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80 Houses

(2) Excellent 

36

Secluded Country Getaway

New York / Highland

Highland house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 31 mi
  • Swimming pool
  • Child Friendly

Price per night from

$115

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$115

57

Hudson Valley Villa - Modern Masterpiece Cantilevered Over Hudson River Bluff

New York / Highland

Highland house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 14 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,195

Responds fast!
avg. 24 minutes

Price per night from

$1,195

15

Nature Lovers Getaway

New York / Highland

Highland house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$150

Responds fast!
avg. 1 hour 4 minutes

Price per night from

$150

(12) Excellent 

18

Hudson Valley 40 Acres With Lake And Hiking

New York / Highland

Highland house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$548

Responds fast!
avg. 29 minutes

Price per night from

$548

Great rentals within 20 miles that match your search

Distance approx 15.28 km from Highland

(2) Excellent 

30

Spacious Rhinebeck Village House w/ Lavish Decor!

New York / Rhinebeck

Rhinebeck house

7 10 min stay varies

  • 7 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ski
  • Suitable for children age 5+

Price per night from

$650

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$650

Distance approx 19.25 km from Highland

24

Cozy Riverfront Pine Bush House w/ Hot Tub & Deck!

Catskill Region / Pine Bush

Pine Bush house

4 12 min stay varies

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

Price per night from

$498

Responds fast!
avg. 55 minutes

Price per night from

$498

Distance approx 14.64 km from Highland

(12) Excellent 

14

The Gallery Inn-A loft style accommodation near the waterfront in Kingston NY

New York / Kingston

Kingston apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Ask about children
“Submerged in art!” We absolutely loved our stay at the Gallery Inn! The space was beautifully renovated, yet comfortable and homey. Terrific artwork decorates the walls. The location is amazing, just steps away from the Hudson River and the fantast
…see more

Price per night from

$175

Responds fast!
avg. 56 minutes

Price per night from

$175

Distance approx 14.46 km from Highland

(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 18.24 km from Highland

(3) Very Good 

43

Stony Mountain House

Catskill Region / Pine Bush

Pine Bush house

5 16 3 nights min

  • 5 bedrooms
  • sleeps 16
  • 3 nights min
  • Child Friendly

Price per night from

$360

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$360

Distance approx 14.17 km from Highland

36

Wild Mountain Getaway - sleeps +20

New York / Gardiner

Gardiner house

5 24 min stay varies

  • 5 bedrooms
  • sleeps 24
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,000

Price per night from

$1,000

Distance approx 11.25 km from Highland

(19) Excellent 

21

Renovated Schoolhouse - Hudson Valley Getaway

New York / New Paltz

New Paltz cottage

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning
“Schoolhouse cottage is an idyllic retreat.” We travelled to the area for a respite from New York City with our two young children. The cottage was perfect for our needs - clean, quiet, well-appointed, and with activities galore for the children. We
…see more

Price per night from

$155

Responds fast!
avg. 3 hours 49 minutes

Price per night from

$155

Distance approx 10.22 km from Highland

(1) Excellent 

18

Cozy Apple House

New York / Gardiner

Gardiner house

3 6 2 nights min

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

Price per night from

$100

Responds fast!
avg. 2 hours 12 minutes

Price per night from

$100

Distance approx 19.71 km from Highland

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 14.31 km from Highland

19

Blue Stone Creek Side Cottage

New York / Accord

Accord house

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Child Friendly
  • Ask about pets
  • Private garden

Price per night from

$350

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$350

Distance approx 7.59 km from Highland Show on Map

(2) Excellent 

22

New Paltz meets Cape May

New York / New Paltz

New Paltz house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$648

Price per night from

$648

Distance approx 14.02 km from Highland

26

Beautiful Streamside Cottage in Dutchess County

New York / Clinton Corners

Clinton Corners house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Child Friendly

Price per night from

$250

Price per night from

$250

Distance approx 14.63 km from Highland

9

Des Artistes Master Bedroom at Church Des Artistes

New York / Kingston

Kingston b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Car not necessary
  • Air conditioning
  • Pet Friendly

Price per night from

$189

Responds fast!
avg. 1 hour 8 minutes

Price per night from

$189

Distance approx 5.02 km from Highland Show on Map

16

Charming Brick House -Hudson Valley

New York / Poughkeepsie

Poughkeepsie house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$299

Price per night from

$299

Distance approx 18.62 km from Highland

(8) Excellent 

21

Enchanting Cottage In The Woods

New York / Accord

Accord cottage

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Peaceful Getaway” A group of childhood friends, our spouses, and my young child just completed a visit to this lovely cottage. We had a wonderful time in the peaceful and beautiful Catskills -- hiked at Minnewaska State park, biked on the O&W; Rail Tr
…see more

Price per night from

$384

Price per night from

$384

Distance approx 9.41 km from Highland

(1) Excellent 

24

Hudson Valley Home w/Mtn View & Fresh Interior

New York / Ulster Park

Ulster Park house

3 8 min stay varies

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

Price per night from

$195

Responds fast!
avg. 2 hours 21 minutes

Price per night from

$195

Distance approx 7.89 km from Highland Show on Map

24

Cozy New Paltz House w/ Views of Shawangunk Ridge!

New York / New Paltz

New Paltz house

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly

Price per night from

$85

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$85

Distance approx 13.65 km from Highland

(3) Excellent 

43

Fiddlers Farmhouse

New York / Rhinebeck

Rhinebeck farmhouse

3 6 2 nights min

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

Price per night from

$349

Price per night from

$349

Distance approx 14.64 km from Highland

16

Kingston/Hurley woodland house

New York / Hurley

Hurley lodge

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Private garden

Price per night from

$175

Price per night from

$175

Distance approx 15.92 km from Highland

(1) Excellent 

17

Orchard home

Catskill Region / Kerhonkson

Kerhonkson house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 12 mi
  • Child Friendly
  • Air conditioning

Price per night from

$249

Price per night from

$249

Distance approx 15.83 km from Highland

(4) Excellent 

6

Comfy Room in Private Home, Ideal Location, Sauna!

New York / Kingston

Kingston room

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$60

Responds fast!
avg. 1 hour 52 minutes

Price per night from

$60

Distance approx 15.88 km from Highland

8

The Wiltwyck Guest House

New York / Kingston

Kingston b and b

1 2 1 night min

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

Price per night from

$80

Price per night from

$80

Distance approx 16.67 km from Highland

(2) Very Good 

35

Guesthouse at 30s Bungalow Colony with 5.5 acres Al yours!

Catskill Region / Kerhonkson

Kerhonkson house

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Pet Friendly

Price per night from

$120

Price per night from

$120

Distance approx 7.81 km from Highland Show on Map

20

Perfect New Paltz Location

New York / New Paltz

New Paltz house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$299

Price per night from

$299

Distance approx 6.28 km from Highland

14

House on Top of the Hill

New York / Marlboro

Marlboro house

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$100

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$100

Distance approx 10.36 km from Highland

(2) Excellent 

26

romantig house at magical lake

New York / Ulster Park

Ulster Park house

2 5 2 nights min

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

Price per night from

$248

Responds fast!
avg. 1 hour 54 minutes

Price per night from

$248

Distance approx 9.38 km from Highland

25

Dutchess County Guest House on Working Horse Farm!

New York / Salt Point

Salt Point house

3 6 min stay varies

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

Price per night from

$280

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$280

Distance approx 12.8 km from Highland

24

Charming Hudson Valley Studio - Walk to Downtown!

New York / Fishkill

Fishkill studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$115

Responds fast!
avg. 2 hours 21 minutes

Price per night from

$115

Distance approx 11.38 km from Highland

31

Newly Renovated Rosendale Getaway

New York / Rosendale

Rosendale apartment

2 4 min stay varies

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

Price per night from

$100

Price per night from

$100

Distance approx 14.34 km from Highland

(3) Excellent 

12

DeMew House

New York / Kingston

Kingston house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min

Price per night from

$175

Price per night from

$175

Distance approx 19.28 km from Highland

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 8.86 km from Highland Show on Map

18

1880s HUDSON VALLEY NEW PALTZ CATSKILLS FARMHOUSE BEAUTIFULLY FURNiSHED POOL

New York / Rifton

Rifton house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$448

Price per night from

$448

Distance approx 8.93 km from Highland

(16) Excellent 

4

Eclectic One Bedroom Cottage in the Hudson Valley

New York / New Paltz

New Paltz cottage

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$150

Price per night from

$150

Distance approx 10.8 km from Highland

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