Windham Private Home Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Private Holiday Homes in Windham

Perfect Family Vacation Home in the Mountains

2.0 star property
Perfect Family Vacation Home in the Mountains

Amazing Hiking Cozy Home Close to Mountns Fireplace

2.0 star property
Amazing Hiking Cozy Home Close to Mountns Fireplace

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

2.0 star property
Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

Hunter Mountain Ski House - Tesla Charger

2.0 star property
Hunter Mountain Ski House - Tesla Charger

The Guest House

3.0 star property
The Guest House

Twin Cabin I - Hot Tub Firepit Hiking Retreat

2.0 star property
Twin Cabin I - Hot Tub Firepit Hiking Retreat

Renovated Grand Woodstock Barn

2.0 star property
Renovated Grand Woodstock Barn

Cortland by Avantstay Charming Heritage Estate w Private Lake Pool

2.0 star property
Cortland by Avantstay Charming Heritage Estate w Private Lake Pool

Shakespeare on the Hudson by Avantstay Two Home Buyout on the Hudson River! 22 Bedrooms!

3.5 star property
Shakespeare on the Hudson by Avantstay Two Home Buyout on the Hudson River! 22 Bedrooms!

West Settlement Ranch by Avantstay Hudson Valley Escape Firepit Patio Yard

2.0 star property
West Settlement Ranch by Avantstay Hudson Valley Escape Firepit Patio Yard

Game Farm Villa by Avantstay 10bdr Private Pond Spa Pool Family-friendly

2.0 star property
Game Farm Villa by Avantstay 10bdr Private Pond Spa Pool Family-friendly

Billingswood by Boutiq

2.0 star property
Billingswood by Boutiq

Windham Mountain Marvel

2.0 star property
Windham Mountain Marvel

River Lodge by Avantstay 11 BR Historic Estate w/ Pool & Views of Hudson!

3.5 star property
River Lodge by Avantstay 11 BR Historic Estate w/ Pool & Views of Hudson!

Wonderful in Windham

3.5 star property
Wonderful in Windham

Modern Catskill Hideaway

3.5 star property
Modern Catskill Hideaway

Hudson Valley Mountain Hideaway

3.5 star property
Hudson Valley Mountain Hideaway

Woodstock Stone Lodge

3.5 star property
Woodstock Stone Lodge

Plum Guide - Soul Of The Willow

3.5 star property
Plum Guide - Soul Of The Willow

River House by Avantstay Historic Secluded Estate on the Hudson River w Pool Sleeps 24

2.0 star property
River House by Avantstay Historic Secluded Estate on the Hudson River w Pool Sleeps 24
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in