Location

Dates

Guests

Vacation rentals in Bloomingburg, New York, United States

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

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

Private Forest Estate - Pool · Theater · Game Room

Private Forest Estate - Pool · Theater · Game Room

Private Forest Estate - Pool · Theater · Game Room

Private Forest Estate - Pool · Theater · Game Room

Private Forest Estate - Pool · Theater · Game Room

Private Forest Estate - Pool · Theater · Game Room

7 bedrooms·5 baths

Pine Bush • New York

$5,900.00 USD $5,360.00 USD total for 3 nights

Oct 30 – Nov 2, 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

Hudson Valley Oasis - Sauna, Hot Tub, Heated Pool!

Hudson Valley Oasis - Sauna, Hot Tub, Heated Pool!

Hudson Valley Oasis - Sauna, Hot Tub, Heated Pool!

Hudson Valley Oasis - Sauna, Hot Tub, Heated Pool!

6 bedrooms·3½ baths

Pine Bush • New York

4.98(40 reviews)

$3,575.00 USD total for 3 nights

Oct 30 – Nov 2, 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

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

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)

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

Chalet retreat with pool, hot tub, fire pit, and stunning great room

Sprawling backyard with fire pit, deck dining, and private pool retreat

Vaulted-ceiling great room with stone fireplace and bright forest views

Family-friendly backyard with playset, swings, and peaceful wooded views

Spacious backyard deck with gazebo dining and private outdoor space

Spacious Retreat w/ Pool, Hot Tub & Great Room

7 bedrooms·4 baths

Monroe • New York

$2,425.00 USD total for 3 nights

Oct 31 – Nov 3, 2026

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

Front of the house and front lawn!

Pool and lake from the deck.

Still more firewood stacked on our front lawn.

Nearby Mount Peter

Lakefront/Legoland/West Point Retreat 1 hr to NYC!

4 bedrooms·2½ baths

Monroe • New York

4.95(55 reviews)

$2,100.73 USD total for 3 nights

Oct 30 – Nov 2, 2026

Resort-style pool, hot tub, and sunset ambiance in a private backyard

Private backyard retreat with pool, hot tub, fire pit & outdoor dining

Private backyard hot tub surrounded by lush landscaping and patio space

Fire pit surrounded by 12 chairs

Private backyard BBQ area with picnic seating and serene wooded views

6BR w/ Heated Pool, Fire Pit & Gazebo | Sleeps 22

6 bedrooms·4 baths

Monroe • New York

$2,807.00 USD total for 3 nights

Nov 16 – 19, 2026

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

Spacious living room designed for relaxing together after a day exploring the Hudson Valley.

Fully equipped kitchen with everything you need to prepare breakfast, family meals and group dinners.

Dine outdoors while enjoying peaceful mountain views and the beauty of your private Hudson Valley retreat.

The secondary suite offers added privacy and convenience with its own private entrance leading directly to the backyard.

Gather everyone together for comfortable meals at the spacious 8-person dining table. Whether you're enjoying a family breakfast, dinner with friends, or planning your day exploring the Hudson Valley.

10-Acre Mountain-View Retreat Near New Paltz

4 bedrooms·3 baths

Highland • New York

4.89(66 reviews)

$1,735.00 USD total for 3 nights

Nov 1 – 4, 2026

Private Deck with Hudson River Views

Apartment Exterior with Private Deck

Kitchen & Living Area

Kitchen with sitting area

Bedroom with King Size Bed

River Suite on Washington

1 bedroom·1 bath

Newburgh • New York

$788.00 USD total for 3 nights

Nov 1 – 4, 2026

Front patio w/ Hudson River views

Sunroom exterior w/ hot tub in background

Hot tub facing Hudson River

Living room looking out onto the Hudson River

Riverview on Washington

2 bedrooms·2 baths

Newburgh • New York

$1,692.97 USD total for 3 nights

Nov 1 – 4, 2026

Aerial view of house

Front patio w/ Hudson River views

Hot tub facing the Hudson River

Sunroom exterior w/ hot tub in background

Private Deck with Hudson River Views

Artisan on Washington

3 bedrooms·3 baths

Newburgh • New York

$2,167.00 USD total for 3 nights

Nov 1 – 4, 2026

Baby Goats and Blue skies: A Micro Farm Stay image 1

Baby Goats and Blue skies: A Micro Farm Stay image 2

Baby Goats and Blue skies: A Micro Farm Stay image 3

Baby Goats and Blue skies: A Micro Farm Stay image 4

Baby Goats and Blue skies: A Micro Farm Stay image 5

Baby Goats and Blue skies: A Micro Farm Stay

2 bedrooms·2 baths

High Falls • New York

5(90 reviews)

$1,600.00 USD total for 3 nights

Nov 26 – 29, 2026

Cozy Ranch Retreat in New Paltz

Cozy Ranch Retreat in New Paltz

Cozy Ranch Retreat in New Paltz

Cozy Ranch Retreat in New Paltz

Cozy Ranch Retreat in New Paltz

2 bedrooms·2 baths

New Paltz • New York

5(2 reviews)

$933.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

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

Side view of cottage

Garden view of cottage

Queen-sized bedroom

Secluded Country Getaway

2 bedrooms·1 bath

Lloyd • New York

4.74(27 reviews)

$977.00 USD total for 3 nights

Dec 31, 2026 – Jan 3, 2027