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 8 – 15

G$138,763 GYD 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 7 – 14

G$20,645 GYD per night

Guest favorite

Apartment in Windham

4.99 out of 5 average rating, 212 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 10 – 17

G$20,221 GYD per night

Guest favorite

Townhouse in Windham

4.91 out of 5 average rating, 112 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

G$36,005 GYD per night

Guest favorite

Cabin in Tannersville

4.99 out of 5 average rating, 146 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 17 – 24

G$30,267 GYD per night

Guest favorite

Cabin in Maplecrest

4.93 out of 5 average rating, 164 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.

Jul 23 – 30

G$35,087 GYD per night

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 134 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.

Jul 27 – Aug 3

G$22,952 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

Apr 24 – May 1

G$33,459 GYD 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 15 – 22

G$22,272 GYD 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!

Jul 13 – 20

G$38,257 GYD per night

Guest favorite

Condo in Hunter

4.98 out of 5 average rating, 538 reviews

Hunter Mtn Liftside Ski In/Out, Slopeside!

Fantastic location! Liftside! Beautifully renovated SLOPESIDE ski on/ski off condo . Spacious one bedroom condo with fully stocked kitchen, luxurious bathroom with jacuzzi tub, large bedroom with queen bed, and comfortable, cozy open concept living and dining room. Real wood burning fireplace. Private deck backs up to the ski slopes at Hunter Mountain! Seconds away from the Kaaterskill Flyer lift , main lodge, and bar. Avail for seasonal rental 11/15-4/15 $15000

Aug 5 – 12

G$22,678 GYD per night

Guest favorite

Home in Windham

4.99 out of 5 average rating, 319 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 :)

Jun 7 – 14

G$53,773 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

Cottage in Gilboa

4.94 out of 5 average rating, 201 reviews

Home Alone Mountain Retreat

Sep 16 – 23

G$31,224 GYD per night

Guest favorite

Condo in Hunter

4.97 out of 5 average rating, 428 reviews

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

Sep 20 – 27

G$22,975 GYD per night

Guest favorite

Apartment in Roxbury

4.93 out of 5 average rating, 215 reviews

"Your Country Getaway at Beulah Land Farm."

Apr 22 – 29

G$17,905 GYD per night

Guest favorite

Home in Durham

4.96 out of 5 average rating, 101 reviews

Wow! Panoramic Mountain View, Minutes to Windham!

Jan 29 – Feb 5

G$51,233 GYD per night

Guest favorite

Cabin in Preston-Potter Hollow

4.98 out of 5 average rating, 288 reviews

Casa Bella Vista with Great Views!

Oct 25 – Nov 1

G$34,146 GYD per night

Guest favorite

Home in Windham

4.93 out of 5 average rating, 166 reviews

Extreme leisure minutes from action and adventure

Jun 1 – 8

G$85,697 GYD per night

Guest favorite

Cottage in Roxbury

4.98 out of 5 average rating, 482 reviews

The Little House

Feb 19 – 26

G$28,047 GYD per night

Guest favorite

Home in East Jewett

4.99 out of 5 average rating, 193 reviews

Modern Ski-Home With Views Near Hunter & Windham

Mar 4 – 11

G$59,664 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

Mar 6 – 13

G$38,029 GYD per night

Guest favorite

Townhouse in Windham

5.0 out of 5 average rating, 59 reviews

Cozy, peaceful-3Br (5 beds)2.5 Bath townhouse

Sep 22 – 29

G$43,322 GYD 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

G$75,890 GYD per night

Guest favorite

Guesthouse in Windham

4.99 out of 5 average rating, 94 reviews

Alpine Chalet on Spectacular Property

Jul 8 – 15

G$47,125 GYD per night

Guest favorite

Home in Hunter

5.0 out of 5 average rating, 60 reviews

Modern House with Mountain View @Getawind

Feb 4 – 11

G$146,045 GYD 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

Jun 25 – Jul 2

G$151,192 GYD per night

Guest favorite

Vacation home in Windham

4.93 out of 5 average rating, 58 reviews

Farmhouse Chic with Mountain and Lake Views

Jan 30 – Feb 6

G$103,834 GYD per night

Guest favorite

Home in Hensonville

4.83 out of 5 average rating, 6 reviews

The Happy Hideaway- 2

Oct 10 – 17

G$22,480 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$14,605 GYD 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 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.
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 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 apartment rentals in Windham have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Windham have a bbq area?
Absolutely! We offer over 10 cabin 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 10 homes with a gym, over 50 homes with self check-in, over 70 homes with a bbq area, over 70 homes with wifi, 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

Cottage in Gilboa

Condo in Hunter

Apartment in Roxbury

Home in Durham

Cabin in Preston-Potter Hollow

Home in Windham

Cottage in Roxbury

Home in East Jewett

Other great vacation rentals in Windham

Condo in Windham

Townhouse in Windham

Home in Windham

Guesthouse in Windham

Home in Hunter

Chalet in Windham

Vacation home in Windham

Home in Hensonville

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 house rentals in Windham?

Are there pet-friendly vacation rentals in Windham?

Do house rentals in Windham have self check-in?

Do apartment rentals in Windham have wifi?

Do cabin 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