Ashland Holiday Rentals

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Holiday Rentals in Ashland

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

9.6 out of 10, Exceptional, (39)
"The house has anything you want . A private house nice town . Quite,"
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (244)
"Cosy room, clean bathroom, useable kitchen with all useful appliances. Loved the back yard with the fire pit. A little bit of a drive from our home but it was worth the effort. I would come again."
The price is AU$224
includes taxes & fees
19 Dec - 20 Dec
Starlite Motel

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (97)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court

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

10.0 out of 10, Exceptional, (144)
"We had another fun stay at the Dancing Horse Farm! The house has been upgraded with a new stove and other amenities. Huge home, to house several large families. Very well maintained and clean. We also visited the near by town for coffee and a nice brisk walk. Overall great time and look forward to coming again!"
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Cozy cabin with great views and fire place!

9.8 out of 10, Exceptional, (80)
"Great space and feel of upstate NY. Will return for sure "
Cozy cabin with great views and fire place!

Updated Cabin on the Esopus

10.0 out of 10, Exceptional, (40)
"We stayed here the weekend of 12/7 and had a lovely time. Cabin is centrally located in a beautiful location and was spotless and well-equipped. Bob was very helpful as the host. We will likely return!"
Updated Cabin on the Esopus

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (176)
"A beautiful, peaceful location to enjoy nature, yet be close enough to restaurants and shopping for convenience. We had four days of quiet and serenity in the warm, cozy, "feels like home" cottage. Our Labrador retriever loved exploring the woods and creekside (and barking at the wild turkeys!) Host Paul was attentive and gracious."
The Cabin at Chichester in the Catskills Mountains

Mountain Chalet with Breathtaking Panoramic Views

9.8 out of 10, Exceptional, (158)
"The property location was beautiful and all prior reviews were spot on. The views were all that and more. Waking up to the sunrise peeking over the mountains was majestic and peaceful. We were incredibly lucky to experience a snowstorm and woke up to 6” on Thxgiving morning. It was just perfect. We had a fire and made a snowman. My dog had a great time in the snow. We all cooked an amazing Thxgiving dinner together in the well equipped kitchen that even had a turkey baster (impressed). ...
Mountain Chalet with Breathtaking Panoramic Views

Birch Creek Retreat ~ 8br, 8ba, New Hot Tub + Sauna

10.0 out of 10, Exceptional, (90)
"My cousins and siblings had a great time from start to finish. The house was very comfortable with multiple places to relax. We had a large group and never felt short for space. All bedrooms were well furnished. The amazing kitchen was perfect for making our large family dinners. The area around the house offered beautiful scenery and nice options for when we wanted to go out. Highly recommend this property and host (Mella)"
Birch Creek Retreat ~ 8br, 8ba, New Hot Tub + Sauna

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (122)
"Our family had a fantastic stay. The house was perfect for kids, with plenty of space and a lovely atmosphere."
Beautiful new house 3/4 mile from Hunter Mountain

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

10.0 out of 10, Exceptional, (212)
"We had a fantastic stay in Valentyna's home. We had a large group of 16 at the home during labor day weekend. We found the house large, clean, updated and had plenty of space. The bedrooms are roomy, the living spaces are even larger than pictured, and the five different outdoor areas are fantastic. The house has every amenity you can ask for. Direct lake access is steps from the house and the house is close to Hunter for the winter months. We had a great time and would happily stay again. "
The price is AU$1,267
includes taxes & fees
19 Dec - 20 Dec
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim

LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

9.6 out of 10, Exceptional, (45)
"We really enjoyed our stay in Hunter. The house met our needs well for a large family gathering. The hot tub and game room were excellent. Beutiful inside.It is close to shopping and hiking trails in the area. We did a lot of cooking and could have used larger cutting boards and baking/roasting pans. Be aware that the house is right on the main road into Hunter. The pinball machine was frustrating at times because the ball would get stuck.Overall it was a great stay."
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

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

9.6 out of 10, Exceptional, (172)
"The property was fantastic. The check-in process was super easy, and the owners stopped by to walk us through the property and answer our questions. If you like using a sauna, then this is the place for you. If you like hot tubbing, then this is the place for you. If you want a wood burning fire place, then this is the place for you. I would absolutely recommend this property, and I will definitely stay again. "
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!

9.8 out of 10, Exceptional, (72)
"This entire place is amazing! I would definitely go back. "
Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!

Your peaceful, private retreat, escape with friends & family! Incredible views!

10.0 out of 10, Exceptional, (30)
"Everything as advertised and much more. The "AMBIANCE" was exceptional. Communications with property management was spot on. We experienced a snow storm (10"+) and the contracted snow plow driver was there to clear the driveway and clear most of the deck area. The owners have taken the time and effort to make this place a place of relaxation and beauty. All you have to bring is your own food (or eat at the local restaurants). If you forget anything, local grocery store would have...
Your peaceful, private retreat, escape with friends & family! Incredible views!

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

10.0 out of 10, Exceptional, (93)
"very beautiful and well-equipped house- everything you need and super comfy and clean!"
The price is AU$1,040
includes taxes & fees
19 Dec - 20 Dec
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE

Moonlight Reflections

10.0 out of 10, Exceptional, (90)
"wonderful experience - excellent host"
Moonlight Reflections

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

9.8 out of 10, Exceptional, (141)
"Most relaxing, the property well situated amongst trees and woods. Plenty of clearing to enjoy the grounds for playing around. Our pitbull absolutely enjoyed the wandering and wooded areas. Local neighbors were very friendly. Many deer on the property every evening they would be out just after dark. Lots of games to keep you busy, WiFi worked great. The cabin was perfect, just bring your food and snacks. Everything else is there."
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

Catskills Windham Hunter Mountain Cabin Getaway

9.0 out of 10, Wonderful, (25)
"Quiet stay in the mountains in the summer."
The price is AU$1,163
includes taxes & fees
7 Jan - 8 Jan 2025
Catskills Windham Hunter Mountain Cabin Getaway

Beautiful House 0,5 Mile From Hunter Mountain

9.8 out of 10, Exceptional, (196)
"Very accommodating host! Thanks for the stay. Definitely consider staying again! Lovely layout, airy, roomy. Host generous with paper goods etc. Thanks for a great vacation!"
Beautiful House 0,5 Mile From Hunter Mountain
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 types of properties in Ashland you may be interested in

Hunter Lodge, a Bluebird by Lark

3.0 star property
9.2 out of 10, Wonderful, (540)
"This place was so cute❤️"
The price is AU$353
includes taxes & fees
19 Dec - 20 Dec
Hunter Lodge, a Bluebird by Lark

Hotel Vienna

2.5 star property
9.4 out of 10, Exceptional, (478)
"Me and my wife stayed here for our anniversary and Thanksgiving dinner, the place is a paradise but the manager was a nightmare, everywhere we went he showed up, all we want it was some time alone that's what hotels are for."
The price is AU$320
includes taxes & fees
23 Dec - 24 Dec
Hotel Vienna

Urban Cowboy Lodge

5.0 star property
9.4 out of 10, Exceptional, (101)
"Great stay ! Will definitely come again "
The price is AU$488
includes taxes & fees
6 Jan - 7 Jan 2025
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.

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?

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge: This holiday home rental outside of Ashland is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Ashland?

With 5 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 Belleayre Beach at Pine Hill Lake. Ashland Town Hall and Hunter Mountain 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.