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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Ashland vacation rentals
1. 'the Mountain House:' Windham Retreat w/ Hot Tub!
'the Mountain House:' Windham Retreat w/ Hot Tub!
2. Windham NY Escape
Windham NY Escape
3. Starlite Motel
Starlite Motel
4. Suites on Main
Suites on MainFind vacation rentals that suit your style
Top Ashland Hotel Reviews
Cave Mountain Motel
Cave Mountain Motel10/10 Excellent
Hotel Vienna
Hotel Vienna10/10 Excellent
Albergo Allegria Hotel
Albergo Allegria Hotel10/10 Excellent
The Colonial Motel
The Colonial Motel10/10 Excellent
Jimmy OConnors Windham Mountain Inn
Jimmy OConnors Windham Mountain Inn10/10 Excellent
Hunter Lodge, a Bluebird by Lark
Hunter Lodge, a Bluebird by Lark10/10 Excellent
Antique Rose Inn Windham
Antique Rose Inn Windham10/10 Excellent
Shandaken Inn
Shandaken Inn10/10 Excellent
Eastwind Windham
Eastwind Windham10/10 Excellent
Mountain Treasure B&B
Mountain Treasure B&B10/10 Excellent
Wylder Hotel Windham
Wylder Hotel Windham10/10 Excellent
Kaatskill Mountain Club & Condos by Vail Resorts
Kaatskill Mountain Club & Condos by Vail Resorts10/10 Excellent
Shadowcrest
Shadowcrest10/10 Excellent
Hotel Mountain Brook
Hotel Mountain Brook10/10 Excellent
The Perch Hotel
The Perch Hotel10/10 Excellent
Find out more about Ashland
Everything you need to know about Ashland vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Ashland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $126 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Ashland rentals
At Expedia, we put the best Ashland vacation 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 vacation.
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 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?
Heart of Hunter Village; across MT!FALL Special3rd nt half OFF!”wknd stay: This vacation home rental near Ashland is located in the mountains and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.
How many vacation rentals will I find in Ashland?
With 3 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.