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  • CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

    Windham, United States

    4.71

    Cabin

    Sleeps: 6
  • Custom-built Catskills retreat

    Windham, United States

    4.95

    Entire place

    Sleeps: 4
  • Sunny, private and peaceful apartment!

    Windham, United States

    4.95

    Guest Suite

    Sleeps: 4
  • One Level 2 bedroom suite on private cul-de-sac

    Windham, United States

    4.66

    Entire place

    Sleeps: 4
  • Cottage on Black Brook Preserve

    Windham, United States

    4.95

    Guesthouse

    Sleeps: 2
  • Small house, Windham, NY

    Windham, United States

    4.80

    Entire place

    Sleeps: 4
  • The Chickadee House on Pettingill Pond

    Windham, United States

    4.80

    Tiny Home

    Sleeps: 2
  • Private Hilltop Cabin, Lakes and Trails Abound..

    Windham, United States

    4.57

    Cabin

    Sleeps: 8
  • Extreme leisure minutes from action and adventure

    Windham, United States

    4.71

    Entire place

    Sleeps: 8
  • Charming Carriage House in Greater Portland

    Windham, United States

    4.95

    Entire place

    Sleeps: 7
  • Alpine Chalet on Spectacular Property

    Windham, United States

    4.95

    Guesthouse

    Sleeps: 4
  • Secluded 55 acre Windham Getaway w/ 6BRs + Hot Tub

    Windham, United States

    4.85

    Entire place

    Sleeps: 16
  • 5 Min to Skiing | Hot Tub | Fire Pit | Games | Bar

    Windham, United States

    4.95

    Cabin

    Sleeps: 12
  • Windham private heated indoor pool up to 12 ppl

    Windham, United States

    4.85

    Entire place

    Sleeps: 12
  • Private riverside retreat

    Windham, United States

    4.90

    Tiny Home

    Sleeps: 2
  • Millers Private Studio on Highland Lake

    Windham, United States

    4.66

    Guest Suite

    Sleeps: 4
  • Beautiful Windham Chalet 2 minutes to the Mountain

    Windham, United States

    4.85

    Chalet

    Sleeps: 11
  • The Roost - lovely one bedroom efficiency unit

    Windham, United States

    4.95

    Entire place

    Sleeps: 2
  • “Spectacular Mountain Views with Tranquility”

    Windham, United States

    4.95

    Entire place

    Sleeps: 10
  • Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing

    Windham, United States

    4.90

    Chalet

    Sleeps: 12
  • Fully Updated and Centrally Located

    Windham, United States

    4.90

    Townhouse

    Sleeps: 8
  • Waterfront Gem walkable to Restaurants!

    Windham, United States

    4.80

    Entire place

    Sleeps: 4
  • The Windham Loft

    Windham, United States

    4.85

    Loft

    Sleeps: 5
  • Luxury Log Home with Ski Windham Views

    Windham, United States

    4.85

    Entire place

    Sleeps: 16
  • Cozy, peaceful-3Br (5 beds)2.5 Bath townhouse

    Windham, United States

    5.00

    Townhouse

    Sleeps: 8
  • Casa Magda - Designer Home near Hiking + Swimming

    Windham, United States

    4.80

    Cabin

    Sleeps: 8
  • Robyn's Nest; A Maine getaway

    Windham, United States

    4.95

    Guesthouse

    Sleeps: 3
  • Waterfront Escape Minutes from Portland

    Windham, United States

    5.00

    Guest Suite

    Sleeps: 2
  • Luxury Lodge with Slope Views - 5 Min to Skiing

    Windham, United States

    4.85

    Chalet

    Sleeps: 12
  • Modern forest retreat with hot tub and sauna

    Windham, United States

    4.95

    Cabin

    Sleeps: 8
  • Little Bear’s Cottage Great location, cozy&cute

    Windham, United States

    4.85

    Guesthouse

    Sleeps: 4
  • Luxurious, 4500 sq foot home in center of Windham

    Windham, United States

    4.95

    Entire place

    Sleeps: 10
  • Charming Home Lg/Mod Kit Hot Tub on Stream FirePit

    Windham, United States

    4.75

    Entire place

    Sleeps: 6

  • Windham, United States

    4.95

    Farm Stay

    Sleeps: 14
  • Big Pond, Big Fish- Fire Pit & Pvt Beach + Lake

    Windham, United States

    4.57

    Cabin

    Sleeps: 4
  • NEW Modern Cabin | 8 Mins From Skiing | Hot Tub

    Windham, United States

    5.00

    Cabin

    Sleeps: 12
  • Sebago Sunrise Yurt

    Windham, United States

    4.95

    Yurt

    Sleeps: 4
  • Lothbrok - the

    Windham, United States

    4.75

    Townhouse

    Sleeps: 4
  • Windham Farmhouse Escape

    Windham, United States

    4.85

    Entire place

    Sleeps: 12
  • Sebago Lakehouse: Hot Tub and Private Beach Access

    Windham, United States

    5.00

    Vacation Home

    Sleeps: 6
  • Cozy Cabin Condo by the Mountain, 5mins to skiing!

    Windham, United States

    4.66

    Guest Suite

    Sleeps: 4
  • Cozy Cottage on Highland Lake

    Windham, United States

    4.71

    Cottage

    Sleeps: 6
  • Romantic waterfront cottage for two in Maine

    Windham, United States

    5.00

    Cottage

    Sleeps: 2
  • Big Red Retreat 3 min to Windham Mountain & Golf!

    Windham, United States

    4.75

    Entire place

    Sleeps: 15
  • Windham Luxury Pet Friendly Retreat

    Windham, United States

    4.71

    Entire place

    Sleeps: 11
  • 1 minute to skiing,hot tub firepit cornhole & pond

    Windham, United States

    4.66

    Townhouse

    Sleeps: 4
  • Secluded Fernwood Chalet, Hot Tub, & Sauna House

    Windham, United States

    4.80

    Chalet

    Sleeps: 6
  • The Creekside Cabin - 5 mins to Windham Mt!

    Windham, United States

    4.90

    Cabin

    Sleeps: 5
  • Cozy English Cottage

    Windham, United States

    4.66

    Cottage

    Sleeps: 4
  • Luxury with pool, tennis courts, hiking and biking

    Windham, United States

    4.90

    Townhouse

    Sleeps: 7
  • The PondeRosa cottage at Cobbett's pond

    Windham, United States

    4.75

    Cottage

    Sleeps: 4
  • Windham Mill House | Walk to town | 2 Mins to Ski

    Windham, United States

    4.90

    Entire place

    Sleeps: 6
  • Year-Round Relaxing Mountain Escape

    Windham, United States

    5.00

    Entire place

    Sleeps: 12
  • 4 Seasons near Windham Mtn and Hunter Mtn

    Windham, United States

    4.90

    Entire place

    Sleeps: 10
  • Golf and Ski Retreat with hot tub and game room

    Windham, United States

    5.00

    Entire place

    Sleeps: 8
  • Blue Spruce Chalet — Hot Tub, Pet Friendly

    Windham, United States

    5.00

    Chalet

    Sleeps: 8
  • Quaint Cottage near Cobbetts Pond

    Windham, United States

    4.90

    Cottage

    Sleeps: 4
  • Artistic Southern Vt Countryside Home at Windham

    Windham, United States

    4.75

    Entire place

    Sleeps: 8
  • Red Lift Cabin - Fall escapades - pool, hiking

    Windham, United States

    4.85

    Townhouse

    Sleeps: 8
  • Cozy 2 bedroom apartment with private entrance

    Windham, United States

    5.00

    Guest Suite

    Sleeps: 4
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