Ashland Rentals

Updating...

age 0-16
82 Results

Relevance

Price: low to high

Price: high to low

Reviews

82 Houses

Affordable Windham Getaway (near private creek!)

Ashland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Match: Parking

All filters match

Price per night from

$172

Great rentals within 20 miles that match your search

1894 Catskills Farmhouse Retreat

Hunter house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Parking

All filters match

Price per night from

$361

Catskill Victorian Fireplaces/ Hot Tub sleeps 12

Margaretville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Parking

All filters match

Price per night from

$516

Match: Parking

All filters match

Price per night from

$567

FAB FUN GREEN BUILT FARMHOUSE ON 17 ACRES

Medusa log cabin

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Lovely, romantic getaway” After a hectic month my husband and I were looking for an easy getaway. The Farmhouse was perfect. It was open and airy, and beautifully designed. A really great find among the stuffier B&B; options normally found upstate. We highly recommend it.

Match: Parking

All filters match

Price per night from

$572

Spectacular Ski Vacation House - Incredible Views!

Shandaken house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Parking

All filters match

Price per night from

$458

“Terrific Rental in Windham” This is a great rental property. The house is very well maintained and comes complete with everything you need for your visit. This includes the kitchen where many other rental properties offer sparse and/or low quality utensils, plates, etc. Angel has literally thought of everything and organized the property to make your stay enjoyable. Also, the hot tub has very potent jets which was nice for a bunch of middle aged golfers after a long day on the course. Angel was extremely helpful and responsive throughout the entire rental process. If you are coming to Windham you will be hard pressed to find a nicer property.

Match: Parking

All filters match

Price per night from

$401

Historic Catskill Mountain House close to Windham

Durham house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Parking

All filters match

Price per night from

$745

Cozy Cottage

Hunter cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Parking

All filters match

Price per night from

$229

Village Suites at Fleischmanns - Suite 1

Fleischmanns apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Parking

All filters match

Price per night from

$155

The Cottage at Chichester

Chichester cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

“Nice place to get away from the hectic city.” Quiet and secluded it was a good fit for me, a couple, their toddler and two small dogs. Property its a good size for a small walk in the woods. Storms have pushed the creek away from the back of the house and it's small and not showing any fish, so wasn't able to fish on the property. I'd advise getting your fishing license before you get there. The house was clean and well kept. The frig had a fair amount of condiments in them, so check the frig before you head to town to buy anything. There were enough pots and pans to cook, but we were glad we brought two cooking knives with us. The gas grill on the deck was OUTSTANDING! I give that grill 5 stars. Quiet with a great view of the stars. We took advantage of the fire pit and picnicked while cooking hot dogs over the open fire. The wifi was intermittent, which can be a good thing if you're looking to truly get away and relax.

Match: Parking

All filters match

Price per night from

$189

Margaretville, Great Vewsi, AC, Fast Internet, near Roxbury Wedding Venues

Margaretville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Wonderful view” Very clean and provided with everything. The view from the hill was amazing. I Enjoyed my stay and would definitely return. Lots to do in the area including some very good restaurants.

Match: Parking

All filters match

Price per night from

$182

Catskill Mountain View House, Belleayre, Fire Pit!

Roxbury house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

“Best house ever” The house is in a beautiful setting. So many things to do in the area from antique shopping, golf in the summer, winter skiing, hiking, really great restaurants. Once you've seen the house though, you won't want to leave. Great layout for families, group of friends, special occasions or just getting away to a special place. everything is provided for your stay. Fully equipped kitchen, comfortable beds, outdoor fire pit!!! Watch shooting stars at night. Jennifer has thought of everything. Even a playroom with toys and games! No preparation is needed on your part. Just show up for a fabulous stay.

Match: Parking

All filters match

Price per night from

$447

***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

Windham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Parking

All filters match

Price per night from

$201

Stately Civil War House near Hunter Mountain Skiing

Palenville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Parking

All filters match

Price per night from

$430

LAKE FRONT NYC DESIGNER Cabin - CATSKILLS, NY.

Stamford log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Parking

All filters match

Price per night from

$458

Windham Cabin

Lexington log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Parking

All filters match

Price per night from

$172

West Kill Retreat

West Kill house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“Awesome getaway!” I came here with a group of friends for a getaway weekend, and it was awesome! The house is big and comfortable. Huge backyard where you can relax and nearby is a little river where you can walk to. The owners of the house are super friendly and always tried to make you feel comfortable. Definitely would recommend this to others and I would sure be coming back.

Match: Parking

All filters match

Price per night from

$298

“Home away from home” My sisters and I rented this cottage on Labor day weekend for our annual sisters get away. Ella was very helpful giving exact directions to the cabin which is important when you are not familiar with a location. She was able to suggest many activities in the area as well as cute little restaurants/taverns in towns nearby. The cabin was truly like a home away from home. Ella clearly takes pride in the upkeep of the property. You are within walking distance to a grocery store, café, liquor store and a little store where you can find many necessities. This is a great get away for any time of the year. I am hoping to return sometime in the next year!

Responds fast! avg. 53 minutes

Match: Parking

All filters match

Price per night from

$113

Country Farmhouse along the Catskill Scenic Trail

Hobart house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Quaint cottage in the peaceful outdoors” My friends and I desperately wanted a weekend away from the grey of New York City and could not have chosen a more perfect place. Barbara was incredibly helpful, as was the manager Scott. Lovely home, spacious despite looking quite small, beautiful kitchen with the most adorable old oven, lots of places to sit, eat and relax. Friends could not stop raving about the beds and nice hot showers. Surrounded by farmland and rolling hills. Very close to most ski resorts via easy routes, lots of small townships along the way. The town of Hobart has great bookstores and a delightful diner/café where the owner breeds cocker spaniels and let's you cuddle them!

Match: Parking

All filters match

Price per night from

$172

charming woodstock cottage with outdoor hottub

Willow cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Parking

All filters match

Price per night from

$201

Stunning Vacation Country & Ski House

Woodstock house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Parking

All filters match

Price per night from

$630

Pet Friendly Cabin Doh-Ray Up At 1450ft

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Relaxing mountain retreat” We enjoyed a very pleasant Thanksgiving week getaway at the cabin, which looks just like the pictures -- nice combination of modern and rustic design. Also very comfortable, clean and well organized. Tv and sound system very high tech. Somehow we did something wrong with the remotes and lost the tv connection, but Raymond was extremely patient troubleshooting over the phone. Kitchen is nicely equipped. Bathrooms, full upstairs and half downstairs (not pictured), were standard but fine. The views of the woods from the many windows were really pretty, especially in the snow. It was a bit of an adventure driving up the somewhat steep mountain road. Definitely need 4wd in bad weather, so car rental was a little expensive. Overall, we had a lovely stay and hope to have a chance to come back in the summer.

Match: Parking

All filters match

Price per night from

$361

“Best weekend ever :)” I have recently rented the bungalow and just have great things to say about it. The place is so cozy, and cute, they had everything we needed and the location couldn't be better. It's very close to any of the skii resorts and many attractions, market...It was only my boyfriend and I and the bungalow was just the perfect choice to spend a holiday weekend. Ella, the owner, was very helpful providing us any info we could need. We are already planning to go back the beggining of the year and summer for sure. Thank you so much Ella!!!

Responds fast! avg. 53 minutes

Match: Parking

All filters match

Price per night from

$102

Mountain House Retreat

Windham house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

“Beautiful! Relaxing! Perfect!” I spent 4th of July weekend with a group of friends at this wonderful mountain retreat, and it was all that we wished and more!! The views are spectacular, the private pond and the mountains added so much to our stay. It was like being on a private resort...the home had everything we needed to have fun and enjoy this long summer weekend, and we are already planning to return next year. Thank you so much for providing such an amazing spot for a long weekend getaway! And it must be noted how accommadating and easy it was to communicate with the owner and with flipkey whenever I had any questions-- 5 Stars!

Match: Parking

All filters match

Price per night from

$287

Catskill Home for Skiing, Fishing, Hiking & biking

Fleischmanns house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 22

Match: Parking

All filters match

Price per night from

$573

Catskill Mountains Retreat for Large Groups

Big Indian villa

  • 20 bedrooms
  • 7 bathrooms
  • sleeps 32

Match: Parking

All filters match

Price per night from

$1,390

Match: Parking

All filters match

Price per night from

$687

Expanded Cabin facing Hunter Mountain in NY

Hunter log cabin

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

“Love it--would return again!” Jeffrey was very friendly, accommodating, helpful and professional as we were booking the cabin. Cabin was beautifully furnished and large enough to fit 8 of us. 5 min drive to Hunter Mountain. Very cozy and comfortable--loved it and would love to return again sometime in the future!

Match: Parking

All filters match

Price per night from

$687

Village Suites at Fleischmanns - Suite 2

Fleischmanns hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Parking

All filters match

Price per night from

$189

Winter Rental For Upstate New York

Hunter apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Parking

All filters match

Price per night from

$134

Charming home with mountain views

Hunter house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Parking

All filters match

Price per night from

$687

charming house in the catskills

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Parking

All filters match

Price per night from

$287

Charming house in great location

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Parking

All filters match

Price per night from

$287

Walk to Hunter Mountain

Hunter house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Parking

All filters match

Price per night from

$172

Sanctuary by the Stream

Phoenicia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“A Little Taste of The Country” The property was exactly as described. When we did arrive John was available to "check us" into the house and show us some of the features. Veronica and John have paid close attention to every detail. A group of four of use stayed in June to attend the Taste of Country Music Festival at Hunter Mountain. The drive to the mountain was very accessible. Since we up there for the weekend for the festival, we did not have much time to explore the surrounding area. We did have dinner at SPORTSMAN’S ALAMO CANTINA right on main street. Great Mexican food and huge portions. It was a nice weekend away and the hospitality was impeccable!

Match: Parking

All filters match

Price per night from

$269

Chickadee Chalet

Windham apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Parking

All filters match

Price per night from

$401

Top of the Pass. Cozy Craftsman Style

Hunter house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Parking

All filters match

Price per night from

$201

Viewing 38 of 82
rentals in Ashland

×

Also consider