
House vacation rentals in Windham
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Top-rated house rentals in Windham
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Popular amenities for Windham house rentals
House rentals with a hot tub

A Cozy’s Woodstock Getaway Home
This space is so lovely, the hot tub worked perfectly and provided many cozy nights outside. The plants are BEAUTIFULLY tender and bring a loving atmosphere to the space. the linen sheets were so wonderful at the end of the day. we made it up the hill in a Honda insight, but if it were a tiny bit icy I don't think we would have been able to make it. definitely use 4wd if you have it. the hosts were very responsive. if the noise is too much in the bedroom at night (critters, rain,etc.) be sure to use the fan they provide, it helped us a lot :) the kitchen was a delight to use. sharp knives. big, metal surfaces. nice gas stove. big fridge.

Secluded Artist's Retreat with Hot tub
We had an amazing stay! The setting was absolutely beautiful, with stunning views and a peaceful atmosphere. The space was impeccably clean, which made our stay even more enjoyable. One of the highlights was the hot tub – it was the perfect way to unwind after a day of exploring. The host was incredibly responsive and saved us with a last-minute booking, which we are so grateful for. We couldn’t have asked for a better experience. Highly recommend!

2 BR , Fireplace & Hot Tub @ heart of Woodstock
We had a wonderful time at Mirav’s place in Woodstock. Made great use of the hot tub and the fireplace. We absolutely plan on returning soon!

Rhinebeck Home with an amazing outdoor space+H/tub
Michael and Enrique were excellent hosts, and left me and my girlfriends ice cream in the freezer to enjoy! They responded quickly when we had any questions. The view from the hottub looking out onto the woods is beautiful and the hottub was just what we needed to relax. A beautiful, cozy getaway, and so close to Rhinebeck!

Mountaintop Lookout with Hot Tub under the Stars
We had a great time at Natalia’s place! The hot tub and fireplace were perfection on a chilly Spring weekend.

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!
Beautiful home with amazing views. The house was very clean and spacious, the views were amazing. Susanna was very responsive and gave clear instructions. We had a very relaxing weekend and enjoyed very much staying at the house. We would love to come back.

Tranquil Chalet with Mountain Views
The best airbnb ever! We stayed at Taylor's place and it was simply the best experience we've ever had in a Airbnb. I wish I could give it more stars. The place is absolutely amazing, beautiful, clean, beautifully decorated, with everything that we needed. Check in easy, communication with her is easy and fast. The place simply delivers all that we could hope for. Me and family loved and we can recommend to everyone.

Catskills home with game room, hot tub, fire pit
We had a wonderful family stay at this beautiful Catskills retreat! The house sits right above the creek with peaceful mountain views, and it's even more charming in person. Catherine was a thoughtful and responsive host from start to finish, everything from early check-in to questions during our stay was handled smoothly. We especially enjoyed the hot tub, outdoor fire pit, and the well-equipped game room that kept everyone entertained. The grill worked great and made our BBQ dinner extra fun. The location is also perfect, quiet and scenic, yet close to town for essentials and only a short drive to nearby mountains and trails. Highly recommended for anyone looking for a peaceful getaway with both comfort and convenience. Thanks again for hosting us, Catherine!
House rentals with free parking

Pied-A-Terre | City of Hudson Entire Apartment
A wonderful host with a wonderful home. We enjoyed our stay so much that we are already planning another trip back. Highly Recommend!

Hudson New York Grey Victorian
This house was perfect for our girls’ weekend in Hudson! It was spacious, clean, and had so much character. The location was great—just a short 5-minute drive to Warren Street. We didn’t walk due to the cold weather but it was definitely close and convenient. Would definitely stay here again!

Welcome to Malden Manor, in a prime location!
Lovely place in Saugerties, close to lots of great hiking and restaurants.

Catskill Getaway!
Great place to stay and super close to the mountain. We were able to walk back and forth. Place looked just like the photos too!

Catskill Lumber House "Blue" - In Catskill Village
truly wonderful and considerate hosts! absolutely a wonderful stay and will 100% be back next time we are in town!

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI
I could not be happier with my stay! my group and I loved the ammenady options. The house was so spacious so no one felt cramped. The house was clean and well cared for! The neighbors aren't too close so there is plenty of privacy. The beds where sooo comfortable. If you do alot of computer work like me. This place is even wonderful for that too as it has many places to "set up shop" where you wont be bothered by others in your group. My only complaint was that I had to leave so soon. I am looking forward to returning.

The Mushroom Palace (Hot Tub, Sauna & Cold Plunge)
Loved the laid back, chill and eclectic vibe of the space. Great place to have a low-key stay with family or friends. The fire pit and hot tub were awesome. Very comfortable beds and living space. Kyle was very friendly and proactive and checked in on us via message. He even dropped off more towels for us. Overall, a really fun place to stay. One of our favorites we’ve stayed at so far!

Marion Manor gorgeous countryside estate w/ views
Impeccable lodging, comfortable,warm and inviting with many amenities that most ARBB don’t offer. Excellent host, a beautiful, quiet place to stay!
House rentals with a pool

Perfect Family Retreat•Pool•Volleyball•Firepit
We stayed as a family of 4, including a 1 year old and 3.5 year old. The place was extremely comfortable and had everything we would need for our stay. The kids enjoyed the playroom and kids room with lot of toys and books. Kitchen was fully stocked with plates, utensils, cooking ware, and a high chair. Place could easily accommodate more people, very clean, comfy beds. Property manager was very responsive. Short drive to downtown area. Lastly, great outdoor area, we’d love to plan a trip there when warmer as well!

Lux Woodstock Pool/ Pvt/Fireplaces /4 mins 2 town
Yanna's house exceeded all expectations. Immaculate throughout the spacious layout offered plenty of room for two families with children. My 10yo son said the bed was the most comfortable bed he ever slept in. Master bedrooms far enough apart so adults can have some privacy. Large kitchen with dining table perfect to cook and hang out. We skied at Belleayre both days (easy drive on 28) and less than 10 min from Woodstock if you want to go out. Also very close to a large grocery store. Would love to stay there again!

Spacious Staycation near HITS & the Hudson
My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

Beaver | Pool, Firepit, Secluded, 10 acres
We had an absolutely wonderful stay at Hava’s Airbnb! From the moment we booked, Hava was an incredible host—warm, welcoming, and unbelievably reachable. She responded to every question we had almost instantly, whether it was about check-in details or local recommendations, making the entire experience seamless and stress-free. The place itself was spotless, cozy, and exactly as described, with thoughtful touches that made us feel right at home. Hava’s communication stood out—she checked in to ensure everything was perfect without ever being intrusive. Her suggestions for nearby spots were spot-on, and it’s clear she genuinely cares about her guests’ comfort. We couldn’t have asked for a better host, and we’d love to stay here again. Highly recommend Hava to anyone looking for a fantastic Airbnb experience!

Little owl Japanese teahouse: pool and tennis
Quiet, peaceful, so cozy. Perfect setting if you need to hibernate a bit.

MODERN FARMHOUSE in the WOODS
We had a terrific stay. The house was exactly as advertised.

Hudson River views with pool and hot tub
The house is amazing, and the host was responsive! The location is beautiful and quiet, perfect spot for a getaway. The only advice I would give is to arrange transportation ahead of time. We relied on Uber/Lfyt, and while we ended up being able to make it work, drivers often weren’t willing to drive all the way out there and we were nearly stranded and had to adjust our plans to make sure we had a ride. But if you have a car or rental, this is the perfect spot! Only 20 minute drive from downtown Kingston, but feels very remote and cozy.

Woodstock Romantic Mountain Studio w/ Pool
We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼
Quick stats about house rentals in Windham
Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ514 before taxes and fees
Total number of reviews
2.5K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
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- Belleayre Mountain Ski Center
- Windham Mountain
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Albany Center Gallery
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Taconic State Park
- Glimmerglass State Park
- Zoom Flume
- Opus 40
- John Boyd Thacher State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Naumkeag
- Thaddeus Hait Farm
- Plattekill Mountain
- Peebles Island State Park
- Pineridge Cross Country Ski Area
- Huck Finn’s Playland, Albany
- Hancock Shaker Village
- Berkshire Botanical Garden