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Top Holiday Rentals in Ashland

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 £1,441
per night
27 May - 28 May
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
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!
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
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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 £572
per night
22 May - 23 May
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
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
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.
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
Fridge, microwave, stovetop, dishwasher
Tannersville Retreat w/ Pool, 6 Mi to Hunter Mtn!
10.0 out of 10, Exceptional, (48)
"Loved the house and it was perfect for our old friends hiking weekend"
Tannersville Retreat w/ Pool, 6 Mi to Hunter Mtn!
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!
Woodstock House on 35 private acres Mtn Views
10.0 out of 10, Exceptional, (35)
"Perfect long weekend getaway for our family of four plus our dog. Plenty of room both inside and out. Close to skiing, hikes, and nearby towns, Woostock, Phoenicia, etc. Thank you!"
Woodstock House on 35 private acres Mtn Views
Fridge, microwave, stovetop, dishwasher
'Bearpen Lodge' on 125 Acres - Near Belleayre Mtn!
10.0 out of 10, Exceptional, (85)
"The cabin was nice and clean and exactly as pictured. Check in was easy and communication with the host was easy and prompt. It was nice to be able to relax by the fire pit and grill outside with our dog. We had a great time."
'Bearpen Lodge' on 125 Acres - Near Belleayre Mtn!
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.
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
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
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!!
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 £645
per night
22 May - 23 May
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Interior
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
9.8 out of 10, Exceptional, (13)
"I recently had the pleasure of renting this fantastic house, and I cannot recommend it enough! From the moment I arrived, I was impressed by the thoughtful amenities and stunning surroundings. The fire pit and fireplace were perfect for cozy evenings, creating a warm and inviting atmosphere. Being near hiking trails added a touch of adventure to my stay, allowing me to explore the beautiful natural surroundings conveniently. The host's attention to detail was exceptional. They provided a...
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
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 £260
per night
22 May - 23 May
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
5 bedrooms, free WiFi, bed sheets
⭐ Spacious Lake House Just Minutes From The Slopes ⭐
9.8 out of 10, Exceptional, (55)
"bill and Nicole were gracious in giving us the best price for the weekend. The spot was clean and though we ran out of a few things there was a grocery store not far to stock up more. Overall a great stay!"
⭐ Spacious Lake House Just Minutes From The Slopes ⭐
Property grounds
Mountain Chalet with Breathtaking Panoramic Views
9.8 out of 10, Exceptional, (143)
"Lee was incredibly communicative and his description of the check in process was spot on! The house is beautiful and was sparkling clean for our arrival. Would absolutely stay again!"
Mountain Chalet with Breathtaking Panoramic Views
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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 Holiday Rental Travel Info

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

Other types of properties in Ashland you may be interested in

The Archaeologist's Digs | Private kitchen | Microwave, coffee/tea maker
The Roxbury
2.0 star property
9.8 out of 10, Exceptional, (33)
"It was a little noisy because the guests next door to us sat outside their room talking loudly while smoking & drinking. "
The price is £86
per night
22 May - 23 May
The Roxbury
Lobby sitting area
Hunter Lodge, a Bluebird by Lark
2.5 star property
9.4 out of 10, Exceptional, (371)
"Perfect mountain lodge with beautiful views - staff was very accommodating. We look forward to going back! "
The price is £99
per night
3 Jun - 4 Jun
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 £168
per night
28 May - 29 May
Urban Cowboy 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.

Everything you need to know about Ashland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ashland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashland holiday rentals we have selected for you start as low as £110 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Ashland?

Yes, there are holiday rentals close to the most popular sights in Ashland, or you can select a more secluded option if you're looking for a relaxing stay.

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

Beautiful House 0,5 Mile From Hunter Mountain: This holiday home rental outside of Ashland is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Ashland?

With 4 Expedia holiday rentals, you're guaranteed 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 wider area.

What are holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.

Recent reviews of Ashland properties
Expedia verified reviews