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)

$1,997.40 USD total for 3 nights

Sep 7 – 10, 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)

$488.45 USD total for 3 nights

Sep 7 – 10, 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

Sep 7 – 10, 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)

$1,255.45 USD total for 3 nights

Sep 12 – 15, 2026

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)

$6,935.00 USD total for 5 nights

Sep 8 – 13, 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)

$558.00 USD total for 3 nights

Sep 8 – 11, 2026

Heated indoor-outdoor pool with retractable enclosure — enjoy swimming year-round

Indoor Heated Pool • Hot Tub • Sauna • Game Room

Stylish lounge with Netflix, French doors to deck & private hot tub

Relax in the private outdoor hot tub overlooking the trees, steps from the pool and lounge area. Perfect for unwinding after a day of adventure-ideal year-round for cozy evenings under the stars.

Rain or shine, the water’s fine

Indoor Heated Pool • Hot Tub • Sauna • Game Room

7 bedrooms·3½ baths

South Fallsburg • New York

$747 – $3,704/ night(excl. fees & taxes)

Catskills-Indoor Pool, Hot Tub, Sauna, Cold Plunge image 1

Magical evenings with a fire pit, hot tub, sauna, heated pool & forest views

Spacious open-concept living room with a huge sectional, custom mountain mural, and dining for 20+ guests. ⭐

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.

Spacious game room: pool, ping pong, hoops, foosball & big TV

Catskills-Indoor Pool, Hot Tub, Sauna, Cold Plunge

7 bedrooms·3 baths

South Fallsburg • New York

4.85(13 reviews)

$1,350/ night(excl. fees & taxes)

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

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)

$1,267.50 USD total for 3 nights

Sep 7 – 10, 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)

$2,676.54 USD total for 4 nights

Sep 7 – 11, 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)

$215/ night(excl. fees & taxes)

♨️ 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)

$268 – $1,612/ night(excl. fees & taxes)

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

Sep 7 – 10, 2026

Private Deck with Hudson River Views

Apartment Exterior with Private Deck

Kitchen with sitting area

Kitchen & Living Area

River Suite on Washington

1 bedroom·1 bath

Newburgh • New York

$677.19 USD total for 3 nights

Sep 14 – 17, 2026

Front patio w/ Hudson River views

Hot tub facing Hudson River

Living room view from kitchen

Living room looking out onto the Hudson River

Riverview on Washington

2 bedrooms·2 baths

Newburgh • New York

$1,452.88 USD total for 3 nights

Sep 8 – 11, 2026

Hot tub facing the Hudson River

Sunroom exterior w/ hot tub in background

Front patio w/ Hudson River views

Living room looking out onto the Hudson River

Living room view from kitchen

Artisan on Washington

3 bedrooms·3 baths

Newburgh • New York

$2,154.69 USD total for 3 nights

Sep 14 – 17, 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

Cozy Ranch Retreat in New Paltz

2 bedrooms·2 baths

New Paltz • New York

5(2 reviews)

$814.20 USD total for 3 nights

Sep 7 – 10, 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)

$2,048.00 USD total for 4 nights

Sep 7 – 11, 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)

$798.18 USD total for 3 nights

Sep 7 – 10, 2026