Town of Ashland, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Ashland, New York on RentalSaver.com!

Town of Ashland Rentals

From $361 per night (USD)
VRBO
Creek house with expansive mountain views
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to our creek house with expansive mountain views and open lush fields. After a long day of hiking, fishing, bike ...
From $361 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Summer fun in the Catskills
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This is a beautiful 1800sq ft. log home built on 8.5 sprawling acres. This private location will give you all the sereni ...
From $344 per night (USD)
Expedia
From $695 per night (USD)
VRBO
Mayfair Manor Mountain Retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Open the door to a great room with vaulted ceilings, stone fireplace, granite kitchen, large dining room and access to a ...
From $695 per night (USD)
VRBO
From $890 per night (USD)
Expedia
Spacious Residence Windham - XL Pool, Movie Room, Hot tub, 6 Bedrooms, Gardens
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Dingley Dell Estate has a long history starting from the British Era. Dingley Dell Estate was originally founded in Sout ...
From $890 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Windham/Hunter Modern Mountain Cabin on 22 acres
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax with family & friends at our serene & magical getaway! Set upon 22 acres, escape to nature, mountain views & inc ...
From $225 per night (USD)
VRBO
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Expedia
NEW! Pastoral Ashland Getaway w/ FIre Pit, Grill!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Leave skyscrapers and city slicking behind when you book this quaint, tranquil vacation rental in woodsy Ashland! This 2 ...
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Expedia
From $1346 per night (USD)
VRBO
Luxury Home on Windham Mountain! Walk to Slopes
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Come enjoy the finest that Windham Mountain has to offer in this spacious, contemporary ski home with breath-taking moun ...
From $1346 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Cutest Cabin in Windham walking trail to MTN views corn hole mini golf BBQ grill
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Cutest Cabin is the perfect stay for 2 people! Located only minutes away to town & ski slope-snow tubing Across the ...
From $196 per night (USD)
Expedia
From $767 per night (USD)
VRBO
Chalet Eglantine Mountain Retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Come to the Catskills and enjoy this Modern Ski Chalet nestled on 7.2 private acres with Impeccable 2,400 foot elevation ...
From $767 per night (USD)
VRBO
$\nStunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna$
From $846 per night (USD)
VRBO
\nStunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Brand new four bedroom cozy log home (Chalet style) nestled on 4 acres on a quiet mountain road. Easily sleeps 10 pe ...
From $846 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Holly Lodge - Ski Windham, Hunter, Catskills
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: Welcome to Holly Lodge in Windham, NY, recently renovated house that has the thoughtful charm to be your home a ...
From $531 per night (USD)
VRBO
From $552 per night (USD)
VRBO
DREAM LOG CABIN 110 Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Tucked away on 110 acres of stunning Catskill Mountain landscape, this charming log cabin awaits any family looking for ...
From $552 per night (USD)
VRBO
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VRBO
Extreme Leisure Minutes from Action and Adventure
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Relax and unwind in uniquely styled home on secluded 14-acre private property. Conveniently located to Windham mountain, ...
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VRBO
From $1380 per night (USD)
Expedia
A'Neils Windham Ski Lodge & Family Retreat
Bedrooms:
9
Bathrooms:
10
Sleeps:
30
This historical Inn is just minutes from the Windham Ski area, as well as 2 professional golf courses, a vineyard, numer ...
From $1380 per night (USD)
Expedia
From $711 per night (USD)
VRBO
(New Listing) Beautiful mountain home on private road
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Newly Listed!! Beautiful mountain home located on a quite private road. This is a large 5 bedroom home only a few minute ...
From $711 per night (USD)
VRBO
From $189 per night (USD)
VRBO
Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
This is a comfy 3-bedroom cottage perfect for unwinding with friends and family. It is small, cozy, and has a wonderful ...
From $189 per night (USD)
VRBO
From $867 per night (USD)
VRBO
Majestic estate in the mountains, over two acres of park-like land,...
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Hilltop Mountain Home Majestic estate in the mountains, over two acres of park-like land, secluded, gorgeous mountain v ...
From $867 per night (USD)
VRBO
From $1000 per night (USD)
VRBO
HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to a wonderful oasis of tranquility. Beautiful bright A-frame home sited on 10 secluded private acres with open ...
From $1000 per night (USD)
VRBO
From $753 per night (USD)
VRBO
Hill Top Villa - 6 bedroom, 4 bathrooms, hot tub, Movie Room, Windham 10min
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
A luxury retreat in the mountains! (Only few mins to Windham/Hunter). This six bedroom/dual lounge/4 bathroom house is f ...
From $753 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Red Fox T.H. & Spa hot tub - mini golf tee off & outside living room & firepit
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Red Fox Townhouse is located in Windham! ...
From $305 per night (USD)
Expedia
From $1183 per night (USD)
VRBO
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Welcome to your Windham Retreat! Enjoy incredibly easy access to some of the best skiing in New York. This home has all ...
From $1183 per night (USD)
VRBO
From $293 per night (USD)
VRBO
Private 7-Acre Retreat: On-Site Pond, Streams
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Seeking some peace and quiet? You’ll find it all, plus stunning views and outdoor entertainment, at this Jewett vacation ...
From $293 per night (USD)
VRBO
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VRBO
Tranquil Cozy Retreat: Views, Brook, Fire Pit, Ski, Hunter, Windham
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to the serene beauty of the Catskills and immerse yourself in the tranquility of our charming Jewett Cabin. This ...
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VRBO
From $854 per night (USD)
VRBO
Stunning Chalet style home with 8 Person Hot Tub, Fire pit & Sauna & steam rm.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
A spectacular open floor plan with a gas fireplace and grand dining room. The entryway has a custom wet bar with wine fr ...
From $854 per night (USD)
VRBO
From $806 per night (USD)
VRBO
Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
*WELCOMING INQUIRIES FOR SKI SEASON 2025-26, and SUMMER-FALL GUESTS!!!** Perfect Windham Mountain slope side chalet. ...
From $806 per night (USD)
VRBO
From $1610 per night (USD)
Expedia
Serene Catskills Escape: Hot Tub, Pond & Game Room
Bedrooms:
3
Bathrooms:
8
Sleeps:
22
Welcome to Bella Vista — your serene Catskills escape where mountain charm meets luxury living. Whether you’re planning ...
From $1610 per night (USD)
Expedia
From $573 per night (USD)
VRBO
Windham Pines Lodge & Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Split level home with Hot Tub and Outdoor Firepit. Conveniently located on private road just 5 miles from Windham Ski ar ...
From $573 per night (USD)
VRBO
From $281 per night (USD)
Expedia
Newly Built 1200sq ft Guest House 4min to Ski & Hiking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful newly built 1200 sq ft cozy log guest house, w vaulted ceiling’s and a gas fireplace for a charming indoor exp ...
From $281 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Grand Windham Retreat w/ Fire Pit & Game Room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Leave all your troubles behind and let the fresh air at this Windham vacation rental take over! This 2-bedroom, 2-bathro ...
From $500 per night (USD)
VRBO
From $203 per night (USD)
VRBO
Seasonal rental: Pet friendly home near Windham and Hunter Ski Resorts
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New, three bedroom, two bath home on three acres, conveniently located a 10 minute/5 mile drive from Windham Ski Mountai ...
From $203 per night (USD)
VRBO
From $1448 per night (USD)
VRBO
Just 6 minutes from Windham Mountain
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Welcome to Antler Ridge Estates! A beautiful, fully furnished, modern but rustic log cabin nestled in the Catskill Mount ...
From $1448 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Stunning Custom Built Lodge on Secluded Streamside Acreage w/ Breathtaking Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
This exquisite custom built full amenity lodge home is located in the heart of the Catskills near the Hunter and Windham ...
From $522 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Fantastic 2 family vacation home with EV charger
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
The perfect luxury vacation gettaway! Fully equipped with everything you need to relax after a day out. Minutes from Win ...
From $270 per night (USD)
VRBO
From $680 per night (USD)
VRBO
Vintage Charm Farmhouse Retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Come and enjoy the mountains all year round! This Farmhouse is conveniently located within minutes from Windham and Hunt ...
From $680 per night (USD)
VRBO
From $2298 per night (USD)
VRBO
*The View* ski in/out modern luxury at Windham Mountain Resort
Bedrooms:
6
Bathrooms:
5
Sleeps:
14
The View is a spectacular new house at the top of Windham Mountain. Ease of ski in/out with all the amenities, from expa ...
From $2298 per night (USD)
VRBO
From $716 per night (USD)
Expedia
Panoramic views four minutes to Windham Mountain skiing.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to the Windham Round Haus located just minutes from Windham Mountain. Our home is located on a private street a ...
From $716 per night (USD)
Expedia
From $741 per night (USD)
VRBO
Windham Mountain Escape - 5bd/4ba Private Home
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Escape to the Catskills and visit this Windham Mountain Home. Stay in this 2 floor, 5 bedroom, 4 bathroom house on a pr ...
From $741 per night (USD)
VRBO
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Expedia
Cozy mountain home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Come enjoy our mountain getaway nestled in the Great Northern Catskills. Our newly updated home is set on 3.5ac with sce ...
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Expedia
From $299 per night (USD)
VRBO
Relaxation Retreat: Home w/Hot Tub, Gym & Sauna
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Come escape the city in this beautifully renovated home, less than 10 minutes from Windham Mountain! This 3 Bed ...
From $299 per night (USD)
VRBO
From $211 per night (USD)
VRBO
Charming Ashland Cottage on 5+ acres—minutes to Windham Mountain
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This retreat, located on over 5 private acres, is just 10 minutes to downtown Windham’s restaurants, bars, local shops a ...
From $211 per night (USD)
VRBO
From $507 per night (USD)
VRBO
Catskills Cabin Retreat: Wood Fired Hot Tub, Firepit & 7 Private Acres
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Welcome to our cozy Catskills retreat, where rustic charm meets modern comfort. Nestled on nearly 7 private wooded acre ...
From $507 per night (USD)
VRBO
$Cozy Cabin Getaway in Windham Catskill Mountains\n$
From $567 per night (USD)
Expedia
Cozy Cabin Getaway in Windham Catskill Mountains\n
Bedrooms:
2
Bathrooms:
5
Sleeps:
15
Welcome! You are viewing our cozy 3500-square-foot cabin tucked away on 5.80 acres in the beautiful and scenic hills of ...
From $567 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to Walnut Grove, your cozy ski retreat near Hunter and Windham! Nestled amidst beautiful black walnut trees, thi ...
From $354 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Charming 3 bedroom, 2 bathroom chalet on the mountain!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Well lit, open floor plan, with wood burning fireplace. You'll be staying right on Windham Mountain - so close to skiin ...
From $270 per night (USD)
VRBO
From $431 per night (USD)
VRBO
Magical Home Located in Windham and Catskills
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Let this Magical Home take you away to your special place in the Catskills. Located nearby the town of Windham and less ...
From $431 per night (USD)
VRBO
From $774 per night (USD)
VRBO
Casa Magda - Designer Home near Hiking + Swimming
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Relax and recharge at Casa Magda—a design-inspiring home on 9 acres in Windham, NY—just 2.5 hrs north of NYC! ...
From $774 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Tiny House on Walnut Grove
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to this charming cottage minutes from Windham and Hunter Mountains. This terrific one-bedroom retreat features ...
From $226 per night (USD)
VRBO
From $3201 per night (USD)
Expedia
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
This Windham cabin minutes from Hunter and Windham Mountains, boasts 6 inviting bedrooms, including 1 king bed, 4 queen ...
From $3201 per night (USD)
Expedia
From $321 per night (USD)
VRBO
Rustic-Chic Farmhouse w/ Firepit, Close to Windham Ski & Catskills Adventures!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to Catskill Park Farm, your Windham escape where rustic charm meets modern comfort on a sprawling, secluded lot. ...
From $321 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Stylish, Luxury Mountain House 10 Mins to Windham
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
Come unwind, play and reconnect with the magic of nature in your own private mountain paradise, close to all the fun! 🌲 ...
From $567 per night (USD)
Expedia
From $998 per night (USD)
VRBO
Cozy Lux Mountain Lodge-Hot Tub-Mountain Views-10min to Skiing-Windham Hunter
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
KEY FEATURES: • Sleeps 10 with 4 queen beds and 1 king bed • Views, Views, Views! Our home, at the end of a cul-de-sac, ...
From $998 per night (USD)
VRBO
From $405 per night (USD)
VRBO
Sauna, Mnt Views, Hot tub, <2 mins to slopes
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You'll love our Ski house for your trip to Windham Mountain! Here's why: - Centrally located to 2 mins from the village ...
From $405 per night (USD)
VRBO
From $804 per night (USD)
VRBO
Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,...
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Wonderful in Windham Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests, ample outdoor seating, ...
From $804 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Delightful 3-bedroom chalet with WiFi in Windham
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This fabulous chalet in Windham offers a cozy retreat for guests. With 3 bedrooms including a queen, twin, and bunk bed, ...
From $234 per night (USD)
Expedia
From $472 per night (USD)
VRBO
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Two Cozy Cabins for Your Perfect Getaway near Hunter and Windham Welcome to the Cabins at Walnut Grove, your ideal esca ...
From $472 per night (USD)
VRBO
From $432 per night (USD)
VRBO
Alpine View: Rustic Charm, Mountain Views & Sauna
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Alpine View is a charming two story 4 bed, 3 bath chalet 3 hours away from NYC. This home features gorgeous mou ...
From $432 per night (USD)
VRBO
From $343 per night (USD)
VRBO
NEW! Fall Leaves, Firepit, Game Room
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Recently renovated and full of charm, this 4BR, 2BA home is just minutes from Windham and Hunter Mountain. Enjoy a spaci ...
From $343 per night (USD)
VRBO
From $677 per night (USD)
Expedia
Unwind Windham, Chalet
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
<p>Welcome to <strong>Unwind Windham</strong>, a stunning mountain chalet designed for relaxation and adventure. </p> ...
From $677 per night (USD)
Expedia

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Town of Ashland Rentals

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Results: 58 Rentals