Ashland Vacation Rentals

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Vacation Rentals in Ashland

Exterior
Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, (229)
"Property was clean. Amenities were as advertised. However, shower temperatures fluctuate from hot to freezing. Stovetop was uneven, making it somewhat difficult to cook. "
The price is CA $170
CA $190 total
includes taxes & fees
May 22 - May 23
Starlite Motel
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (165)
"Very clean, good area"
The Cabin at Chichester in the Catskills Mountains
Terrace/patio
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
10.0 out of 10, Exceptional, (7)
"House and location were great, would definitely come back."
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
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Outdoor dining
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
9.8 out of 10, Exceptional, (86)
"Stayed here with a group of friends, and loved it! We had terrible weather, but the house was the best place to be stuck inside. We made pizzas in the outdoor oven, and enjoyed the hot tub. Can't recommend enough! The property manager Alan was awesome."
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
Exterior
Catskills Windham Hunter Mountain Cabin Getaway
9.4 out of 10, Exceptional, (19)
"This was such a great house! The property is beautiful. Running stream, plenty of room inside and out, hot tub, etc. Perfect place for couples or families to relax and get away from the hassle of life."
The price is CA $366
CA $821 total
includes taxes & fees
May 19 - May 20
Catskills Windham Hunter Mountain Cabin Getaway
Exterior
Beautiful House 0,5 Mile From Hunter Mountain
9.8 out of 10, Exceptional, (188)
"It was a great family time. Play and rest"
Beautiful House 0,5 Mile From Hunter Mountain
Property grounds
Updated Cabin on the Esopus
10.0 out of 10, Exceptional, (17)
"The cabin was excellent, very clean, and they gave us everything we needed"
Updated Cabin on the Esopus
Property grounds
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
9.8 out of 10, Exceptional, (80)
"Natalya was a great host! Property was very nice and great location to Hunter!"
The price is CA $680
CA $1,088 total
includes taxes & fees
May 19 - May 20
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Fridge, microwave, oven, stovetop
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
9.6 out of 10, Exceptional, (42)
"We decided on a trip to Hunter Mountain with our family and some of my sons friends. I came across this house and let me tell you the pictures do not do it justice it’s even better in person!! We were beyond happy with the house and the location…. The house was fully stocked with everything you could imagine. So much room for our group of 13 including our golden retriever! The kids and adults loved the game room some adults even had a Pac-Man competition. We will definitely stay at this house...
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Property grounds
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (131)
"We had a great time at Greg’s property. The house is huge and easily accommodated the 25 guests we had. It is very conveniently located for those that like to take advantage of skiing between Hunter and Windham mountains. Greg was extremely responsive and very easy to work with anytime we had questions arise. I would definitely recommend to others and will most certainly keep this place in mind for future trips! Thanks again!"
The price is CA $1,489
CA $2,376 total
includes taxes & fees
May 23 - May 24
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
1 bedroom, iron/ironing board, free WiFi, bed sheets
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
10.0 out of 10, Exceptional, (10)
"This property was perfect for a quick weekend getaway with my partner. The place was clean and inviting. There were a few snacks along with coffee and tea provided by the hosts. The bathroom was well stocked. The town itself is adorable with some good restaurants within close driving/walking distance and lots of outdoor activities. I definitely recommend staying here!"
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
Outdoor spa tub
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
9.6 out of 10, Exceptional, (163)
"The house was fantastic. Close to Hunter Mountain Ski Resort and a cute one street town. Peter and Lara had both wood burning stoves going for us when we arrived. The house is wonderful with a fun separate hang out place for the kids. Well equipped kitchen. Comfortable beds. Hot tub with wonderful views. All the firewood you could ever need. We will be back for sure!"
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
2 bedrooms, free WiFi, bed sheets
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
9.8 out of 10, Exceptional, (19)
"Great little cabin, very clean, and the host was extremely responsive and helpful. Very close to a bunch of nice restaurants and a nice little town. Amazing hiking trails all around. Definitely recommended for a getaway from the city."
The price is CA $184
CA $437 total
includes taxes & fees
May 20 - May 21
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
Fridge, microwave, oven, stovetop
Your peaceful, private retreat to get away with friends & family!
10.0 out of 10, Exceptional, (22)
"The place and host were amazing. The property was well kept and well appointed for our stay. It is nicely secluded, and the hot tub was perfect for relaxing."
Your peaceful, private retreat to get away with friends & family!
Fridge, microwave, oven, stovetop
FOUR SEASON Catskills Home - Secluded & Spacious w/ Secret Waterfall
10.0 out of 10, Exceptional, (29)
"Wonderful very large home in the mountains. Quiet and peaceful. Enjoyed our Thanksgiving holiday here with plenty of room for cooking and lounging. Able to bring our dog too which was an added plus. Small village nearby with cute shops for Saturday shopping and grocery store within 5 miles. House has everything you need."
FOUR SEASON Catskills Home - Secluded & Spacious w/ Secret Waterfall
Property grounds
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
9.6 out of 10, Exceptional, (37)
"Great Mountain View’s,very relaxing"
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Property grounds
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
10.0 out of 10, Exceptional, (208)
"House came with great amenities and host was very communicative and flexible"
The price is CA $443
CA $966 total
includes taxes & fees
May 20 - May 21
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
Terrace/patio
Moonlight Reflections
10.0 out of 10, Exceptional, (85)
"Stayed here for a family of 6 ski trip to Belleayre. It was very clean and well stocked, with comfortable furnishings . Enjoyed the gas firepit on the deck, which has lots of comfortable seating around it. This is a perfect all-season house. I highly recommend it. Will definitely return!"
Moonlight Reflections
Interior
Private Contemporary Cottage with heated pool, hot tub and wide mountain views.
9.8 out of 10, Exceptional, (70)
"Beautiful well appointed home. Great for large groups. The kitchen is well stocked with everything to cook and serve meals. The beds were comfortable. Gorgeous views and the hot tub on a chilly November night was amazing."
Private Contemporary Cottage with heated pool, hot tub and wide mountain views.
Aerial view
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
9.8 out of 10, Exceptional, (67)
"We travel to the Catskills at least once a year and stay at various locations. What sets this property apart is the true seclusion and absolutely no distractions from the nature around you. Even though it is close to hubs like Wyndham and Hunter (less than 20 to both) when sitting outside it feels like you are in the middle of nowhere. Inside is clean, cosey by the fire, and lots of fun things to do with our teenagers. Definitely would stay again."
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
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See all available properties in Ashland
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.

Ashland Vacation Rental Travel Info

Number of vacation rentals
45
Popular accommodation
Ashland private vacation homes
International airport
Albany, NY (ALB-Albany Intl.)

Other types of properties in Ashland you may be interested in

Lobby sitting area
Hunter Lodge, a Bluebird by Lark
2.5 star property
9.4 out of 10, Exceptional, (362)
"Perfect mountain lodge with beautiful views - staff was very accommodating. We look forward to going back! "
The price is CA $164
CA $178 total
includes taxes & fees
May 21 - May 22
Hunter Lodge, a Bluebird by Lark
Chalet, 1 Bedroom, Hot Tub, Mountain View | Private kitchen
Urban Cowboy Lodge
5.0 star property
9.4 out of 10, Exceptional, (67)
"Property was absolutely gorgeous quiet, staff was accommodating. Our room was perfect with the Mountain View and tub. The restaurant had a very small menu and food was not that great. We had to order 2 appetizers and 5 dinners just get to full. Overall satisfied. "
The price is CA $260
CA $291 total
includes taxes & fees
May 28 - May 29
Urban Cowboy Lodge
Exterior
Hotel Vienna
2.5 star property
9.2 out of 10, Wonderful, (352)
"Solid not spectacular. Staff was great"
The price is CA $187
CA $202 total
includes taxes & fees
May 29 - May 30
Hotel Vienna
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Ashland?

Yes, we offer vacation rentals near popular attractions in Ashland, or you can choose a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Ashland has to offer?

Beautiful House 0,5 Mile From Hunter Mountain: This vacation home near Ashland is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Ashland?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Ashland stay.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Zoom Flume, or get outside and enjoy nature at Mountain Top Arboretum. Ashland Town Hall and Windham Vineyards and Winery are a couple of places you'll find in the larger area.

What are vacation rentals like in Ashland?

Vacation rentals are private properties you can book for several days or longer in Ashland. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip.

Recent reviews of Ashland properties
Expedia verified reviews