Top Winter Vacations - Vacation Rentals in Overlook Mountain Trailhead

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From US $747

         

9.8 (101 Reviews)

House

Family-Friendly Retreat Close to Town w/Heated Pool & Hot Tub on 3 Acres

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Bearsville

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From US $132

         

|

10.0 (1 Review)

Apartment

Private countryside apartment suite 1.5 miles to Woodstock

• Air Conditioner
• Parking
• Balcony/Terrace

• Kingston
• Woodstock

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From US $197

         

|

9.6 (90 Reviews)

House

The Herwood Inn

• Air Conditioner
• Parking
• TV

• Kingston
• Woodstock

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From US $258

         

9.8 (137 Reviews)

Cottage

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

• Parking
• Pet Friendly
• TV

• Kingston
• Woodstock

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From US $272

         

|

9.3 (4 Reviews)

House

Cozy Woodstock Home with Fire Pit!

• Air Conditioner
• Parking
• Accessibility

• Kingston
• Woodstock

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From US $212

         

|

8.4 (155 Reviews)

Bed & Breakfast

Morning Glory B n B Woodstock NY

• Parking
• Balcony/Terrace
• Security/Safety

• Kingston
• Woodstock

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From US $311

         

10.0 (67 Reviews)

House

Pet Friendly Cabin Doh-Ray up @ 1500 ft

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Woodstock

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From US $199

         

8.4 (62 Reviews)

Bed & Breakfast

Morning Glory B&B Woodstock NY

• Air Conditioner
• Parking
• View

• Kingston
• Woodstock

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From US $178

         

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9.8 (189 Reviews)

Hotel

Twin Gables of Woodstock

• Air Conditioner
• Parking
• Pool

• Kingston
• Woodstock

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From US $317

         

9.8 (124 Reviews)

Cottage

Private Cozy Home ~ Hot Tub ~ All Yours ~ In town ~ fenced in yard ~Pets welcome

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Woodstock

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From US $309

         

10.0 (12 Reviews)

Cottage

Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

• Air Conditioner
• Parking
• TV

• Kingston
• Woodstock

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From US $541

         

10.0 (68 Reviews)

House

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

• Parking
• Pet Friendly
• Pool

• Kingston
• Woodstock

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From US $388

         

10.0 (261 Reviews)

Cottage

Streamside Cottage Half Mile to Town of Woodstock

• Air Conditioner
• Parking
• TV

• Kingston
• Woodstock

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From US $299

         

10.0 (188 Reviews)

House

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

• Air Conditioner
• Parking
• TV

• Kingston
• Woodstock

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From US $270

         

10.0 (187 Reviews)

House

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

• Air Conditioner
• Parking
• TV

• Kingston
• Woodstock

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From US $368

         

10.0 (172 Reviews)

Cottage

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Woodstock

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From US $397

         

10.0 (133 Reviews)

House

Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Woodstock

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From US $307

         

10.0 (124 Reviews)

Cottage

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Woodstock

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From US $934

         

10.0 (116 Reviews)

House

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

• Air Conditioner
• Parking
• Pool

• Kingston
• Woodstock

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From US $479

         

10.0 (102 Reviews)

House

HOT TUB w/POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Woodstock

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From US $416

         

10.0 (100 Reviews)

House

Brookside Retreat: streamside patio outdoor fireplace fenced yard walk to town!

• Air Conditioner
• Parking
• Pet Friendly

• Kingston
• Woodstock

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From US $225

         

10.0 (78 Reviews)

Cottage

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

• Air Conditioner
• Parking
• TV

• Kingston
• Woodstock

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From US $404

         

10.0 (36 Reviews)

House

JUST LISTED! Romance +history +luxury +privacy in heart of village = Maple House

• Air Conditioner
• Parking
• TV

• Kingston
• Woodstock

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From US $128

         

10.0 (19 Reviews)

Apartment

Relax near Catskills in our cozy Woodstock Apartment

• Air Conditioner
• Parking
• Pool

• Kingston
• Woodstock

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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 Overlook Mountain Trailhead.