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Highland Rentals

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Price: high to low

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64 Houses

Secluded Country Getaway

Highland house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$269

Hudson Valley Villa - Modern Masterpiece Cantilevered Over Hudson River Bluff

Highland house

4 bedrooms / 6 bathrooms / sleeps 8

Responds fast! avg. 1 hour 33 minutes

Price per night from

$1,706

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

Highland b&b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 31 minutes

Price per night from

$286

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

Highland b&b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 31 minutes

Price per night from

$251

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

Highland b&b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 31 minutes

Price per night from

$286

Black Creek Bed and Breakfast

Highland house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 31 minutes

Price per night from

$1,142

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

Highland b&b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 31 minutes

Price per night from

$257

Great rentals within 20 miles that match your search

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

$2,283

Base Camp - Dutch Colonial Estate

Beacon apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$257

50 Mins from Manhattan River view

Cornwall on Hudson house

5 bedrooms / 3 bathrooms / sleeps 17

“Spectacular view” We loved this house. It has probably the best view of the Hudson River. The house was very comfortable and had everything we needed. Susan was very helpful with information about the sights and restaurants. We will definitely be back.

Price per night from

$1,507

THE STABLES IN THE CARRIAGE HOUSE

Kingston villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$286

Carriage House on private English Tudor Estate

Kingston house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$337

Blue Stone Creek Side Cottage

Accord house

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 30 minutes

Price per night from

$685

Charming Brick House -Hudson Valley

Poughkeepsie house

3 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 1 hour 47 minutes

Price per night from

$457

Earth Berm House at Terra Casa Retreat Center

Plattekill house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$326

Phillie's Country Comfort Space -

New Paltz b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$132

DeMew House in Historic Rondout, Kingston NY

Kingston house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$200

Tentrr - Cooke's Creek

East Fishkill tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$159

Tentrr Signature Site - Kamp Kimberg North

Rifton tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$115

Eagles Nest - Lakefront Contemporary Home 3200 Sq' w Piano - 5 Queen Beds

Newburgh house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$685

Tentrr Signature Site - Honeybug Hill near Omega

Clinton Corners tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$129

Famous Liberty View Farm

Clintondale house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$856

Tentrr Signature Site - Indica Way

Pine Bush tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$128

Gorgeous Hudson Valley Villa

Wallkill villa

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$1,142

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

Cold Spring cottage

2 bedrooms / 1 bathroom / sleeps 7

Price per night from

$410

Cozy cottage in Hudson Valley-Dog friendly

Arlington apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$172

Happy Minnewaska- Welcome Home

Kerhonkson house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$62

Just steps from the Rondout waterfront, shops and restaurants.

Kingston apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$143

Gatehouse Gardens

New Paltz apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$411

Modern, Luxury Vintage CAMPER with Swimming Pool in the Hudson Valley

Port Ewen camper van

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$485

Renovated Schoolhouse - Hudson Valley Getaway

New Paltz cottage

2 bedrooms / 1 bathroom / sleeps 7

“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 fed the horses and donkies carrots and apples, played with the three friendly farm dogs, and enjoyed a couple of proper horseback riding lessons for the kids. The owners of the farm are warm and friendly, and have taken every effort to be accomodating to their cottage guests. The farm is absolutely beautiful, with a backdrop of the Gunks - the horses are extremely lucky and well-cared for!

Price per night from

$177

Tentrr Signature Site - Mini Yosemite in the Hudson Valley

High Falls tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$124

Private King Bed w/Bath in SHARED Charming House, good for business travelers

New Paltz house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$75

Tentrr Signature Site - Orchard Tent Overlooking Mohonk Golden Russet

Stone Ridge tented camp

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$137

Tentrr Signature Site - Dogwood Tree Camp

Accord tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$92

Tentrr Signature Site - Newtown Pippin

Stone Ridge tented camp

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$137

Tentrr Signature Site - Reservoir Retreat

High Falls tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$115

Tentrr Signature Site - A Riverwalk

Stanfordville tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$129

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