Discover a selection of 476 vacation rentals in Ashland, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $232 per night, and houses and condos are popular options for a stay in Ashland. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Ashland
Destination guide

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.

Things to do

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:

  • Hunter Mountain (9 mi / 14.5 km)
  • Windham Mountain Resort (3.9 mi / 6.3 km)
  • Windham Country Club (5.1 mi / 8.2 km)
  • Zoom Flume (10.9 mi / 17.6 km)
  • Belleayre Mountain (15 mi / 24.1 km)
  • Plattekill Mountain (16.5 mi / 26.6 km)
Natural features

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:

  • Belleayre Beach at Pine Hill Lake (14.2 mi / 22.8 km)
  • Catskill Mountains (20.5 mi / 33 km)
  • Esopus Creek (29.9 mi / 48.2 km)
  • Mine Kill State Park (11.1 mi / 17.9 km)
  • Mountain Top Arboretum (11.6 mi / 18.7 km)
  • Max V. Shaul State Park (17.3 mi / 27.9 km)

What are the top vacation rentals in or near Ashland?

Whatever you're seeking in a vacation, you'll find a rental in or around Ashland that's right up your alley. Take a peek at these favorites:

  • "Luxury Waterfront Escape Perfect For Families And Corporate Retreats" is popular with guests. Around 30 miles from Ashland, it has 6 bedrooms and loads of amenities to help you feel at home, including beach sun loungers and a kitchen island.
  • Another appealing choice is "Charming Mountain Retreat Lg Mod", which is around 6 miles from Ashland. Offering 3 bedrooms, a living room and a nearby river, it has everything you need to make your visit comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Ashland vacation rental for you.

Can I find log cabins to rent in or near Ashland?

Choose a lovely log cabin from the many scattered in or near Ashland and you'll soon be inside your wooden sanctuary, vino in hand, relaxing next to a roaring fire. But adventure will be right there on your doorstep too. These cabins offer a great mix of comfort and fun:

  • "Dream Log Cabin 110 Acres/hot Tub": This is the ideal base to enjoy some of the fun outdoor activities this region has to offer, including parasailing and hiking and biking.
  • "Luxury Log Cabin With Amazing Views Of Windham Mountain": Spend your much needed break taking advantage of all the creature comforts at this hideout. When it's time for some fresh air, cycling and fishing are waiting for you.

What are the top-rated vacation rentals for weekend getaways in or near Ashland?

Get away from the daily grind at one of our weekend getaways in or near Ashland. Whether you want to catch up with pals or spend quality time with your partner, there'll be something to suit your style. These are some of our top-rated options:

  • "Carriage House 110 Acres In Catskills Golf Hike Swing Set Bbq" is perfect for a weekend of relaxation and fun. It comes with a range of amenities, such as nearby museums and golf, and is located roughly 18 miles to the east of Ashland.
  • Otherwise, create new memories with your loved ones at "Hunter Mountain Condo 2 Minutes From Ski Area", which is around 11 miles to the southeast of Ashland. Take advantage of internet services, a garden and more here.

Can I find studio apartments for rent in and around Ashland?

Studio apartments are a simple yet stylish pick, perfectly suited for traveling couples or solo adventurers. Spend your days familiarizing yourself with your new surroundings and your nights chilling out in your comfy hideaway. These properties in or near Ashland are sure to please:

  • After a fun-filled day of urban exploration, enjoy peace, quiet and privacy at "Tentrr Signature Site - Pleasant Valley Maplecroft Camp". A balcony and mountain views are among the useful amenities on offer here.
  • "The Loft At Bearpen Mountain" is another superb stay, offering all you need for the perfect Ashland adventure. Useful amenities here include free toiletries and beach towels.

Can I find short term rentals in or near Ashland?

From funky apartments to extravagant houses, Vrbo has your mini break sorted. Here are just two of our most popular picks in and around Ashland:

  • If you only need to stay a night or two, "7bdr/5bth, Amazing View, Lake, 1" is a good choice. It's close to the center of Ashland, so you'll be within easy reach of all the top attractions.
  • Another great option is "5 Star Lakefront Lodge, 4 Acre Peninsula. Wifi". Round up your squad and enjoy a relaxing stay close to the heart of Ashland.

What are the best romantic weekend getaways in or near Ashland?

Forget roses and chocolates. Sometimes all you need is to take off for the weekend, just the two of you. At Vrbo, we've got romantic getaways in and around Ashland that would make Cupid green with envy. Here are some we think you'll adore:

  • Put on some love songs and chill together at "Luxury Waterfront Escape Perfect For Families And Corporate Retreats". Around 30 miles from Ashland, this property has everything you need for a couple's weekend away, including a fireplace and beauty services.
  • Otherwise, spend your escape drinking wine and canoodling at "Charming Mountain Retreat Lg Mod", around 6 miles from Ashland. Winery tours and a fireplace will help set the mood.

What are the best houses for rent with a pool in or near Ashland?

From energetic games of freeze tag to refreshing morning dips, a pool promises hours of fun for grown-ups and kids alike. Earn some brownie points with the family by renting a house with a place to swim in or near Ashland:

  • First on our list of cool pool escapes is "Carriage House 110 Acres In Catskills Golf Hike Swing Set Bbq". Traveling families will feel right at home here, with useful amenities like a theme park and a travel crib also at hand.
  • "Guest House Catskill Mountains Private Backyard Fire Pit Deck 150" is another top-rated option. After you've enjoyed a refreshing dip with the kids, make use of childrens activities and a stereo.

What are the best large family vacation rentals in or near Ashland?

Whether your idea of the perfect escape is up in the hills or near the beach, you'll have a lot more fun if you share it with people you love. Consider one of these large family vacation rentals in or near Ashland and bring the entire crew along:

  • Around 30 miles to the east of Ashland, "Luxury Waterfront Escape Perfect For Families And Corporate Retreats" has 6 bedrooms and sleeps up to 27 guests. It comes with a range of amenities, including a dining table and a living room.
  • Another popular option is "7bdr/5bth, Amazing View, Lake, 1". This large rental is 10 miles southeast of Ashland and features a video library, on-site watersports and more. With 7 bedrooms accommodating up to 20 people, you won't need to leave anyone off your invitation list.

If you're after family-friendly attractions in the area, you're spoiled for choice. Kaaterskill Falls, Zoom Flume and Bailiwick Ranch and Discovery Zoo offer fun for all the crew.

Can I find family cabin rentals in or near Ashland?

Vacation with your kids in a family cabin rental in or near Ashland and get set to make some fantastic memories together. Here are some of our favorites:

  • "Dream Log Cabin 110 Acres/hot Tub" - Enjoy great times with your gang at this getaway, which is around 2 miles east of the center of Ashland. Childrens activities and a separate dining area are among its family-friendly amenities.
  • "Cabin - Windham Mountain Ski Retreat - Hot Tub" - This stay is also ideal for families and is around 6 miles east of Ashland. Offering coffee and tea making facilities, childrens activities and more, it'll get everyone's nod of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Ashland vacation rental that's perfect for your needs.

What are the best large houses to rent with indoor pools in or near Ashland?

Add a serve of indulgence to your getaway by booking somewhere with a private indoor pool. These amazing large houses in or near Ashland have a swimming space that's just for you, as well as loads of room for whoever is fortunate enough to be joining you:

  • With 5 bedrooms that can fit up to 12 guests, "Windham Private Heated Indoor Pool" is the perfect place to escape to with close friends. Take advantage of this property's host of amenities, such as a fireplace and a swimming pool.
  • In addition to its inviting indoor pool, "Condo In Windham Mountain Village" comes with a swimming pool and a fireplace. It has 3 bedrooms that can accommodate up to 12 guests, so you can bring your entire crew along.

Want to see more options? Find your dream stay by using the search bar at the top of the page. Simply adjust the filters to find the Ashland vacation rental that's perfect for you.