Windham vacation rentals

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Top-rated vacation rentals in Windham

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

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Guest favorite

Cabin in Durham

4.99 out of 5 average rating, 117 reviews

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

Welcome to Chalet LaRosa, a new 2,450 SF custom cabin just 10 minutes from Windham Mountain & easily accessible to the area's hottest attractions! This idyllic 4BR, 3BA retreat w/ an 8" cedar sauna, hot tub, & full game/bar area is situated on the Durham Scenic Byway w/ some of the Catskills' most breathtaking views. The cabin provides a rare amenity package & truly authentic Catskills experience w/ decor & materials sourced from dozens of local shops & antique collectors. Come enjoy the Chalet!

Sep 22 – 29

G$138,997 GYD per night

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 30 – Oct 7

G$22,057 GYD per night

Guest favorite

Townhouse in Windham

4.91 out of 5 average rating, 108 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.

Nov 19 – 26

G$32,179 GYD 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.

Oct 5 – 12

G$20,255 GYD per night

Guest favorite

Cabin in Maplecrest

4.94 out of 5 average rating, 163 reviews

Fraxinus House - Ideal for Windham & Hunter

Scenic country cabin located between Hunter Mountain and Windham Mountain, in the charming hamlet of Maplecrest. Surrounded by trees and the wilderness, it creates an idyllic mountainside escape, private and secluded grounds with only night stars and the sounds of wildlife. The decor is a mix of modern, color, and comfort, with lots of natural wood details. Both ski mountains are only a short 10 mins drive away. This is a great place for a romantic getaway or an outdoor trip in the Catskills.

Apr 30 – May 7

G$31,666 GYD per night

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 130 reviews

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Sep 7 – 14

G$16,552 GYD per night

Superhost

Condo in Windham

4.84 out of 5 average rating, 112 reviews

Studio 3 BEDS-SLEEP 4

Light-filled studio in downtown Windham. Beautiful mountain views from your balcony; at night gaze at the moon & stars If you want solitude, this is the place to be! Daytime, take a walk down to the river & enjoy! Walking distance to restaurants & small grocery. Studio is big, with closet, full bathroom, well-stocked coffee area with microwave and refrigerator. Maximum 3 people; 1 double & 2 twins. Check-in: From 4PM off-street parking, Free Wifi /Basic Cable /Linens/Coffee

Jun 29 – Jul 6

G$33,516 GYD per night

Superhost

Townhouse in Windham

4.82 out of 5 average rating, 177 reviews

Redwood Retreat in Windham - minutes to Mtn!

True mountain getaway, just 2.5 hours from NYC!! Modern and clean 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Complex amenities include outdoor pool (open from Memorial Day through Labor Day) 2 tennis courts and a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails. NOW OPEN FOR 2024/25 SKI SEASON!!

Jun 2 – 9

G$31,348 GYD per night

Guest favorite

Cottage in Gilboa

4.93 out of 5 average rating, 199 reviews

Home Alone Mountain Retreat

The cottage is beautifully located in the small vacation community on the hill with a stunning mountain view from the wrap-around deck. Nature and sport enthusiasts will love the area. Take on the early morning stroll in the woods, wander around the historic villages, take a swim in the pond, enjoy the country roads on the mountain bike, and visit neighboring Windham and Hunter Mountain Resort. The kitchen is equipped with cooking essentials such as pots, pans, and utensils.

Oct 26 – Nov 2

G$27,290 GYD per night

Guest favorite

Tiny home in Lexington

4.95 out of 5 average rating, 297 reviews

Diamond Notch - Mini A-frame, Spectacular Views

The Diamond Notch is a site-specific, passive-house level insulated, off-grid mini A-frame - locally designed & built by the architects in co-operation with Lexington Arts + Science (LA+S). Requires a 5 minute hike in. Bring hiking boots. Micro spikes or snow shoes provided if needed. Yes, there is a cozy propane fireplace inside which provides plenty of heat for cold winter nights. We provide bedding, limited cooking utensils and a fire pit. (no T mobile cell coverage)

Nov 24 – Dec 1

G$23,179 GYD per night

Guest favorite

Apartment in Freehold

5.0 out of 5 average rating, 218 reviews

Mountain View Retreat~Sunny Hill Golf / Skiing

Welcome to Sunny Hill Road ! We are located in a small community of private homes in an open space overlooking the mountains. This one bedroom unit has everything you need to enjoy your stay in the Catskills. Relax on the private deck or inside with amazing views from every window. The kitchen is fully equipped and ready to cook a full meal and then enjoy it in the dining room overlooking the mountains. It is quiet and restful here, amazingly beautiful in all four seasons!

Jun 8 – 15

G$37,708 GYD per night

Guest favorite

Home in Windham

4.93 out of 5 average rating, 165 reviews

Extreme leisure minutes from action and adventure

Relax and unwind in uniquely styled home on secluded 14-acre private property. Conveniently located to Windham mountain, vineyard, horseback riding and hiking trails The Bridge as we lovingly call our home, was designed to be a space where extreme leisure is met with adventure. Wake up early enough, you will see deer and wild turkey graze through the meadow. Stay awake late enough and gaze upon the endless stars. Now with hi-speed wifi!! Follow us @TheBridge_windhamNY

Mar 12 – 19

G$97,433 GYD per night

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

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

Guest favorite

Condo in Hunter

4.97 out of 5 average rating, 425 reviews

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

Jun 17 – 24

G$17,297 GYD per night

Superhost

Cabin in Jewett

4.92 out of 5 average rating, 237 reviews

The Barnhouse - Ski House near Hunter and Windham

May 9 – 16

G$131,254 GYD per night

Guest favorite

Cabin in Tannersville

4.99 out of 5 average rating, 142 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Sep 21 – 28

G$30,993 GYD per night

Guest favorite

Cabin in Jefferson

5.0 out of 5 average rating, 430 reviews

"Far from the Madding Crowd" Cozy Cabin Retreat

Feb 23 – Mar 2

G$21,814 GYD per night

Guest favorite

Home in Durham

4.96 out of 5 average rating, 100 reviews

Wow! Panoramic Mountain View, Minutes to Windham!

Feb 25 – Mar 4

G$51,320 GYD per night

Guest favorite

Cottage in Roxbury

4.98 out of 5 average rating, 476 reviews

The Little House

Feb 7 – 14

G$28,094 GYD per night

Guest favorite

Cabin in Windham

4.88 out of 5 average rating, 109 reviews

The Windham Cabin w/ Hot Tub

May 27 – Jun 3

G$45,299 GYD per night

Guest favorite

Cabin in Windham

4.83 out of 5 average rating, 247 reviews

Hunter / Windham Ski Loft

Aug 18 – 25

G$41,071 GYD per night

Show all

Other great vacation rentals in Windham

Guest favorite

Condo in Windham

4.97 out of 5 average rating, 58 reviews

Beautiful, modern, newly remodeled 1 bedroom condo

Nov 15 – 22

G$38,094 GYD per night

Guest favorite

Apartment in Windham

5.0 out of 5 average rating, 17 reviews

Black Dome - a 2B, 2B Condo 5 min from Windham Mt.

Jun 23 – 30

G$30,148 GYD per night

Guest favorite

Townhouse in Windham

5.0 out of 5 average rating, 11 reviews

Sunny 3 BR Getaway in Windham | The Mill House 1

Nov 2 – 9

G$40,433 GYD per night

Guest favorite

Townhouse in Windham

4.96 out of 5 average rating, 23 reviews

First Floor Condo with full kitchen.

Feb 24 – Mar 3

G$39,620 GYD per night

Guest favorite

Home in Windham

4.96 out of 5 average rating, 54 reviews

The Ski Ranch – 5min from Windham Mountain

Jun 27 – Jul 4

G$76,718 GYD per night

Guest favorite

Home in Hunter

5.0 out of 5 average rating, 56 reviews

Modern House with Mountain View @Getawind

Dec 1 – 8

G$144,308 GYD per night

Guest favorite

Chalet in Windham

4.99 out of 5 average rating, 83 reviews

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

Jun 12 – 19

G$171,310 GYD per night

Superhost

Cabin in Jewett

4.92 out of 5 average rating, 36 reviews

YAYFrame - Catskills Mountains Cozy Cabin Getaway

May 15 – 22

G$25,451 GYD per night

Show all

Quick stats about vacation rentals in Windham

Total rentals
160 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
G$14,629 GYD before taxes and fees

Frequently Asked Questions

Are there townhouse rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 10 townhouse rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Windham?
Experience the best of Windham with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cabin rentals in Windham have self check-in?
Absolutely! We offer over 10 cabin 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 70 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 townhouse rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 10 townhouse rentals for guests traveling with pets.
Are there family-friendly condo rentals in Windham?
Windham has more than 10 family-friendly condo 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 wifi, over 50 homes with self check-in, over 70 homes with a bbq area, 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!

Windham vacation rentals

Top-rated vacation rentals in Windham

Vacation rentals for every style

Houses

Chalets

Hotels

Popular amenities for Windham vacation rentals

Stay near Windham's top sights

Other great vacation rentals in Windham

Condo in Hunter

Cabin in Jewett

Cabin in Tannersville

Cabin in Jefferson

Home in Durham

Cottage in Roxbury

Cabin in Windham

Cabin in Windham

Other great vacation rentals in Windham

Condo in Windham

Apartment in Windham

Townhouse in Windham

Townhouse in Windham

Home in Windham

Home in Hunter

Chalet in Windham

Cabin in Jewett

Quick stats about vacation rentals in Windham

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there townhouse rentals with a dedicated workspace in Windham?

How much does it cost to stay in house rentals in Windham?

Do cabin rentals in Windham have self check-in?

Do house rentals in Windham have wifi?

Do house rentals in Windham have a bbq area?

Do house rentals in Windham have a gym?

Are there pet-friendly townhouse rentals in Windham?

Are there family-friendly condo rentals in Windham?

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

Are there Windham vacation rentals on Airbnb with pools?

Destinations to explore