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Windham Holiday Apartments

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50 rentals in Windham.
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Poetic Mountaintop Log Cabin nestled in the woods, holiday rental in Windham
Poetic Mountaintop Log Cabin nestled in the woods, holiday rental in Windham
Poetic Mountaintop Log Cabin nestled in the woods, holiday rental in Windham

Poetic Mountaintop Log Cabin nestled in the woods

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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5-Bedroom Winter Wonderland with 3 fireplaces

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Private and Secluded Escape in Rural Vermont! Mountain Views, Hot Tub., holiday rental in Windham
Private and Secluded Escape in Rural Vermont! Mountain Views, Hot Tub., holiday rental in Windham
Private and Secluded Escape in Rural Vermont! Mountain Views, Hot Tub., holiday rental in Windham

Private and Secluded Escape in Rural Vermont! Mountain Views, Hot Tub.

Holiday Rental House
8 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
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Magic Haven 3+ Bdrms 2+flrs (1400 sq ft) near Magic, Stratton, Bromley, Okemo ., holiday rental in Windham
Magic Haven 3+ Bdrms 2+flrs (1400 sq ft) near Magic, Stratton, Bromley, Okemo ., holiday rental in Windham
Magic Haven 3+ Bdrms 2+flrs (1400 sq ft) near Magic, Stratton, Bromley, Okemo ., holiday rental in Windham

Magic Haven 3+ Bdrms 2+flrs (1400 sq ft) near Magic, Stratton, Bromley, Okemo .

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Artistic Southern Vermont Home at Windham, holiday rental in Windham
Artistic Southern Vermont Home at Windham, holiday rental in Windham
Artistic Southern Vermont Home at Windham, holiday rental in Windham

Artistic Southern Vermont Home at Windham

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Modern Farmhouse minutes to Skiing & Golf, holiday rental in Windham
Modern Farmhouse minutes to Skiing & Golf, holiday rental in Windham
Modern Farmhouse minutes to Skiing & Golf, holiday rental in Windham

Modern Farmhouse minutes to Skiing & Golf

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Escape in Rural Vermont!  Pool, Hot Tub, Mountain Views., holiday rental in Windham
Secluded Escape in Rural Vermont!  Pool, Hot Tub, Mountain Views., holiday rental in Windham
Secluded Escape in Rural Vermont!  Pool, Hot Tub, Mountain Views., holiday rental in Windham

Secluded Escape in Rural Vermont! Pool, Hot Tub, Mountain Views.

Holiday Rental House
8 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
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1830's Recently Renovated Rustic Farmhouse, Windham Vermont, holiday rental in Windham
1830's Recently Renovated Rustic Farmhouse, Windham Vermont, holiday rental in Windham
1830's Recently Renovated Rustic Farmhouse, Windham Vermont, holiday rental in Windham

1830's Recently Renovated Rustic Farmhouse, Windham Vermont

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton, holiday rental in Windham
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton, holiday rental in Windham
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton, holiday rental in Windham

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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4 bedroom Vermont Farmhouse centrally located near ski resorts and lakes, holiday rental in Windham
4 bedroom Vermont Farmhouse centrally located near ski resorts and lakes, holiday rental in Windham
4 bedroom Vermont Farmhouse centrally located near ski resorts and lakes, holiday rental in Windham

4 bedroom Vermont Farmhouse centrally located near ski resorts and lakes

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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70 Acres, 9 Bedrooms, Hiking Trails, Fly Fishing, Country Retreat - Londonderry, holiday rental in Windham
70 Acres, 9 Bedrooms, Hiking Trails, Fly Fishing, Country Retreat - Londonderry, holiday rental in Windham
70 Acres, 9 Bedrooms, Hiking Trails, Fly Fishing, Country Retreat - Londonderry, holiday rental in Windham

70 Acres, 9 Bedrooms, Hiking Trails, Fly Fishing, Country Retreat - Londonderry

Holiday Rental House
9 bedrooms
9 bathrooms
Sleeps 21
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Fall Foliage and Winter Skiing!!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun, holiday rental in Windham
8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun, holiday rental in Windham
8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun, holiday rental in Windham

8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun

Holiday Rental House
8 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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RED BRICK RETREAT - 8br 6ba Hot Tub Sauna Home Gym, holiday rental in Windham
RED BRICK RETREAT - 8br 6ba Hot Tub Sauna Home Gym, holiday rental in Windham
RED BRICK RETREAT - 8br 6ba Hot Tub Sauna Home Gym, holiday rental in Windham

RED BRICK RETREAT - 8br 6ba Hot Tub Sauna Home Gym

Holiday Rental House
8 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Slopeside 2BR 2BTH Condo at Magic Mountain, holiday rental in Windham
Slopeside 2BR 2BTH Condo at Magic Mountain, holiday rental in Windham
Slopeside 2BR 2BTH Condo at Magic Mountain, holiday rental in Windham

Slopeside 2BR 2BTH Condo at Magic Mountain

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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VT home with a PRIVATE INDOOR POOL - Stratton, Magic, Bromley, Okemo SLEEPS 12, holiday rental in Windham
VT home with a PRIVATE INDOOR POOL - Stratton, Magic, Bromley, Okemo SLEEPS 12, holiday rental in Windham
VT home with a PRIVATE INDOOR POOL - Stratton, Magic, Bromley, Okemo SLEEPS 12, holiday rental in Windham

VT home with a PRIVATE INDOOR POOL - Stratton, Magic, Bromley, Okemo SLEEPS 12

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Log cabin on 25 acres bordering state forest with trails nearby., holiday rental in Windham
Log cabin on 25 acres bordering state forest with trails nearby., holiday rental in Windham
Log cabin on 25 acres bordering state forest with trails nearby., holiday rental in Windham

Log cabin on 25 acres bordering state forest with trails nearby.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious mountainside retreat - Fireplaces, New kitchen, Great for groups, holiday rental in Windham
Spacious mountainside retreat - Fireplaces, New kitchen, Great for groups, holiday rental in Windham
Spacious mountainside retreat - Fireplaces, New kitchen, Great for groups, holiday rental in Windham

Spacious mountainside retreat - Fireplaces, New kitchen, Great for groups

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Apartment at Viking Nordic Center; sleeps 8; rent with Farmhouse to sleep 18, holiday rental in Windham
Apartment at Viking Nordic Center; sleeps 8; rent with Farmhouse to sleep 18, holiday rental in Windham
Apartment at Viking Nordic Center; sleeps 8; rent with Farmhouse to sleep 18, holiday rental in Windham

Apartment at Viking Nordic Center; sleeps 8; rent with Farmhouse to sleep 18

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quality Vermont Home in the heart of Ski Country, holiday rental in Windham
Quality Vermont Home in the heart of Ski Country, holiday rental in Windham
Quality Vermont Home in the heart of Ski Country, holiday rental in Windham

Quality Vermont Home in the heart of Ski Country

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Vermont getaway house within 10 minutes of three ski resorts, holiday rental in Windham
Vermont getaway house within 10 minutes of three ski resorts, holiday rental in Windham
Vermont getaway house within 10 minutes of three ski resorts, holiday rental in Windham

Vermont getaway house within 10 minutes of three ski resorts

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vermont Country Home, holiday rental in Windham
Vermont Country Home, holiday rental in Windham
Vermont Country Home, holiday rental in Windham

Vermont Country Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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SPECIAL! Perfect Family Getaway! Book 4 nights get 5th half off!, holiday rental in Windham
SPECIAL! Perfect Family Getaway! Book 4 nights get 5th half off!, holiday rental in Windham
SPECIAL! Perfect Family Getaway! Book 4 nights get 5th half off!, holiday rental in Windham

SPECIAL! Perfect Family Getaway! Book 4 nights get 5th half off!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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New listing! Very accommodating home on 170+ acres w/ multiple living spaces, holiday rental in Windham
New listing! Very accommodating home on 170+ acres w/ multiple living spaces, holiday rental in Windham
New listing! Very accommodating home on 170+ acres w/ multiple living spaces, holiday rental in Windham

New listing! Very accommodating home on 170+ acres w/ multiple living spaces

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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4 Bedroom 100 Yr Old Bungalow, holiday rental in Windham
4 Bedroom 100 Yr Old Bungalow, holiday rental in Windham
4 Bedroom 100 Yr Old Bungalow, holiday rental in Windham

4 Bedroom 100 Yr Old Bungalow

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Reboot & Relax while surrounded by Vermont beauty., holiday rental in Windham
Reboot & Relax while surrounded by Vermont beauty., holiday rental in Windham
Reboot & Relax while surrounded by Vermont beauty., holiday rental in Windham

Reboot & Relax while surrounded by Vermont beauty.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Trout House (private pond, fire pit & hot tub) *summer discount!*, holiday rental in Windham
Trout House (private pond, fire pit & hot tub) *summer discount!*, holiday rental in Windham
Trout House (private pond, fire pit & hot tub) *summer discount!*, holiday rental in Windham

Trout House (private pond, fire pit & hot tub) *summer discount!*

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Contemporary Ski Chalet Minutes to Hiking Dining Parks, holiday rental in Windham
Contemporary Ski Chalet Minutes to Hiking Dining Parks, holiday rental in Windham
Contemporary Ski Chalet Minutes to Hiking Dining Parks, holiday rental in Windham

Contemporary Ski Chalet Minutes to Hiking Dining Parks

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Dog-friendly vacation home with fast WiFi & washer/dryer - near ski areas, holiday rental in Windham
Dog-friendly vacation home with fast WiFi & washer/dryer - near ski areas, holiday rental in Windham
Dog-friendly vacation home with fast WiFi & washer/dryer - near ski areas, holiday rental in Windham

Dog-friendly vacation home with fast WiFi & washer/dryer - near ski areas

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historic Farm House,12+ acres Ski, Shop, Relax., holiday rental in Windham
Historic Farm House,12+ acres Ski, Shop, Relax., holiday rental in Windham
Historic Farm House,12+ acres Ski, Shop, Relax., holiday rental in Windham

Historic Farm House,12+ acres Ski, Shop, Relax.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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In the Ski Zone. 3 minutes past Magic Mtn. Private snowmobile trails., holiday rental in Windham
In the Ski Zone. 3 minutes past Magic Mtn. Private snowmobile trails., holiday rental in Windham
In the Ski Zone. 3 minutes past Magic Mtn. Private snowmobile trails., holiday rental in Windham

In the Ski Zone. 3 minutes past Magic Mtn. Private snowmobile trails.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Chalet on Magic Mountain, holiday rental in Windham
Cozy Chalet on Magic Mountain, holiday rental in Windham
Cozy Chalet on Magic Mountain, holiday rental in Windham

Cozy Chalet on Magic Mountain

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Grand Londonderry Home w/ Ski Mountain Views!, holiday rental in Windham
NEW! Grand Londonderry Home w/ Ski Mountain Views!, holiday rental in Windham
NEW! Grand Londonderry Home w/ Ski Mountain Views!, holiday rental in Windham

NEW! Grand Londonderry Home w/ Ski Mountain Views!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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NEW! Ski-In/Ski-Out Magic Mountain Condo w/ Deck!, holiday rental in Windham
NEW! Ski-In/Ski-Out Magic Mountain Condo w/ Deck!, holiday rental in Windham
NEW! Ski-In/Ski-Out Magic Mountain Condo w/ Deck!, holiday rental in Windham

NEW! Ski-In/Ski-Out Magic Mountain Condo w/ Deck!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tiny house overlooking a stream, holiday rental in Windham
Tiny house overlooking a stream, holiday rental in Windham
Tiny house overlooking a stream, holiday rental in Windham

Tiny house overlooking a stream

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Vermont Chalet with Spacious Deck Near Skiing, holiday rental in Windham
Vermont Chalet with Spacious Deck Near Skiing, holiday rental in Windham
Vermont Chalet with Spacious Deck Near Skiing, holiday rental in Windham

Vermont Chalet with Spacious Deck Near Skiing

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Trailside Condo at Magic Mountain - Ski In/Ski Out, holiday rental in Windham
Trailside Condo at Magic Mountain - Ski In/Ski Out, holiday rental in Windham
Trailside Condo at Magic Mountain - Ski In/Ski Out, holiday rental in Windham

Trailside Condo at Magic Mountain - Ski In/Ski Out

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Spectacular view takes your breath away, holiday rental in Windham
Spectacular view takes your breath away, holiday rental in Windham
Spectacular view takes your breath away, holiday rental in Windham

Spectacular view takes your breath away

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Majestic estate on Magic Mtn! Ski in also minutes to Stratton, Bromley, Okemo!, holiday rental in Windham
Majestic estate on Magic Mtn! Ski in also minutes to Stratton, Bromley, Okemo!, holiday rental in Windham
Majestic estate on Magic Mtn! Ski in also minutes to Stratton, Bromley, Okemo!, holiday rental in Windham

Majestic estate on Magic Mtn! Ski in also minutes to Stratton, Bromley, Okemo!

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Mountain chalet, holiday rental in Windham
Mountain chalet, holiday rental in Windham
Mountain chalet, holiday rental in Windham

Mountain chalet

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious + Sunny Contemporary Mountain Chalet Close to Hiking, Parks, & Fun, holiday rental in Windham
Spacious + Sunny Contemporary Mountain Chalet Close to Hiking, Parks, & Fun, holiday rental in Windham
Spacious + Sunny Contemporary Mountain Chalet Close to Hiking, Parks, & Fun, holiday rental in Windham

Spacious + Sunny Contemporary Mountain Chalet Close to Hiking, Parks, & Fun

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Vermont Lake, Fishing & Ski Carriage Home, holiday rental in Windham
Vermont Lake, Fishing & Ski Carriage Home, holiday rental in Windham
Vermont Lake, Fishing & Ski Carriage Home, holiday rental in Windham

Vermont Lake, Fishing & Ski Carriage Home

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Magic View in Scenic Vermont - Mtn View & Hot Tub, holiday rental in Windham
Magic View in Scenic Vermont - Mtn View & Hot Tub, holiday rental in Windham
Magic View in Scenic Vermont - Mtn View & Hot Tub, holiday rental in Windham

Magic View in Scenic Vermont - Mtn View & Hot Tub

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Wild Blossom Farmhouse- a lovely Vermont Getaway, holiday rental in Windham
Wild Blossom Farmhouse- a lovely Vermont Getaway, holiday rental in Windham
Wild Blossom Farmhouse- a lovely Vermont Getaway, holiday rental in Windham

Wild Blossom Farmhouse- a lovely Vermont Getaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake, Ski, Hiking, Shopping Vermont Getaway! Just Steps Away From Everything!, holiday rental in Windham
Lake, Ski, Hiking, Shopping Vermont Getaway! Just Steps Away From Everything!, holiday rental in Windham
Lake, Ski, Hiking, Shopping Vermont Getaway! Just Steps Away From Everything!, holiday rental in Windham

Lake, Ski, Hiking, Shopping Vermont Getaway! Just Steps Away From Everything!

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic.1820 Brick Federal home in Grafton..., holiday rental in Windham
Historic.1820 Brick Federal home in Grafton..., holiday rental in Windham
Historic.1820 Brick Federal home in Grafton..., holiday rental in Windham

Historic.1820 Brick Federal home in Grafton...

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Trailside Condo on Magic Mountain!, holiday rental in Windham
Cozy Trailside Condo on Magic Mountain!, holiday rental in Windham
Cozy Trailside Condo on Magic Mountain!, holiday rental in Windham

Cozy Trailside Condo on Magic Mountain!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Four Bedroom with a Hot Tub in Londonderry VT, holiday rental in Windham
Cozy Four Bedroom with a Hot Tub in Londonderry VT, holiday rental in Windham
Cozy Four Bedroom with a Hot Tub in Londonderry VT, holiday rental in Windham

Cozy Four Bedroom with a Hot Tub in Londonderry VT

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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70's Style Ski House on Magic Mountain, holiday rental in Windham
70's Style Ski House on Magic Mountain, holiday rental in Windham
70's Style Ski House on Magic Mountain, holiday rental in Windham

70's Style Ski House on Magic Mountain

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Londonderry Lodge with Hot Tub and Porch!, holiday rental in Windham
Londonderry Lodge with Hot Tub and Porch!, holiday rental in Windham
Londonderry Lodge with Hot Tub and Porch!, holiday rental in Windham

Londonderry Lodge with Hot Tub and Porch!

Holiday Rental House
8 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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