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Our top choices for Ashland hotels

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
Hunter
9.2 out of 10, Wonderful, (365 reviews)
"Spacious room. Beautiful Mountain View s."
United States
Richard
3 days ago
$212 nightly
The price is $229
Jun 3 - Jun 4
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (805 reviews)
"Family run eclectic hotel. Stay here again. Staff was friendly."
United States
Kenneth
21 hours ago
$164 nightly
The price is $177
Jul 1 - Jul 2
Total with taxes and fees
Hotel Vienna

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (955 reviews)
"Huge comfortable rooms. This place was amazing. A gorgeous property."
United States
katelyn
8 days ago
$138 nightly
The price is $149
Jun 10 - Jun 11
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark

Urban Cowboy Lodge

Urban Cowboy Lodge
5.0 star property
Big Indian
9.4 out of 10, Exceptional, (240 reviews)
"Everything was wonderful! Perfect for a long weekend getaway."
United States
Bonnie
25 days ago
$206 nightly
The price is $231
Jun 9 - Jun 10
Total with taxes and fees
Urban Cowboy Lodge

Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (104 reviews)
"Clean and such friendly staff would definitely recommend!"
United States
Anthony
April 26th, 2026
$243 nightly
The price is $262
Jun 24 - Jun 25
Total with taxes and fees
Eastwind Windham

AutoCamp Catskills

AutoCamp Catskills
5.0 star property
Saugerties
9.0 out of 10, Wonderful, (511 reviews)
"We all really loved our stay."
United States
Katelyn
4 days ago
$187 nightly
The price is $209
Jun 24 - Jun 25
Total with taxes and fees
AutoCamp Catskills

Silas House

Silas House
3.0 star property
Lexington
10.0 out of 10, Exceptional, (16 reviews)
"Had a lovely stay at Silas House. I hope to stay here again."
United States
Sophie
Silas House

Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (142 reviews)
"Great stay at Cave Mountain Motel."
United States
Marc
March 14th, 2026
$139 nightly
The price is $150
Jun 2 - Jun 3
Total with taxes and fees
Cave Mountain Motel

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (98 reviews)
"Family Weekend Getaway. Enough to come back several times. The staff amazing."
United States
Herendira
14 days ago
$360 nightly
The price is $389
Jun 4 - Jun 5
Total with taxes and fees
Wylder Hotel Windham

Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (136 reviews)
"We enjoyed our stay very much."
United States
Briana
April 13th, 2026
$149 nightly
The price is $161
Jul 1 - Jul 2
Total with taxes and fees
Black Bear Lodge

The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (353 reviews)
"Great option for visiting Windham mountain!"
United States
Maria
March 10th, 2026
$169 nightly
The price is $183
Jun 2 - Jun 3
Total with taxes and fees
The Winwood Condominiums

The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (444 reviews)
"A spacious room close to the downtown good place to lay your head."
United States
Peggy
2 days ago
$94 nightly
The price is $103
Jun 16 - Jun 17
Total with taxes and fees
The Colonial Motel

Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (279 reviews)
"The coffee was awesome. All were great."
United States
Christopher
12 days ago
$163 nightly
The price is $176
Jun 2 - Jun 3
Total with taxes and fees
Albergo Allegria Hotel

Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.8 out of 10, Excellent, (169 reviews)
"Hot showers with great pressure."
United States
John
January 4th, 2026
$120 nightly
The price is $130
Jun 2 - Jun 3
Total with taxes and fees
Moore's Motel

Fairlawn Inn

Fairlawn Inn
3.0 star property
Hunter
8.8 out of 10, Excellent, (437 reviews)
"Room was lovely and Sandy, the host, was so attentive."
United States
Tina
$259 nightly
The price is $280
Jun 13 - Jun 14
Total with taxes and fees
Fairlawn Inn

Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.0 out of 10, Wonderful, (68 reviews)
"Just all around a good experience."
United States
Mihai
28 days ago
$188 nightly
The price is $211
Jun 30 - Jul 1
Total with taxes and fees
Emerson Resort & Spa

Xenia Resort

Xenia Resort
2.5 star property
Jewett
9.2 out of 10, Wonderful, (67 reviews)
"Nice rear porch. Close to Hunter Mtn."
United States
john delbert
March 3rd, 2026
Xenia Resort

Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
Tannersville
9.8 out of 10, Exceptional, (566 reviews)
"Fantastic place to stay in the Catskills. With charming rooms."
United States
Flavio M
1 day ago
$229 nightly
The price is $247
Jun 2 - Jun 3
Total with taxes and fees
Hotel Mountain Brook

Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (277 reviews)
"Amazing an unique place to stay."
United States
Mary
9 days ago
$289 nightly
The price is $319
Jun 9 - Jun 10
Total with taxes and fees
Woodstock Way Hotel

The Outpost by Windham Mountain Club

The Outpost by Windham Mountain Club
2.5 star property
Windham
8.4 out of 10, Very Good, (5 reviews)
"Cozy and warm. I think it would be better to visit during the winter season."
United States
TAEJUN
$350 nightly
The price is $378
Jun 4 - Jun 5
Total with taxes and fees
The Outpost by Windham Mountain Club
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Where to stay near Ashland

Ashland offers a delightful blend of adventure and relaxation, perfect for ski enthusiasts and outdoor lovers. Nearby towns provide friendly atmospheres and stunning scenery, making it an ideal destination for family-friendly excursions and sports vacations. Discover the charm and excitement that awaits in this beautiful region.

Windham

Discover Windham, a picturesque destination ideal for nature lovers and adventure seekers looking for a weekend getaway. With stunning attractions like Kaaterskill Falls, the serene Huntersfield State Forest, and the charming Ashland Park, Windham invites travelers to explore its natural beauty year-round. Located about 6 miles by car from Ashland, this city offers easy access to thrilling ski resorts during the winter months. Choosing Windham for your stay ensures a memorable experience in the heart of the Catskills.

Hunter

Experience the charm of Hunter, a fantastic hub for adventure seekers and families eager to explore the stunning Catskill Mountains and enjoy outdoor activities year-round. With attractions like Kaaterskill Falls and Catskill State Park, visitors can immerse themselves in nature's beauty while enjoying skiing and sports during the peak winter months. Located about 14 miles by car from Ashland, Hunter offers a convenient base for your vacation, making it an excellent choice for your next getaway.

Jewett

If you are a nature lover or an adventure seeker, look no further than Jewett, known for its stunning landscapes and outdoor activities. This charming city offers easy access to the beautiful Catskill State Park, the breathtaking Kaaterskill Falls, and the inviting Ashland Park. While visitor numbers peak from June to August, Jewett remains a great choice for a weekend getaway year-round. Located about 3 miles from Ashland, Jewett provides a perfect base for exploring the area's natural wonders.

Prattsville

Prattsville stands out as a prime spot for families and outdoor enthusiasts interested in a nature-filled getaway. Nestled near the beautiful Bearpen Mountain State Forest, visitors can enjoy skiing and explore scenic lakes and parks, including the delightful Ashland Park. With its rich history showcased at the Zadock Pratt Museum, Prattsville offers diverse experiences year-round. Located about 4 miles by car from Ashland, it’s an ideal choice for your next vacation, providing easy access to adventure and relaxation.

Lexington

Travelers seeking a weekend getaway will find Lexington to be the ideal base for their vacation, featuring stunning landscapes and an abundance of outdoor activities. With the majestic Catskill Mountains and Catskill State Park nearby, nature enthusiasts can indulge in hiking, skiing, and exploring picturesque lakes. Just about 5 miles from Ashland, Lexington offers easy access to local landmarks like Ashland Park, making it a smart choice for your stay. Enjoy the perfect blend of adventure and relaxation in this charming destination.

Stay near popular attractions in and around Ashland

Discover the charm of Ashland, where adventure awaits! Whether you're seeking thrilling ski slopes, serene parks, or cultural experiences, this destination offers something for everyone. Embrace the outdoors and create unforgettable memories with family and friends in this picturesque setting.

Top Ashland Hotel Reviews

More cheap stays in Ashland

Hotels in Ashland with star-rating

Find out more about Ashland

Top reasons to visit Ashland

  • Winter Sports Paradise: Ashland is perfect for skiing enthusiasts with local resorts offering thrilling slopes and winter activities.
  • Cultural Enrichment: Experience the renowned Shakespeare Festival, adding a unique cultural dimension to your visit.
  • Outdoor Adventures: Explore nearby national and state parks, ideal for hiking and family-friendly excursions.
  • Scenic Views: Enjoy picturesque landscapes in Ashland Hills, perfect for relaxation and picnics.
  • Welcoming Atmosphere: Experience the friendly vibe of downtown Ashland, complemented by charming accommodations.

Find great hotels near Ashland

Discover a range of hotel accommodations in Ashland, New York, perfect for any traveler seeking adventure or a cozy family getaway. From affordable hotels to charming motels, Ashland offers pet-friendly options to ensure everyone can enjoy their vacation. Whether you're looking for a comfortable stay or unique agritourism experiences, you'll find the ideal lodging to suit your needs in this picturesque destination.

  • Hunter Lodge, a Bluebird by Lark: Nestled 11 miles away from Ashland, Hunter Lodge, a Bluebird by Lark is a budget-friendly escape rated 9.2 by guests. This lodge is perfect for adventure seekers and pet owners alike, offering a host of outdoor activities like snowboarding, canoeing, and fishing nearby. With a pet-friendly policy allowing dogs in rooms, guests can enjoy a cozy stay with their furry companions. The lodge emphasizes recreation, making it an ideal choice for those looking to embrace the great outdoors while enjoying a comfortable and welcoming atmosphere.
  • Hotel Vienna: Located just 6 miles from Ashland, Hotel Vienna is a charming budget-friendly option with an impressive guest rating of 9.4. This hotel is especially suited for golf enthusiasts and business travelers, boasting opportunities for golf-themed activities. Guests can also take advantage of nearby adventure sports, including kayaking and zip-lining. The warm ambiance and friendly service create an inviting atmosphere, making Hotel Vienna a delightful choice for those seeking both leisure and business amenities.
  • Kaatskill Mountain Club & Condos by Vail Resorts: Situated 10 miles from Ashland, Kaatskill Mountain Club & Condos by Vail Resorts offers a budget-friendly stay with a guest rating of 9.2. Ideal for ski lovers and adventure seekers, this property provides easy access to ski shuttles and lifts. Guests can enjoy a variety of thrilling activities, including downhill skiing and snowboarding, making it a paradise for winter sports enthusiasts. With spacious accommodations and a focus on outdoor adventure, this destination is perfect for those looking to create unforgettable mountain memories.

Where to stay near Ashland

Ashland, New York, is a hidden gem perfect for adventurous travelers. Enjoy the vibrant atmosphere of downtown Ashland, where friendly locals welcome you. Explore the picturesque Ashland Hills for scenic views and picnic areas ideal for relaxation. Whether you're skiing or seeking family-friendly excursions, Ashland offers an unforgettable experience. Nearby towns also provide a charming backdrop for your vacation, ensuring a delightful blend of adventure and tranquility.

  • Windham: Located 5 miles from Ashland, Windham is a delightful city that attracts visitors year-round, with a peak in winter from December to February. Known for its vibrant ski culture, Windham offers thrilling adventures in skiing and sports, making it a popular destination for outdoor enthusiasts. Visitors can enjoy a variety of ski resorts and fields, while the breathtaking natural landmarks, including mountains, lakes, and waterfalls, provide stunning backdrops for both relaxation and exploration. The charming local vibe and seasonal events ensure there's always something happening.
  • Hunter: Situated 9 miles from Ashland, Hunter is a charming city that draws a moderate influx of travelers, especially during the winter months. Known for its excellent skiing opportunities, Hunter caters to adventure seekers and sports lovers alike. The area boasts several ski resorts and fields, offering an exhilarating experience for both novices and experts. Surrounded by majestic mountains, tranquil lakes, and picturesque waterfalls, Hunter invites visitors to immerse themselves in the beauty of nature while enjoying outdoor activities throughout the year.
  • Jewett: Just 3 miles from Ashland, Jewett is a hidden gem that captivates visitors with its scenic charm. The city sees a spike in tourism during the summer months of June to August, making it a fantastic spot for those seeking outdoor adventure. Like its neighbors, Jewett is known for skiing and sports, with several ski fields and resorts nearby. Visitors can explore local landmarks, including stunning mountains, serene lakes, and well-maintained urban parks, providing a perfect blend of relaxation and adventure for all ages.

Things to do in Ashland

Ashland, New York, is an ideal destination for ski enthusiasts and adventure seekers, offering a range of activities like skiing at local resorts. In addition to winter sports, visitors can enjoy the renowned Shakespeare Festival, which adds a cultural flair to your trip. Whether you're hitting the slopes or appreciating the arts, Ashland provides a unique blend of excitement and entertainment for your vacation.

Shopping

In Ashland, visit local shops for unique gifts and souvenirs. If you're up for a drive, check out the Hudson Valley Mall, around 15 miles away, which features a mix of well-known retailers and smaller boutiques for a great shopping experience.

Recreation

Experience rejuvenation at the Ashland Wellness Spa, where you can indulge in soothing massages and holistic treatments. For outdoor fun, explore the scenic hiking trails in the Catskills, offering breathtaking views and an opportunity to connect with nature while enjoying fresh air and exercise.

Adventure

Explore the thrilling hiking trails of the Catskill Mountains, offering stunning vistas and diverse wildlife. For a unique adventure, try kayaking on the nearby lakes, where you can paddle through serene waters surrounded by nature's beauty.

Nightlife

Ashland boasts a cozy nightlife with local bars and taverns like The Ashland Tavern, where you can enjoy live music and craft beers. For a more laid-back vibe, check out the nearby café scene, perfect for evening hangouts and conversations with friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Ashland

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Ashland are March to April and November, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Ashland is Tuesday. The most expensive day to stay in Ashland is Friday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your search based on your preferences, such as budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Ashland with your flights and activities through an Expedia package.

Find the best attractions near Ashland

Ashland, New York, is a fantastic destination for skiing and adventure sports, offering a variety of outdoor activities. Visitors can explore nearby national and state parks, as well as nature reserves, perfect for families and culture enthusiasts alike. Whether you're looking to hit the slopes or enjoy a scenic hike, Ashland provides a range of attractions that cater to outdoor lovers and those seeking memorable experiences in the great outdoors.

  • Catskill State Park: Experience the stunning natural beauty of Catskill State Park, just 14 miles from Ashland. With endless hiking trails, scenic vistas, and vibrant wildlife, it’s a paradise for outdoor enthusiasts and nature lovers alike.
  • Belleayre Beach: Relax and soak up the sun at Belleayre Beach, also 14 miles away. This serene beach offers a perfect spot for swimming, picnicking, and enjoying the tranquil atmosphere of the surrounding mountains.
  • Mountain Top Arboretum: Explore the diverse plant collections at Mountain Top Arboretum, located 12 miles from Ashland. This family-friendly destination provides a peaceful outdoor experience with beautiful landscapes and educational programs for all ages.

Best time to go to Ashland

The best time to visit Ashland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.9°F (-5.6°C)Light RainMostly CloudyAverageAverage
February24.1°F (-4.4°C)Light RainMostly CloudyAverageAverage
March31.6°F (-0.2°C)Light RainMostly CloudySlightly LowSlightly Low
April43.3°F (6.3°C)Light RainMostly CloudySlightly LowSlightly Low
May55.6°F (13.1°C)Light RainMostly SunnyAverageAverage
June63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
July68.7°F (20.4°C)Light RainMostly SunnySlightly HighSlightly High
August66.7°F (19.3°C)Light RainMostly SunnySlightly HighSlightly High
September59.9°F (15.5°C)Light RainMostly SunnyAverageAverage
October48.9°F (9.4°C)Light RainMostly SunnySlightly HighSlightly High
November36.9°F (2.7°C)Light RainMostly SunnySlightly LowSlightly Low
December28.2°F (-2.1°C)Light RainMostly CloudyAverageAverage

The nearest major airports for your trip to Ashland

When planning your visit to Ashland, New York, you have several airport options. ALBany International Airport (ALB) is the closest, located 41 miles away, with nearby hotels such as The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both just 8 miles from the airport. Bradley International Airport (BDL) in Hartford, CT, is 89 miles away, offering hotels like DoubleTree by Hilton Hartford - Bradley Airport, which is 1 mile from the airport. For those considering Westchester County Airport (HPN), it is located 92 miles from Ashland, with hotel options like The Opus Westchester, just 4 miles away, providing convenient transportation services.

Frequently asked questions

What is the best area to stay in Ashland?
The best area to stay in Ashland is downtown, particularly around Main Street, for its central location and access to local attractions.

Downtown Ashland is the heart of the city's activity, characterized by its historic buildings and a walkable layout. Main Street is where you'll find a concentration of local shops, art galleries, and diverse dining options. The Ashland Creek runs through the downtown area, adding to its pleasant setting.

Couples will find downtown an excellent choice due to its proximity to the Oregon Shakespeare Festival theaters, which are a major draw. Evening strolls to dinner or a performance are convenient, and there are many cozy cafes and wine bars for a relaxed experience.

Families also benefit from staying downtown. Lithia Park, a large and well-maintained urban park with playgrounds, walking trails, and open spaces, is directly adjacent to the downtown area.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Ashland.
How can I save on a Ashland hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Ashland hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Ashland hotel?
Prices for hotels in Ashland often vary, but you can find a great deal from $91 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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