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Windham Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

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5 mi
49 rentals in Windham.
The Windham Hill A-Frame - Close to 3 Ski Resorts!, vacation rental in Windham
The Windham Hill A-Frame - Close to 3 Ski Resorts!, vacation rental in Windham
The Windham Hill A-Frame - Close to 3 Ski Resorts!, vacation rental in Windham

The Windham Hill A-Frame - Close to 3 Ski Resorts!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Magic Haven 3 Bdrms 2+flrs near Magic, Stratton, Okemo & Bromley & Manchester !, vacation rental in Windham
Magic Haven 3 Bdrms 2+flrs near Magic, Stratton, Okemo & Bromley & Manchester !, vacation rental in Windham
Magic Haven 3 Bdrms 2+flrs near Magic, Stratton, Okemo & Bromley & Manchester !, vacation rental in Windham

Magic Haven 3 Bdrms 2+flrs near Magic, Stratton, Okemo & Bromley & Manchester !

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Your perfect Vermont Getaway, vacation rental in Windham
Your perfect Vermont Getaway, vacation rental in Windham
Your perfect Vermont Getaway, vacation rental in Windham

Your perfect Vermont Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Farmhouse Central to Six Vermont Ski Resorts and 5 minutes from Magic Mountain, vacation rental in Windham
Farmhouse Central to Six Vermont Ski Resorts and 5 minutes from Magic Mountain, vacation rental in Windham
Farmhouse Central to Six Vermont Ski Resorts and 5 minutes from Magic Mountain, vacation rental in Windham

Farmhouse Central to Six Vermont Ski Resorts and 5 minutes from Magic Mountain

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Brand New Luxury “Tiny” House, Immersed In Nature, vacation rental in Windham
Brand New Luxury “Tiny” House, Immersed In Nature, vacation rental in Windham
Brand New Luxury “Tiny” House, Immersed In Nature, vacation rental in Windham

Brand New Luxury “Tiny” House, Immersed In Nature

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Winter Getaway at the Octagon w/ 3 Fireplaces!, vacation rental in Windham
Winter Getaway at the Octagon w/ 3 Fireplaces!, vacation rental in Windham
Winter Getaway at the Octagon w/ 3 Fireplaces!, vacation rental in Windham

Winter Getaway at the Octagon w/ 3 Fireplaces!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Single-Level Duplex with Fast WiFi & a Full Kitchen - Close to Magic Mountain, vacation rental in Windham
Single-Level Duplex with Fast WiFi & a Full Kitchen - Close to Magic Mountain, vacation rental in Windham
Single-Level Duplex with Fast WiFi & a Full Kitchen - Close to Magic Mountain, vacation rental in Windham

Single-Level Duplex with Fast WiFi & a Full Kitchen - Close to Magic Mountain

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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1830's Recently Renovated Rustic Farmhouse, Windham Vermont, vacation rental in Windham
1830's Recently Renovated Rustic Farmhouse, Windham Vermont, vacation rental in Windham
1830's Recently Renovated Rustic Farmhouse, Windham Vermont, vacation rental in Windham

1830's Recently Renovated Rustic Farmhouse, Windham Vermont

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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| Handmade 4 Bed Log Cabin | 5 Min From Skiing |, vacation rental in Windham
| Handmade 4 Bed Log Cabin | 5 Min From Skiing |, vacation rental in Windham
| Handmade 4 Bed Log Cabin | 5 Min From Skiing |, vacation rental in Windham

| Handmade 4 Bed Log Cabin | 5 Min From Skiing |

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views., vacation rental in Windham
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views., vacation rental in Windham
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views., vacation rental in Windham

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

Rental Home
11 bedrooms
7 bathrooms
Sleeps 30
Match: Sleeps
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Vermont Ski Chalet ~ 5 Mi to Magic Mountain, vacation rental in Windham
Vermont Ski Chalet ~ 5 Mi to Magic Mountain, vacation rental in Windham
Vermont Ski Chalet ~ 5 Mi to Magic Mountain, vacation rental in Windham

Vermont Ski Chalet ~ 5 Mi to Magic Mountain

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Artistic Southern Vermont home at Windham, vacation rental in Windham
Artistic Southern Vermont home at Windham, vacation rental in Windham
Artistic Southern Vermont home at Windham, vacation rental in Windham

Artistic Southern Vermont home at Windham

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New! Cozy private ski chalet with incredible views, close to Mountains!, vacation rental in Windham
New! Cozy private ski chalet with incredible views, close to Mountains!, vacation rental in Windham
New! Cozy private ski chalet with incredible views, close to Mountains!, vacation rental in Windham

New! Cozy private ski chalet with incredible views, close to Mountains!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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The following properties within 20 miles of Windham match all your filters:
Cozy Ski-In/Ski-Out Condo on Magic Mountain, vacation rental in Windham
Cozy Ski-In/Ski-Out Condo on Magic Mountain, vacation rental in Windham
Cozy Ski-In/Ski-Out Condo on Magic Mountain, vacation rental in Windham

Cozy Ski-In/Ski-Out Condo on Magic Mountain

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stratton, Okemo, Bromley, Viking Nordic XC, Skiing!!, vacation rental in Windham
Stratton, Okemo, Bromley, Viking Nordic XC, Skiing!!, vacation rental in Windham
Stratton, Okemo, Bromley, Viking Nordic XC, Skiing!!, vacation rental in Windham

Stratton, Okemo, Bromley, Viking Nordic XC, Skiing!!

Rental Home
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Ski-In/Ski-Out Magic Mountain Condo w/ Deck!, vacation rental in Windham
Ski-In/Ski-Out Magic Mountain Condo w/ Deck!, vacation rental in Windham
Ski-In/Ski-Out Magic Mountain Condo w/ Deck!, vacation rental in Windham

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Ski Carriage Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont, vacation rental in Windham
Ski Carriage Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont, vacation rental in Windham
Ski Carriage Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont, vacation rental in Windham

Ski Carriage Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Chalet on Magic Mountain, vacation rental in Windham
Cozy Chalet on Magic Mountain, vacation rental in Windham
Cozy Chalet on Magic Mountain, vacation rental in Windham

Cozy Chalet on Magic Mountain

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Apartment at Viking Nordic Center; sleeps 8. Rent with The Farmhouse to sleep 18, vacation rental in Windham
Apartment at Viking Nordic Center; sleeps 8. Rent with The Farmhouse to sleep 18, vacation rental in Windham
Apartment at Viking Nordic Center; sleeps 8. Rent with The Farmhouse to sleep 18, vacation rental in Windham

Apartment at Viking Nordic Center; sleeps 8. Rent with The Farmhouse to sleep 18

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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South Londonderry Home, Walk to Magic Mtn Ski Area, vacation rental in Windham
South Londonderry Home, Walk to Magic Mtn Ski Area, vacation rental in Windham
South Londonderry Home, Walk to Magic Mtn Ski Area, vacation rental in Windham

South Londonderry Home, Walk to Magic Mtn Ski Area

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Cozy Chalet on Magic Mountain, vacation rental in Windham
Cozy Chalet on Magic Mountain, vacation rental in Windham
Cozy Chalet on Magic Mountain, vacation rental in Windham

Cozy Chalet on Magic Mountain

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Minutes to a Magical Apres Ski!, vacation rental in Windham
Minutes to a Magical Apres Ski!, vacation rental in Windham
Minutes to a Magical Apres Ski!, vacation rental in Windham

Minutes to a Magical Apres Ski!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Leaf Peep Magic VT Country Home, vacation rental in Windham
Leaf Peep Magic VT Country Home, vacation rental in Windham
Leaf Peep Magic VT Country Home, vacation rental in Windham

Leaf Peep Magic VT Country Home

Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stay where you can Ski the Fab Four, vacation rental in Windham
Stay where you can Ski the Fab Four, vacation rental in Windham
Stay where you can Ski the Fab Four, vacation rental in Windham

Stay where you can Ski the Fab Four

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Farmhouse in South Londonderry - great amenities and really close to ski resorts, vacation rental in Windham
Farmhouse in South Londonderry - great amenities and really close to ski resorts, vacation rental in Windham
Farmhouse in South Londonderry - great amenities and really close to ski resorts, vacation rental in Windham

Farmhouse in South Londonderry - great amenities and really close to ski resorts

Rental Home
5 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Insanely romantic treehouse perched next to a stream and rolling hills., vacation rental in Windham
Insanely romantic treehouse perched next to a stream and rolling hills., vacation rental in Windham
Insanely romantic treehouse perched next to a stream and rolling hills., vacation rental in Windham

Insanely romantic treehouse perched next to a stream and rolling hills.

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!, vacation rental in Windham
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!, vacation rental in Windham
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!, vacation rental in Windham

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SEPTEMBER SPECIAL! 15% Off mid week bookings at the Secluded Trout Cabin, vacation rental in Windham
SEPTEMBER SPECIAL! 15% Off mid week bookings at the Secluded Trout Cabin, vacation rental in Windham
SEPTEMBER SPECIAL! 15% Off mid week bookings at the Secluded Trout Cabin, vacation rental in Windham

SEPTEMBER SPECIAL! 15% Off mid week bookings at the Secluded Trout Cabin

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Maple Retreat | 20 Min to Stratton w/ Sauna, vacation rental in Windham
The Maple Retreat | 20 Min to Stratton w/ Sauna, vacation rental in Windham
The Maple Retreat | 20 Min to Stratton w/ Sauna, vacation rental in Windham

The Maple Retreat | 20 Min to Stratton w/ Sauna

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Magic Mountain Trailside Condo - Ski In / Ski Out, vacation rental in Windham
Magic Mountain Trailside Condo - Ski In / Ski Out, vacation rental in Windham
Magic Mountain Trailside Condo - Ski In / Ski Out, vacation rental in Windham

Magic Mountain Trailside Condo - Ski In / Ski Out

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Baby Barn, Architect Owner, vacation rental in Windham
Baby Barn, Architect Owner, vacation rental in Windham
Baby Barn, Architect Owner, vacation rental in Windham

Baby Barn, Architect Owner

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Historic Farmhouse, Quaint Vermont Experience, vacation rental in Windham
Historic Farmhouse, Quaint Vermont Experience, vacation rental in Windham
Historic Farmhouse, Quaint Vermont Experience, vacation rental in Windham

Historic Farmhouse, Quaint Vermont Experience

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Cozy 2-bedroom cabin in enjoyable Londonderry with AC with hot tub and sauna, vacation rental in Windham
Cozy 2-bedroom cabin in enjoyable Londonderry with AC with hot tub and sauna, vacation rental in Windham
Cozy 2-bedroom cabin in enjoyable Londonderry with AC with hot tub and sauna, vacation rental in Windham

Cozy 2-bedroom cabin in enjoyable Londonderry with AC with hot tub and sauna

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful country cabin with hot tub and outdoor shower in Londonderry, vacation rental in Windham
Beautiful country cabin with hot tub and outdoor shower in Londonderry, vacation rental in Windham
Beautiful country cabin with hot tub and outdoor shower in Londonderry, vacation rental in Windham

Beautiful country cabin with hot tub and outdoor shower in Londonderry

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ski-in/ski-out, dog-friendly condo with 2 decks & fireplace - steps to lifts, vacation rental in Windham
Ski-in/ski-out, dog-friendly condo with 2 decks & fireplace - steps to lifts, vacation rental in Windham
Ski-in/ski-out, dog-friendly condo with 2 decks & fireplace - steps to lifts, vacation rental in Windham

Ski-in/ski-out, dog-friendly condo with 2 decks & fireplace - steps to lifts

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lake, Ski, Hiking, Shopping Vermont Getaway! Just Steps Away From Everything!, vacation rental in Windham
Lake, Ski, Hiking, Shopping Vermont Getaway! Just Steps Away From Everything!, vacation rental in Windham
Lake, Ski, Hiking, Shopping Vermont Getaway! Just Steps Away From Everything!, vacation rental in Windham

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

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tranquil Mountain Chalet- fireplace, deck, sauna, hiking trails, close to skiing, vacation rental in Windham
Tranquil Mountain Chalet- fireplace, deck, sauna, hiking trails, close to skiing, vacation rental in Windham
Tranquil Mountain Chalet- fireplace, deck, sauna, hiking trails, close to skiing, vacation rental in Windham

Tranquil Mountain Chalet- fireplace, deck, sauna, hiking trails, close to skiing

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Green Mt Getaway: Close to Magic, Stratton, Bromley, Okemo Parks, vacation rental in Windham
Green Mt Getaway: Close to Magic, Stratton, Bromley, Okemo Parks, vacation rental in Windham
Green Mt Getaway: Close to Magic, Stratton, Bromley, Okemo Parks, vacation rental in Windham

Green Mt Getaway: Close to Magic, Stratton, Bromley, Okemo Parks

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby, vacation rental in Windham
Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby, vacation rental in Windham
Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby, vacation rental in Windham

Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely home on 500 acres w/private lake near great skiing - for all-season fun, vacation rental in Windham
Lovely home on 500 acres w/private lake near great skiing - for all-season fun, vacation rental in Windham
Lovely home on 500 acres w/private lake near great skiing - for all-season fun, vacation rental in Windham

Lovely home on 500 acres w/private lake near great skiing - for all-season fun

Rental Home
8 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Cozy Chalet in Vermont's Golden Triangle, vacation rental in Windham
Cozy Chalet in Vermont's Golden Triangle, vacation rental in Windham
Cozy Chalet in Vermont's Golden Triangle, vacation rental in Windham

Cozy Chalet in Vermont's Golden Triangle

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Spacious mountainside retreat - Fireplaces, New kitchen, Great for groups, vacation rental in Windham
Spacious mountainside retreat - Fireplaces, New kitchen, Great for groups, vacation rental in Windham
Spacious mountainside retreat - Fireplaces, New kitchen, Great for groups, vacation rental in Windham

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Charming and Spacious Vermont farmhouse WINTER RENTAL JAN-MARCH AVAILABLE, vacation rental in Windham
Charming and Spacious Vermont farmhouse WINTER RENTAL JAN-MARCH AVAILABLE, vacation rental in Windham
Charming and Spacious Vermont farmhouse WINTER RENTAL JAN-MARCH AVAILABLE, vacation rental in Windham

Charming and Spacious Vermont farmhouse WINTER RENTAL JAN-MARCH AVAILABLE

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Londonderry Chalet w/ Deck, Fire Pit & Views!, vacation rental in Windham
Londonderry Chalet w/ Deck, Fire Pit & Views!, vacation rental in Windham
Londonderry Chalet w/ Deck, Fire Pit & Views!, vacation rental in Windham

Londonderry Chalet w/ Deck, Fire Pit & Views!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Mtn View & Hot Tub - Magic View in Scenic Vermont, vacation rental in Windham
Mtn View & Hot Tub - Magic View in Scenic Vermont, vacation rental in Windham
Mtn View & Hot Tub - Magic View in Scenic Vermont, vacation rental in Windham

Mtn View & Hot Tub - Magic View in Scenic Vermont

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Spacious Family getaway near Magic Mountain, VT, vacation rental in Windham
Spacious Family getaway near Magic Mountain, VT, vacation rental in Windham
Spacious Family getaway near Magic Mountain, VT, vacation rental in Windham

Spacious Family getaway near Magic Mountain, VT

Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Mountain chalet, vacation rental in Windham
Mountain chalet, vacation rental in Windham
Mountain chalet, vacation rental in Windham

Mountain chalet

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym, vacation rental in Windham
Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym, vacation rental in Windham
Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym, vacation rental in Windham

Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym

Rental Home
8 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
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Cozy Condo w/ Magic Mountain Ski-In Access!, vacation rental in Windham
Cozy Condo w/ Magic Mountain Ski-In Access!, vacation rental in Windham
Cozy Condo w/ Magic Mountain Ski-In Access!, vacation rental in Windham

Cozy Condo w/ Magic Mountain Ski-In Access!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Showing results 1-49 of 49
Frequently Asked Questions about Windham