Ashland Vacation Rentals
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50 rentals in Ashland.
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A'Neils West Windham Ski House & Family Retreat
Rental Home
10 bedrooms
10 bathrooms
Sleeps 30
Match: Sleeps
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Holly Lodge - Ski Windham, Hunter, Catskills
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Affordable Windham Getaway (near private creek!)
Rental Home
3 bedrooms
1 bathroom
Sleeps 7
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The Millbrook Farmhouse- HIKE, FISH, RELAX
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dingley Dell Estate II with Movie Theater(6 Bedroom/ 4 bathrooms, large house)
Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Windham Estate w/ 8 BRs, 5800 sq. feet and Hot Tub
Rental Home
8 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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*NEW* Catskills Getaway Tucked into a Beautiful Landscape
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Pastoral Ashland Getaway w/ FIre Pit, Grill!
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Elegant4bedroom home near slopes, high speed internet, firepits ,also monthly
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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DREAM LOG CABIN 110 Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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FRESH SNOWSTORM Cutest Cabin in Windham for 2 People
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Snowy Winter Wonderland
Rental Home
4 bedrooms
2 bathrooms
Sleeps 4
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Ready for your family if you need a retreat.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Foot of fresh SNOW Amazing skiing & snowboarding
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Quiet Getaway With Mountain Views and Heated Private Pool
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Stunning Custom Built Lodge on Secluded Streamside Acreage w/ Breathtaking Views
Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
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Le Chalet: Modern Luxury retreat with Mountain views, Chef's Kitchen & Hot Tub
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Windham Mountain A Frame Ski House with Central A/C
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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(New Listing) Beautiful mountain home on private road
Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
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New Two Family House 5 minutes to Windham Resort
Rental Home
5 bedrooms
4 bathrooms
Sleeps 13
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NEW! Private 7-Acre Retreat: On-Site Pond, Streams
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Charming house in great location
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain
Rental Home
3 bedrooms
1 bathroom
Sleeps 7
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Extreme Leisure Minutes from Action and Adventure
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Bella Vista - Steps away from Windham Vineyard
Rental Home
8 bedrooms
4 bathrooms
Sleeps 8
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Windham Mountain Ski House
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Tentrr Signature Site - Pleasant Valley Maplecroft Camp
Rental Home
1 bedroom
1 bathroom
Sleeps 6
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Tentrr Signature Site - Pleasant Valley Maplecroft Camp
Rental Home
1 bedroom
1 bathroom
Sleeps 6
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Amazing 4 BR Villa on Windham
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ski house in Windham near Hunter and Windham mountains
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Perfect Retreat with an Amazing View
Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
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The Farmehouse at Firefly Run
Rental Home
5 bedrooms
2 bathrooms
Sleeps 15
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Beautiful home conveniently located 5 minutes windham 10 minutes to hunter
Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
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Perfect retreat with an amazing view
Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
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Creek house with expansive mountain views
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sutton Hollow Lodge - Catskills, Windham Mountain
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Serenity Mountain Cabin- 5 miles to Windham Mtn
Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
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Home Theatre Game Room Private Driving Range
Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Fox Run Escape: Modern Ski Getaway w/ Sunset Views, Near Windham Mountain
Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,...
Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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The Cedar Arch - Windham Getaway!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Windham and Hunter Mountain Ski House.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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House , outdoor heated swim spa , outdoor lounge area , near skiing
Rental Home
4 bedrooms
4 bathrooms
Sleeps 14
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Windham Streamside Country House
Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
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Spacious Modern Chalet 8 minutes from Hunter and Windham Mountain with hot tub
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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CLARKS NEST
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Catskill's Getaway - 8/13 min to Windham/Hunter. Hiking Golf Waterfalls.
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Windham Pines Lodge & Hot Tub
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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A Feel Good Family Home Amongst Leafy Serenity
Rental Home
4 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Ashland
- Yes, here are some popular vacation rentals in Ashland that have a pool:
- Affordable Windham Getaway (near private creek!)
- *NEW* Catskills Getaway Tucked into a Beautiful Landscape
- Holly Lodge - Ski Windham, Hunter, Catskills
- Yes, here are some popular vacation rentals in Ashland that have internet access:
- Affordable Windham Getaway (near private creek!)
- *NEW* Catskills Getaway Tucked into a Beautiful Landscape
- Holly Lodge - Ski Windham, Hunter, Catskills
- Some of the most popular kid friendly rentals in Ashland are:
- Affordable Windham Getaway (near private creek!)
- *NEW* Catskills Getaway Tucked into a Beautiful Landscape
- Holly Lodge - Ski Windham, Hunter, Catskills