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Four-season spacious and modern Catskill / Ashokan retreat on 11 wooded acres

Bedrooms 5
Half Baths1
Space 4,000 sq. ft.
Property type chalet
Minimum Stay 2 nights


About the property


- 4-season getaway with retreat-like feel

- Privately nestled in 11 acres of woodland

- Wifi, air conditioning, radiant under-floor heat

- Brand new, state-of-the-art, fully equipped kitchen with German appliances

- All furniture, beds, mattresses, towels, and linens are brand new

- Entertainment area in finished basement with TV area, pool table, air hockey, wet bar, refrigerator

- Stone fireplace and wood-burning stove

- Outdoor activities on the property (basketball, tennis, volleyball, fire pit, children’s area, stream)

- 5 bedrooms (1 king, 4 queen, and 3 twin beds) with views of surrounding woodland

- 3.5 bathrooms

Modern and spacious post and beam home privately nestled back from the road in 11 acres of peaceful woodland. This home is the perfect 4-season getaway for families or friends to unwind and reunite, and it is great for children. It has a retreat-like feel, perfectly combining the rustic peace and tranquility of the mountains with every modern convenience and home comfort, including wifi internet, high definition cable TV, radiant under-floor heating, air conditioning, washer/dryer, and dishwasher.

It is located in picturesque Olivebridge, 2 hours from NYC, and is 5 mins from the beautiful Ashokan reservoir. It is also close to Woodstock, Phonecia, Stone Ridge, New Paltz, Kingston, and Saugerties. The ski areas of Bellayre, Hunter, and Wyndham are within easy driving distance while there is cross-country skiing in nearby Minnewaska state park. In the summer and fall, the area is perfect for hiking, biking, climbing, tubing, horse riding, and boating.

The 4,000 sq ft, 5 bedroom, 3.5 bathroom house easily accommodates 12 guests and has sofa and additional living space for more. The main floor features a great room– a large living area with stone fireplace, cathedral ceiling, large sofa, and window seat; dining area with seating for 10; and a brand new kitchen with large refrigerator, and Bosch dishwasher, microwave, and state-of-the-art induction range, and bar seating for 5. Off the great room is a bright sun room with screened windows. French doors lead from the great room and the sun room out to the large deck, complete with new propane grill and patio furniture, perfect for relaxing on long summer days. Also on the main floor is a laundry room with washer, dryer, and powder room; master suite with king bed, en-suite bathroom, and skylight; two guest bedrooms with queen beds, one of which has a loft with an additional queen bed and a skylight; and guest bathroom with over-sized tub and shower. Above the great room is a balcony and a beautiful queen bedroom with cathedral ceiling and exposed beams.

Downstairs also has radiant under-floor heating and features a large TV/movie area with a 60” LED high definition TV, wireless surround sound, cable TV, DVD/blu-ray player, comfortable sectional sofa with space for 12+, and a wood-burning stove. The downstairs also has a games and entertainment area complete with pool table, air hockey, wet bar, and refrigerator, an additional bedroom with 3 twin beds, and a bathroom. French doors lead out of the downstairs area to a secluded patio area below the deck.

The 11 acre grounds feature an enclosed and floodlit tennis / volleyball / basketball court, fire pit, children’s play area, natural rock outcroppings, original stone walls, and a year-round stream.

More Details

Member since: 2014
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
February 20, 2018

About Jonathan

We are a professional 30-something couple who live in Manhattan.

Jonathan purchased this chalet in 2014

Why Jonathan chose Olivebridge

We wanted a weekend getaway from the city that was peaceful and off the beaten track but not too remote. We also wanted a home that we could use to host friends and family and use as a base for hiking and skiing.

What makes this chalet unique

We loved that the house was so perfect for entertaining yet was also peaceful and relaxing. The first thing we did with the place was to renovate the kitchen to make the main floor even more open.


Olivebridge Chalet Accommodation and Amenities

Property Type:
  • chalet
  • Guests provide their own meals
Floor Area:
  • 4000 sq. ft.
House Rules:
  • Check-in: Flexible / Check-out: Flexible
  • Max. occupancy: 12
  • children welcome
  • pets not allowed
  • non smoking only ...
Location Type:
  • Rural ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Telephone ...
  • Towels Provided ...
  • Washing Machine
  • Wood Stove
  • Coffee Maker
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Room
  • seating for 10 people
  • 3 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , combination tub/shower
    Bathroom 2 - toilet , combination tub/shower
    Bathroom 3 - toilet , shower
    Bathroom 4 - toilet
  • 5 Bedrooms, Sleeps 12
  • Bedroom 1 - 1 king , En-suite
    Bedroom 3 - 1 queen
    Bedroom 4 - 1 queen
    Bedroom 2 - 2 queen , Bedroom with additional sleeping loft
    Bedroom 5 - 3 twin/ single , Downstairs bedroom
  • Bedrooms all have brand new beds, mattresses, and linens
  • DVD Player ...
  • Game Room ...
  • Games
  • Pool Table
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • Ski & Snowboard ...
  • Tennis ...
  • Long-term Renters Welcome
  • autumn foliage
  • forests
  • waterfalls
Leisure Activities:
  • antiquing
  • bird watching
  • photography
  • sight seeing
  • walking
Sports & Adventure Activities:
  • basketball court
  • cycling
  • fishing
  • freshwater fishing
  • hiking
  • hunting
  • mountain biking
  • mountain climbing
  • skiing
  • swimming
  • tennis
  • water tubing


Wonderful! 4.9/5 -
(31 traveler reviews)

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Four-season spacious and modern Catskill / Ashokan retreat on 11 wooded acres
average rating of 4.935484 based on 31 reviews

Clean Large House with Lots of Fun Things to Do

  • 5 of 5

We had a great time playing on the court outside and playing pool and air hockey downstairs. We were able to play our music throughout the house with Sonos and really enjoyed all the beautiful natural light. I would definitely recommend this house to friends. We had a little trouble with the induction stove, but we were okay once we figured it out. LOVED it!

  • Submitted: Nov 13, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
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New York, NY

Great for Annual Getaway

  • 4 of 5

Great space for our friends and family getaway. Each family had their own room and the house had plenty of space for everyone to spread out. The downstairs games were a big hit with adults and kids. The playground was also a big hit with kids and adults! The house was clean and fully stocked. The reason I did not give five stars was because some of the outside light bulbs were out and the outdoor deck where the grill and chairs are needs some love.

Would recommend as a great choice for an upstate getaway.

  • Submitted: Oct 26, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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smithville, nj

Wonderful time 3 years in a row!

  • 5 of 5

My husband, kids and grandkids had a wonderful family get away for the 3rd year in a row! Plenty of space so no one is underfoot. Wonderful kitchen and large table that can fit us all. We also LOVE the outdoor space with huge firepit, playground, basketball, and tennis court. It was very warm when we recently stayed so this was the first time we spent time on the could use some TLC as well as doors leading out to it. Other than that, a most wonderful home!!!!

  • Submitted: Oct 5, 2017
  • Stayed: September 2017
  • Source: HomeAway
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  • 5 of 5

This house was perfect for our visit. It was clean and organized, with plenty of amenities. Jonathan was great to deal with and quick with responses. The sound system was a wonderful addition, and the basement was a fantastic play area. Would stay here again when visiting Woodstock. Thanks Jonathan for sharing your beautiful home!!

  • Submitted: Aug 31, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Kaukauna, WI

Great Place for Family Gathering

  • 5 of 5

This was a very spacious and comfortable place for a family gathering celebrating our parents 45th anniversary. The air conditioning was a savior from the heat and humidity outside. The kitchen was extremely well stocked and the beds were all very comfortable. Our only complaints were minor. For example, the bedrooms are missing window coverings so lots of light is let into the rooms, which means you are up with the sun. The deck is showing its age and may need some repair in spots. Otherwise our mom loved the Roland piano upstairs. And the games in the basement were very enjoyable when cooling off from using the outside courts. The grounds are gorgeous and private. We even got to see the solar eclipse from the deck! Overall an easy place to recommend to anyone needing a place of its size.

  • Submitted: Aug 27, 2017
  • Stayed: August 2017
  • Source: HomeAway
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Fantastic home

  • 5 of 5

Lovely home! 11 of us spent the weekend there. The house was clean and in great condition, exactly as described. We enjoyed the game room and all other things on the property.

  • Submitted: Aug 10, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Nearest Barpub
1.5 Miles
Country Inn
Nearest Golf
9 Miles
Rondout Golf Course
Nearest Train
30 Miles
Nearest Restaurant
1.5 Miles
Country Inn
Nearest Ski
30 Miles
Car: necessary

The house is conveniently located 2 hours north of NYC. While in a beautifully rural setting, it is close to many of the Catskills' and Hudson Valley's key attractions and activities, including:

The Country Inn: Locals come from miles around because of its excellent food, 300+ beers from around the world, and rustic charm. Only 1.5 miles from the house!

Ashokan reservoir: Beautiful views and perfect for cycling, a summer evening walk, or a morning run. Less than 5 mins from the house.

Boiceville: 10 mins away. Supermarket, liquor store, and pharmacy.

Phonecia: Tubing down the Esopus, cafes, hiking, biking.

Woodstock: Famous for many reasons, not least its art galleries, cafes, restaurants, and eclectic shops.

Stone Ridge: Lots of historic architecture and stone houses, as well as cafes and shops.

Minnewaska state park: Great for hiking and biking.

Mohonk preserve: Hiking in the Shawangunk Ridge, golf, Mohonk Mountain House resort.

Ski areas: Bellayre, Hunter, and Windham mountains are within easy reach.

New Paltz: Cafes, shops, restaurants, and historic stone houses built by the Huguenots.

Kingston: Beautiful waterfront area with bars and cafes, lively nightlife, and all the large stores and supermarkets.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Damage Deposit $500

Once a reservation has been made, Traveler agrees to Owners' Rental Agreement.
Price and minimum stay requirements for holidays may be different - contact owner for details.
Deposit and cleaning fee may be higher for stays of longer than six nights or more than 10 guests.
Property damage protection available upon request in lieu of deposit.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.