House vacation rentals in Windham

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Popular amenities for Windham house rentals

House rentals with a pool

Guest favorite
An aerial view captures the lush green landscape surrounding the property, highlighting a swim pond at the center, framed by natural stones. Scenic mountains rise in the background, offering a serene backdrop, while trees provide shade around the area. Hanging swing chairs are visible nearby.
Home in Saugerties
4.88 out of 5 average rating, 132 reviews

Shaggerties - fun cozy catskill mountain getaway

OhadRating, 5 stars2 weeks ago
Awesome property for a weekend getaway from the city. Sonny made this place into a fun playground - the pond is amazing, the hot tub, sauna, and back deck felt like a spa, and we enjoyed the fire pit and taking a short hike to the creek. The house itself is simple but has everything you need and we even managed to order Uber eats once from Kingston. The area is great, and we enjoyed the villages and a nice hike in the area. We will definitely come back.
Guest favorite
A stock tank plunge pool is surrounded by a wooden deck and gravel, featuring a pink flamingo float. A lounge chair rests nearby, inviting relaxation in the natural setting of greenery.
Home in Hudson
4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars2 weeks ago
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!
Guest favorite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck
4.89 out of 5 average rating, 141 reviews

4Br Mountain Brook House on 130 acres w/ trails

DanielaRating, 5 stars2 weeks ago
Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!
Guest favorite
A serene heated saltwater pool is framed by lush greenery, reflecting the sky above. A rustic wooden edge provides a natural transition between the pool and the surrounding landscape, which includes a prominent tree adding to the tranquil ambiance.
Home in Woodstock
4.92 out of 5 average rating, 244 reviews

Little owl Japanese teahouse: pool is OPEN

JaneRating, 5 stars1 week ago
My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.
Top guest favorite
A spacious deck features two comfortable chairs and a round table at its center, offering a clear view of the expansive Catskill Mountain landscape. Lush greenery and rolling hills stretch into the distance under a bright blue sky.
Home in Stamford
4.98 out of 5 average rating, 113 reviews

Hawk View

ZacharyRating, 5 stars2 weeks ago
The house is really gorgeous. Everything was very new/modern, clean, and comfortable. We enjoyed cooking meals in the kitchen overlooking the stunning view out the back. The hot tub and fire put were nice amenities to enjoy. The BBQ seemed to not be working, but other than that, no complaints. Location wise, the property is located in the northwest Catskills, near Stamford, NY, and convenient to many hiking spots in the area as well as nearby towns. The property itself its up on a hill, in what felt like a secluded and private spot, which made it feel like a real getaway and retreat. In sum, recommend this Airbnb for the nice amenities, modern touches, and amazing view.
Guest favorite
Home in Saugerties
5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars2 weeks ago
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***
Guest favorite
A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.
Home in Woodstock
4.98 out of 5 average rating, 146 reviews

Woodstock Historic Artist Estate- The Museum House

EmilyRating, 5 stars2 weeks ago
We had the best weekend at the house with our two young children and dog. We loved the house, we loved exploring the property and close by water. We couldn't be closer to town. I can't wait to go back again!
Guest favorite
A scenic aerial view showcases an outdoor pool surrounded by greenery, with mountain vistas in the background. Lounge chairs line the poolside, inviting relaxation. The property features a blend of manicured gardens and natural landscaping, creating a peaceful environment.
Home in Woodstock
4.91 out of 5 average rating, 201 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars8 months ago
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 👍🏼

Weekly house rentals

Top guest favorite
An open living and dining area features high vaulted ceilings and large arched windows, allowing natural light to fill the space. A long dining table with upholstered chairs sits centrally, while a comfortable seating area with a sofa is visible in the background.
Home in Windham
4.94 out of 5 average rating, 53 reviews

EAT, DRINK, PLAY ... and Relax in Windham

ARating, 5 stars4 months ago
Great stay! Marquis was very responsive and helpful. Great house for a weekend ski trip.
Top guest favorite
A spacious living area features light wood flooring and large windows allowing natural light. A dining table with chairs is positioned near a cozy wood-burning stove. Sofas include a pullout bed, while decorative elements and bookshelves add warmth to the inviting space.
Home in Prattsville
4.98 out of 5 average rating, 40 reviews

Ashland Cottage—Minutes to Windham Mountain

LuisRating, 5 stars1 month ago
Amazing place to get away from the city! Close to all of the big windham attractions yet super peaceful and private. The cottage itself is very comfortable and the kitchen offers everything you need to cook a nice meal. We also had deer and wild turkey roaming in the large yard out back. Highly recommend!
Guest favorite
A comfortable living area features a stone fireplace with a flickering flame. A modern couch adorned with patterned cushions faces an entertainment setup. A wooden table and chairs are situated nearby, creating a cozy space for relaxation and conversation.
Home in Windham
4.97 out of 5 average rating, 74 reviews

Walk to town | 2 Mins to Ski | Windham Mill House

Taryn LynRating, 5 stars3 months ago
Thanks for a great stay. We loved the location and proximity to the mountain. Your place was clean and comfortable.
Guest favorite
The circular exterior of the home is showcased, featuring large windows that provide abundant natural light. Surrounding greenery and landscaped gardens enhance the inviting atmosphere, while a wraparound deck can be seen above. A well-maintained lawn borders the residence, creating a serene outdoor setting.
Home in Windham
4.89 out of 5 average rating, 57 reviews

Designer upstate home perfect for family holidays!

JoannaRating, 5 stars4 months ago
We had a wonderful stay at this house! It was incredibly convenient to Windham, had everything we needed/wanted in a weekend getaway. The house is excellent for all ages with the most spectacular windows and views. The hosts were also super responsive and accommodating. Definitely highly recommend to anybody visiting Windham.
Guest favorite
The exterior of the house features a welcoming deck area with seating and a hot tub, set against a backdrop of trees. A cozy game room and entertainment space with a pool table is visible indoors, complemented by natural lighting from the windows. The outdoor patio is elegantly lit for evening gatherings.
Home in Windham
4.95 out of 5 average rating, 57 reviews

The Hensonville Honeypot- HotTub/Game Room/Bikes

VarunRating, 5 stars2 weeks ago
Amazing host and amazing home which made my friends and I fit right in and feel comfortable. Cant wait to come here again maybe one day for longer, super easy to just chill and relax, the hot tub is too good!!!
Superhost
Home in Windham
4.83 out of 5 average rating, 47 reviews

The Lost Toboggan

SiavashRating, 5 stars1 week ago
I decided to take my friends to a cabin and make a road trip out of it for my bday and after days of searching for the right AirBnb, I chose James’ house. I did NOT regret it at all. Very private and peaceful location, absolutely beautiful surroundings, only 10 minutes away from everything you might need (gas station, grocery stores, book stores, pharmacy and even a movie theater). The house pretty much had everything that we needed. We weren’t lucky enough to explore the nature more as it rained most of the time, but it only made sitting in front of the fireplace and watching movies more ‘romantic’. The cabin was very clean (not squeaky, but clean enough, can’t expect a cabin to be spotless). It had plenty of firewood for the fireplaces, the grill was gas powered so very easy to use, there was A POT of cutlery, dishes and utensils for anything. In short, if you want to celebrate any occasion or just go and have a peaceful weekend with your friends/ family, this is THE cabin.
Superhost
A cottage is seen against a vibrant sunset sky, surrounded by tall trees. The outdoor area features a deck, with light spilling warmly from inside. A grassy yard is visible in the foreground, enhancing the tranquil, natural setting.
Home in Maplecrest
4.86 out of 5 average rating, 43 reviews

Birchwood Cottage - Scenic Valley Getaway

LauraRating, 5 stars3 weeks ago
This place was perfect for our girls weekend getaway. The space was very private and beautiful with tons of little wildflowers. The deck with the hammock was a great outdoor hangout spot and so was the sun room with its full openable screened windows. So peaceful. The kitchen had everything we needed. It was also located near a cute park with a lake we could picnic at. Host was super nice and made everything easy for us.
Guest favorite
An inviting fire pit area is surrounded by six green Adirondack chairs arranged in a circle, set on a stone path of gray gravel. In the background, a multi-level deck extends from the house, surrounded by trees in a serene outdoor setting.
Home in Hensonville
4.92 out of 5 average rating, 88 reviews

GreeneHaus - Modern Mountain Escape - EV Charger

DeborahRating, 5 stars3 months ago
We had an absolutely wonderful stay at this Airbnb! The home was spacious, cozy, and even better in person than we imagined. There was plenty of room for our family to spread out, and the assortment of games provided kept everyone entertained for hours. The home was impeccably clean and beautifully decorated, creating a warm and welcoming atmosphere. The check-in and check-out process was a breeze, and Genevieve and Yahve were fantastic hosts. They were incredibly responsive and easy to communicate with, offering excellent recommendations for local activities and dining spots. Their tips really helped us make the most of our stay! Overall, this is a perfect home for families looking for a relaxing and fun getaway. We would absolutely stay here again and highly recommend it to anyone looking for a great place to stay.

Private house rentals

Top guest favorite
A cozy living area features a sectional couch set against a wooden wall with a decorative hanging. A warm electric fireplace creates a focal point, while a soft dog bed is positioned nearby. A patterned area rug complements the wooden flooring beneath.
Home in East Durham
5 out of 5 average rating, 25 reviews

Pawfect Family Retreat w/DogPark. <1mi toWaterPark

OwenRating, 5 stars3 days ago
Maryana & Scott literally saved our group’s weekend (and sanity) after our RV had flooded and ruined our original camping plans. After frantically shooting out messages to every nearby Airbnb that looked somewhat doable to see if our RV would fit, they were the first to respond by a long shot and were so thoughtful and attentive to detail from the jump to make sure we had what we needed. The place was spotless when we arrived, and gave us a space to finally relax. The backyard is gigantic, beautiful, and so well equipped we ended up cooking dinner out there and hanging out for most of the night to at least enjoy the outdoors. We were able to make the most of a bad situation thanks to Maryana & Scott, and I cannot thank them enough. Would love to stay at any of their properties again in the future, they’re just all around A+ human beings.
Guest favorite
A cozy living area showcases a stone fireplace, with soft lighting highlighting a grey sectional sofa and an accent chair. Natural light filters in through two windows, illuminating the warm wood flooring and decorative elements on the wall.
Home in Windham
5 out of 5 average rating, 10 reviews

Peaceful Woods at The Johnson Cottage

CatherineRating, 5 stars1 month ago
Thoroughly enjoyed our stay at the Johnson Cottage. Super quiet area making it so peaceful and house was very cozy. Home was extremely clean and everything was nicely appointed and all seemed brand new. Bathroom floor with radiant heat was a treat. Plenty of space for my husband and I and our 2 older (mid 20’s) boys. All loved golfing at Christman’s & always a great stop at The Chicken Run! Our dog also loved the property and exploring the woods and the extra dog items left in the mudroom for us to use was so thoughtful of the owners:) Would love to return in the Summer & utilize the deck area!
Guest favorite
A welcoming living room features leather seating along with a coffee table and a warm fireplace. Large windows invite natural light, offering views of the outdoors. Light-colored curtains frame the windows, enhancing the spacious ambiance, while a ceiling fan adds a cooling touch.
Home in Cairo
4.98 out of 5 average rating, 63 reviews

Couples' Mountain Escape |HotTub|GameRoom|MtnViews

ThomasRating, 5 stars1 week ago
Janet was an excellent host and her home was beautiful. Extremely spacious and clean. One thing that stood out was every (light) switch had a label of what it was for. Kitchen had many appliances and seasonings, master bath had an awesome jacuzzi (and many toiletries), and the hot tub outside was easy to operate. Patio is also a beautiful amenity at night. Overall an excellent experience - can’t wait to come back!
Guest favorite
A view from beneath a wooden gazebo showcases a serene landscape of green grass and evergreen trees. The distant mountains are visible against a bright blue sky, creating a peaceful outdoor setting.
Home in Jewett
4.95 out of 5 average rating, 78 reviews

6-Acres Lux Oasis with 3BR/2BA - Hunter Mnt Views

ErickRating, 5 stars2 weeks ago
Me and my family really enjoyed our stay. Host was very communicative, gave great suggestions of nearby places to check out, and made sure we were comfortable during our visit. Place has a great view, big backyard, and was very clean. Would come back again for sure.
Top guest favorite
Aerial view of a modern A-frame chalet surrounded by autumn-colored trees, with a vibrant sunset sky. The property features outdoor lighting, creating a warm ambiance in the backyard, complemented by the natural wooded landscape.
Home in Prattsville
4.98 out of 5 average rating, 52 reviews

Scandi A-Frame w/Hot Tub & Sauna

JulianaRating, 5 stars5 days ago
My friends and I loved our stay at Wilderkaat. The cabin was clean, comfortable, and well supplied with thoughtful amenities. We immediately felt at home and were able to relax and enjoy our time there -- we only wished we could have stayed longer.
Top guest favorite
The living area features a spacious open floor plan with cathedral ceilings and a wall of windows allowing natural light. A wood-burning stove is positioned centrally, surrounded by comfortable seating. The decor includes warm wood elements, enhancing the overall inviting ambiance.
Home in Windham
4.93 out of 5 average rating, 55 reviews

Creekside Lodge

CarolRating, 5 stars2 months ago
Our family of 11 had a great time at the house! The layout of the house was great, we all had plenty of room to relax and hangout. The deck had a beautiful view and over all house was great. The bedrooms were a good size and cozy. It was super close to Windham mountain and made for a great location and house for the weekend!
Guest favorite
Two glasses of red wine are placed on a wooden tray, accompanied by decorative nuts. A white vase filled with vibrant orange flowers adds a touch of color to the light-colored countertop.
Home in Hensonville
4.94 out of 5 average rating, 48 reviews

CreeksideHome, 2-5min to Ski,Hiking,Lake,Cafe&Bars

LinusRating, 5 stars5 months ago
We had a wonderful time staying here over the Christmas holiday. The house was comfortable, clean, and well-equipped with everything we needed to cook, which was especially helpful since most restaurants were closed for Christmas. Its location is fantastic, close to ski resorts, restaurants, and beautiful sights.
Top guest favorite
A spacious living area is presented, featuring a light-colored sectional sofa adorned with throw pillows in varying tones. A wooden coffee table is positioned in front of the sofa, complemented by a simple mug. Large windows allow natural light to illuminate the room, with views of the outdoors.
Home in Tannersville
4.96 out of 5 average rating, 52 reviews

Luxury Retreat Experience Modern Mountain Hideaway

AshRating, 5 stars3 weeks ago
This is a really special place and a hidden gem in Hudson Valley. With its modern architecture, well curated furniture, engaging art, beautiful open fields and a canopy of tall trees all add up to create a truly unique experience. The place has a full kitchen, a big and cozy living room, a patio perfect for lounging and very comfy bedrooms. The strategically positioned glass windows blur the indoor / outdoors. Michael is the perfect host with clear and responsive communication. My wife and I look forward to our next visit!

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

Destinations to explore

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