Ashland Holiday Rentals from AU$199: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Ashland holiday rentals

A two-story building with large windows and a storefront.

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

Windham

Ahmad O.

includes taxes & fees

29 Sept - 30 Sept

A wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

2. Cozy Cabin-Catskills secluded Mountain retreat

Gilboa

Joshua

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

3. Starlite Motel

Big Indian

Sarah

includes taxes & fees

28 Sept - 29 Sept

A log cabin with a porch, a staircase, and a garage.

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

Hunter

alain

includes taxes & fees

27 Sept - 28 Sept

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

Windham

"Overall great experience. Very central location. Host lives in building, so is always available. They grow tomato's and cucumbers on the balcony that they invited us to "take as much as you want" My only discomfort with this place was the dust and dirty dishes. The people before us half-washed the things they used and the place seemed like it needed a pass with a vacuum cleaner. The floors were not very clean. In general, I greatly enjoyed my stay here."

David

includes taxes & fees

29 Sept - 30 Sept

A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

6. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham

Cristina L.

includes taxes & fees

5 Oct - 6 Oct

A natural landscape with a lake, rocky cliffs, and a bench.

7. Cozy Mountain Dome Escape in the Catskills

Gilboa

kim h.

includes taxes & fees

28 Sept - 29 Sept

A wooden cabin interior with a kitchen area, wooden cabinets, a black stove, and a black refrigerator.

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

Roxbury

Gabrielle G.

includes taxes & fees

4 Oct - 5 Oct

A kitchen with green cabinets, a stainless steel stove, and a microwave.

9. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

Windham

Anthony M.

includes taxes & fees

28 Sept - 29 Sept

A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

10. West Kill Barnhouse: Ski, Work & Unwind

West Kill

Vijay S.

includes taxes & fees

27 Sept - 28 Sept

Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

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

Hensonville

Kimberly K.

includes taxes & fees

27 Sept - 28 Sept

A cozy cabin interior with a wooden interior, a spiral staircase, a kitchen area, and a seating area with a view.

12. Spacious Catskill Mountains ski cabin with fire pit

Maplecrest

Lily

includes taxes & fees

27 Sept - 28 Sept

13. Windham NY Escape

Hensonville

Miguel

includes taxes & fees

5 Oct - 6 Oct

A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

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

Windham

Melissa R.

includes taxes & fees

27 Sept - 28 Sept

A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

15. Jessie's Harvest House

Tannersville

Dan

includes taxes & fees

29 Sept - 30 Sept

A picnic setup with a wine glass, bottle, cheese, tomatoes, and grapes on a wooden table with a view of a grassy field and hills.

16. Relaxing Mountain Hideaway - Hot Tub & Outdoors

Hensonville

Kyrill A.

includes taxes & fees

27 Sept - 28 Sept

A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

17. Pines Vignette • Modern 3BR Home in Windham

Windham

William H.

includes taxes & fees

27 Sept - 28 Sept

A deck with a fire pit, outdoor seating, and a view of the landscape.

18. Romantic Catskill Getaway | HotTub w/Mountain View

Prattsville

Ramsey

includes taxes & fees

29 Sept - 30 Sept

19. Suites on Main

Margaretville

"You get what you pay for - cheap, not value. Spent the first 2 hours cleaning because it was barely touched - even dining table and chairs had crumbs and spill stains. The coffee maker was black inside the water compartment. I had to pick up silverware and dish soap from the dollar store because there was only 2 forks and spoons for a place advertised for 6 and no dish soap to clean dishes. I’m confident my cleaning and items I left behind for the next guests will be reimbursed by karma. Oh,...

Jonathan

includes taxes & fees

27 Sept - 28 Sept

A wooden structure with a circular entrance, two red Adirondack chairs, a small table, and a bottle of water.

20. Sauna Belleayre Cozy Cabin

Fleischmanns

Jordan W.

includes taxes & fees

28 Sept - 29 Sept

View all properties

Find holiday rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Ashland Hotel Reviews

Urban Cowboy Lodge

10/10 Excellent

"A fabulous establishment, lots to do on site!"

Jimmy OConnors Windham Mountain Inn

10/10 Excellent

"Cool little spot with the inn at the back of the property and the restaurant at the front. It’s been passed down through the family and I met the owner inside during a quick dinner, down to earth guy. The room is very vey clean and still sporting the original textures and fixtures, real retro feeling, I loved it."

Emerson Resort & Spa

10/10 Excellent

"If you are looking for a very peaceful, serene getaway to completely reset, book this place immediately. The quiet, beautiful atmosphere makes it a true sanctuary.The hospitality here is next level. Jackie was incredibly nice and welcoming from start to finish. Jonathan went out of his way to take gorgeous birthday pictures for me the second I asked. The absolute hero of my trip was Kristine, who literally saved me when I found myself stranded in the middle of nowhere!This team protects your peace of mind, I am telling everyone about this gem, and I am definitely coming back to the Emerson!"

Shandaken Inn

8/10 Good

"The hotel staff is very friendly and provides excellent service . The room is clean and comfortable. The breakfast is not really good. The potatoes are too spicy. We asked the waitress if we could change. She rejected directly and didn’t give us any choices. However, when we had the breakfast in second day morning, we required to change too spicy potatoes. The waitress was very nice and helped change to fruit after she talked with supervisor. If the breakfast could give more choices, the hotel would be more attractive."

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$199 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?

Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend: This holiday home rental outside of Ashland is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 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, an arcade/games room 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.

Room 1

Change your mind

Treat yourself

Be picky

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. Cozy Cabin-Catskills secluded Mountain retreat

3. Starlite Motel

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

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

6. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

7. Cozy Mountain Dome Escape in the Catskills

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

9. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

10. West Kill Barnhouse: Ski, Work & Unwind

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

12. Spacious Catskill Mountains ski cabin with fire pit

13. Windham NY Escape

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

15. Jessie's Harvest House

16. Relaxing Mountain Hideaway - Hot Tub & Outdoors

17. Pines Vignette • Modern 3BR Home in Windham

18. Romantic Catskill Getaway | HotTub w/Mountain View

19. Suites on Main

20. Sauna Belleayre Cozy Cabin

Find holiday rentals that suit your style

Top Ashland Hotel Reviews

Urban Cowboy Lodge

The Colonial Motel

Hunter Lodge, a Bluebird by Lark

Jimmy OConnors Windham Mountain Inn

Emerson Resort & Spa

SunView Motel

Shandaken Inn

Starlite Motel

The Graham & Co.

Find out more about Ashland

Frequently asked questions

Go further with the Expedia app