Family-friendly holiday rentals in Windham

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Top-rated family-friendly rentals in Windham

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Guest favourite
An inviting interior features custom birch furniture, including a love seat and a dining table with two chairs. A small wooden coffee table enhances the cozy atmosphere. Natural light filters through patterned curtains, while a retro-style fridge adds a pop of color.
Dome in Hensonville
4.89 out of 5 average rating, 183 reviews

Catskill Domeo- Magical, Romantic and Unique Geodesic Dome

CatskillDomeo, bringing the nature inside! Soak up the cozy, romantic ambiance under the stars and moon skylights. This one-of-a-kind retreat features bespoke furniture and lighting, fabrics, and art inspired by mountain scenery and wildlife. This Geodesic Dome is 12 feet tall at peak, located in host's backyard. Ground level features custom-built birch furniture, love seat, large bay window, bedroom with full bed, table, chairs, bench/coffee table. Bathroom: standing shower with RV toilet. Small loft with sitting area, star and moon skylights add romantic atmosphere and sky view at night. Experience the sweetest, romantic and most unique Dome in the Catskills! Right in our back yard! Truly magical Glamorous Camping experience! (Glamping) Domeo is 12 feet tall at peak, has two stars for skylights, and a moon window in addition to a large bay window. Ground level: Custom built Birch Table, two chairs, bench (used for extra sitting when renting for 4, or as a coffee table when renting for 2), bedroom with 1 full/double bed. Custom built birch love seat, custom built birch vanity/sink, retro style fridge and microwave. Coffee maker, electric water kettle. Cedar sliding barn door with birch moon for bathroom entry, custom made. Birch tree and it's lights add romantic ambiance day or night. Small loft with a double/full foldable mattress for sitting (when renting for 2) or additional sleep space (when renting for 4). If you are booking for two, only the main bed will be made. Loft mattress is to be used as a SEAT ONLY, unless otherwise requested in advance, and set up by us ($25 additional fee applies for the setup). When booking for 3 or 4, loft mattress will be set up as bed (at no extra fee). Please Note: you are welcome to grill and cook outside (grill also has a gas burner). Inside you can use Microwave to re-heat food, coffee maker and electric water boiling kettle. Our Domeo is equipped with AC in the summer, heaters in the winter. This is a tent and you are camping, please keep this in mind. In the very cold winter days (below 0 F) temperature inside might not raise above 72 degrees F, so feel free to bring extra blankets, sweaters, etc in case you need them. In the summer, our Geodesic Dome is equipped with an AC and it cools the Glamping Dome nicely, but you should still keep in mind you are in a tent, not a house. We require that heaters and AC are used on Low or Medium setting only. Our Domeo is located in our back yard, and we are located in Town of Hensonville, NY (part of Windham, NY) NOTE: Cell phone reception is very spotty in our town. You can log in to WI-FI to make phone calls. You are welcome to use the back yard around the dome area. House, front yard etc are NOT a part of this rental. We live on the property but if not there, we are also available via phone, email and/or text. The quaint Catskills hamlet of Hensonville is just two miles from Ski Windham and seven miles from Hunter Mountain. Explore hundreds of acres of picturesque state forest preserves, hike or bike to nearby C.D. Lane Park or BlackDome State Forest. Dome is situated in host's backyard, 25 feet from the house. Located in town, not in the woods. Walking distance to local diner, bar and restaurant. Location ideal for skiing, hiking, mt. biking, hunting or just relaxing. Several golf courses nearby. Free Village Shuttle to downtown Windham and Windham Mountain base during winter on weekends and holidays! Local cab services throughout the mountaintop are also available, as well as Lyft and Uber. You can get here by Bus from NYC, which will leave you within a short 2 minutes walk! ★ Please Note: We require an authorization hold for any damages and/or violation of house rules that leads to additional expenditures. Usually the required authorization hold is for $200 - but it varies depending on length of stay and number or age of guests. Hold gets released/voided after check out. It is to make sure there's no damage, no smoking inside or within 10 feet of the dome, place is left in neat condition and check out list is followed (lowering heaters, removing garbage, putting dishes away etc). Please see our "House Rules" for full details and Rental Agreement. ★ Cell phone reception is spotty in our town. There is WIFI at the house. ★ We supply things to start you off with. Grocery store is within 10 minutes walk if you need more or other supplies etc. ★ Domeo has an RV / self sustained toilet. We recommend that you use public restrooms anytime you are out. The tank holds 5.3 gallons of waste total which should be more than sufficient for at least 3 night stay. There is a $25 charge each time you need to empty or exchange the tank during your stay, unless you are using it more than 3 nights. We will supply you with RV toilet paper, which is the only thing you should use in the toilet. Please be Frugal and keep in mind that you are camping and not on a "City septic" setup. No wipes or feminine products should ever be flushed. ★ Cooking is allowed outside on the provided grill which also has a gas burner. Inside guests can use microwave to re-heat food, coffee maker and electric water boiling kettle. ★ Only the amount of people that you book for are allowed in the unit at any time. ★ Check In/Check Out: Domeo is ready for guests from 3:30PM on the day of arrival. Check out hour is at or before 11AM. Earlier check in or later check out might be available for a fee, but can only be confirmed last minute, if there are no guests checking out on your arrival day, or checking in on your departure day. ★ When booking for two, only the main bed will be made. Loft mattress is to be used as a SEAT ONLY, (see pictures) unless otherwise requested in advance, and set up by us. $25 additional fee applies for the setup. When booking for three or four, the top mattress will be made as a bed (at no additional fee). ★ SAME DAY BOOKINGS/ARRIVALS: if you're booking the day you would like to arrive, please know that it may take few/several hours to prepare and/or heat the place for you. If you spontaneously decide that you would like to visit Catskill Mountains please check if our Domeo is available for your last minute getaway trip. We welcome last minute guests! ★ Contact owner if you're looking for a larger unit or a cabin. ★ We are located in Town, not in the woods, in walking distance from a diner, post office, bar etc. ★ This is a tent and you are camping, please keep this in mind. In the very cold winter days (below 0 F) temperature inside might not raise above 72 degrees F, so feel free to bring extra blankets, sweaters, etc. In the event of extremely cold temperatures we reserve the right to cancel your booking (for your and our property safety), and will issue a refund.

Top guest favourite
An open floor plan living area features vaulted wooden ceilings and large windows offering views of the outdoors. Comfortable seating areas include a tan couch, black chairs, and a decorative coffee table. A dining space with a large table and an island kitchen is also visible.
Chalet in Windham
4.98 out of 5 average rating, 168 reviews

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

Plan your all-seasons escape to this gorgeous new mid-century modern chalet with can't-beat direct views of Windham Mtn, less than a 5 minute drive away. Situated between state land and an active creek, enjoy this mountain getaway's hot tub, firepit, game room, open floor plan and other luxury 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!

Top guest favourite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties
5 out of 5 average rating, 102 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Top guest favourite
The exterior of a charming A-frame house is depicted under a dusk sky, adorned with warm lights that outline the roof. A welcome sign is displayed beside a green front door, which is enhanced by a decorative wreath. Soft landscaping and pathway lighting create a cozy ambiance.
Home in Windham
4.99 out of 5 average rating, 393 reviews

Private cabin - 7 mins from ski mountain

This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

Guest favourite
Apartment in Windham
4.9 out of 5 average rating, 228 reviews

Hideaway Windham/Hunter Fireplace, Snow & Skiing

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.

Top guest favourite
A cozy living space features a gray sectional sofa adorned with textured pillows and a soft throw. A rustic wooden coffee table sits within reach, complemented by a gas fireplace framed in warm wood. Natural light floods the area through a skylight, enhancing the inviting ambiance.
Guest house in Windham
4.99 out of 5 average rating, 186 reviews

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.

Superhost
An outdoor seating area is presented alongside a hot tub and a fire pit. The seating features a sectional sofa with light-colored cushions. Dividing panels with a leaf design create a sense of privacy, while surrounding trees provide a natural backdrop.
Cabin in Prattsville
4.87 out of 5 average rating, 293 reviews

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

Top guest favourite
Cabin in Windham
4.96 out of 5 average rating, 180 reviews

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.

Top guest favourite
A warm and inviting living space is seen, featuring a round wooden dining table surrounded by four rustic chairs. An adobe wood-burning fireplace is visible in the background, with seating arranged nearby for relaxation. Natural light flows in through a window, enhancing the cozy atmosphere.
Home in East Jewett
4.98 out of 5 average rating, 102 reviews

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.

Top guest favourite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top
4.99 out of 5 average rating, 134 reviews

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Top guest favourite
An outdoor deck area features a hot tub surrounded by a wooden railing. Two comfortable chairs and a wooden table provide a relaxing spot to enjoy the scenery. Large windows reflect a serene natural setting, enhancing the peaceful atmosphere of the cabin.
Cabin in Windham
4.98 out of 5 average rating, 161 reviews

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing pond and a deck offering panoramic resort views, it's a perfect outdoor retreat. Inside, enjoy a pool table, Pac-Man arcade, and shuffleboard for endless fun. A 2-minute drive to town makes dining and shopping convenient. The cabin's modern amenities, cozy fireplace, outdoor firepit, and hot tub guarantee a comfortable and relaxing stay.

Guest favourite
Guest suite in Windham
4.93 out of 5 average rating, 121 reviews

Cozy Cabin Condo by the Mountain, 5mins to skiing!

Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from the slopes of Windham and just 15 minutes from Hunter! A short walk or drive from the charming town of Windham, you're perfectly located for a country getaway. The town itself is a wonderful mountain community with many great shops, restaurants and activities all within a short drive.

Popular amenities for Windham family-friendly rentals

When is the best time to visit Windham?

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Avg. price$644 SGD$668 SGD$522 SGD$383 SGD$400 SGD$445 SGD$460 SGD$465 SGD$417 SGD$442 SGD$471 SGD$610 SGD
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Quick stats about holiday rentals that are family-friendly in Windham

  • Total holiday rentals

    Explore 160 holiday rentals in Windham

  • Nightly prices starting at

    Windham holiday rentals start at $114 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,920 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 60 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

    160 of Windham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Windham rentals

  • 4.9 Average rating

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

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