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Windham Holiday Rentals

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50 rentals in Windham.
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3+ Bedrooms 2+flrs of living space (1400 sq ft) near Magic, Stratton & Bromley., holiday rental in Windham

3+ Bedrooms 2+flrs of living space (1400 sq ft) near Magic, Stratton & Bromley.

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Vermont Hillside Cottage w/Great View - Pet Friendly, holiday rental in Windham

Vermont Hillside Cottage w/Great View - Pet Friendly

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Lakefront Home Nestled in the Woods on Cole Pond . Close to Stratton, holiday rental in Windham

Beautiful Lakefront Home Nestled in the Woods on Cole Pond . Close to Stratton

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Fully Renovated One-Room Schoolhouse on 22+ acres, holiday rental in Windham

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Western Mountain Lodge on River and Close to Stratton, holiday rental in Windham

Western Mountain Lodge on River and Close to Stratton

5 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
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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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Log Cabin in Beautiful Weston, VT, holiday rental in Windham

Luxury Log Cabin in Beautiful Weston, VT

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Light-Filled Octagon Getaway, wifi, close to ski areas, holiday rental in Windham

Light-Filled Octagon Getaway, wifi, close to ski areas

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful log cabin w/covered porch, fire pit, secluded - close to Stratton Mtn!, holiday rental in Windham

Beautiful log cabin w/covered porch, fire pit, secluded - close to Stratton Mtn!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Secluded, cozy and affordable!  Beautiful setting in the woods, holiday rental in Windham

Secluded, cozy and affordable! Beautiful setting in the woods

3 bedrooms
2 bathrooms
Sleeps 7
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

8 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Private Mountain Cottage

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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Family-friendly cabin with a deck, excellent home base for skiing, holiday rental in Windham

Family-friendly cabin with a deck, excellent home base for skiing

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Slopeside 2BR 2BTH Condo at Magic Mountain, holiday rental in Windham

Slopeside 2BR 2BTH Condo at Magic Mountain

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Isolated Luxury-Camp!  Pool, Private Tavern, Hot Tub, Hiking, Fire Pit, Meadow-W, holiday rental in Windham

Isolated Luxury-Camp!  Pool, Private Tavern, Hot Tub, Hiking, Fire Pit, Meadow-W

9 bedrooms
10 bathrooms
Sleeps 16
Match: Sleeps
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Available Monthly during non-ski season, holiday rental in Windham

Available Monthly during non-ski season

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Post and Beam with beautiful Okemo View-Plan a Spring Golf Get Away Weekend, holiday rental in Windham

Post and Beam with beautiful Okemo View-Plan a Spring Golf Get Away Weekend

7 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Home Sweet Grafton Home, holiday rental in Windham

Home Sweet Grafton Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Slopeside Condominium In The Heart Of Southern Vermont, holiday rental in Windham

Slopeside Condominium In The Heart Of Southern Vermont

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded log cabin on 25 acres bordering state forest with trails nearby, holiday rental in Windham

Secluded log cabin on 25 acres bordering state forest with trails nearby

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Isolated Luxury-Camp!  Pool, Hot Tub, Hiking, Fire Pit, Meadow-Woods-Pond, 5 Spa, holiday rental in Windham

Isolated Luxury-Camp!  Pool, Hot Tub, Hiking, Fire Pit, Meadow-Woods-Pond, 5 Spa

7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Vermont Ski Chalet - Fireplace, Walk to Mountain, Great for Groups, holiday rental in Windham

Vermont Ski Chalet - Fireplace, Walk to Mountain, Great for Groups

3 bedrooms
3 bathrooms
Sleeps 12
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

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax, holiday rental in Windham

Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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PERU - Rustic retreat in picturesque location near 4 ski areas -, holiday rental in Windham

PERU - Rustic retreat in picturesque location near 4 ski areas -

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Isolated Rural Inn! Private Water, Generator, 3000MG Wifi, Scenic Weston Inn Nea, holiday rental in Windham

Isolated Rural Inn! Private Water, Generator, 3000MG Wifi, Scenic Weston Inn Nea

7 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Isolated Rural Inn & Cottages! Private Water, Generator, Wifi! Scenic Weston Inn, holiday rental in Windham

Isolated Rural Inn & Cottages! Private Water, Generator, Wifi! Scenic Weston Inn

10 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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Perfect 2 Family - Stratton Mountain Ski House - 2 mi to base, holiday rental in Windham

Perfect 2 Family - Stratton Mountain Ski House - 2 mi to base

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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6 Bedroom House Located near Magic , Stratton and Okemo Mountain, holiday rental in Windham

6 Bedroom House Located near Magic , Stratton and Okemo Mountain

6 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Award-Winning Log Cabin, Top 5 in New England!, holiday rental in Windham

Award-Winning Log Cabin, Top 5 in New England!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Enjoy Every Season at this Incredible Estate with Serene Mountain Views !, holiday rental in Windham

Enjoy Every Season at this Incredible Estate with Serene Mountain Views !

8 bedrooms
5 bathrooms
Sleeps 23
Match: Sleeps
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Charming VT Farmhouse with awesome mountain views. Children welcome., holiday rental in Windham

Charming VT Farmhouse with awesome mountain views. Children welcome.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious, 1 Mile to Stratton, Separate Family Room for Kids, holiday rental in Windham

Luxurious, 1 Mile to Stratton, Separate Family Room for Kids

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Mountain Getaway, holiday rental in Windham

Cozy Mountain Getaway

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quaint 4 bedroom cabin in the woods of Vermont, holiday rental in Windham

Quaint 4 bedroom cabin in the woods of Vermont

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lovely Vermont House, holiday rental in Windham

Lovely Vermont House

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Live & Breathe VT- Village Home, Yoga Studio, Ski!, holiday rental in Windham

Live & Breathe VT- Village Home, Yoga Studio, Ski!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Hugging Bear Inn RENT ENTIRE INN, holiday rental in Windham

Hugging Bear Inn RENT ENTIRE INN

6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Newly Remodeled Townhome, holiday rental in Windham

Newly Remodeled Townhome

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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5 STAR HOME - HOT TUB SAUNA BUS TO STRATTON LIFTS, holiday rental in Windham

5 STAR HOME - HOT TUB SAUNA BUS TO STRATTON LIFTS

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historic Chester House 10-30 Mins to 5 Mountains!, holiday rental in Windham

Historic Chester House 10-30 Mins to 5 Mountains!

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Private Rustic Home, 10 Min. to Bromley Mtn!, holiday rental in Windham

Private Rustic Home, 10 Min. to Bromley Mtn!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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*NEWLY RENOVATED* Road-trippers Oasis - 3min walk to Grafton Inn & Tavern, holiday rental in Windham

*NEWLY RENOVATED* Road-trippers Oasis - 3min walk to Grafton Inn & Tavern

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Reboot & Relax while surrounded by Vermont beauty., holiday rental in Windham

Reboot & Relax while surrounded by Vermont beauty.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Luxury Mountain Home with Private Shuttle to Mountain, holiday rental in Windham

Spacious Luxury Mountain Home with Private Shuttle to Mountain

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Luxurious 'Mountainview' House-10acres, o/door Hot Tub, mins to Bromley, holiday rental in Windham

Luxurious 'Mountainview' House-10acres, o/door Hot Tub, mins to Bromley

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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10 min from Stratton! Log Cabin w/ Beautiful Views, holiday rental in Windham

10 min from Stratton! Log Cabin w/ Beautiful Views

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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NEW! Warm & Inviting Jamaica Cabin: Ski & Hike!, holiday rental in Windham

NEW! Warm & Inviting Jamaica Cabin: Ski & Hike!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog-friendly mountain cabin w/forest views & large deck - close to ski resorts!, holiday rental in Windham

Dog-friendly mountain cabin w/forest views & large deck - close to ski resorts!

1 bedroom
2 bathrooms
Sleeps 4
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

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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