Location

Dates

Guests

Vacation rentals in Smallwood, New York, United States

Private kitchen

Gorgeous Pet & Family Friendly 3-bedroom Smallwood home for a relaxing getaway

3 bedrooms·2 baths

Smallwood • New York

5(60 reviews)

$820.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

♨️ Your private spa under the trees—unwind anytime in this spacious hot tub.

Hot Tub + Game Room + Fire Pit + Deck + Near Lake image 2

Hot Tub + Game Room + Fire Pit + Deck + Near Lake image 3

Hot Tub + Game Room + Fire Pit + Deck + Near Lake image 4

Hot Tub + Game Room + Fire Pit + Deck + Near Lake image 5

Hot Tub + Game Room + Fire Pit + Deck + Near Lake

4 bedrooms·2 baths

Monticello • New York

5(33 reviews)

$1,265.65 USD total for 3 nights

Nov 1 – 4, 2026

Heated Indoor Swimming Pool All Year

Sauna + Cold Plunge + Wellness Deck
Enjoy a spa-like experience with a cedar barrel sauna, cold plunge, Adirondack seating, robes, and ambient lighting surrounded by nature.

Indoor Heated Pool • Hot Tub • Sauna • Game Room image 3

⭐ One of our guests' favorite amenities—relax in the hot tub while overlooking the year-round indoor pool and barrel sauna

Epic garage game room pool, ping pong, arcades + cozy lounge

Indoor Heated Pool • Hot Tub • Sauna • Game Room - Holiday Home

7 bedrooms·3½ baths

South Fallsburg • New York

4.9(20 reviews)

$3,000.25 USD total for 3 nights

Nov 2 – 5, 2026

Bear Lodge cabin surrounded by trees.

Relax on the front porch Adirondack chairs.

Living room fireplace for ambiance and/or supplemental heat. Bose bluetooth speaker, flatscreen TV.

Living room with ample seating for all.

Living room wall shows vintage winter sports decor

Escape to a 3-Bedroom Cabin in Lower Catskills

3 bedrooms·2 baths

Woodridge • New York

5(93 reviews)

$527.55 USD total for 3 nights

Nov 1 – 4, 2026

Catskills Cottage, Relax By The Lake

Window view of the lake

Catskills Cottage, Relax By The Lake

Catskills Cottage, Relax By The Lake

Catskills Cottage, Relax By The Lake

Catskills Cottage, Relax By The Lake

2 bedrooms·1 bath

Rock Hill • New York

5(50 reviews)

$1,049.65 USD total for 3 nights

Mar 1 – 4, 2027

Spacious Catskills Delaware River Gap Retreat

Spacious Catskills Delaware River Gap Retreat

Spacious Catskills Delaware River Gap Retreat

Spacious Catskills Delaware River Gap Retreat

Spacious Catskills Delaware River Gap Retreat

Spacious Catskills Delaware River Gap Retreat

3 bedrooms·3 baths

Glen Spey • New York

4.91(34 reviews)

$1,590.83 USD total for 3 nights

Nov 24 – 27, 2026

Schönes Haus in Sparrow Bush mit privatem Parkplatz und Bergblick

Schönes Haus in Sparrow Bush mit privatem Parkplatz und Bergblick

Kitchen / Dining Room

Schönes Haus in Sparrow Bush mit privatem Parkplatz und Bergblick

Schönes Haus in Sparrow Bush mit privatem Parkplatz und Bergblick

1 bedroom·1 bath

Sparrow Bush • New York

Fence surrounding the house showing the back patio and the large backyard

3 bedroom, 2 bath, dog and child friendly -front of house enclosed with a split rail fence

Living Room with a bay window

The patio with seasonal chairs, umbrella, seating and electric grill

Enjoy resting in the hammock and enjoy the outside campfire pit with seating for 6, children chairs and lighting surrounding the pit

A & R Hacienda-Top Rated-near the Delaware River

3 bedrooms·2 baths

Callicoon • New York

5(80 reviews)

$350/ night(excl. fees & taxes)

Front of House | Stone Patio

40' x 8' Deck | Blackstone Grill | 6 Adirondack Chairs

Outdoor Movie Theater

Living Room | 1930s Antique Players Piano | Smart TV

Spacious Home on 5 Acres 2 Hrs to NYC

4 bedrooms·2 baths

Pond Eddy • New York

5(19 reviews)

$1,935.00 USD total for 4 nights

Nov 2 – 6, 2026

Escape to a Streamside Cabin in the Catskills

Escape to a Streamside Cabin in the Catskills

Bedroom with Queen Bed

Escape to a Streamside Cabin in the Catskills

1 bedroom·1 bath

Wurtsboro • New York

5(25 reviews)

$577.70 USD total for 3 nights

Oct 31 – Nov 3, 2026

A mountain, a view that runs for miles. image 1

A mountain, a view that runs for miles. image 2

A mountain, a view that runs for miles. image 3

A mountain, a view that runs for miles. image 4

A mountain, a view that runs for miles. image 5

A mountain, a view that runs for miles.

4 bedrooms·4 baths

Otisville • New York

$5,085.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

Spacious 6BR Villa Sleeps 16 Near NYC

6 bedrooms·3 baths

Bloomingburg • New York

4.85(102 reviews)

$2,164.64 USD total for 3 nights

Nov 1 – 4, 2026

Welcome to Breezy Hills NY! Amazing mountain views, fire pits, 4 burner propane grill with side burner, zero gravity lounge chairs

Private Mountain View★ Fire Pit ★ 30Min Legoland

Fall at Breezy Hills is like no place you've ever been. The mountain views, highlighted with the changing of colors and seasons. Truly spectacular!

Propane fire pit and two zero gravity lounge chairs. Perfect chairs for catching some rays of sunshine or star gazing at night.

Do you see the Pot of Gold?

Private Mountain View★ Fire Pit ★ 30Min Legoland

3 bedrooms·1 bath

Port Jervis • New York

$999/ night(excl. fees & taxes)