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Ashland Vacation Rentals

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5 mi
47 rentals in Ashland.
NEW! Pastoral Ashland Getaway w/ FIre Pit, Grill!, vacation rental in Ashland
NEW! Pastoral Ashland Getaway w/ FIre Pit, Grill!, vacation rental in Ashland
NEW! Pastoral Ashland Getaway w/ FIre Pit, Grill!, vacation rental in Ashland

NEW! Pastoral Ashland Getaway w/ FIre Pit, Grill!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chalet near Windham w/ hot tub, vacation rental in Ashland
Chalet near Windham w/ hot tub, vacation rental in Ashland
Chalet near Windham w/ hot tub, vacation rental in Ashland

Chalet near Windham w/ hot tub

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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All Year-Round Retreat Near Windham Mountain, vacation rental in Ashland
All Year-Round Retreat Near Windham Mountain, vacation rental in Ashland
All Year-Round Retreat Near Windham Mountain, vacation rental in Ashland

All Year-Round Retreat Near Windham Mountain

Rental Home
7 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ashland · Home Theatre, Game Room, Private Driving Range, vacation rental in Ashland
Ashland · Home Theatre, Game Room, Private Driving Range, vacation rental in Ashland
Ashland · Home Theatre, Game Room, Private Driving Range, vacation rental in Ashland

Ashland · Home Theatre, Game Room, Private Driving Range

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stylish, Luxury Mountain House 10 Mins to Windham, vacation rental in Ashland
Stylish, Luxury Mountain House 10 Mins to Windham, vacation rental in Ashland
Stylish, Luxury Mountain House 10 Mins to Windham, vacation rental in Ashland

Stylish, Luxury Mountain House 10 Mins to Windham

Rental Home
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Tiny House on Walnut Grove, vacation rental in Ashland
Tiny House on Walnut Grove, vacation rental in Ashland
Tiny House on Walnut Grove, vacation rental in Ashland

Tiny House on Walnut Grove

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!, vacation rental in Ashland
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!, vacation rental in Ashland
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!, vacation rental in Ashland

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The following properties within 20 miles of Ashland match all your filters:
Tranquil Cozy Retreat: Views, Brook, Fire Pit, Ski, Hunter, Windham, vacation rental in Ashland
Tranquil Cozy Retreat: Views, Brook, Fire Pit, Ski, Hunter, Windham, vacation rental in Ashland
Tranquil Cozy Retreat: Views, Brook, Fire Pit, Ski, Hunter, Windham, vacation rental in Ashland

Tranquil Cozy Retreat: Views, Brook, Fire Pit, Ski, Hunter, Windham

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain, vacation rental in Ashland
Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain, vacation rental in Ashland
Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain, vacation rental in Ashland

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

Rental Home
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Grand Windham Retreat w/ Fire Pit & Game Room, vacation rental in Ashland
Grand Windham Retreat w/ Fire Pit & Game Room, vacation rental in Ashland
Grand Windham Retreat w/ Fire Pit & Game Room, vacation rental in Ashland

Grand Windham Retreat w/ Fire Pit & Game Room

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ready for your family if you need a retreat., vacation rental in Ashland
Ready for your family if you need a retreat., vacation rental in Ashland
Ready for your family if you need a retreat., vacation rental in Ashland

Ready for your family if you need a retreat.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Woodsy Ashland Home - 6 Mi to Windham Mountain, vacation rental in Ashland
Woodsy Ashland Home - 6 Mi to Windham Mountain, vacation rental in Ashland
Woodsy Ashland Home - 6 Mi to Windham Mountain, vacation rental in Ashland

Woodsy Ashland Home - 6 Mi to Windham Mountain

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rustic Family Log Cabin 4 miles to Windham & Hunter Mountains, vacation rental in Ashland
Rustic Family Log Cabin 4 miles to Windham & Hunter Mountains, vacation rental in Ashland
Rustic Family Log Cabin 4 miles to Windham & Hunter Mountains, vacation rental in Ashland

Rustic Family Log Cabin 4 miles to Windham & Hunter Mountains

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Private 7-Acre Retreat: On-Site Pond, Streams, vacation rental in Ashland
Private 7-Acre Retreat: On-Site Pond, Streams, vacation rental in Ashland
Private 7-Acre Retreat: On-Site Pond, Streams, vacation rental in Ashland

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Windham resort area. Pet friendly home with mountain views, near hiking trails., vacation rental in Ashland
Windham resort area. Pet friendly home with mountain views, near hiking trails., vacation rental in Ashland
Windham resort area. Pet friendly home with mountain views, near hiking trails., vacation rental in Ashland

Windham resort area. Pet friendly home with mountain views, near hiking trails.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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CLARKS NEST, vacation rental in Ashland
CLARKS NEST, vacation rental in Ashland
CLARKS NEST, vacation rental in Ashland

CLARKS NEST

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Summer fun in the Catskills, vacation rental in Ashland
Summer fun in the Catskills, vacation rental in Ashland
Summer fun in the Catskills, vacation rental in Ashland

Summer fun in the Catskills

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Custom Built Lodge on Secluded Streamside Acreage w/ Breathtaking, vacation rental in Ashland
Stunning Custom Built Lodge on Secluded Streamside Acreage w/ Breathtaking, vacation rental in Ashland
Stunning Custom Built Lodge on Secluded Streamside Acreage w/ Breathtaking, vacation rental in Ashland

Stunning Custom Built Lodge on Secluded Streamside Acreage w/ Breathtaking

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Relaxation Retreat: Home w/Hot Tub, Gym & Sauna, vacation rental in Ashland
Relaxation Retreat: Home w/Hot Tub, Gym & Sauna, vacation rental in Ashland
Relaxation Retreat: Home w/Hot Tub, Gym & Sauna, vacation rental in Ashland

Relaxation Retreat: Home w/Hot Tub, Gym & Sauna

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Farmehouse at Firefly Run, vacation rental in Ashland
The Farmehouse at Firefly Run, vacation rental in Ashland
The Farmehouse at Firefly Run, vacation rental in Ashland

The Farmehouse at Firefly Run

Rental Home
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Hot tub! Modern Catskills Charmer - Hunter/Windham, vacation rental in Ashland
Hot tub! Modern Catskills Charmer - Hunter/Windham, vacation rental in Ashland
Hot tub! Modern Catskills Charmer - Hunter/Windham, vacation rental in Ashland

Hot tub! Modern Catskills Charmer - Hunter/Windham

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Windham Pines Lodge & Hot Tub, vacation rental in Ashland
Windham Pines Lodge & Hot Tub, vacation rental in Ashland
Windham Pines Lodge & Hot Tub, vacation rental in Ashland

Windham Pines Lodge & Hot Tub

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Windham Mountain A Frame Ski House with Central A/C, vacation rental in Ashland
Windham Mountain A Frame Ski House with Central A/C, vacation rental in Ashland
Windham Mountain A Frame Ski House with Central A/C, vacation rental in Ashland

Windham Mountain A Frame Ski House with Central A/C

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Creek house with expansive mountain views, vacation rental in Ashland
Creek house with expansive mountain views, vacation rental in Ashland
Creek house with expansive mountain views, vacation rental in Ashland

Creek house with expansive mountain views

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views, vacation rental in Ashland
HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views, vacation rental in Ashland
HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views, vacation rental in Ashland

HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Extreme Leisure Minutes from Action and Adventure, vacation rental in Ashland
Extreme Leisure Minutes from Action and Adventure, vacation rental in Ashland
Extreme Leisure Minutes from Action and Adventure, vacation rental in Ashland

Extreme Leisure Minutes from Action and Adventure

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Cozy mountain home, vacation rental in Ashland
Cozy mountain home, vacation rental in Ashland
Cozy mountain home, vacation rental in Ashland

Cozy mountain home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful home conveniently located 5 minutes windham 10 minutes to hunter, vacation rental in Ashland
Beautiful home conveniently located 5 minutes windham 10 minutes to hunter, vacation rental in Ashland
Beautiful home conveniently located 5 minutes windham 10 minutes to hunter, vacation rental in Ashland

Beautiful home conveniently located 5 minutes windham 10 minutes to hunter

Rental Home
6 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Holly Lodge - Ski Windham, Hunter, Catskills, vacation rental in Ashland
Holly Lodge - Ski Windham, Hunter, Catskills, vacation rental in Ashland
Holly Lodge - Ski Windham, Hunter, Catskills, vacation rental in Ashland

Holly Lodge - Ski Windham, Hunter, Catskills

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the, vacation rental in Ashland
DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the, vacation rental in Ashland
DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the, vacation rental in Ashland

DREAM LOG CABIN 110 Acres/Hot Tub/ 5 Minutes to the

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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(New Listing) Beautiful mountain home on private road, vacation rental in Ashland
(New Listing) Beautiful mountain home on private road, vacation rental in Ashland
(New Listing) Beautiful mountain home on private road, vacation rental in Ashland

(New Listing) Beautiful mountain home on private road

Rental Home
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Windham Mountain Escape - 5bd/4ba Private Home, vacation rental in Ashland
Windham Mountain Escape - 5bd/4ba Private Home, vacation rental in Ashland
Windham Mountain Escape - 5bd/4ba Private Home, vacation rental in Ashland

Windham Mountain Escape - 5bd/4ba Private Home

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Chalet Eglantine Mountain Retreat, vacation rental in Ashland
Chalet Eglantine Mountain Retreat, vacation rental in Ashland
Chalet Eglantine Mountain Retreat, vacation rental in Ashland

Chalet Eglantine Mountain Retreat

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Just 6 minutes from Windham Mountain, vacation rental in Ashland
Just 6 minutes from Windham Mountain, vacation rental in Ashland
Just 6 minutes from Windham Mountain, vacation rental in Ashland

Just 6 minutes from Windham Mountain

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,..., vacation rental in Ashland
Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,..., vacation rental in Ashland
Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,..., vacation rental in Ashland

Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,...

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Mayfair Manor Mountain Retreat, vacation rental in Ashland
Mayfair Manor Mountain Retreat, vacation rental in Ashland
Mayfair Manor Mountain Retreat, vacation rental in Ashland

Mayfair Manor Mountain Retreat

Rental Home
5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Dingley Dell Villa Windham - Movie Room, Hot tub, 6 Bedrooms, 4 bathrooms, vacation rental in Ashland
Dingley Dell Villa Windham - Movie Room, Hot tub, 6 Bedrooms, 4 bathrooms, vacation rental in Ashland
Dingley Dell Villa Windham - Movie Room, Hot tub, 6 Bedrooms, 4 bathrooms, vacation rental in Ashland

Dingley Dell Villa Windham - Movie Room, Hot tub, 6 Bedrooms, 4 bathrooms

Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Elegant Catskill Retreat: 8BR Windham Getaway with Hot Tub & Vineyard Views, vacation rental in Ashland
Elegant Catskill Retreat: 8BR Windham Getaway with Hot Tub & Vineyard Views, vacation rental in Ashland
Elegant Catskill Retreat: 8BR Windham Getaway with Hot Tub & Vineyard Views, vacation rental in Ashland

Elegant Catskill Retreat: 8BR Windham Getaway with Hot Tub & Vineyard Views

Rental Home
9 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
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Windham Cabin 5 mins to Mtn with 2 Fireplaces & Games, vacation rental in Ashland
Windham Cabin 5 mins to Mtn with 2 Fireplaces & Games, vacation rental in Ashland
Windham Cabin 5 mins to Mtn with 2 Fireplaces & Games, vacation rental in Ashland

Windham Cabin 5 mins to Mtn with 2 Fireplaces & Games

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A'Neils Windham Ski Lodge & Family Retreat, vacation rental in Ashland
A'Neils Windham Ski Lodge & Family Retreat, vacation rental in Ashland
A'Neils Windham Ski Lodge & Family Retreat, vacation rental in Ashland

A'Neils Windham Ski Lodge & Family Retreat

Rental Home
10 bedrooms
10 bathrooms
Sleeps 30
Match: Sleeps
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Cozy Lux Mountain Lodge- Hot Tub- Mountain Views- 10min to Skiing Windham Hunter, vacation rental in Ashland
Cozy Lux Mountain Lodge- Hot Tub- Mountain Views- 10min to Skiing Windham Hunter, vacation rental in Ashland
Cozy Lux Mountain Lodge- Hot Tub- Mountain Views- 10min to Skiing Windham Hunter, vacation rental in Ashland

Cozy Lux Mountain Lodge- Hot Tub- Mountain Views- 10min to Skiing Windham Hunter

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Windham Mountain House *redfallslanding -- A Catskill Mountains Retreat, vacation rental in Ashland
Windham Mountain House *redfallslanding -- A Catskill Mountains Retreat, vacation rental in Ashland
Windham Mountain House *redfallslanding -- A Catskill Mountains Retreat, vacation rental in Ashland

Windham Mountain House *redfallslanding -- A Catskill Mountains Retreat

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Mountain Paradise - Hot Tub / Games / Ski, vacation rental in Ashland
Mountain Paradise - Hot Tub / Games / Ski, vacation rental in Ashland
Mountain Paradise - Hot Tub / Games / Ski, vacation rental in Ashland

Mountain Paradise - Hot Tub / Games / Ski

Rental Home
6 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Rustic-Chic Farmhouse w/ Firepit, Close to Windham Ski & Catskills Adventures!, vacation rental in Ashland
Rustic-Chic Farmhouse w/ Firepit, Close to Windham Ski & Catskills Adventures!, vacation rental in Ashland
Rustic-Chic Farmhouse w/ Firepit, Close to Windham Ski & Catskills Adventures!, vacation rental in Ashland

Rustic-Chic Farmhouse w/ Firepit, Close to Windham Ski & Catskills Adventures!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Casa Magda - Designer Home near Hiking + Swimming, vacation rental in Ashland
Casa Magda - Designer Home near Hiking + Swimming, vacation rental in Ashland
Casa Magda - Designer Home near Hiking + Swimming, vacation rental in Ashland

Casa Magda - Designer Home near Hiking + Swimming

Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Magical Home Located in Windham and Catskills, vacation rental in Ashland
Magical Home Located in Windham and Catskills, vacation rental in Ashland
Magical Home Located in Windham and Catskills, vacation rental in Ashland

Magical Home Located in Windham and Catskills

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury waterfront ski cabin, 4-bedroom house and office, monthly only, vacation rental in Ashland
Luxury waterfront ski cabin, 4-bedroom house and office, monthly only, vacation rental in Ashland
Luxury waterfront ski cabin, 4-bedroom house and office, monthly only, vacation rental in Ashland

Luxury waterfront ski cabin, 4-bedroom house and office, monthly only

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Showing results 1-47 of 47
Frequently Asked Questions about Ashland