Poughkeepsie, NY, USA Vacation Rentals

United States New York Marlboro vacation rental compare prices direct by owner 40422813

The Bluff - Designer Home with Views, Pool & Hot T

4.9 (18)

3 Bedrooms • 8 Guests

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United States New York Milton vacation rental compare prices direct by owner 40689642

Maple Branch Manor

0.0 (0)

7 Bedrooms • 14 Guests

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United States New York Milton vacation rental compare prices direct by owner 40913559

Cozy Escape with Stunning Hudson River Views

5.0 (14)

4 Bedrooms • 8 Guests

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United States New York Highland vacation rental compare prices direct by owner 9586761

Charming Vacation House w/ Pool & HotTub

5.0 (47)

3 Bedrooms • 8 Guests

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United States New York Highland vacation rental compare prices direct by owner 11669691

Hudson Valley Estate 90 min from NYC Pool&GameRoom

5.0 (53)

4 Bedrooms • 10 Guests

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United States New York Hyde Park vacation rental compare prices direct by owner 29311409

Wooded Rhinebeck-Beacon area Escape w/Outdoor Spa

5.0 (170)

2 Bedrooms • 6 Guests

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United States New York Highland vacation rental compare prices direct by owner 203328

Splendid Isolation @ Extraordinary Country Retreat

5.0 (155)

4 Bedrooms • 8 Guests

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United States New York Poughkeepsie vacation rental compare prices direct by owner 30002028

Spacious and stylish entire one bedroom apartment.

5.0 (390)

1 Bedroom • 4 Guests

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United States New York Highland vacation rental compare prices direct by owner 29540027

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

5.0 (109)

4 Bedrooms • 8 Guests

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United States New York Poughkeepsie vacation rental compare prices direct by owner 34496438

Hudson Pond · Hideaway King Suite · GF Breakfast

5.0 (256)

1 Bedroom • 2 Guests

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United States New York Poughkeepsie vacation rental compare prices direct by owner 11654972

3rd Floor- Lovely, spacious, modern 1-bedroom apt.

4.9 (138)

1 Bedroom • 4 Guests

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United States New York Milton vacation rental compare prices direct by owner 15406073

Hamptons on the Hudson: Pool, SPA, BBQ, Views!

4.9 (51)

6 Bedrooms • 10 Guests

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United States New York Poughkeepsie vacation rental compare prices direct by owner 1432596

Be in Nature at this Gorgeous Riverfront Cabin

4.9 (440)

3 Bedrooms • 6 Guests

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United States New York Highland vacation rental compare prices direct by owner 2007517

Classic Hudson Valley Riverfront House with Pool

4.9 (55)

3 Bedrooms • 6 Guests

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United States New York Highland vacation rental compare prices direct by owner 5367062

Beautiful Home - 4BR/2.5BA - Hot Tub and Patio

4.8 (94)

4 Bedrooms • 8 Guests

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United States New York Poughkeepsie vacation rental compare prices direct by owner 10590191

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

5.0 (6)

3 Bedrooms • 6 Guests

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United States New York Highland vacation rental compare prices direct by owner 11416109

The House in Highland

5.0 (6)

3 Bedrooms • 6 Guests

$870 avg/night

United States New York Poughkeepsie vacation rental compare prices direct by owner 36092858

The Secret Cottage-A Stylish Retreat in Prime Location!

5.0 (1)

1 Bedroom • 2 Guests

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United States New York Highland vacation rental compare prices direct by owner 44354387

Hudson Riverfront Escape

5.0 (1)

2 Bedrooms • 4 Guests

$834 avg/night

United States New York Highland vacation rental compare prices direct by owner 38566333

Zen Peaks Retreat

4.9 (27)

4 Bedrooms • 8 Guests

$594 avg/night

United States New York Marlboro vacation rental compare prices direct by owner 37346304

Scenic Hudson Valley Getaway • Farms & Vineyards

4.9 (23)

2 Bedrooms • 4 Guests

$434 avg/night

United States New York Poughkeepsie vacation rental compare prices direct by owner 33560557

Historic Spacious Home 5 bed/2 bath

4.8 (27)

5 Bedrooms • 10 Guests

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United States New York Poughkeepsie vacation rental compare prices direct by owner 27873743

Modern Getaway Retreat House, on 2 Acres!

4.8 (53)

4 Bedrooms • 8 Guests

$492 avg/night

United States New York Milton vacation rental compare prices direct by owner 36539046

Historic 1 BR Family Home Near Buttermilk Falls

4.8 (218)

1 Bedroom • 4 Guests

$338 avg/night

United States New York Milton vacation rental compare prices direct by owner 1102861

Historic 4BR Family Home Near Buttermilk Falls

4.8 (256)

4 Bedrooms • 10 Guests

$487 avg/night

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