Windham vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Windham

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Prattsville

4.91 out of 5 average rating, 270 reviews

Yanity House

You will have access to the entire house fully furnished. Pet's are welcome just keep paws clean its a beige rug. We want everyone to be comfortable, so please let us know how and what you would like to see improved if you rent the unit. We will improve the unit as per guest suggestions. Currently we do not have cable but we do have a dvd and game system in the living room - All the bedrooms have TV's, dvd players or bring your streaming device There currently is no phone but cell service works

Sep 17 – 24

R2,036 ZAR per night
Guest favorite

Apartment in Windham

4.99 out of 5 average rating, 210 reviews

Main Street, The Heart of Windham

The perfect base to explore Windham & spend time in the Mountains! Just 0.7 mi. to Windham Mtn/9 mi. to Hunter. Located where Main St. begins, this immaculate 1 Bdrm has a queen bed, open concept EIK/LR, Full Bath & Balcony. Roll-away bed avail. Hiking/ski/snowboard/music/dining/exploring. Near Wedding Venues-Wylder Hotel, Hayfield & Windham Manor. Walkable to restaurants, movies, pubs, galleries & shops. Parking. WIFI. Smart TV/NO CABLE. Bring your Roku/Amazon/Netflex/Hulu codes. DVDs avail.

Aug 2 – 9

R1,838 ZAR per night
Guest favorite

Townhouse in Windham

4.92 out of 5 average rating, 107 reviews

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

Sep 22 – 29

R2,809 ZAR per night

Popular amenities for Windham vacation rentals

Stay near Windham's top sights

Chicken Run Family Restaurant and Steak House214 locals recommend
Michael's Diner- Now Windham Diner53 locals recommend
Catskill Mountain Country Store - Windham105 locals recommend
The Windham Local129 locals recommend
Millrock Restaurant105 locals recommend
Tap House Grille72 locals recommend

Other great vacation rentals in Windham

Superhost

Cabin in Maplecrest

4.95 out of 5 average rating, 167 reviews

The Cabin - Ski House near Windham

Jul 17 – 24

R8,258 ZAR per night
Guest favorite

Cabin in Durham

4.99 out of 5 average rating, 115 reviews

Stunning Cabin, Sauna, HT, MtnView, Mins 2 Windham

Sep 11 – 18

R12,611 ZAR per night
Guest favorite

Cottage in Gilboa

4.93 out of 5 average rating, 193 reviews

Home Alone Mountain Retreat

Sep 27 – Oct 4

R2,643 ZAR per night
Guest favorite

Home in Windham

4.99 out of 5 average rating, 314 reviews

Custom-built Catskills retreat, 7 mins from skiing

Sep 14 – 21

R6,705 ZAR per night
Guest favorite

Condo in Hunter

4.97 out of 5 average rating, 424 reviews

*Great Reviews* Hunter Mtn. Clean/Close/Cozy Condo

Jun 2 – 9

R1,785 ZAR per night
Guest favorite

Cottage in Roxbury

4.98 out of 5 average rating, 473 reviews

The Little House

Nov 18 – 25

R2,436 ZAR per night
Guest favorite

Home in East Jewett

4.99 out of 5 average rating, 189 reviews

Modern Ski-Home With Views Near Hunter & Windham

Apr 29 – May 6

R3,753 ZAR per night
Guest favorite

Apartment in Roxbury

4.93 out of 5 average rating, 208 reviews

"Your Country Getaway at Beulah Land Farm."

Apr 15 – 22

R1,506 ZAR per night
Guest favorite

Tiny home in Saugerties

4.94 out of 5 average rating, 217 reviews

Gorgeous Tiny House with Mountain View

Sep 5 – 12

R2,319 ZAR per night
Guest favorite

Cabin in Tannersville

4.99 out of 5 average rating, 140 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Aug 2 – 9

R2,907 ZAR per night
Superhost

Townhouse in Windham

4.82 out of 5 average rating, 177 reviews

Redwood Retreat in Windham - minutes to Mtn!

Sep 10 – 17

R3,346 ZAR per night
Guest favorite

Guest suite in Windham

5.0 out of 5 average rating, 35 reviews

Cozy 2 bedroom apartment with private entrance

Apr 27 – May 4

R2,740 ZAR per night

Other great vacation rentals in Windham

Guest favorite

Home in Hunter

5.0 out of 5 average rating, 53 reviews

Modern House with Mountain View @Getawind

Nov 22 – 29

R15,012 ZAR per night
Guest favorite

Home in Windham

4.96 out of 5 average rating, 54 reviews

The Ski Ranch – 5min from Windham Mountain

May 13 – 20

R6,897 ZAR per night
Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 86 reviews

Alpine Chalet on Spectacular Property

Aug 3 – 10

R6,348 ZAR per night
Superhost

Cabin in West Kill

4.95 out of 5 average rating, 63 reviews

Cozy Cabin/Hiking/Trout Fishing/Fresh Mountain Air

Jun 5 – 12

R2,356 ZAR per night
Guest favorite

Chalet in Windham

4.99 out of 5 average rating, 80 reviews

Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing

May 30 – Jun 6

R12,133 ZAR per night
Guest favorite

Townhouse in Windham

4.87 out of 5 average rating, 30 reviews

Ski-in Ski-out Windham Mountain Village Townhouse

Apr 6 – 13

R3,113 ZAR per night
Guest favorite

Condo in Lanesville

4.94 out of 5 average rating, 36 reviews

Cozy Downtown Hunter Mountain Getaway

Apr 27 – May 4

R1,538 ZAR per night
Guest favorite

Vacation home in Windham

4.93 out of 5 average rating, 55 reviews

Farmhouse Chic with Mountain and Lake Views

Sep 25 – Oct 2

R6,997 ZAR per night
Guest favorite

Home in Windham

4.96 out of 5 average rating, 51 reviews

Bluebird Cabin: Modern Home With Ski Windham View

Aug 3 – 10

R7,147 ZAR per night
Guest favorite

Townhouse in Windham

4.94 out of 5 average rating, 36 reviews

Sunny 3 BR Escape in Windham | The Mill House 2

Aug 14 – 21

R3,384 ZAR per night
Guest favorite

Condo in Lanesville

4.98 out of 5 average rating, 43 reviews

Quiet, Cozy, Catskills

Jun 7 – 14

R2,079 ZAR per night
Guest favorite

Home in Windham

5.0 out of 5 average rating, 32 reviews

NEW stylish Farm house on the golf course

Aug 14 – 21

R14,153 ZAR per night

Quick stats about vacation rentals in Windham

Total rentals

170 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

150 properties are a good fit for families

Total number of reviews

5.6K reviews

Nightly prices starting at

R1,707 ZAR before taxes and fees

Frequently Asked Questions

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

    Yes! Work meets play with ease at over 40 house rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Experience the best of Windham with our apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

  • 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 70 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 pet-friendly house rentals in Windham?

    Four-legged friends are welcome in Windham. Choose from more than 20 house rentals for guests traveling with pets.

  • 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.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with a bbq area, over 80 homes with wifi, over 50 homes with self check-in, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there Windham vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Windham, available on Airbnb. Make a splash and soak up the sun in style!

Destinations to explore

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