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244 Houses

32

mid century modern ranch woodstock pool

New York / Bearsville

Bearsville house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$450

Price per night from

$450

(1) Excellent 

29

Woodstock Modern House with Pool and Hot Tub

New York / Bearsville

Bearsville house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$450

Price per night from

$450

24

NEW! Bearsville Cabin - Pet Friendly - Near Hikes!

New York / Bearsville

Bearsville cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$155

Responds fast!
avg. 16 minutes

Price per night from

$155

Great rentals within 20 miles that match your search

Distance approx 7.4 km from Bearsville Show on Map

(25) Excellent 

14

The Cottage at Chichester

Catskill Region / Chichester

Chichester cottage

3 5 2 nights min

  • 3 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“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 hous
…see more

Price per night from

$150

Responds fast!
avg. 1 hour 33 minutes

Price per night from

$150

Distance approx 6.57 km from Bearsville

(13) Very Good 

21

A 50 Mile View in the Hudson Valley

Catskill Region / Saugerties

Saugerties apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 8 mi
  • Child Friendly
  • Air conditioning
“Truly spectatcular view amidst a tranquill setting!” My husband and I stayed at this lovely place for a week. Sitting in the screened in porch, overlooking the beautiful Hudson Valley, was so relaxing. Ihe place was clean, quiet and a wonderful retr
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Price per night from

$135

Price per night from

$135

Distance approx 15.63 km from Bearsville

24

Two-Story, 3-Bedroom Family Home

Catskill Region / Windham

Windham house

3 4 2 nights min

  • 3 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$200

Price per night from

$200

Distance approx 10.89 km from Bearsville

40

Peaceful & Secluded Olive Star Cottage IN OLIVEBRIDGE NY (MAP ERROR BY Tripadvs)

New York / Olivebridge

Olivebridge house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$200

Price per night from

$200

Distance approx 12.95 km from Bearsville

(11) Very Good 

17

Calder's Cottage in the historic artistic Rondout

New York / Kingston

Kingston house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Car not necessary
“Charming Historic House and Great Hosts” We rented Calder's Cottage for a trip with friends to visit nearby historic sites. The house is a delight...fresh and comfortable in every respect. The hosts made it even better with their warmth, helpful inf
…see more

Price per night from

$175

Price per night from

$175

Distance approx 10.5 km from Bearsville

7

Hunter Mountain Ski House Condo Ski Season Rental

Catskill Region / Hunter

Hunter apartment

1 6 3 nights min

  • 1 bedroom
  • sleeps 6
  • 3 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$100

Price per night from

$100

Distance approx 6.93 km from Bearsville Show on Map

24

Newly Built Hunter Home w/ Stream & Mountain View!

New York / Edgewood

Edgewood house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$195

Responds fast!
avg. 38 minutes

Price per night from

$195

Distance approx 18.09 km from Bearsville

(1) Excellent 

26

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

Catskill Region / Windham

Windham house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$175

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$175

Distance approx 12.49 km from Bearsville

10

Hunter Mt-REDUCED-5 minutes to Ski Slopes- Amazing Mt. Views~

Catskill Region / Hunter

Hunter house

5 16 min stay varies

  • 5 bedrooms
  • sleeps 16
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$474

Price per night from

$474

Distance approx 11.06 km from Bearsville

(1) Excellent 

16

Charming Star Sapphire Cabin with Luxury Hot Tub near Windham & Hunter Mtn.

Catskill Region / Hunter

Hunter house

3 2 1 night min

  • 3 bedrooms
  • sleeps 2
  • 1 night min
  • Child Friendly

Price per night from

$350

Price per night from

$350

Distance approx 7.76 km from Bearsville Show on Map

11

Streamside Cabin in the New York Catskills

Catskill Region / Chichester

Chichester house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$285

Price per night from

$285

Distance approx 11.3 km from Bearsville

(7) Excellent 

45

THE LAKE HOUSE AT HUNTER FOUR SEASON FUN!

Catskill Region / Hunter

Hunter chalet

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Ski
  • Child Friendly

Price per night from

$350

Responds fast!
avg. 2 hours 0 minutes

Price per night from

$350

Distance approx 15.91 km from Bearsville

(2) Very Good 

40

3400 Sq Ft 5 Bedroom House for Rent Near Hunter/Windham mountains ,cable/WIFI

New York / Jewett

Jewett house

5 17 2 nights min

  • 5 bedrooms
  • sleeps 17
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$499

Price per night from

$499

Distance approx 16.31 km from Bearsville

(7) Excellent 

14

Sunbeam Guest House Retreat

Catskill Region / West Kill

West Kill house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly
“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 supe
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Price per night from

$350

Responds fast!
avg. 2 hours 52 minutes

Price per night from

$350

Distance approx 15.16 km from Bearsville

(16) Excellent 

60

Panther Mt Crater Lodge-Private studio apt.-Catskill Mts

Catskill Region / Big Indian

Big Indian apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 3 mi
  • Child Friendly
  • Air conditioning
“Peace, quiet, and the magic of nature” My stay at Stephen's place in Big Indian was magical. I was stressed from city life and this was exactly what I needed. My boyfriend and I stopped at a farm stand along the way on Rte. 28 and loaded up on good st
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Price per night from

$85

Responds fast!
avg. 57 minutes

Price per night from

$85

Distance approx 11.36 km from Bearsville

12

Antique Stone House

New York / Kingston

Kingston b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$225

Price per night from

$225

Distance approx 9.94 km from Bearsville

(1) Very Good 

20

SAUGERTIES, New York... on SKI ROUTE

Catskill Region / Saugerties

Saugerties house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Ask about children
  • Ask about pets

Price per night from

$150

Price per night from

$150

Distance approx 2.7 km from Bearsville Show on Map

24

Woodstock Oasis. 3 acres of secluded nature. Walkable to town

Catskill Region / Woodstock

Woodstock house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$220

Price per night from

$220

Distance approx 6.34 km from Bearsville Show on Map

4

Cozy and comfortable

New York / Boiceville

Boiceville apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$95

Price per night from

$95

Distance approx 16.62 km from Bearsville

17

Charming Estate Property w/Luxury Hot Tub! Close to Ski

New York / Jewett

Jewett house

3 2 3 nights min

  • 3 bedrooms
  • sleeps 2
  • 3 nights min
  • Child Friendly

Price per night from

$350

Price per night from

$350

Distance approx 0.1 km from Bearsville Show on Map

17

Woodstock Peace, Privacy, Views

Catskill Region / Woodstock

Woodstock house

4 9 3 nights min

  • 4 bedrooms
  • sleeps 9
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$999

Price per night from

$999

Distance approx 3.61 km from Bearsville Show on Map

30

'Casa Reál' Expansive Woodstock House w/ Hot Tub!

Catskill Region / Woodstock

Woodstock house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$290

Responds fast!
avg. 26 minutes

Price per night from

$290

Distance approx 17.33 km from Bearsville

(4) Very Good 

23

On A Road Less Traveled -Catskill Mountain Retreat

New York / Lexington

Lexington house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning
“Great place to get away” The house very clean inside and had everything we wanted. The outside had a huge deck, as well as a hot tub for extreme relaxation and tranquility. Would definitely go back.
…see more

Price per night from

$215

Price per night from

$215

Distance approx 2.31 km from Bearsville Show on Map

16

The Waterfall House - near Woodstock NY

Catskill Region / Saugerties

Saugerties house

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Ask about pets

Price per night from

$465

Price per night from

$465

Distance approx 13.59 km from Bearsville

14

JW LODGING- Comfortable Country Home, Ideal for Groups Touring Bethel Complexes!

New York / Red Hook

Red Hook apartment

2 8 5 nights min

  • 2 bedrooms
  • sleeps 8
  • 5 nights min
  • Nearest beach 10 mi
  • Child Friendly
  • Air conditioning

Price per night from

$200

Price per night from

$200

Distance approx 9.71 km from Bearsville

22

four season vacation rental

Catskill Region / Tannersville

Tannersville house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Ski
  • Child Friendly

Price per night from

$100

Price per night from

$100

Distance approx 1.17 km from Bearsville Show on Map

20

Historic Southwestern Chalet

Catskill Region / Woodstock

Woodstock house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly

Price per night from

$350

Price per night from

$350

Distance approx 17.3 km from Bearsville

29

The Yellow Dutch Cottage

New York / Ulster Park

Ulster Park house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$325

Price per night from

$325

Distance approx 3.98 km from Bearsville Show on Map

6

Classic Mid-Century Modern in Woodstock, 5 minutes from town.

Catskill Region / Woodstock

Woodstock house

5 8 3 nights min

  • 5 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$395

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$395

Distance approx 8.68 km from Bearsville Show on Map

49

Brand New European Style Home+Sauna,Olivebridge NY

New York / Olivebridge

Olivebridge house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$310

Price per night from

$310

Distance approx 11.74 km from Bearsville

17

Your Catskills basecamp

Catskill Region / Hunter

Hunter house

4 7 2 nights min

  • 4 bedrooms
  • sleeps 7
  • 2 nights min
  • Ski
  • Pet Friendly
  • Private garden

Price per night from

$225

Price per night from

$225

Distance approx 13.59 km from Bearsville

8

JW LODGING- Visiting Bethel? Ideal for groups traveling together!

New York / Red Hook

Red Hook house

4 10 5 nights min

  • 4 bedrooms
  • sleeps 10
  • 5 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$400

Price per night from

$400

Distance approx 6.9 km from Bearsville

(9) Excellent 

19

Secluded, Luxury Home with Hot Tub

Catskill Region / Woodstock

Woodstock house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Woodstock cabin with hotel” Great place, great service, clean and very nice, looking forward to renting this on a yearly basis , lots to do around the surrounding towns., visited the overlook mountain hiking trail and the Christmas light shows.
…see more

Price per night from

$235

Responds fast!
avg. 1 hour 23 minutes

Price per night from

$235

Distance approx 3.64 km from Bearsville Show on Map

24

Tranquil Retreat Stunning Views+Hot Tub, Woodstock Area -The Glenford House

Catskill Region / Glenford

Glenford house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$275

Price per night from

$275

Distance approx 16.23 km from Bearsville

9

Mirror Lake Cabins Ulster Park New York

New York / Ulster Park

Ulster Park bungalow

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$125

Price per night from

$125