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Compare 530 Vacation Homes in Ashland with updated reviews, rates, and availability.

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

9.2 out of 10, Wonderful, (40)
"Really lovely place right in the heart of town. Owner and manager were great."
The price is SAR 413
SAR 675 total
includes taxes & fees
1 Apr - 2 Apr
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.6 out of 10, Exceptional, (39)
"The property was well maintained and a great space. The views along side the creek were amazing. "
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

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

9.2 out of 10, Wonderful, (9)
"Just as advertised. Clean, comfortable, and inviting cabin perfect for relaxing after a day of skiing. The roads leading to the cabin are rural, and the driveway is a bit steep, so keep that in mind if you’ll be driving during or after a snowfall in the area. "
The price is SAR 747
SAR 1,957 total
includes taxes & fees
23 Mar - 24 Mar
A world where time stands still, close to Belleayre Ski & Wedding venues.

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

9.8 out of 10, Exceptional, (16)
"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 597
SAR 1,142 total
includes taxes & fees
12 Mar - 13 Mar
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE

10.0 out of 10, Exceptional, (102)
"Thanks for a great place to hang for a ski weekend!"
The price is SAR 1,032
SAR 2,033 total
includes taxes & fees
6 Apr - 7 Apr
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (98)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court

Victorian Catskill House w/ Game Room, Fire Pit, and Strong Wi-Fi

9.4 out of 10, Exceptional, (92)
"This house offered plenty of space and a great place to unwind after a day on the slopes. We enjoyed the closeness to the slopes (less than 15 minute drive) and cooked some great meals in the kitchen, dining on the glorious table in the dining room. My 9.5 month old grandson loved crawling through the “tunnel” under the long table;/)"
Victorian Catskill House w/ Game Room, Fire Pit, and Strong Wi-Fi

Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

9.8 out of 10, Exceptional, (70)
"Located close to Belleayre, easy check in and clean tidy place. Would use again for a visit."
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

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

10.0 out of 10, Exceptional, (215)
"The house has hot tub, sauna and game room. It is perfect for both youths and adults."
The price is SAR 1,107
SAR 2,529 total
includes taxes & fees
12 Mar - 13 Mar
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

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

Phoenicia Retreat: Massive Private Entertaining Home with Fireplace & Pond

9.0 out of 10, Wonderful, (16)
"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

Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

9.6 out of 10, Exceptional, (178)
"We had an amazing time at this beautiful home! The house was spotless when we arrived, and we were welcomed with a warm fire already going in the wood stove – such a nice touch. Peter and Lara were there to greet us and give us a tour, making us all feel right at home. We also really appreciated how responsive they were when we had a small issue with the hot tub – they took care of it right away. The place is absolutely gorgeous and so unique – you can really see the love and care they put into...
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

Catskill Mountain Retreat -- private, beautiful views

9.8 out of 10, Exceptional, (103)
"Rick was super nice and easy to get in contact with. Everything went super smooth! The house is great and was clean when we arrived and the kitchen is full of cooking equipment."
Catskill Mountain Retreat -- private, beautiful views

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (128)
"Always a great stay at this beautiful house!"
Beautiful new house 3/4 mile from Hunter Mountain

Catskills Quaint Cottage w/ Peloton & Sauna near Hiking - Hunter and Belleayre

9.6 out of 10, Exceptional, (14)
"I stayed in this property for a total of 4 weeks. It was close to our work location, easily accessed, comfortable and clean. The shining star was the frequent and clear communication with the property manager CinthyaIf we find ourselves working in the area again, we'd look to book here as our first choice!"
Catskills Quaint Cottage w/ Peloton & Sauna near Hiking - Hunter and Belleayre

GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.

9.8 out of 10, Exceptional, (9)
"We had the best time! The property was perfect! Plenty of bedrooms and bathrooms plus gathering spaces galore ! The kitchen was stocked with all the necessities. We had 6 children age 8 and under so the outside property was perfect. Just enough snow for a snowman and some sledding! Plus an enormous deck and wrap around porch. There was a laundry and plenty of towels , pillows and cozy blankets! We will definitely be back! "
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.

◆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

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

9.8 out of 10, Exceptional, (37)
"Worked out perfectly"
5 Min to Windham Mtn! Luxury Retreat w/ Mountain Views! Natural Swimming Pond

LOOKING FOR A HEAVENLY GETAWAY

9.6 out of 10, Exceptional, (91)
"Very nice stay. Warm and cozy despite freezing weather. Host was incredibly attentive "
LOOKING FOR A HEAVENLY GETAWAY

Brand New 2 Bdr. Townhome Minutes from Windham Mtn

10.0 out of 10, Exceptional, (7)
"We look forward to renting again next season."
The price is SAR 581
SAR 1,144 total
includes taxes & fees
12 Mar - 13 Mar
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
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

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (250)
"Works great for our family of seven to Ski at Belleayre Mountain resort. Thank you. "
The price is SAR 469
SAR 541 total
includes taxes & fees
18 Mar - 19 Mar
Starlite Motel

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.6 out of 10, Exceptional, (39)
"The property was well maintained and a great space. The views along side the creek were amazing. "
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10.0 out of 10, Exceptional, (154)
"Large home with everything you’ll need. Plenty of towels, kitchen supplies, fridge space for a large party. Bedding was nice, with plenty of extra blankets. Greg was very easy to work with and answered all of our questions quickly. We would definitely book this property again. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
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.