Private Holiday Homes in Dutchess County

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Top cities in Dutchess County

A large steel bridge spanning a wide river, with a cityscape and hills in the background.
Hotels

Poughkeepsie

Poughkeepsie

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
Cottage image
Cottages
Cottages

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Dutchess County holiday homes

A large, two-story log cabin with a prominent front porch and a wrap-around deck.

1. Luxury Private Estate w Pool Near Rhinebeck

Luxury Private Estate w Pool Near Rhinebeck
2.0 star property
Red Hook
Luxury Private Estate w Pool Near Rhinebeck
A dining area with a wooden table and green chairs, a patterned wall, and a fireplace in the background.

2. Huge HV Retreat Pool spa Home Theater gym

Huge HV Retreat Pool spa Home Theater gym
2.0 star property
Pleasant Valley
Huge HV Retreat Pool spa Home Theater gym
Exterior

3. Red Hook Retreat

Red Hook Retreat
3.5 star property
Red Hook
Red Hook Retreat
Outdoor dining

4. Salt Point Serenity

Salt Point Serenity
3.5 star property
Salt Point
Salt Point Serenity
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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