Ashland Holiday Rentals from AU$198: Search Short-Term Rentals

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Our top choices for Ashland holiday rentals

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

Windham

Ahmad O.

includes taxes & fees

11 Aug - 12 Aug

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

Windham

Michael C.

includes taxes & fees

11 Aug - 12 Aug

3. Cozy Cabin-Catskills secluded Mountain retreat

Gilboa

Joshua

includes taxes & fees

12 Aug - 13 Aug

4. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Hunter

Mary C.

includes taxes & fees

11 Aug - 12 Aug

Premium House, Kitchen, Mountain View | Private kitchen

5. Starlite Motel

Big Indian

Sean

includes taxes & fees

11 Aug - 12 Aug

6. West Kill Barnhouse: Ski, Work & Unwind

West Kill

Vijay S.

includes taxes & fees

12 Aug - 13 Aug

7. Boutique Glamping Dome in the Catskill Mountains

Gilboa

includes taxes & fees

11 Aug - 12 Aug

8. Relaxing Mountain Hideaway - Hot Tub & Outdoors

Hensonville

Kyrill A.

includes taxes & fees

31 Aug - 1 Sept

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Top Ashland Hotel Reviews

Hotel Vienna

10/10 Excellent

"Great weekend visit at Hotel Vienna with our 2 small dogs! Check in and check out were super easy, staff was helpful and accommodating, and the property was really quiet, very clean and super well maintained. The bathrooms were obviously recently renovated and very tastefully done, the bed was firm and linens soft and comfy. Breakfast was pastries, cereal, and yogurt; all were high quality, fresh and delicious. Cappuccino and tea were lovely. Shower pressure could have been a bit better, but that was literally the only downside. We did not have a chance to use the pool, but it looked very clean, located in a nice, stand-alone building with windows and skylights. Barrel sauna is just outside on the deck, and both are is surrounded by beautiful landscaping. The main building also has two sunny, well furnished decks, and there are fire pits with Adirondack chairs located about the property, and there's direct access to the Windham Path and dog park. Sad I missed the free Saturday morning yoga, but I'll definitely try to make it next time. All in all, this hotel was perfect, peaceful, and we'll definitely be back to explore all the things we missed!"

Wylder Hotel Windham

10/10 Excellent

"The staff were wonderful and went out of their way to make sure you had whatever you wanted. There are plenty of things to do right at the hotel and you are right by the mountains if you want to take advantage of that. The pool is heated and you can have drinks by the pool. There are several locations for fire pits and the staff will help you get a raging fire going immediately upon request. The golf course was simply beautiful and if that is your thing, absolutely a must. The restaurant on the grounds was terrific as was the bakery for breakfast and goodies. The buildings themselves are 150 years old and are lovely to check out just for that. I would certainly return in the future."

The Colonial Motel

10/10 Excellent

"Beautiful historic Inn and motel, set in the heart of the Catskills. I stayed in the main Inn and enjoyed a boutique style stay. My room was beautifully decorated with attention given to details from the time period. Very clean with one of the most comfortable beds I've slept in. Really enjoyed the pool and the staff. Can't wait to return."

Hotel Mountain Brook

10/10 Excellent

"We stayed in the 3 bedroom apt and it was so cute and very clean! There was an ample supply of towels for the three of us and all the room amenities you would need. Lots of board games and movies to borrow from the lobby den and coffee and tea are always available. They are welcoming to dogs and had bowls and treats for our two fur babies. The fire pit was on each night and there are delicious s’mores kits in the lobby to take out to the fire which we LOVED!!! Wish they offered lunch and dinner but they don’t so make sure you plan around that. Also mondays and Tuesdays many of the restaurants around there are closed."

The Graham & Co.

10/10 Excellent

"This was my family’s third time staying at the Graham & Co. and every single stay has been wonderful. My family has grown a lot since our first stay 10 years ago, so staying in the bungalow gave everyone enough space while keeping us close. The room and grounds are very clean and well kept. The staff were so attentive. We arrived very late and they were great about giving us an option of seamless access to our room. We will certainly be back soon."

Find out more about Ashland

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, 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 favourite 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 depend 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 AU$198 per night. Entering your travel dates in the search wizard might find you 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?

Catskill Mountain Retreat -- private, beautiful views, hot tub, game rm, firepit: This holiday home rental outside of Ashland is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 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 library 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 Mountain Resort 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.

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Check prices for these dates

Our top choices for Ashland holiday rentals

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

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

3. Cozy Cabin-Catskills secluded Mountain retreat

4. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

5. Starlite Motel

6. West Kill Barnhouse: Ski, Work & Unwind

7. Boutique Glamping Dome in the Catskill Mountains

8. Relaxing Mountain Hideaway - Hot Tub & Outdoors

9. Brand New 2 Bdr. Townhome Minutes from Windham Mtn

10. Cozy Downtown Hunter Mountain Getaway

11. King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4

12. Hunter Mountain 2 Bedroom Condo - Steps to Ski Slopes!!

13. Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly

14. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

15. Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

16. Cozy Waterfall Home | Close to All Mountains/Hikes

17. Windham NY Escape

18. Cozy 2-bedroom house in Haines Falls near Katterskill falls .

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

20. Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

Find holiday rentals that suit your style

Top Ashland Hotel Reviews

Hotel Vienna

Wylder Hotel Windham

The Colonial Motel

Hotel Mountain Brook

Jimmy OConnors Windham Mountain Inn

The Graham & Co.

Phoenicia Lodge

Emerson Resort & Spa

Urban Cowboy Lodge

Find out more about Ashland

Frequently asked questions

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