Windham Private Holiday Homes
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United States of America
Private Holiday Homes
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Featured Private Holiday Homes in Windham

Enjoy al fresco dining on the deck, surrounded by a serene forest and snowy landscape.

Welcome to a serene retreat with a deck and stone pathway leading to the front door.

Kitchen features a central island, refrigerator, microwave, and stove, with a hanging light fixture above.

Enjoy meals and meetings in this spacious dining area with a large table and comfortable seating for six.

Perfect Family Vacation Home in the Mountains

2.0 star property

Windham

Perfect Family Vacation Home in the Mountains

Enjoy cooking in this well-equipped kitchen with a stainless steel sink and ample countertop space.

Relax in a warm and inviting space with a large window offering a view into the adjacent living area.

Cozy living room with a fireplace, comfortable sofa, and a wooden coffee table.

Enjoy cooking in this kitchen with a stove, oven, and refrigerator, and dine in the adjacent dining area with a table and chairs.

Amazing Hiking Cozy Home Close to Mountns Fireplace

2.0 star property

Prattsville

Amazing Hiking Cozy Home Close to Mountns Fireplace

Kitchen features a refrigerator, dishwasher, microwave, oven, and sink, with ample counter space for meal preparation.

Escape to a serene forest setting, where a snow-covered picnic table invites relaxation and outdoor activities.

Relax in the spacious living room with a large sofa, coffee table, and flat-screen TV.

Enjoy meals in the kitchen with an oven and dining table, or relax on the sofa in the adjacent living area.

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

2.0 star property

Maplecrest

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

Enjoy al fresco dining on the deck with a grill and glass table.

Situated in a secluded forest, this cozy retreat features a front door and a small window.

Relax in a spacious living area with a high ceiling and exposed beams, featuring a stone fireplace and comfortable seating.

Enjoy meals in this dining area with a long table, flanked by benches, and a unique chandelier.

Hunter Mountain Ski House - Tesla Charger

2.0 star property

Hunter

Hunter Mountain Ski House - Tesla Charger

Relax in the living room with a sofa, fireplace, and dining area, leading to an outdoor patio with a deck and picnic table.

Relax on the covered deck with lounge chairs and a picnic table amidst lush surroundings.

Relax in this spacious living room with a high ceiling, featuring a large sofa, a smaller sofa, and a stone fireplace.

Relax in this stylish room featuring a comfortable bed, flat-screen TV, and cozy seating area.

The Guest House

3.0 star property

Margaretville

The Guest House

Stroll up to the inviting porch, surrounded by lush trees and shrubs.

Cozy cabin with a charming front porch and gabled roof, surrounded by lush greenery.

Enjoy the serene outdoor space with a swimming pool, hot tub, and covered patio area.

Modern kitchen with central island, sink, stove, and microwave, adjacent to a dining area with a round table and chairs.

Twin Cabin I - Hot Tub Firepit Hiking Retreat

2.0 star property

Jewett

Twin Cabin I - Hot Tub Firepit Hiking Retreat

Cozy seating area with a piano, fireplace, and large windows offering views of the surrounding landscape.

Rustic cabin with a central entrance, flanked by two windows, and a small porch area.

Relax in a cozy living room with a large window offering a view of the surrounding landscape, a comfortable sofa, and a wooden coffee table.

Relax in this inviting bedroom with a large bed, nightstand, and bookshelf.

Renovated Grand Woodstock Barn

2.0 star property

Bearsville

Renovated Grand Woodstock Barn

Relax by the pool on a furnished deck surrounded by lush trees and shrubs.

Relax in a warm and inviting space with a bench and a round table.

Cozy retreat with a large bed, ceiling fan, and a comfortable chair by the window.

Enjoy meals in this elegant dining area with a large table, comfortable bench, and beautiful views.

Cortland by Avantstay Charming Heritage Estate w Private Lake Pool

2.0 star property

Saugerties

Cortland by Avantstay Charming Heritage Estate w Private Lake Pool

Enjoy cooking in this well-equipped kitchen with a large island, sink, and high ceilings.

Enjoy a serene retreat with a spacious balcony overlooking a forested area, perfect for taking in the views.

Relax in a spacious room with high ceilings and large windows, surrounded by artwork and a mix of traditional and modern elements.

Enjoy meals in this stylish dining area with a long table, chandelier, and framed artwork.

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

3.5 star property

Catskill

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

Enjoy al fresco dining on the covered porch with a beautiful garden view.

Kitchen features white cabinetry, a stainless steel range hood, and a central island with a countertop.

Enjoy cooking in this well-appointed kitchen with a central island and ample counter space.

Enjoy a warm and inviting living space with a fireplace, comfortable seating, and a large window offering a view of the outdoors.

West Settlement Ranch by Avantstay Hudson Valley Escape Firepit Patio Yard

2.0 star property

Ashland

West Settlement Ranch by Avantstay Hudson Valley Escape Firepit Patio Yard

Relax in the outdoor space with a hot tub and grill.

Moored boats and a picturesque bridge span the serene lake, surrounded by lush greenery.

Relax in this serene bedroom with a large bed, desk, and comfortable seating areas.

Relax in this inviting living room with a comfortable sofa set, armchairs, and a round coffee table.

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

2.0 star property

Palenville

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

Enjoy a relaxing moment on the deck with a sofa and two chairs, overlooking a serene body of water.

Relax in this spacious room with a sofa, chair, and potted plant, surrounded by large windows and a high ceiling.

Relax in this serene bedroom with a large bed, ceiling fan, and comfortable seating area.

Enjoy cooking in this well-lit kitchen with a refrigerator, microwave, and oven.

Billingswood by Boutiq

2.0 star property

Athens

Billingswood by Boutiq

Windham Mountain Marvel

2.0 star property

Windham

Windham Mountain Marvel

Cozy living space with a high ceiling, staircase, and comfortable seating area.

Relax in this inviting living room with a comfortable sofa, fireplace, and large window offering a view of the outdoors.

Enjoy a refreshing swim in the outdoor pool surrounded by a deck area and a white picket fence.

Enjoy a warm breakfast in this inviting dining area, complete with a table set for a meal, comfortable chairs, and a selection of breakfast items.

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

3.5 star property

Catskill

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

Wonderful in Windham

3.5 star property

Windham

Wonderful in Windham

Modern Catskill Hideaway

3.5 star property

Palenville

Modern Catskill Hideaway

Hudson Valley Mountain Hideaway

3.5 star property

Gilboa

Hudson Valley Mountain Hideaway

Woodstock Stone Lodge

3.5 star property

Woodstock

Woodstock Stone Lodge

Plum Guide - Soul Of The Willow

3.5 star property

Willow

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

Catskill

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.

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Find out more about Windham

Windham Private Holiday Homes information

Number of reviews
Accommodation	30 Private Holiday Homes
Lowest Price
Highest Price

Recent Reviews in Windham

5/5 Excellent

"The staff is absolutely incredible and the property has everything you need. We were taken care of the entire time we were there. The grounds are lovely. We would definitely stay here again."

A verified traveller stayed at Wylder Hotel Windham

Posted 16 hours ago

Wylder Hotel Windham

5/5 Excellent

"Fantastic "

A verified traveller stayed at Hunter Lodge, a Bluebird by Lark

Posted 2 days ago

Hunter Lodge, a Bluebird by Lark

5/5 Excellent

"Great view!"

A verified traveller stayed at The Haüs Windham

Posted 3 days ago

The Haüs Windham

5/5 Excellent

"good place to stay at"

A verified traveller stayed at Hotel Vienna

Posted 5 days ago

Hotel Vienna

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

5/5 Excellent

"Did not like truck noise on highway."

A verified traveller stayed at Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Posted 6 days ago

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

5/5 Excellent

"room was ok for the price- just needed one night"

A verified traveller stayed at Howard Johnson by Wyndham Saugerties

Posted 7 days ago

Howard Johnson by Wyndham Saugerties

Kaatskill Mountain Club at Hunter Mountain

5/5 Excellent

"I really like the location and property amenities. "

A verified traveller stayed at Kaatskill Mountain Club at Hunter Mountain

Posted 7 days ago

Kaatskill Mountain Club at Hunter Mountain

Albergo Allegria Hotel & Breakfast Restaurant

5/5 Excellent

Wonderful stay!

"We enjoyed our stay, the room was very comfortable, the bathroom very clean and convenient to town."

A verified traveller stayed at Albergo Allegria Hotel & Breakfast Restaurant

Posted 8 days ago

Albergo Allegria Hotel & Breakfast Restaurant

5/5 Excellent

"Great and unique property with all the conveniences that one expects."

A verified traveller from New York stayed at The Roxbury at Stratton Falls

Posted 8 days ago

The Roxbury at Stratton Falls

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Windham Private Home Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Featured Private Holiday Homes in Windham

Perfect Family Vacation Home in the Mountains

Perfect Family Vacation Home in the Mountains

Amazing Hiking Cozy Home Close to Mountns Fireplace

Amazing Hiking Cozy Home Close to Mountns Fireplace

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

Hunter Mountain Ski House - Tesla Charger

Hunter Mountain Ski House - Tesla Charger

The Guest House

The Guest House

Twin Cabin I - Hot Tub Firepit Hiking Retreat

Twin Cabin I - Hot Tub Firepit Hiking Retreat

Renovated Grand Woodstock Barn

Renovated Grand Woodstock Barn

Cortland by Avantstay Charming Heritage Estate w Private Lake Pool

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!

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

West Settlement Ranch by Avantstay Hudson Valley Escape Firepit Patio Yard

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

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

Billingswood by Boutiq

Billingswood by Boutiq

Windham Mountain Marvel

Windham Mountain Marvel

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

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

Wonderful in Windham

Wonderful in Windham

Modern Catskill Hideaway

Modern Catskill Hideaway

Hudson Valley Mountain Hideaway

Hudson Valley Mountain Hideaway

Woodstock Stone Lodge

Woodstock Stone Lodge

Plum Guide - Soul Of The Willow

Plum Guide - Soul Of The Willow

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

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

Find out more about Windham

Find out more about Windham

Windham Private Holiday Homes information

Recent Reviews in Windham

Recent Reviews in Windham

Wylder Hotel Windham

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Top Private Holiday Homes destinations

More Accommodation Types in Windham

All Accommodation Types

Be inspired: Top Private Holiday Homes destinations in 2025

More ways to book

Expedia's Latest Trends