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, 120 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!

Oct 23 – 30

ﺩ.ﺇ2,443 per night

Guest favorite

Home in Prattsville

4.91 out of 5 average rating, 271 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 6 – 13

ﺩ.ﺇ363 per night

Guest favorite

Apartment in Windham

4.99 out of 5 average rating, 211 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 11 – 18

ﺩ.ﺇ356 per night

Guest favorite

Townhouse in Windham

4.91 out of 5 average rating, 111 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.

Apr 11 – 18

ﺩ.ﺇ626 per night

Guest favorite

Cabin in Tannersville

4.99 out of 5 average rating, 145 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

Sep 15 – 22

ﺩ.ﺇ533 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.

Jun 1 – 8

ﺩ.ﺇ556 per night

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 133 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.

Aug 21 – 28

ﺩ.ﺇ340 per night

Guest favorite

Condo in Hunter

4.97 out of 5 average rating, 428 reviews

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

*Clean, cozy studio condo in the Village of Hunter featuring vintage decor. Short walk to the Ski Slopes, Snowtubing Park, Scenic Skyride, Dolan's Lake/Beach, Schoharie Creek, Fly Fishing, Hiking, Disc Golf, Stores, Eateries & Trailways Bus Stop. A Murphy bed w/ full size comfy Casper Mattress, a sectional couch, kitchen, microwave, electric wood stove, dinette, full bath, strong WiFi, Smart TV (no cable) w/Netflix, HBOGO, Pandora. No Pets/No Smoking or vaping in or on the property. Thanks

Jun 12 – 19

ﺩ.ﺇ278 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

Sep 17 – 24

ﺩ.ﺇ589 per night

Guest favorite

Tiny home in Lexington

4.95 out of 5 average rating, 302 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 7 – 14

ﺩ.ﺇ392 per night

Guest favorite

Apartment in Freehold

5.0 out of 5 average rating, 225 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 7 – 14

ﺩ.ﺇ663 per night

Guest favorite

Home in Windham

4.99 out of 5 average rating, 318 reviews

Custom-built Catskills retreat, 7 mins from skiing

Located 7 mins from Windham mountain, the house is surrounded by scenic land. Skiing in the winter, foliage in the fall, swimming holes in the summer, sweet air in the spring. Mountain biking, hiking, golf, antiquing, horseback riding, local farms and so much more! The house itself is a true retreat, you will leave totally re-charged. Bird chirping, star gazing, grilling, baking, pancakes, yoga or simply enjoy a few days of not seeing another soul :)

Oct 17 – 24

ﺩ.ﺇ1,278 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

Cabin in Preston-Potter Hollow

4.98 out of 5 average rating, 288 reviews

Casa Bella Vista with Great Views!

Aug 23 – 30

ﺩ.ﺇ597 per night

Superhost

Cabin in Maplecrest

4.95 out of 5 average rating, 173 reviews

The Cabin - Ski House near Windham

Jul 13 – 20

ﺩ.ﺇ1,599 per night

Guest favorite

Home in Durham

4.96 out of 5 average rating, 101 reviews

Wow! Panoramic Mountain View, Minutes to Windham!

Oct 12 – 19

ﺩ.ﺇ1,504 per night

Guest favorite

Cottage in Gilboa

4.94 out of 5 average rating, 201 reviews

Home Alone Mountain Retreat

Nov 6 – 13

ﺩ.ﺇ581 per night

Guest favorite

Home in Windham

4.93 out of 5 average rating, 166 reviews

Extreme leisure minutes from action and adventure

May 5 – 12

ﺩ.ﺇ1,674 per night

Guest favorite

Cottage in Roxbury

4.98 out of 5 average rating, 481 reviews

The Little House

Jan 10 – 17

ﺩ.ﺇ485 per night

Guest favorite

Home in East Jewett

4.99 out of 5 average rating, 192 reviews

Modern Ski-Home With Views Near Hunter & Windham

Nov 7 – 14

ﺩ.ﺇ1,050 per night

Guest favorite

Home in Durham

4.95 out of 5 average rating, 20 reviews

Charming retreat near Windham NY

Apr 8 – 15

ﺩ.ﺇ496 per night

Show all

Other great vacation rentals in Windham

Guest favorite

Guest suite in Windham

5.0 out of 5 average rating, 35 reviews

Cozy 2 bedroom apartment with private entrance

Apr 16 – 23

ﺩ.ﺇ580 per night

Guest favorite

Condo in Windham

4.97 out of 5 average rating, 58 reviews

Beautiful, modern, newly remodeled 1 bedroom condo

Jun 8 – 15

ﺩ.ﺇ669 per night

Guest favorite

Home in Windham

4.96 out of 5 average rating, 54 reviews

The Ski Ranch – 5min from Windham Mountain

May 12 – 19

ﺩ.ﺇ1,336 per night

Guest favorite

Home in Hunter

5.0 out of 5 average rating, 59 reviews

Modern House with Mountain View @Getawind

Apr 26 – May 3

ﺩ.ﺇ2,638 per night

Guest favorite

Home in Windham

5.0 out of 5 average rating, 33 reviews

NEW stylish Farm house on the golf course

Jan 14 – 21

ﺩ.ﺇ3,654 per night

Guest favorite

Chalet in Windham

4.99 out of 5 average rating, 84 reviews

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

Sep 24 – Oct 1

ﺩ.ﺇ2,877 per night

Guest favorite

Guesthouse in Windham

4.99 out of 5 average rating, 93 reviews

Alpine Chalet on Spectacular Property

Jul 9 – 16

ﺩ.ﺇ842 per night

Guest favorite

Vacation home in Windham

4.93 out of 5 average rating, 58 reviews

Farmhouse Chic with Mountain and Lake Views

Apr 1 – 8

ﺩ.ﺇ1,713 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
ﺩ.ﺇ257 before taxes and fees

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 townhouse rentals in Windham?
Experience the best of Windham with our townhouse 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.
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.
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 condo rentals in Windham have wifi?
Absolutely! We offer over 20 condo 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 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 70 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!

Windham vacation rentals

Top-rated vacation rentals in Windham

Vacation rentals for every style

Chalets

Houses

Hotels

Popular amenities for Windham vacation rentals

Stay near Windham's top sights

Other great vacation rentals in Windham

Cabin in Preston-Potter Hollow

Cabin in Maplecrest

Home in Durham

Cottage in Gilboa

Home in Windham

Cottage in Roxbury

Home in East Jewett

Home in Durham

Other great vacation rentals in Windham

Guest suite in Windham

Condo in Windham

Home in Windham

Home in Hunter

Home in Windham

Chalet in Windham

Guesthouse in Windham

Vacation home in Windham

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 vacation rentals with a dedicated workspace in Windham?

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

Are there pet-friendly vacation rentals in Windham?

Do cabin rentals in Windham have self check-in?

Do condo rentals in Windham have wifi?

Do house rentals in Windham have a bbq area?

Do house rentals in Windham have a gym?

Are there family-friendly townhouse 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