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Ashland Holiday Rentals

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50 rentals in Ashland.
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Affordable Windham Getaway (near private creek!), holiday rental in Ashland

Affordable Windham Getaway (near private creek!)

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Windham Mtn.-Walking distance to trail and base lodge!, holiday rental in Ashland

Windham Mtn.-Walking distance to trail and base lodge!

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Windham:  Ski Season: Wkds & Midweek- High Speed WIFI, Private deck, Watch Video, holiday rental in Ashland

Windham: Ski Season: Wkds & Midweek- High Speed WIFI, Private deck, Watch Video

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!, holiday rental in Ashland

****ON Mountain!*** Steps From Slopes! Welcome to our Windham Mountain Escape!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Tranquil Catskill Mountains Log Cabin - Minutes to Skiing and Hiking, holiday rental in Ashland

Tranquil Catskill Mountains Log Cabin - Minutes to Skiing and Hiking

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Mountain Oasis is open for your skiing pleasure!, holiday rental in Ashland

Mountain Oasis is open for your skiing pleasure!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Custom Built Luxury Cabin on 2.5 Acres, 10 Mins to Windham & Hunter Mountains!, holiday rental in Ashland

Custom Built Luxury Cabin on 2.5 Acres, 10 Mins to Windham & Hunter Mountains!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Escape Winter... above & beyond. Perfect house for family, friends & fresh air., holiday rental in Ashland

Escape Winter... above & beyond. Perfect house for family, friends & fresh air.

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Getaway - HUNTER & WINDHAM! Beautiful , Cozy and Private new home, holiday rental in Ashland

Perfect Getaway - HUNTER & WINDHAM! Beautiful , Cozy and Private new home

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Windham Family Getaway (Brand New!), holiday rental in Ashland

Windham Family Getaway (Brand New!)

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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5-Star Luxury Condo On Mountain: Ski-in & Ski-out, holiday rental in Ashland

5-Star Luxury Condo On Mountain: Ski-in & Ski-out

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet, holiday rental in Ashland

Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Retreat with Luxurious View, holiday rental in Ashland

Spacious Retreat with Luxurious View

5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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'New Home' Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, holiday rental in Ashland

'New Home' Idyllic Mt Views ,Pond & Horse farm views 2 min to Town

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Escape:  Gorgeous Mountain View Hideaway: AC, big deck & fire pit, holiday rental in Ashland

Escape: Gorgeous Mountain View Hideaway: AC, big deck & fire pit

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Luxury Home on Windham Mountain! Walk to Slopes, holiday rental in Ashland

NEW! Luxury Home on Windham Mountain! Walk to Slopes

4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Gorgeous, First Class, 2 King apartment in downtown Windham, holiday rental in Ashland

Gorgeous, First Class, 2 King apartment in downtown Windham

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo, holiday rental in Ashland

Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Windham Townhouse - Base of Mountain, holiday rental in Ashland

Windham Townhouse - Base of Mountain

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham, holiday rental in Ashland

Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Charming Water Front Log Home, holiday rental in Ashland

Secluded Charming Water Front Log Home

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Charming house in great location, holiday rental in Ashland

Charming house in great location

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain, holiday rental in Ashland

Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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3400 Sq Ft 5 Bedroom House for Rent Near Hunter/Windham mountains ,cable/WIFI, holiday rental in Ashland

3400 Sq Ft 5 Bedroom House for Rent Near Hunter/Windham mountains ,cable/WIFI

5 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
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The Presidential Suite at Brie & Bordeaux, holiday rental in Ashland

The Presidential Suite at Brie & Bordeaux

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ski Chalet with Mountain Views - Grill & Firepit, holiday rental in Ashland

Ski Chalet with Mountain Views - Grill & Firepit

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Luxury Ski Windham Resort directly on Ski Mountain. Enjoy direct ski in/out, holiday rental in Ashland

Luxury Ski Windham Resort directly on Ski Mountain. Enjoy direct ski in/out

6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Windham Cabin, holiday rental in Ashland

Windham Cabin

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chickadee Chalet, holiday rental in Ashland

Chickadee Chalet

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Mountain House: The Perfect 4 Season Retreat, holiday rental in Ashland

The Mountain House: The Perfect 4 Season Retreat

8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Foot of fresh SNOW Amazing skiing & snowboarding, holiday rental in Ashland

Foot of fresh SNOW Amazing skiing & snowboarding

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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FRESH SNOWSTORM Cutest Cabin in Windham for 2 People, holiday rental in Ashland

FRESH SNOWSTORM Cutest Cabin in Windham for 2 People

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Windham Mountain Ski House, holiday rental in Ashland

Windham Mountain Ski House

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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'The Mountain House' Windham Retreat w/ Hot Tub!, holiday rental in Ashland

'The Mountain House' Windham Retreat w/ Hot Tub!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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charming house in the catskills, holiday rental in Ashland

charming house in the catskills

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Elegant4bedroom home near golf, slopes, WiFi, firepits ,also monthly, holiday rental in Ashland

Elegant4bedroom home near golf, slopes, WiFi, firepits ,also monthly

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious House - 1 Mi. to Windham Ski Resort!, holiday rental in Ashland

Spacious House - 1 Mi. to Windham Ski Resort!

5 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Tentrr Signature Site - Pleasant Valley Maplecroft Camp, holiday rental in Ashland

Tentrr Signature Site - Pleasant Valley Maplecroft Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Fish, Golf, Bike, Hike; steps to Windham Ski resort., holiday rental in Ashland

Fish, Golf, Bike, Hike; steps to Windham Ski resort.

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Luxe Windham Home w/Hot Tub - Walk to Ski Resort!, holiday rental in Ashland

Luxe Windham Home w/Hot Tub - Walk to Ski Resort!

8 bedrooms
3 bathrooms
Sleeps 17
Match: Sleeps
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Luxe Family Home 2Mi to Windham Mountain & Resort, holiday rental in Ashland

Luxe Family Home 2Mi to Windham Mountain & Resort

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Catskills House w/Yard, 1Mi to Windham Mtn Resort!, holiday rental in Ashland

Catskills House w/Yard, 1Mi to Windham Mtn Resort!

6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Windham Mountain Retreat!  5 Bedroom, 3.5 Bathroom beautiful appointed home, holiday rental in Ashland

Windham Mountain Retreat! 5 Bedroom, 3.5 Bathroom beautiful appointed home

9 bedrooms
6 bathrooms
Sleeps 22
Match: Sleeps
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New Custom Built Catskill Mountain Chalet with Elevator, holiday rental in Ashland

New Custom Built Catskill Mountain Chalet with Elevator

6 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Retreat with an Amazing View, holiday rental in Ashland

Perfect Retreat with an Amazing View

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Private 7-Acre Retreat: On-Site Pond, Streams, holiday rental in Ashland

NEW! Private 7-Acre Retreat: On-Site Pond, Streams

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Modern & Cozy Windham Mountain Home: Hike & Tennis, holiday rental in Ashland

Modern & Cozy Windham Mountain Home: Hike & Tennis

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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On Windham Mountain - Westside Chalet, holiday rental in Ashland

On Windham Mountain - Westside Chalet

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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5 Min to Windham Mtn! Luxury Retreat w/Amazing Views! Natural Swimming Pond, holiday rental in Ashland

5 Min to Windham Mtn! Luxury Retreat w/Amazing Views! Natural Swimming Pond

8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Windham - Hunter - Catskill Retreat, holiday rental in Ashland

Windham - Hunter - Catskill Retreat

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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