Renovated condo, walk to dining, on bus route to ski slopes, holiday rental in Proctorsville

Renovated condo, walk to dining, on bus route to ski slopes

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
More info
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Cozy Tiny Home on Black River - Walk to Town!, holiday rental in Proctorsville
Cozy Tiny Home on Black River - Walk to Town!, holiday rental in Proctorsville
Cozy Tiny Home on Black River - Walk to Town!, holiday rental in Proctorsville

Cozy Tiny Home on Black River - Walk to Town!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Family Ski & Summer  house 1.5 miles to Okemo, Close to Lakes, holiday rental in Proctorsville
Family Ski & Summer  house 1.5 miles to Okemo, Close to Lakes, holiday rental in Proctorsville
Family Ski & Summer  house 1.5 miles to Okemo, Close to Lakes, holiday rental in Proctorsville

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

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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A distinctive family retreat for an epic ski vacation!, holiday rental in Proctorsville
A distinctive family retreat for an epic ski vacation!, holiday rental in Proctorsville
A distinctive family retreat for an epic ski vacation!, holiday rental in Proctorsville

A distinctive family retreat for an epic ski vacation!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Vermont charm 8 minutes to Okemo Mountain!, holiday rental in Proctorsville
Vermont charm 8 minutes to Okemo Mountain!, holiday rental in Proctorsville
Vermont charm 8 minutes to Okemo Mountain!, holiday rental in Proctorsville

Vermont charm 8 minutes to Okemo Mountain!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Okemo Mountain - VT Barns, Unit 2, holiday rental in Proctorsville
Okemo Mountain - VT Barns, Unit 2, holiday rental in Proctorsville
Okemo Mountain - VT Barns, Unit 2, holiday rental in Proctorsville

Okemo Mountain - VT Barns, Unit 2

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Corona? My Sharona! Enjoy the Ski Season Safely In Your Own Home Away From Home!, holiday rental in Proctorsville
Corona? My Sharona! Enjoy the Ski Season Safely In Your Own Home Away From Home!, holiday rental in Proctorsville
Corona? My Sharona! Enjoy the Ski Season Safely In Your Own Home Away From Home!, holiday rental in Proctorsville

Corona? My Sharona! Enjoy the Ski Season Safely In Your Own Home Away From Home!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo, holiday rental in Proctorsville
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo, holiday rental in Proctorsville
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo, holiday rental in Proctorsville

Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

Holiday Rental House
7 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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Village Home with 15 acre backyard on the river, holiday rental in Proctorsville
Village Home with 15 acre backyard on the river, holiday rental in Proctorsville
Village Home with 15 acre backyard on the river, holiday rental in Proctorsville

Village Home with 15 acre backyard on the river

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Gone Ski Inn near Okemo, holiday rental in Proctorsville
Gone Ski Inn near Okemo, holiday rental in Proctorsville
Gone Ski Inn near Okemo, holiday rental in Proctorsville

Gone Ski Inn near Okemo

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
More info
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Home located 5 minutes to Okemo Mountain, Lake Rescue, and nearby Fox Run Golf., holiday rental in Proctorsville
Home located 5 minutes to Okemo Mountain, Lake Rescue, and nearby Fox Run Golf., holiday rental in Proctorsville
Home located 5 minutes to Okemo Mountain, Lake Rescue, and nearby Fox Run Golf., holiday rental in Proctorsville

Home located 5 minutes to Okemo Mountain, Lake Rescue, and nearby Fox Run Golf.

Holiday Rental House
7 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Great house for 2 families, views of Okemo, newly renovated, minutes to mountain, holiday rental in Proctorsville
Great house for 2 families, views of Okemo, newly renovated, minutes to mountain, holiday rental in Proctorsville
Great house for 2 families, views of Okemo, newly renovated, minutes to mountain, holiday rental in Proctorsville

Great house for 2 families, views of Okemo, newly renovated, minutes to mountain

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Summer fun in VT! Enjoy all that Ludlow, the Lake Regions & Okemo Mtn offers!, holiday rental in Proctorsville
Summer fun in VT! Enjoy all that Ludlow, the Lake Regions & Okemo Mtn offers!, holiday rental in Proctorsville
Summer fun in VT! Enjoy all that Ludlow, the Lake Regions & Okemo Mtn offers!, holiday rental in Proctorsville

Summer fun in VT! Enjoy all that Ludlow, the Lake Regions & Okemo Mtn offers!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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In Town Location!!!Okemo Ski House in Town. 7 Guests 5 Beds 2 Baths, holiday rental in Proctorsville
In Town Location!!!Okemo Ski House in Town. 7 Guests 5 Beds 2 Baths, holiday rental in Proctorsville
In Town Location!!!Okemo Ski House in Town. 7 Guests 5 Beds 2 Baths, holiday rental in Proctorsville

In Town Location!!!Okemo Ski House in Town. 7 Guests 5 Beds 2 Baths

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
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Cottage On Main, holiday rental in Proctorsville
Cottage On Main, holiday rental in Proctorsville
Cottage On Main, holiday rental in Proctorsville

Cottage On Main

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cozy Chalet Cabin near Okemo Mountain, holiday rental in Proctorsville
Cozy Chalet Cabin near Okemo Mountain, holiday rental in Proctorsville
Cozy Chalet Cabin near Okemo Mountain, holiday rental in Proctorsville

Cozy Chalet Cabin near Okemo Mountain

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
More info
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Sunny, new centrally located condo!, holiday rental in Proctorsville
Sunny, new centrally located condo!, holiday rental in Proctorsville
Sunny, new centrally located condo!, holiday rental in Proctorsville

Sunny, new centrally located condo!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Welcoming Condo Featuring Wood-Burning Fireplace, WiFi, & Shared Seasonal Pool, holiday rental in Proctorsville
Welcoming Condo Featuring Wood-Burning Fireplace, WiFi, & Shared Seasonal Pool, holiday rental in Proctorsville
Welcoming Condo Featuring Wood-Burning Fireplace, WiFi, & Shared Seasonal Pool, holiday rental in Proctorsville

Welcoming Condo Featuring Wood-Burning Fireplace, WiFi, & Shared Seasonal Pool

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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2-Story Riverfront home with washer/dryer, partial A/C, river views & wifi, holiday rental in Proctorsville
2-Story Riverfront home with washer/dryer, partial A/C, river views & wifi, holiday rental in Proctorsville
2-Story Riverfront home with washer/dryer, partial A/C, river views & wifi, holiday rental in Proctorsville

2-Story Riverfront home with washer/dryer, partial A/C, river views & wifi

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
More info
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2-Story riverfront home + studio with washer/dryer, river views, & free WiFi, holiday rental in Proctorsville
2-Story riverfront home + studio with washer/dryer, river views, & free WiFi, holiday rental in Proctorsville
2-Story riverfront home + studio with washer/dryer, river views, & free WiFi, holiday rental in Proctorsville

2-Story riverfront home + studio with washer/dryer, river views, & free WiFi

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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A Stylish Ski Retreat near Okemo Mountain Resort and heart of Ludlow Village, holiday rental in Proctorsville
A Stylish Ski Retreat near Okemo Mountain Resort and heart of Ludlow Village, holiday rental in Proctorsville
A Stylish Ski Retreat near Okemo Mountain Resort and heart of Ludlow Village, holiday rental in Proctorsville

A Stylish Ski Retreat near Okemo Mountain Resort and heart of Ludlow Village

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Frequently Asked Questions about Proctorsville