Roundout Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Roundout

Price found within the past 48 hours. Click for updated prices.
Econo Lodge Lee - Great Barrington
The Equinox Golf Resort & Spa
Valley Craft Ales
Kimpton Taconic Hotel by IHG
South Shire

Where to stay in Roundout

Find the best Roundout areas and neighborhoods for the activities you enjoy most. Learn more about Roundout

Roundout Hotel Deals

Kingston Carriage House

Kingston Carriage House

4 out of 5
85 Abeel St, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Sep 2 to Sep 3
CA $267
CA $311 total
Sep 2 - Sep 3
includes taxes & fees
Kingston Carriage House
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Sep 28 to Sep 29
CA $139
CA $162 total
Sep 28 - Sep 29
includes taxes & fees
7.6/10 Good! (402 reviews)
"Overall good stay"

Reviewed on Aug. 24, 2025

Quality Inn Poughkeepsie
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is CA $1,343 per night from Sep 17 to Sep 18
CA $1,343
CA $1,564 total
Sep 17 - Sep 18
includes taxes & fees
9.4/10 Exceptional! (52 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on May 15, 2025

Wildflower Farms, Auberge Resorts Collection
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.