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Featured Vacation Rentals in Poughkeepsie

C$107
Farm House ON 30 Acres, 3 Miles TO Omega Private BED & Bath USE OF 1ST Floor

Farm House ON 30 Acres, 3 Miles TO Omega Private BED & Bath USE OF 1ST Floor

233 Nine Partners Rd, Clinton Corners, NY
Situated in a rural location, this historic holiday home is 3 mi (4.9 km) from Omega Institute and within 9 miles (15 km) of Clinton Vineyards and Center for Performing Arts at Rhinebeck. Northern Dutchess Botanical Gardens and Red Hook Golf Club are also within 9 miles (15 km).
 
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Tentrr - Clove Mountain Meadow

Tentrr - Clove Mountain Meadow

81 Clove Valley Road, High Falls, NY
Situated in High Falls, this holiday home is within 9 miles (15 km) of Century House Historical Society, Minnewaska State Park and State University of New York-New Paltz. Mohonk Preserve Visitor Center and World's Second Largest Garden Gnome are also within 9 miles (15 km).
 
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New! Modern-industrial Farmhouse Mountain Views 1 Minute Walk to Rail Trail

New! Modern-industrial Farmhouse Mountain Views 1 Minute Walk to Rail Trail

7 Coffey Road, New Paltz, NY
Situated in New Paltz, this holiday home is within 3 miles (5 km) of New Paltz Golf Course, Huguenot Street Historic District and G. Steve Jordan Gallery. State University of New York-New Paltz and Loren Campbell Memorial Field are also within 6 miles (10 km).
 
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THE Modern Farmhouse Unit B

THE Modern Farmhouse Unit B

1019 Albany Post Rd, Gardiner, NY
Situated in Gardiner, this historic holiday home is within 3 miles (5 km) of DM Weil Gallery, Robibero Winery and Whitecliff Vineyard. Mohonk Preserve Visitor Center and Testimonial Gateway are also within 6 miles (10 km).
 
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Charming and Artsy Getaway in Historic Cold Spring

Charming and Artsy Getaway in Historic Cold Spring

50 Parsonage St, Cold Spring, NY
Situated in Cold Spring, this holiday home is within 1 mile (2 km) of Putnam History Museum, Boscobel House and Gardens and West Point Foundry Preserve. Foundry Dock Park and Chapel Restoration are also within 1 mile (2 km).
 
C$183
House on Appalachian Trail, Walking Distance From NYC Trains. 3bd/1ba, 3 Acres

House on Appalachian Trail, Walking Distance From NYC Trains. 3bd/1ba, 3 Acres

72 Hurds Corner Rd, Pawling, NY
Situated in Pawling, this historic holiday home is within 9 miles (15 km) of John Kane House, Thunder Ridge Ski Resort and Bull's Bridge. Candlewood Lake and Emmanuel Williamson Park are also within 12 miles (20 km). Appalachian Trail is 13 minutes by foot.
 
C$270
Tentrr - Downing Wood

Tentrr - Downing Wood

23 Bird Lane, Garrison, NY
Situated in Philipstown, this holiday home is within 6 miles (10 km) of Graymoor - The Holy Mountain, Oscawana Lake and Paramount Hudson Valley Theater. Peekskill Museum and Garrison Art Center are also within 6 miles (10 km).
 
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Tentrr - Orchard View

Tentrr - Orchard View

699 New York 208, Gardiner, NY
Situated in Gardiner, this holiday home is within 6 miles (10 km) of Adair Vineyards, DM Weil Gallery and Robibero Winery. Whitecliff Vineyard and Loren Campbell Memorial Field are also within 6 miles (10 km).
 
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Lake! Pool! HOT Tub! Fishing! Boating! Volleyball! Grill! Mohonk!

Lake! Pool! HOT Tub! Fishing! Boating! Volleyball! Grill! Mohonk!

490 Route 299 West, New Paltz, NY
Located in the heart of New Paltz, this romantic holiday home is 2.6 mi (4.2 km) from Mohonk Preserve Visitor Center and within 6 miles (10 km) of State University of New York-New Paltz and Testimonial Gateway. Robibero Winery and DM Weil Gallery are also within 6 miles (10 km).
 
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1800s Farmhouse set on 165 Acre Estate-- Does not Include Caretaker's Apartment

1800s Farmhouse set on 165 Acre Estate-- Does not Include Caretaker's Apartment

628 Lattintown Rd, Marlboro, NY
Situated on a lake, this holiday home is within 9 miles (15 km) of Marlboro Free Library, Benmaryle Wineries and Berean Park Beach. Adair Vineyards and Walkway Over the Hudson State Historic Park are also within 9 miles (15 km).
 
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Modern Ranch Centrally Located

Modern Ranch Centrally Located

96 Orange St, Marlboro, NY
Situated in Marlboro, this holiday home is within 1 mile (2 km) of Marlboro Free Library and Benmaryle Wineries. Mount Saint Mary's College Newburgh and David Crawford House are also within 9 miles (15 km).
 
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THE Modern Farmhouse Unit A

THE Modern Farmhouse Unit A

1019 Albany Post Rd, Gardiner, NY
Situated in Gardiner, this holiday home is within 3 miles (5 km) of DM Weil Gallery, Robibero Winery and Whitecliff Vineyard. Mohonk Preserve Visitor Center and Testimonial Gateway are also within 6 miles (10 km).
 
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Vacation Rentals in Poughkeepsie

What kind of vacation do you want in Poughkeepsie? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Poughkeepsie that will speak to you.

Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Poughkeepsie, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.

Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.

Top Trending Hotels in Poughkeepsie

See all 213 properties in Poughkeepsie
HYATT house Fishkill/Poughkeepsie C$139
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

100 Westage Business Center Dr., Fishkill, NY
     
    3.0 out of 5.0 Stars

    Situated in Fishkill, this hotel is within 1 mile (2 km) of Van Wyck Homestead Museum and Blodgett Memorial Library. Fishkill Golf Course and SplashDown Beach are also within 2 miles (3 km).

    Hyatt Place Poughkeepsie C$127
    Hyatt Place Poughkeepsie

    Hyatt Place Poughkeepsie

    2165 South Road, Poughkeepsie, NY
       
      3.0 out of 5.0 Stars

      Located in the heart of Poughkeepsie, this hotel is within 1 mile (2 km) of Casperkill Golf Club and Poughkeepsie Galleria. Bowdoin Park and Locust Grove are also within 3 miles (5 km).

      Hampton Inn by Hilton New Paltz C$141
      Hampton Inn by Hilton New Paltz

      Hampton Inn by Hilton New Paltz

      4 South Putt Corners Road, New Paltz, NY
         
        2.5 out of 5.0 Stars

        Located in the heart of New Paltz, this hotel is 8.3 mi (13.3 km) from Walkway Over the Hudson State Historic Park and 11.7 mi (18.8 km) from Minnewaska State Park. Home of Franklin D. Roosevelt National Historic Site and Poughkeepsie Galleria are also within 20 mi (32 km).

        *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.