House vacation rentals in Windham

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Windham house rentals

House rentals with a hot tub

Guest favorite
A two-story red cottage is nestled among tall trees, showcasing a classic design with multiple windows and balconies. A gravel driveway leads to the entrance, providing access to outdoor spaces. The surrounding wooded landscape adds to the cottage's natural setting.
Home in Bearsville
4.92 out of 5 average rating, 230 reviews

A Cozy’s Woodstock Getaway Home

ClancyRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Bearsville
4.92 out of 5 average rating, 134 reviews

Secluded Artist's Retreat with Hot tub

DavidRating, 5 stars3 months ago
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!
Superhost
Home in Woodstock
4.84 out of 5 average rating, 110 reviews

2 BR , Fireplace & Hot Tub @ heart of Woodstock

AndrewRating, 5 stars2 months ago
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!
Top guest favorite
A modern house is surrounded by trees with colorful autumn leaves. The exterior features a wraparound deck, and snow lightly covers the ground and plants. Clear blue skies enhance the peaceful outdoor setting, creating a serene atmosphere.
Home in Rhinebeck
4.91 out of 5 average rating, 230 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

AudreyRating, 5 stars1 month ago
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!
Guest favorite
A spacious wooden deck is surrounded by lush greenery, featuring a hot tub and a grill. Neatly stacked logs are positioned against the wall, providing a rustic touch. Large windows showcase the scenic views, allowing natural light to brighten the space.
Home in Lanesville
4.93 out of 5 average rating, 158 reviews

Mountaintop Lookout with Hot Tub under the Stars

SarahRating, 5 stars2 weeks ago
We had a great time at Natalia’s place! The hot tub and fireplace were perfection on a chilly Spring weekend.
Guest favorite
Home in Woodstock
4.86 out of 5 average rating, 132 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

HelaRating, 5 stars1 month ago
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.
Top guest favorite
The exterior of a modern chalet is framed by lush greenery, featuring dark wood accents. A spacious patio raises above the landscape, complete with a hot tub. Adirondack chairs are positioned nearby, inviting relaxation amidst the serene natural setting.
Home in Hunter
5 out of 5 average rating, 100 reviews

Tranquil Chalet with Mountain Views

AlexandreRating, 5 stars3 weeks ago
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.
Top guest favorite
A serene outdoor area features a stone patio with wooden seating around a fire pit amidst lush greenery. A charming single-story house is visible, surrounded by a manicured lawn. An indoor game room is equipped with a pool table and dart board, while an outdoor hot tub is shaded by a large red umbrella.
Home in Prattsville
4.94 out of 5 average rating, 111 reviews

Catskills home with game room, hot tub, fire pit

LawrenceRating, 5 stars1 week ago
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

Guest favorite
A cozy living area is presented with a green couch positioned in front of a rustic wooden coffee table. A small blue vase holds fresh flowers, while magazines and a candle adorn the table, inviting relaxation and comfort.
Home in Hudson
4.86 out of 5 average rating, 458 reviews

Pied-A-Terre | City of Hudson Entire Apartment

MichaelRating, 5 stars1 month ago
A wonderful host with a wonderful home. We enjoyed our stay so much that we are already planning another trip back. Highly Recommend!
Guest favorite
A spacious living area is highlighted by two large artworks: a framed image of a person holding oranges and a striking mural featuring two figures near a vintage train. The warm wooden floors add a sense of openness to the room.
Home in Hudson
4.92 out of 5 average rating, 202 reviews

Hudson New York Grey Victorian

KarlaRating, 5 stars2 months ago
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!
Top guest favorite
A wooden dining table is set with a floral centerpiece and a decorative runner. Soft lighting from three pendant lights illuminates the space, with light wood floors extending throughout. Nearby, a window is adorned with sheer curtains, and a cozy seating area is visible in the background.
Home in Saugerties
4.97 out of 5 average rating, 126 reviews

Welcome to Malden Manor, in a prime location!

OrionRating, 5 stars2 months ago
Lovely place in Saugerties, close to lots of great hiking and restaurants.
Superhost
A spacious living area is highlighted by a vintage piano against a light wall. Comfortable seating includes a cushioned sofa and an accent chair. Natural light enters through windows, illuminating the hardwood floor and detailing in the coffered ceiling.
Home in Hunter
4.89 out of 5 average rating, 141 reviews

Catskill Getaway!

LaurenRating, 5 stars1 month ago
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!
Superhost
A comfortable living room showcases wooden beams on the ceiling and warm hardwood flooring. Two seating areas are present, one featuring a light sofa and the other a turquoise armchair. A decorative rug lies beneath, and a fireplace with plants adds a cozy touch.
Home in Catskill
4.94 out of 5 average rating, 109 reviews

Catskill Lumber House "Blue" - In Catskill Village

PaulRating, 5 stars4 months ago
truly wonderful and considerate hosts! absolutely a wonderful stay and will 100% be back next time we are in town!
Superhost
A cozy living area features a soft sofa and a leather chair, complemented by a round coffee table. A gas fireplace with a stone surround adds warmth, while large windows allow natural light to fill the space. A modern light fixture and decorative accents enhance the inviting atmosphere.
Home in Durham
4.85 out of 5 average rating, 131 reviews

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI

Fur-EliseRating, 5 stars3 weeks ago
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.
Top guest favorite
A cozy living room is furnished with a large sectional sofa and a wooden coffee table. A flat-screen TV is placed on a stand, with vibrant red chairs nearby. A doorway leads to a dining area with natural light, decorated with art and personal touches.
Home in Saugerties
4.98 out of 5 average rating, 168 reviews

The Mushroom Palace (Hot Tub, Sauna & Cold Plunge)

AlexRating, 5 stars2 weeks ago
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!
Top guest favorite
Home in Stamford
5 out of 5 average rating, 9 reviews

Marion Manor gorgeous countryside estate w/ views

PatRating, 5 stars5 months ago
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

Guest favorite
A modern entryway is highlighted by a circular mirror and potted plant, with a sleek console table underneath. A spiral staircase leads to an upper level, while natural light streams through nearby windows, illuminating the elegant hardwood floor and inviting blue sofa.
Home in Saugerties
4.94 out of 5 average rating, 68 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

YuliaRating, 5 stars2 months ago
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!
Guest favorite
A heated salt-water pool is surrounded by greenery, with lounge chairs positioned nearby. A bright yellow rubber duck floats on the water, while the pool is bordered by textured pavers. Tall trees provide a natural backdrop, ensuring privacy and tranquil views.
Home in Woodstock
4.86 out of 5 average rating, 211 reviews

Lux Woodstock Pool/ Pvt/Fireplaces /4 mins 2 town

JoshuaRating, 5 stars2 months ago
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!
Top guest favorite
An outdoor deck surrounds a circular swimming pool, complemented by a patio table and chairs. Several lounge chairs are arranged near the pool, and a large umbrella offers shade. Lush greenery borders the space, creating a private and serene environment.
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars6 months ago
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!
Guest favorite
Home in Kingston
4.83 out of 5 average rating, 70 reviews

Beaver | Pool, Firepit, Secluded, 10 acres

GraemeRating, 5 stars2 months ago
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!
Guest favorite
Home in Woodstock
4.92 out of 5 average rating, 240 reviews

Little owl Japanese teahouse: pool and tennis

JessicaRating, 5 stars3 weeks ago
Quiet, peaceful, so cozy. Perfect setting if you need to hibernate a bit.
Guest favorite
A modern farmhouse exterior is visible beside a crystal-clear swimming pool surrounded by grassy areas. Colorful pool floats are placed in the water, while a wooden fence and tall trees frame the peaceful setting.
Home in Saugerties
4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars6 months ago
We had a terrific stay. The house was exactly as advertised.
Guest favorite
The exterior of the house showcases a combination of stone and brick, framed by well-kept landscaping. A mature tree offers shade in the front yard, while a pathway leads to the entrance. The roof features a peak with multiple gables.
Home in Kingston
4.86 out of 5 average rating, 99 reviews

Hudson River views with pool and hot tub

EvanRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Woodstock
4.91 out of 5 average rating, 199 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars6 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 👍🏼

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

  1. Airbnb
  2. United States
  3. New York
  4. Greene County
  5. Windham
  6. House rentals