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Compare 645 Vacation Homes in Ashland with updated reviews, rates, and availability.

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (128)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain

A world where time stands still, close to Belleayre Ski & Wedding venues.

9.6 out of 10, Exceptional, (14)
"Had a great "
The price is SAR 563
SAR 1,827 total
includes taxes & fees
7 May - 8 May
A world where time stands still, close to Belleayre Ski & Wedding venues.

Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

9.8 out of 10, Exceptional, (72)
"We'll come again "
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

9.6 out of 10, Exceptional, (25)
"Had a great 2 night stay. Location is close to Hunter. "
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

A'Neils Windham Ski Lodge & Family Retreat

10.0 out of 10, Exceptional, (28)
"A wonderful space for a family reunion ski get away. Enough personal space for each while also offering great shared space for warm gatherings and meals. Host was very accommodating and easily available. We would definitely stay again!"
A'Neils Windham Ski Lodge & Family Retreat

7Bdr/5Bth, Amazing View, Lake/Swim. 1/2 ml Ski Hunter Resort, Hot Tub/Sauna.Golf

10.0 out of 10, Exceptional, (217)
"Excellent communication. Cozy home. Really enjoyed our stay. "
The price is SAR 1,496
SAR 3,155 total
includes taxes & fees
7 May - 8 May
7Bdr/5Bth, Amazing View, Lake/Swim. 1/2 ml Ski Hunter Resort, Hot Tub/Sauna.Golf

Quaint Cottage w/ Peloton & Sauna near Hiking

9.6 out of 10, Exceptional, (18)
"Once you connect to the wifi you can use your phone. The landlord as well as property manager are helpful and actually respond. Property is very peaceful!"
Quaint Cottage w/ Peloton & Sauna near Hiking

◆DREAM Modern Cabin in the Woods ◆ Hot tub + Sauna

9.6 out of 10, Exceptional, (5)
"Property is beautiful - hot tub, sauna, heated toilet seats, abundant spaces to meet and hang out. Only drawback was uneven temperatures in house - heaters in every room but it was cold almost everywhere. "
◆DREAM Modern Cabin in the Woods ◆ Hot tub + Sauna

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

9.2 out of 10, Wonderful, (44)
"Really lovely place right in the heart of town. Owner and manager were great."
The price is SAR 64
SAR 352 total
includes taxes & fees
6 Jun - 7 Jun
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

9.8 out of 10, Exceptional, (18)
"After a day of skiing at Bellayre Mtn this very clean, comfortable cabins’ great location was the perfect place to unwind for the night."
The price is SAR 596
SAR 1,250 total
includes taxes & fees
7 May - 8 May
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

Game Room + Deck: Secluded Catskills Retreat

10.0 out of 10, Exceptional, (4)
"Another great stay at this beautiful home!"
Game Room + Deck: Secluded Catskills Retreat

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.6 out of 10, Exceptional, (40)
"The property was well maintained and a great space. The views along side the creek were amazing. "
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

10.0 out of 10, Exceptional, (267)
"This place is the best! We’ll keep coming back. "
The price is SAR 2,561
SAR 4,783 total
includes taxes & fees
1 Jun - 2 Jun
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

Phoenicia Retreat: Massive Private Entertaining Home with Fireplace & Pond

9.2 out of 10, Wonderful, (17)
"5 adults, 2 kids, one dog. Had plenty of room. Beautiful weather and enjoyed the outdoor decks. Overall very comfortable for us."
Phoenicia Retreat: Massive Private Entertaining Home with Fireplace & Pond

Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

9.8 out of 10, Exceptional, (145)
"Great property for families ! The game room got a ton of use and the loft beds were a big hit ! Having a loft in each bedroom upstairs was helpful ! Property is gorgeous and the kids had a ton of fun exploring! "
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

Catskill Mountain Retreat -- private, beautiful views,

9.8 out of 10, Exceptional, (103)
"We had an excellent stay at this property, highly recommended."
Catskill Mountain Retreat -- private, beautiful views,

6 Mi to Hunter Mtn: Tannersville Retreat w/ Pool

10.0 out of 10, Exceptional, (64)
"The house was beautiful, clean and very accommodating. Very close to downtown shopping and restaurants. Would definitely recommend staying in this beautiful family friendly home. "
6 Mi to Hunter Mtn: Tannersville Retreat w/ Pool

Woodstock Ski House on 35 private acres Mtn Views

10.0 out of 10, Exceptional, (45)
"Easy to book and directions were spot on."
Woodstock Ski House on 35 private acres Mtn Views

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

9.4 out of 10, Exceptional, (34)
"Great place for an incredible price. We would definitely stay here again."
The price is SAR 281
SAR 506 total
includes taxes & fees
7 May - 8 May
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Chateau Bungalow - Ski Belleayre, Hunter

10.0 out of 10, Exceptional, (2)
"We enjoyed 4 days staying for skiing at Belleayre. This fully renovated house was perfect for us, and I would definately come back again"
Chateau Bungalow - Ski Belleayre, Hunter
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Ashland

Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain

8.6 out of 10, Excellent, (14)
"It was a nice getaway in a quaint area!"
Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (252)
"Great Upstate location! Very welcoming."
The price is SAR 469
SAR 541 total
includes taxes & fees
7 May - 8 May
Starlite Motel

Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year

10.0 out of 10, Exceptional, (20)
"Beautiful house and excellent location between Hunter and Windham mountains "
Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.