Highland Rentals

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40 Houses

Secluded Country Getaway

Highland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$270

Black Creek Bed and Breakfast (Paris Room w/Shared Bathroom)

Highland b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$287

Black Creek Bed and Breakfast (Arbor Room w/Shared Bathroom)

Highland b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$253

Black Creek Bed and Breakfast (Zen Room w/Shared Bathroom)

Highland b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$287

Black Creek Bed and Breakfast

Highland house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,148

Great rentals within 20 miles that match your search

Blue Stone Creek Side Cottage

Accord house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$689

Carriage House on private English Tudor Estate

Kingston house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$339

Church Des Artistes

Kingston villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

“Wonderful!” This was one of the most unusual places we've ever stayed- a renovated old church, at the same time classic, modern, absolutely spotless, warm, bright, cozy and if you appreciate the arts you are in for a treat as both Julie and Peter are accomplished artists (Julie is a painter and Peter a musician).

Price per night from

$2,295

Phillie's Country Comfort Space -

New Paltz b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$161

Earth Berm House at Terra Casa Retreat Center

Plattekill house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$327

FARM HOUSE ON 30 ACRES PRIVATE BED AND BATH USE OF 1ST FLOOR

Clinton Corners house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 6 minutes

Price per night from

$229

Famous Liberty View Farm

Clintondale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$861

Rustic Countryside Cottage w/ Spa/Fire Pit/Wood Pellet Stove

Cold Spring cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$412

Happy Minnewaska- Welcome Home

Kerhonkson house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$582

Quiet Cottage with free Parking

Cornwall on Hudson house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Price per night from

$120

Spectacular views! Scenic Hilltop Home on Organic Farm

High Falls house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$746

Cozy 2 Bedroom Cottage with Fireplace!!

Newburgh house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$170

Lovely 2 Bedroom Cottage Just Off Orange Lake

Newburgh house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$298

Charming Brick House -Hudson Valley

Poughkeepsie house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$373

Secluded Mountain View House on 10 Acres

Plattekill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$402

Cozy Hudson Valley 1880 Carriage House with FIRE PLACE

Clintondale house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$201

The Blue House

Kerhonkson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$339

Gorgeous Hudson Valley Villa

Wallkill villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 15

Price per night from

$1,033

Huge new modern house with movie theater

Cold Spring house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$802

True American Hippie House - A Country Home with History and Heart

Rosendale house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$603

Private Studio Close to Downtown Rhinebeck

Rhinebeck apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$109

Price per night from

$75

Gatehouse Gardens

New Paltz apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$413

Mountain View Vacation Home Near Mohonk Preserv

Gardiner house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$574

Private Mountain top Lakehouse Retreat

Pawling house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$259

Quiet and peaceful cape cod on rural lake setting!

Rhinebeck house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$573

Cliff Haven In The Catskills

Kingston house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$459

2Br Private Victorian Apartment in convenient City location on 5 acre, Sleeps 5

Poughkeepsie apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$211

THE STABLES IN THE CARRIAGE HOUSE

Kingston villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$338

2 Br Victorian Apt, 2800 sq ft, 2 floors with Full Kitchen , 2 baths and Laundry

Poughkeepsie apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$299

Newly Built Private Home & Pool In Accord, NY

Accord house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$916

1 Br Private Victorian Apt in convenient City location on 5 acre, sleeps 4

Poughkeepsie private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$192

Sun-Drenched Retreat in the Hearth of Hudson Valley

Stone Ridge house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$572

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