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Holiday rentals in Windham

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Quick stats about holiday rentals in Windham

  • Total holiday rentals

    Explore 170 holiday rentals in Windham

  • Nightly prices starting at

    Windham holiday rentals start at $115 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,500 verified reviews to help you choose

  • Family-friendly holiday rentals

    160 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    170 of Windham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Windham rentals

  • 4.9 Average rating

    Windham stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Windham

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

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Guest favourite
Chalet in Windham

Beautiful Windham Ski/Summer House

A spacious 4 bedroom house located in Windham, NY just 5 minutes from the mountain. Built in 2012. Brand new comfy couches just purchased March 2021. Beautifully decorated with large wood doors, stone fireplace, and granite countertops. Wake up to view of the slopes from the large windows. Truly breathtaking views year round. Four bedrooms three with queen beds and 1 with a bunk beds (full size beds/twin trundle on the bottom). Plus a couch located in the loft area. The house sleeps 12. Full basement with television and couch with a ping pong table, a basketball game and a fooseball table. There are 3 full bathrooms along with one half. The main floor has a fire place along with tv and a full kitchen and dining area all with full views of Windham mountain. Come see the leaves turn and enjoy Great hiking, biking, golf and skiing when the snow comes. One mile from town and Windham Mountain. Pricing for a week goes from Friday to Friday. Renters must be at least 25 years old. Please no pets are allowed at the house, this is a strict policy no exceptions. No parties allowed Cleaning fee additional Christmas and New Years week have a 4 day min. and MLK and Presidents day week have a 3 day min.

4.88 out of 5 average rating, 194 reviews
Top guest favourite
A spacious kitchen features modern blue cabinetry and light countertops, complemented by natural light from large windows. An island with seating offers additional workspace, and hanging cookware is neatly arranged above, providing a practical yet stylish cooking environment.
Home in Windham

Cozy Modern: Views, 3 min ski, fire pit, game room

Welcome to Windy Hollow! A spacious and newly renovated vacation home with stunning views of Windham Mtn and a block to town. Thoughtfully designed to provide multiple gathering spaces for guests over two levels. We are ideally setup for families & groups. Ski the slopes, hike the trails, bike, golf, swim in the lakes, enjoy a winery, fancy the spa, visit our wonderful local restaurants. However you decide to spend your vacation, Windy Hollow offers a home-away-from-home experience year-around.

4.98 out of 5 average rating, 40 reviews
Top guest favourite
The living room features a modern design with tall windows allowing natural light to fill the space. A black fireplace serves as a focal point, surrounded by comfortable seating. A cozy area rug enhances the atmosphere, while decor items add subtle artistic touches.
Cabin in Windham

Catskills Designer Retreat near Hiking + Swimming

★ One of Airbnb’s Most-Loved Design Homes in the Catskills ★ Relax & recharge at Casa Magda—a design-forward retreat on 9 acres in Windham, just 2.5 hours from NYC. Perfect for design lovers and nature seekers, this renovated 1980s gem blends modern style w/peaceful seclusion. Unwind in the hot tub, cozy up by the fireplace w/a record, or gather around the firepit beneath star-filled skies. Explore nearby restaurants and trails, ski Windham Mountain 7 mins away or head to Hunter in 15 mins.

4.97 out of 5 average rating, 142 reviews
Luxe
The spacious living area features high, vaulted ceilings with natural wood beams and an elegant antler chandelier. Large windows allow abundant natural light, offering views of the surrounding greenery. A central coffee table is complemented by a cozy sofa and several armchairs, creating an inviting atmosphere.
Cabin in Windham

NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym

Immerse yourself in luxury at Timber Trail Lodge, an opulent 5-bedroom, 4 full bathroom estate nestled in Windham’s premier location. This expansive 4,000 ft² home offers the ultimate mountain escape, high-end amenities such as a modern spa, chef’s kitchen, Sonos, and an outdoor fire pit, perfect for entertaining. Adventure seekers can enjoy a private zip-line and proximity to Windham Mountain 8 minutes away. Timber Trail Lodge combines modern comfort, outdoor fun, and serene Mountain View’s

5.0 out of 5 average rating, 45 reviews
Guest favourite
Cabin in Windham

Cozy Family-Friendly A-Frame - Windham with AC

Escape to this peaceful A -Frame mountain retreat in the Catskills. Windham is know as the “Gem of the Catskills” and was recently named as a big charm town and perfect for a weekend getaway in New York by World Atlas. Only 5 minutes from Windham Mountain with skiing and snowboarding, hiking, golfing, restaurants and shops. Relax and enjoy with the whole family and friends around the fireplace, game room, or large deck. We believe without a doubt you will love this home as much as we do!

4.96 out of 5 average rating, 24 reviews
Guest favourite
An above ground pool is situated in a spacious yard surrounded by lush greenery. The pool's clear blue water reflects the sky, while a nearby patio area is equipped with seating and umbrellas. A charming red house serves as a backdrop, completing the serene outdoor scene.
Home in Windham

Luxury Windham | 6BDRM, Pool, Hot Tub & Movie Room

A spectacular six-bedroom estate blending refined luxury, comfort, and privacy. Nestled within the exclusive Dingley Dell Estate, just six minutes from Windham town and 25 minutes from Hunter Ski Resort. Enjoy beautifully landscaped grounds, inviting outdoor spaces, complete privacy, and breathtaking mountain views. Fully renovated for exceptional comfort, the home features a private pool, movie room, premium sound system, and everything needed for an unforgettable luxury mountain escape.

4.95 out of 5 average rating, 109 reviews
Top guest favourite
Chalet in Windham

Stargazing Dome|Sauna|Firepit|HotTub|Pet Frndly

Now featuring our brand-new GeoDome Lounge in Windham, NY Nestled in the heart of the Catskills, this Windham retreat is just 5 minutes away from Windham Mountain resort! Wake up to breathtaking views of Windham Mountain, with skiing, hiking, biking, and more just minutes away. After exploring, unwind in the hot tub, rejuvenate in the sauna, relax in the NEW dome lounge, walk around the 1.4-acre property, or gather around the fire pit. Our mountain escape invites unforgettable memories.

4.98 out of 5 average rating, 101 reviews
Top guest favourite
The living room features a wall of large windows that offer views of surrounding mountains. A combination of leather and upholstered seating is arranged around a coffee table, with a light area rug underfoot. Wooden ceilings and natural light contribute to a spacious atmosphere.
Chalet in Windham

Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm

Plan your all-seasons escape to this beautiful, luxury chalet with direct views of Windham Mt., just a 5 minute drive to the slopes. Situated at the end of a private road on 3+ acres, enjoy this mountain getaway's hot tub, oversized deck, pond, firepit, huge game room, and other modern amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

4.98 out of 5 average rating, 175 reviews
Guest favourite
An A-frame cabin is nestled among snow-covered trees, showcasing large glass windows that reflect the sunset sky. The deck extends outward, surrounded by a natural landscape of snow and evergreens, creating a serene and inviting atmosphere.
Cabin in Windham

The Windham A

Discover year-round comfort and style at this beautifully designed A-frame cabin just 5 minutes from Windham Mountain and 20 minutes from Hunter Mountain. With 3Beds, 3Baths, and a loft, this modern retreat is perfect for families, couples, or friends seeking a peaceful escape in the Catskills. Step downstairs to a fully finished basement that features a game room, private theater room, and a stylish bar area—perfect for après-ski gatherings, movie nights, or fun with friends and family.

4.95 out of 5 average rating, 40 reviews
Guest favourite
The chalet stands amidst vibrant autumn foliage, showcasing a green exterior and a spacious deck. The well-maintained yard features a lush green lawn, with a variety of trees surrounding the property that enhance the natural setting.
Guest house in Windham

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

4.98 out of 5 average rating, 198 reviews
Top guest favourite
Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

4.99 out of 5 average rating, 158 reviews
Top guest favourite
Cabin in Windham

Cozy Creekside Cabin | 5 Mins to Windham Mt!

Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

4.95 out of 5 average rating, 231 reviews

Popular amenities for Windham holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Windham's top sights

Windham Mountain

786 locals recommend

Windham Theatre

64 locals recommend

Briars & Brambles Books

37 locals recommend

Other great holiday rentals in Windham

Top guest favourite
Home in Windham

Modern Forest Retreat with Hot Tub and Sauna

5.0 out of 5 average rating, 19 reviews
Top guest favourite
A modern kitchen is showcased with a large island featuring ample seating for six. Stainless steel appliances, including a refrigerator and a microwave, complement white cabinetry. Natural light enters through windows above the sink, highlighting the open space and wooden ceiling beam.
Home in Windham

Beautifully restored 6 BR in the heart of Windham

4.98 out of 5 average rating, 58 reviews
Top guest favourite
The spacious living area is defined by a high wood-beamed ceiling and large windows that offer views of the surrounding greenery. A stylish pool table is centered in the room, surrounded by various seating options, including a sectional sofa in muted tones and accent chairs.
Home in Windham

Family-ready retreat, games and BBQ

5.0 out of 5 average rating, 55 reviews
Top guest favourite
A spacious living area features high wooden ceilings and large windows that provide abundant natural light. A comfortable sofa and armchairs are arranged around a central coffee table, while a television is mounted on a wooden wall. A dining area with a table for six is visible in the background.
Home in Windham

Modern Ski House Minutes From The Slopes

4.94 out of 5 average rating, 94 reviews
Guest favourite
Apartment in Windham

Slope Side Luxe | Views, Decks, Walk to Mtn & Town

4.98 out of 5 average rating, 45 reviews
Top guest favourite
A spacious living area contains a light grey sofa with decorative pillows and a wooden coffee table on a patterned rug. Large windows allow natural light to filter in, highlighting a green potted plant. A red wood stove is visible on the side.
Cottage in Windham

Cozy Cottage Retreat Close to Main St/Windham Mtn

4.99 out of 5 average rating, 70 reviews
Guest favourite
Home in Windham

Luxury Modern Windham 5BR/4.5BA, Sleeps 12.

5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Windham

Comfy-Cozy Quads Hideaway

4.87 out of 5 average rating, 15 reviews

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$638 SGD$603 SGD$512 SGD$448 SGD$448 SGD$448 SGD$438 SGD$460 SGD$405 SGD$448 SGD$448 SGD$598 SGD
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Windham?

    Many travelers choose accommodations near Main Street or by Windham Mountain for walkable access to restaurants, trails, and seasonal activities. Vacation rentals, cabins, and historic inns are frequently suggested for a variety of group sizes.

  • What are the best things to do in Windham with kids?

    Families often enjoy the Windham Path, kid-friendly activities at Windham Mountain Adventure Park, and interactive workshops at local art centers. Community events and small farms also create opportunities for hands-on learning.

  • What are some of the best things to do in Windham?

    Explore skiing or biking at Windham Mountain, enjoy walking Main Street’s shops and galleries, and unwind in local parks. Seasonal festivals and outdoor adventure activities are central to the area’s rhythm.

  • How is the weather in Windham?

    Windham has cold, snowy winters around 16–38°F (-9–3°C) and mild summers near 62–84°F (17–29°C), with rain scattered throughout the year. Layered clothing and waterproof gear help adjust to quick weather changes in the mountains.

  • When is the best time to visit Windham?

    Late spring through early fall is often recommended for mild temperatures and outdoor festivals, while winter draws those interested in skiing and snow activities. Each season highlights a different side of Windham's landscape and community events.

  • What are the best places to visit in Windham?

    Explore Windham Mountain for skiing or mountain biking, stroll the picturesque Main Street shops, or wander local galleries. Nature parks around Windham showcase scenic trails and peaceful views.

  • What are some hiking trails in Windham?

    Try the Windham Path for a gentle, scenic walk, or the Windham High Peak Trail for more elevation and wide-ranging views. Nearby preserves feature routes through mixed forests and lively streams.

  • What are some family activities we can do in Windham?

    Families can explore easy trails at Windham Path, enjoy outdoor adventures at Windham Mountain Adventure Park, or visit local farms for hands-on experiences. Main Street provides ice cream shops and cozy cafes for relaxed outings.

  • What are some of the best day trip ideas from Windham?

    Explore nearby state parks with waterfalls, wander through small Catskill towns known for arts and antiques, or visit historic sites that share the region’s story. Outdoor enthusiasts frequently suggest hiking, swimming, or seasonal festivals in the surrounding countryside.

  • Are there any pet friendly accommodations available in Windham?

    Windham has a range of pet-friendly accommodations, including cabins, lodges, and vacation rentals. You can explore options that welcome pets, making it easier to enjoy the area's outdoor spaces together.

  • What are some local tips for visiting Windham?

    Locals often suggest checking trail conditions before heading out, layering clothes for sudden weather changes, and visiting independent shops for regional treats. Early evenings are a popular time for gathering at local cafes or enjoying live music.

  • What is Windham known for?

    Windham is known for its mountain scenery, winter sports scene, and lively arts community. The town has a welcoming Main Street, access to hiking trails, and hosts community festivals throughout the year.

  • What are the best hidden gems to explore in Windham?

    Windham has quieter nature preserves, small art galleries, and locally owned shops that reveal a distinct character. Exploring forest trails or visiting a community farmers market gives a glimpse into local traditions.

  • What are the best foods to try in Windham?

    Windham has restaurants with locally sourced meats, New York-style pizza, and American comfort foods. Seasonal produce, baked goods, and offerings from regional breweries or cideries often feature on menus.

  • What should I bring for a trip to Windham?

    Pack layers for varied mountain weather, especially between seasons; waterproof outerwear is often useful. In winter, bring insulated clothing for 16–38°F (-9–3°C) temperatures, and consider sturdy footwear for trail exploration year-round.

  • What is the nightlife in Windham like?

    Nightlife in Windham consists of casual bars, taverns with live music, and local restaurants with relaxed atmospheres. Seasonal events sometimes feature evening entertainment or open-air concerts.

  • What are the most popular events or festivals in Windham?

    Windham hosts festivals with live music, craft vendors, and celebrated food traditions, often around holidays and during summer or fall weekends. Annual events at Windham Mountain, such as mountain biking and winter sports competitions, are also frequently suggested.

  • Are there family friendly vacation rentals in Windham?

    Windham has a variety of family-friendly vacation rentals, including multi-bedroom homes, cabins, and apartments with kitchen and outdoor space. Many are located near parks and recreation areas for convenient access to activities.

Destinations to explore