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

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

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.

Guest favorite

Townhouse in Windham

4.91 out of 5 average rating, 109 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.

Guest favorite

Cabin in Tannersville

4.99 out of 5 average rating, 144 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.

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 132 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.

Guest favorite

Condo in Hunter

4.97 out of 5 average rating, 427 reviews

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

Guest favorite

Tiny home in Lexington

4.95 out of 5 average rating, 299 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)

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.

Guest favorite

Apartment in Freehold

5.0 out of 5 average rating, 222 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!

Guest favorite

Condo in Hunter

4.98 out of 5 average rating, 535 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

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 :)

Guest favorite

Tiny home in Saugerties

4.94 out of 5 average rating, 218 reviews

Gorgeous Tiny House with Mountain View

Enjoy our little cabin and feel off the grid, without being far from the charming village of Saugerties and close to Woodstock. Enjoy the beautiful Catskills area and retreat in our beautifully renovated “tiny haven” ... complete with a Mountain View! “The Haven” at Blue Mountain! ******Can also be booked together with the Main House on the property, listed as Blue Mountain Haven! https://abnb.me/SMQTSu5LQpb

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 Durham

4.99 out of 5 average rating, 120 reviews

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

Guest favorite

Cabin in Chichester

4.99 out of 5 average rating, 514 reviews

Garden Cottage In The Catskills

Guest favorite

Cottage in Roxbury

4.98 out of 5 average rating, 478 reviews

The Little House

Guest favorite

Home in Durham

4.96 out of 5 average rating, 101 reviews

Wow! Panoramic Mountain View, Minutes to Windham!

Guest favorite

Cabin in Maplecrest

4.94 out of 5 average rating, 163 reviews

Fraxinus House - Ideal for Windham & Hunter

Guest favorite

Home in Windham

4.93 out of 5 average rating, 166 reviews

Extreme leisure minutes from action and adventure

Superhost

Condo in Windham

4.84 out of 5 average rating, 112 reviews

Studio 3 BEDS-SLEEP 4

Guest favorite

Home in East Jewett

4.99 out of 5 average rating, 192 reviews

Modern Ski-Home With Views Near Hunter & Windham

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Other great vacation rentals in Windham

Guest favorite

Townhouse in Windham

4.88 out of 5 average rating, 99 reviews

Windham Mountain Village 2 bedroom townhouse

Guest favorite

Townhouse in Windham

5.0 out of 5 average rating, 57 reviews

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

Guest favorite

Condo in Windham

4.97 out of 5 average rating, 58 reviews

Beautiful, modern, newly remodeled 1 bedroom condo

Guest favorite

Guest suite in Windham

5.0 out of 5 average rating, 35 reviews

Cozy 2 bedroom apartment with private entrance

Guest favorite

Guesthouse in Windham

4.99 out of 5 average rating, 91 reviews

Alpine Chalet on Spectacular Property

Guest favorite

Home in Hunter

5.0 out of 5 average rating, 57 reviews

Modern House with Mountain View @Getawind

Guest favorite

Home in Windham

4.96 out of 5 average rating, 54 reviews

The Ski Ranch – 5min from Windham Mountain

Guest favorite

Home in Windham

5.0 out of 5 average rating, 33 reviews

NEW stylish Farm house on the golf course

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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
$70 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 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 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 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 Cabin Rentals in Windham?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with self check-in, 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

Cabin in Durham

Cabin in Chichester

Cottage in Roxbury

Home in Durham

Cabin in Maplecrest

Home in Windham

Condo in Windham

Home in East Jewett

Other great vacation rentals in Windham

Townhouse in Windham

Townhouse in Windham

Condo in Windham

Guest suite in Windham

Guesthouse in Windham

Home in Hunter

Home in Windham

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 townhouse rentals with a dedicated workspace in Windham?

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

Do house 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 pet-friendly house rentals in Windham?

Are there family-friendly townhouse rentals in Windham?

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

Are there Windham vacation rentals on Airbnb with pools?

Destinations to explore