Top Winter Vacations - Vacation Rentals in Olana

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From US $558

         

10.0 (17 Reviews)

Cabin

Mountain Ridge Retreat - Private & Peaceful Getaway. Family & Pet Friendly

• Air Conditioner
• Parking
• TV

• Poughkeepsie
• Highland

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From US $9,099

         

|

10.0 (1 Review)

House

Private 37 Acre Lake Estate On 164 Acres - 11 Br

• Air Conditioner
• Pet Friendly
• View

• Poughkeepsie
• Highland

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From US $99

         

7.8 (938 Reviews)

Hotel

SureStay Plus Hotel by Best Western Highland Poughkeepsie

• Air Conditioner
• Parking
• TV

• Poughkeepsie
• Town of Lloyd

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From US $368

         

10.0 (12 Reviews)

House

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

• Air Conditioner
• Parking
• TV

• Poughkeepsie
• Town of Lloyd

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From US $389

         

|

9.5 (4 Reviews)

House

Spacious 4bd Country Gem - Fire Pit & Chill Vibes

• Air Conditioner
• Parking
• View

• Poughkeepsie
• Town of Lloyd

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From US $101

         

7.2 (683 Reviews)

Hotel

Rodeway Inn & Suites New Paltz - Hudson Valley

• Air Conditioner
• Parking
• TV

• Poughkeepsie
• New Paltz

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From US $744

         

10.0 (11 Reviews)

Ski Chalet

Spacious A-Frame w/Game Room, Fire Pit & Modern Comforts in Hudson Valley

• Air Conditioner
• Parking
• Pet Friendly

• Poughkeepsie
• New Paltz

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From US $210

         

1.0 (1 Review)

Apartment

Chic New York Studio with Kitchen

• Air Conditioner
• Parking
• Balcony/Terrace

• Poughkeepsie
• Town of Lloyd

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From US $185

         

10.0 (11 Reviews)

Apartment

Studio with private pool, firepit, cabana, grill, & washer/dryer-Dogs ok

• Air Conditioner
• Parking
• Pet Friendly

• Poughkeepsie
• Town of Lloyd

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From US $298

         

10.0 (1 Review)

Apartment

Highland 1850s Studio Barn on Sprawling 4.5 Acres!

• Air Conditioner
• Parking
• Pet Friendly

• Poughkeepsie
• New Paltz

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From US $250

         

9.8 (26 Reviews)

Apartment

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

• Air Conditioner
• Parking
• Pet Friendly

• Poughkeepsie
• Town of Lloyd

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From US $408

         

9.6 (5 Reviews)

House

Charming 4-bedrm Colonial Farmhouse amidst the mountains with WiFi in Highland.

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Poughkeepsie
• Town of Lloyd

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From US $5,681

         

9.4 (3 Reviews)

House

Private 37 Acre Lake Estate on 164 Acres - 11 BR

• Air Conditioner
• Pet Friendly
• TV

• Poughkeepsie
• Highland

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From US $644

         

New

House

NEW: Chalet Getaway, 5 min to Main St

• Security/Safety
• Child Friendly
• Internet

• Poughkeepsie
• New Paltz

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New

From US $247

         

New

Apartment

1850s Barn Studio on 4.5 Hudson Valley Acres!

• Poughkeepsie
• Highland

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From US $1,838

         

10.0 (71 Reviews)

House

Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs.

• Air Conditioner
• Parking
• Pet Friendly

• Poughkeepsie
• Town of Lloyd

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From US $2,621

         

10.0 (6 Reviews)

House

Bright & Spacious Hudson Valley Home with Pool

• Air Conditioner
• Parking
• Pet Friendly

• Poughkeepsie
• West Park

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From US $487

         

10.0 (2 Reviews)

Villa

Charming 4-bedroom villa with Art, Sauna, Cold Plunge and Yoga in New Paltz

• Air Conditioner
• Pet Friendly
• Security/Safety

• Poughkeepsie
• Highland

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From US $612

         

9.8 (27 Reviews)

House

Classic Hudson Riverfront Home & Pool with Spectacular View

• Air Conditioner
• Parking
• Pool

• Poughkeepsie
• Town of Lloyd

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From US $375

         

10.0 (15 Reviews)

House

Unit 2 Spring Summer Fall Winter

• Air Conditioner
• Parking
• Pool

• Poughkeepsie
• West Park

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From US $268

         

9.8 (33 Reviews)

Apartment

Unit 1 Hudson RiverView Sleeps 4 4213344- Queen Bedroom 1 pullout

• Air Conditioner
• Parking
• Pool

• Poughkeepsie
• Town of Lloyd

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From US $120

         

8.6 (4 Reviews)

Apartment

Large Private Apt w King bed near New Paltz

• Air Conditioner
• Parking
• Pet Friendly

• Poughkeepsie
• Town of Lloyd

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From US $360

         

5.0 (1 Review)

House

1st floor of Historic home -

• Air Conditioner
• Pool
• TV

• Poughkeepsie
• West Park

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From US $913

         

New

House

Private mountain forest escape

• Air Conditioner
• Parking
• Pet Friendly

• Poughkeepsie
• Town of Lloyd

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★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Olana.