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Vacation rentals in Windham

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windham vacation rentals

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Other great vacation rentals in Windham

Top guest favorite
Home in Windham
5 out of 5 average rating, 24 reviews

Cozy Modern: views, 3 min ski, fire pit, games,BBQ

CharlesRating, 5 stars1 month ago
Paula’s place was excellent! If I could give it more than five stars I would! Paula’s place was clean had everything it said it would looked like the pictures! One of the best places I’ve stayed at, and she was great at communicating and responding to everything we messaged! Thank you
Top guest favorite
The exterior of the chalet is showcased, featuring a large wrap-around deck and multiple windows that invite natural light. A fire pit surrounded by seating is visible, along with a swing set for children. Lush greenery frames the property, enhancing the sense of privacy.
Chalet in Windham
5 out of 5 average rating, 38 reviews

Mountain Views-Game Room-Hot Tub-5 minutes to town

NikkiRating, 5 stars2 weeks ago
Melanie was a fantastic host. She was responsive and helpful. The house is beautiful, nestled in the trees on your own little piece of the mountain. There are many great hikes and restaurants close by. There is a great little coffee shop and breakfast spot within five minutes. The property even has some little waterfalls and areas to explore. Our daughters had fun playing games in the game room and have developed a love of shuffleboard. We were able to cook dinners and have a nice fire outside under the stars with everything we needed. This is a great house for a mountain getaway.
Top guest favorite
Home in East Jewett
4.98 out of 5 average rating, 41 reviews

Creekside Couple's Retreat w/Hot tub, Sauna & More

IzabelaRating, 5 stars4 days ago
My husband and I were blown away by the beauty and thought that was put into this private destination. The moment you step on property, the freshness of the air and sounds of the creek are immediately calming. Diana was incredibly nice and very communicative before and during the entire stay. Activities: The sauna, creek, hot tub, pizza oven, grill, fire place/pits, hammocks- the amenities are amazing and unlike any other Airbnb I have ever been in before. So much that besides a quick dinner out one night (12 min away) and a nice walk around the Mountain Top Arboretum with our dog, we wanted to spend our time at the property. We called it our personal sanctuary spa!! The home: The home style is minimalistic but homey and every single item is top notch quality. There are no shortcuts- the entire place is a work of art. The bedroom and bathroom inspired me to reanalyze my own bedroom style. Thank you for upping the Airbnb game!! Can’t wait to come back to this magical spot! ✨
Top guest favorite
The spacious living room features large windows with scenic views of the woods, allowing natural light to fill the area. A sectional couch offers ample seating, while a round dining table accommodates gatherings. A wall-mounted TV is visible, enhancing the entertainment options.
Chalet in Windham
4.97 out of 5 average rating, 39 reviews

Après Chalet|Ski|Luxury|Sauna|HotTub|Firepit|Disco

DianeRating, 5 stars1 week ago
Our families stay at Emma’s place was really enjoyable! Her home is beautiful, clean and more than accommodating for all our needs. We all loved the sauna, jacuzzi and game room. Our toddlers loved the playroom as well. The town of Windham is 2miles away with some nice places to eat or have a drink. There are many places close by to go hiking for all different levels, we opted for The Windham Path, a nice 2mile walk. We highly recommend Emma’s place for your stay in the Catskills!
Top guest favorite
A scenic view of a creek bordered by a mix of lush greenery and wildflowers. The gentle flow of the water is visible alongside a rocky riverbank, with trees in the background, creating a natural and serene environment.
Home in Gilboa
5 out of 5 average rating, 18 reviews

Charming Catskills Cottage

TamarRating, 5 stars5 days ago
Had a great stay. Cozy and sweet cabin, designed well and comfortable to stay in. Also loved the little creek behind it.
Guest favorite
Tiny home in Haines Falls
5 out of 5 average rating, 5 reviews

Romantic tiny Pod for two/HotTub/LakeView/FirePit

AveryRating, 5 stars5 days ago
Wow - we just enjoyed a long weekend here and it was a dream! Serg’s place is beautiful, thoughtfully designed, and a great way to relax and enjoy some natural beauty. The pond is beautiful to watch throughout the day with fish and frogs jumping between the lily pads. One morning we awoke to a pair of red shouldered hawks swooping over the pond, and each night we saw a doe come graze on the other side. There are hiking trails and groceries within minutes, with Woodstock and Kingston around 30 away if you want a longer day trip. We spent each day hiking and came back to have s’mores over the fire and enjoy the hot tub. At night, the stars are beautiful and it’s great to watch the sunset through the huge windows. Serg was also very communicative and helpful as well.
Guest favorite
An outdoor fire pit is surrounded by four sturdy chairs, set against a serene snowy landscape. Evergreen trees provide a natural backdrop, while a gentle sky reveals soft clouds. The scene evokes a peaceful environment perfect for gatherings in nature.
Cabin in Windham
4.93 out of 5 average rating, 43 reviews

Windham Cabin Escape (3BR)

KyleRating, 5 stars5 days ago
lovely stay in Windham, great outdoor fireplace and plenty of space to enjoy inside and out
Superhost
A spacious living area showcases a leather couch and a cozy armchair, positioned around a round coffee table on a textured area rug. Large windows invite natural light and frame views of the landscape, while exposed wooden beams and a stone fireplace enhance the room's character.
Condo in Windham
4.91 out of 5 average rating, 11 reviews

Brand New Outdoor Hot Tub - Luxury 2 Bedroom Suite

YadiraRating, 5 stars2 days ago
We had an amazing stay! The home was exactly as pictured. The location was perfect—just a 30 min drive to Kaaterskill Falls and 5 mins to the local restaurants, but tucked away enough to enjoy peace and quiet. Michael was responsive and made check-in a breeze. We especially loved the beautiful views from the hot tub and how comfortable the space felt after a day of hiking and exploring. The sauna was a great surprise! Highly recommend this place for anyone looking for a peaceful escape to the Catskills. We’d absolutely stay again!
Show all

Quick stats about vacation rentals in Windham

  • Total rentals

    160 properties

  • Nightly prices starting at

    R1,440 ZAR before taxes and fees

  • Total number of reviews

    6.2K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Windham?

    Yes! Work meets play with ease at over 80 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in condo rentals in Windham?

    Experience the best of Windham with our condo rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Windham?

    Four-legged friends are welcome in Windham. Choose from more than 50 vacation rentals for guests traveling with pets.

  • What are the most popular amenities for Cabin Rentals in Windham?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with self check-in, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Windham have self check-in?

    Absolutely! We offer over 50 house rentals with self check-in in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Are there Windham house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Windham, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Windham have wifi?

    Absolutely! We offer over 80 house rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windham have a bbq area?

    Absolutely! We offer over 60 house rentals with a bbq area in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windham have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly townhouse rentals in Windham?

    Windham has more than 20 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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