Town of Milan Rentals
From $1053 per night (USD)VRBO
PRIVATE 65 ACRE ESTATE - POOL, TENNIS, PICKLEBALL, 4BR\nBOOK JULY OR AUG 2026 NOW
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
A bucolic retreat, this completely secluded estate, nestled on over 50 acres, offering your exclusive use of on site ac ...
From $1053 per night (USD)VRBO
From $1034 per night (USD)VRBO
Stylish Farmhouse with heated pool - 35 acres
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Drive down a small, quiet one-lane road to this stylishly renovated 1890's farmhouse. Enjoy 35 private acres with garden ...
From $1034 per night (USD)VRBO
From $815 per night (USD)VRBO
Blissful 1848 Farmhouse: AVAILABLE THANKSGIVING 2025
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Wonderful restored 1848 farmhouse with swimming, canoeing, fishing & ice-skating pond in an idyllic, 11-acre setting. Fo ...
From $815 per night (USD)VRBO
From $1594 per night (USD)Expedia
Luxury Private Estate with heated pool near Rhinebeck
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Perched at the top of a hill on 20 private acres, this upscale, modern log home serves as an ideal home base to ...
From $1594 per night (USD)Expedia
From $370 per night (USD)VRBO
Hudson Valley Artist Sanctuary
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This home, an artists sanctuary, is located on a country road with farms in every direction. You're twelve minutes from ...
From $370 per night (USD)VRBO
From $240 per night (USD)Expedia
WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WELCOME TO THE HUDSON VALLEY! Spend a romantic, cozy weekend in front of a warm fireplace, enjoy a book at the lake, o ...
From $240 per night (USD)Expedia
From $1297 per night (USD)VRBO
Upstate Idyll
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in in the heart of the Hudson Valley in Northern Dutchess County, our custom home is beautiful sighted away from ...
From $1297 per night (USD)VRBO
From $365 per night (USD)Expedia
rural, serene + sophisticated space
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
In the country, yet short drives to the Hudson River Valley's towns. So many guests have a hard time leaving to go out ...
From $365 per night (USD)Expedia
From $335 per night (USD)VRBO
Willow Glen House - Architectural Gem in the Hudson Valley with European Vibes
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Nestled in the heart of the Hudson Valley, in Dutchess County, Willow Glen House is a refined, European-style retreat wh ...
From $335 per night (USD)VRBO
From $333 per night (USD)Expedia
Classy Comfort in Upstate New York
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Repeat booking?? Let us know! We offer a 5% discount on the nightly rate! *Exclusions apply. See below Open-concept, ...
From $333 per night (USD)Expedia
From $357 per night (USD)VRBO
Rhinebeck Perfection - One Level w/ 2 Living Areas
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
What’s not to love? A gorgeous, architecturally interesting 1830’s schoolhouse, sited along a quiet lane, but within min ...
From $357 per night (USD)VRBO
From $615 per night (USD)VRBO
Firebrook - a peaceful retreat near Rhinebeck
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our home is perfectly situated for outdoor adventures during the day and cozy evenings by the fire. Perched on a hill, w ...
From $615 per night (USD)VRBO
From $554 per night (USD)VRBO
Milan Hill A-Frame - Heated Pool near Rhinebeck
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Milan Hill A-Frame is a charming A-Frame style home in the heart of the Hudson Valley, 10 minutes from Rhinebec ...
From $554 per night (USD)VRBO
From $373 per night (USD)VRBO
Baby friendly home surrounded by nature w/ creative suite & meditation/yoga room
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Surrounded by nature, on a quiet road, this newly furnished home is a unique 3 bedroom, 3.5 bath in Hudson Valley ideal ...
From $373 per night (USD)VRBO
From $253 per night (USD)VRBO
the suite @ barn & bike - private, bucolic, serene setting
- Bedrooms:
- 0
- Bathrooms:
- 1
- Sleeps:
- 2
A 675 sq ft. fully private suite with your own entrance in an early American eyebrow colonial. The well appointed space ...
From $253 per night (USD)VRBO
From $760 per night (USD)Expedia
The George is an elegant restored home in the Hudson Valley
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The George is a beautiful perfectly restored turn of the century home in the heart of Hudson Valley horse country. On a ...
From $760 per night (USD)Expedia
From $354 per night (USD)VRBO
Perfect upstate home in Rhinebeck w /low fees
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to our charming retreat near Rhinebeck! This spacious home offers a perfect blend of relaxation and pro ...
From $354 per night (USD)VRBO
From $767 per night (USD)VRBO
Golden Hill: Light Filled w. Sunroom + Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Golden Hill, a beautifully designed 3-bed, 2.5-bath modern retreat in Rhinebeck—just 1.5 hours from ...
From $767 per night (USD)VRBO
From $1424 per night (USD)VRBO
Hudson Valley Luxury Lodge w/ Saltwater Pool, Yoga & Massage Room & Nature Trail
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
About this space Thoughtfully designed by a husband-and-wife team—one a hospitality specialist, the other a healing exp ...
From $1424 per night (USD)VRBO
From $625 per night (USD)VRBO
Willow Brook: Historic Farmhouse w/ Fun Playroom
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Welcome to Willow Brook, a beautifully restored 4-bedroom, 3-bathroom 1800s Colonial farmhouse near Rhinebeck a ...
From $625 per night (USD)VRBO
From $152 per night (USD)VRBO
Three bedroom house near Bard College with wood burning stove & baby grand piano
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to this beautifully renovated 3-bedroom house on a quiet, untrafficked country road—perfect for relaxing getaway ...
From $152 per night (USD)VRBO
From $406 per night (USD)VRBO
Forget your worries in this serene Modern Farm House.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Your Red Hook adventure begins at this marvelous 3-bedroom Modern Farmhouse. Inside, you'll find a king bed, queen bed, ...
From $406 per night (USD)VRBO