Ashland vacation rentals

We found 643 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Ashland that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you need and want for your stay, which might include parking and a pool. What you'll find is a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Ashland

Showing deals for:Jul 17 - Jul 24

Image gallery for Spacious Catskill Mountains ski cabin with fire pit

Room
9.8 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)

Spacious Catskill Mountains ski cabin with fire pit

Maplecrest

8% off
Price is $217
$1,516 for 7 nights
All fees included
Spacious Catskill Mountains ski cabin with fire pit

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Find out more about Ashland

Why visit Ashland

  • Outdoor Adventure: Ashland is perfect for skiing and exploring state parks, offering thrilling activities for adventure seekers.
  • Charming Neighborhoods: South Ashland features delightful accommodations and family-friendly experiences in a welcoming atmosphere.
  • Diverse Accommodations: Choose from cozy cabins, private homes, and charming cottages to suit every traveler's needs.
  • Scenic Landscapes: Enjoy breathtaking views and picturesque surroundings, perfect for relaxation and outdoor exploration.
  • Family Fun: Ashland offers a variety of activities suitable for all ages, making it a great destination for families.

Popular types of accommodation in Ashland

If you're looking for the perfect getaway in Ashland, you've come to the right place. Our most popular vacation rentals include houses, cozy cabins, and charming cottages. Whether you're seeking pet-friendly options, a place to enjoy breakfast, or simply the best houses to stay in, we've got a variety of choices to suit your needs. Explore Ashland and find the ideal rental for your next adventure.

  • Houses: These are the top choice for travelers seeking spacious and comfortable accommodations, perfect for families or groups.
  • Cabins: A close second, cabins offer a rustic charm and a tranquil escape surrounded by nature.
  • Cottages: Ideal for a cozy getaway, cottages provide a quaint and inviting atmosphere.
  • Chalets: These unique stays combine comfort with alpine aesthetics, perfect for those seeking a mountain retreat.
  • Apartments: Offering convenience and flexibility, apartments are a great option for shorter stays or city explorers.**

Top attractions near Ashland

Ashland, New York, is a fantastic destination for ski enthusiasts and adventure seekers alike. With popular attractions like ski resorts, state parks, and nearby beaches, visitors can enjoy a range of outdoor activities. Whether you're looking for cultural experiences or family-friendly fun, Ashland offers something for everyone, making it an ideal spot for your next vacation.

  • Windham Mountain Resort: Located 5 miles from Ashland, this ski resort offers thrilling winter sports, including skiing and snowboarding, along with breathtaking mountain views and a vibrant adventure atmosphere year-round.
  • Belleayre Beach at Pine Hill Lake: Just 14 miles away, this charming beach provides a serene escape with sandy shores, swimming, and picnic areas, perfect for relaxing under the sun.
  • Mine Kill State Park: Situated 11 miles from Ashland, this national park features stunning scenery, hiking trails, and outdoor activities, making it an adventure lover’s paradise.

Things to do recommended for couples

For a romantic getaway in Ashland, explore Windham Mountain Resort for thrilling skiing or unwind at Windham Vineyards and Winery, perfect for wine tasting. Don't miss a scenic ride on the Kaatskill Flyer Ski Lift for breathtaking views and adventure together.

Things to do recommended for families

Families will love visiting the Pine Hill Community Center, a recreation hub located 14 miles from Ashland. With its wellness and relaxation vibes, it's a perfect spot for kids to play and parents to unwind together in a friendly, community atmosphere.

Things to do recommended for groups

Experience the outdoor vibes at the Windham Country Club, only 6 miles from Ashland, perfect for a round of golf. For a touch of romance, visit the Union Grove Distillery, 18 miles away, or enjoy culture and family fun at Mount Tremper Arts, also 18 miles from Ashland.

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

What do I need to keep in mind when booking a vacation in Ashland

If you're traveling with a group, family, or pets, or if you're planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Ashland with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily narrow down your options on Vrbo to find exactly what you need and more.
  • Traveling to Ashland with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Ashland: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Ashland: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Ashland

Ashland, New York, offers a perfect blend of adventure and relaxation, making it an ideal vacation spot. Explore the scenic landscapes and friendly atmosphere while enjoying outdoor activities like skiing and sports. Nearby neighborhoods, such as South Ashland, provide charming accommodations and family-friendly experiences. Whether you're seeking cozy holiday apartments or planning excursions, Ashland promises memorable moments in a welcoming environment.

  • Windham: Located 5 miles from Ashland, Windham is a premier destination for outdoor enthusiasts and adventure seekers. Renowned for its ski slopes, this charming city offers an array of sports experiences year-round. Visitors can enjoy skiing and snowboarding in the winter, while the warmer months reveal hiking trails and scenic vistas. The nearby mountain landscapes, tranquil lakes, and picturesque waterfalls enhance the natural beauty of the area, making it a perfect spot for both relaxation and adventure.
  • Hunter: Situated 9 miles from Ashland, Hunter is another fantastic city for those craving outdoor activities. Known for its ski resorts, Hunter attracts visitors with its thrilling winter sports and breathtaking mountain views. In addition to skiing, the area offers opportunities for hiking, biking, and exploring its stunning natural landmarks, including lakes and waterfalls. The vibrant local community also provides a welcoming atmosphere for tourists looking to enjoy unique shops and eateries after a day of adventure.
  • Jewett: Just 3 miles from Ashland, Jewett is a hidden gem for outdoor lovers. This small city is known for its access to ski fields and recreational sports, making it a great spot for winter activities. Jewett's close proximity to stunning mountains, serene lakes, and beautiful waterfalls allows visitors to immerse themselves in nature's splendor. Whether you are hitting the slopes or enjoying a peaceful day by the water, Jewett provides a tranquil yet adventurous getaway.

Best time to go to Ashland

If you're planning a trip to Ashland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in July to August and October, while off-peak times, like March to April and November tend to have fewer bookings and better deals.

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

Booking with Vrbo is simple

Looking to save money on your next trip? Consider being flexible with your travel dates, as prices can change significantly. Additionally, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental. We’re here to help you find the best options for your needs.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can start new trip ideas, pick up right where you left off, or easily manage and organize your existing plans. Any properties you’ve saved or booked before can now be accessed under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Ashland getaway

Learn about the unique charm of Ashland with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Ashland

Are you hoping to discover attractions to visit while you're in town? Venture out of your vacation home and check out everything that makes Ashland a one-of-a-kind vacation spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Windham Mountain Resort (5.6 mi / 8.9 km)
  • Windham Country Club (6.5 mi / 10.4 km)
  • Hunter Mountain (10.6 mi / 17 km)
  • Zoom Flume (11.7 mi / 18.8 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (13.9 mi / 22.3 km)
  • Belleayre Mountain Ski Center (14.2 mi / 22.9 km)

Exploring the natural features in Ashland

Whether you're an active traveler or just want to take in the scenery, Ashland is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Mountain Top Arboretum (13.2 mi / 21.3 km)
  • Belleayre Beach (14.5 mi / 23.3 km)
  • East Branch Delaware River (18.9 mi / 30.4 km)
  • Catskill Mountains (21.3 mi / 34.3 km)
  • Elm Ridge Wild Forest (9 mi / 14.4 km)
  • Relay State Forest (13.4 mi / 21.5 km)

Frequently asked questions

What is the best area to stay in Ashland, New York, United States of America when booking a vacation rental?
When planning a vacation in Ashland, New York, one of the best areas to consider for your stay is the vicinity around the charming village center. This area offers a delightful blend of natural beauty and local culture, making it an ideal spot for visitors. The village is home to scenic views and outdoor activities, with opportunities for hiking and exploring the picturesque landscapes that surround the region.

In particular, you can enjoy proximity to attractions such as the nearby Catskill Mountains, which provide excellent options for hiking and outdoor adventures. Additionally, the area is close to local parks and recreational spots where you can relax and take in the serene environment.

Ashland has a range of vacation rental properties, suiting various preferences, whether you're looking for a cozy cabin or a spacious home.
How much does it cost to rent a vacation home in Ashland?
Prices for vacation rentals in Ashland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Ashland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Ashland vacation house rentals?
You can find great discounts on house rentals in Ashland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Ashland?
In Ashland, vacation houses are a popular choice, with several available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many vacation houses also come with outdoor areas for relaxation, such as patios or decks, where guests can enjoy the serene surroundings.

Additionally, cabins and cottages are also widely available, providing a cozy, rustic atmosphere that appeals to travelers seeking a more intimate experience with nature. These accommodations generally offer similar amenities, including kitchen facilities and comfortable living spaces, but often emphasize a charming, cabin-like aesthetic.
Are there any family house rentals in Ashland?
In Ashland, New York, there are several family-friendly house rentals available, making it a great choice for family getaways. The area is known for its beautiful landscapes and proximity to outdoor activities. Many of these homes feature spacious living areas, full kitchens great for preparing family meals, and cozy dining spaces. Some properties also offer yards where children can play and explore.

Visitors can enjoy easy access to local attractions such as the scenic Catskill Mountains, which provide opportunities for hiking, biking, and enjoying nature. Additionally, the charming town center has shops and restaurants that cater to families.
Can I find long-stay vacation rentals in Ashland?
A long-stay vacation rental in Ashland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Ashland?
In Ashland, there are several pet-friendly house rentals available, making it a great destination for travelers who want to bring their furry companions along. Many of these vacation homes offer amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, providing a comfortable stay for both pets and their owners.

The area around Ashland features beautiful landscapes and outdoor activities, ideal for pet owners looking to explore. Nearby hiking trails and parks provide ample opportunities for walking and enjoying nature with pets. Additionally, some rentals may be located close to local shops and restaurants that welcome pets, enhancing the overall experience for those traveling with animals.
Are there any remote work vacation rentals in Ashland?
In Ashland, New York, there are several vacation rentals that cater to remote work needs. Many of these properties come equipped with essential amenities such as high-speed internet, dedicated workspaces, and comfortable desks and chairs, allowing travelers to maintain productivity while enjoying their stay. The scenic surroundings provide a peaceful backdrop for remote work, enhancing the overall experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Ashland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Ashland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Ashland?
In Ashland, popular vacation rental amenities include kitchens, which allow travelers to prepare their own meals, and coffee or tea makers for a cozy start to the day. Many properties feature fireplaces, providing a warm and inviting atmosphere, especially during cooler months. Onsite parking is also a common amenity, making it convenient for guests with vehicles. Additionally, several rentals boast gardens, offering outdoor spaces for relaxation and enjoyment of the natural surroundings.
How early should I book a Ashland vacation rental?
Book your Ashland vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Ashland, New York, United States of America?
In Ashland, New York, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural offerings. The nearby Catskill Mountains provide excellent opportunities for hiking, with trails that offer stunning views and access to picturesque waterfalls.

The Ashland Town Park is a lovely spot for picnicking and enjoying the outdoors, featuring walking paths and playgrounds for families. Additionally, the area is known for its close-knit community atmosphere, often hosting local events and farmers' markets that showcase regional produce and crafts.

For those interested in arts and culture, the nearby town of Catskill also offers galleries, antique shops, and venues for live music performances. The scenic Hudson River is not far away, providing activities such as boating, fishing, and riverside relaxation.
Can I change or cancel my Ashland home rental booking on Vrbo?
To find Ashland vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Ashland vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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