Top Wing's Castle vacation deals
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Staatsburg NY
9.8/10 Exceptional! (89 reviews)
My family and I had such a wonderful stay. Glen was very responsive and proactive. The space was beautiful as it was decorated for Christmas. It was very warm and peaceful. Definitely looking forward to returning!
Reviewed on Dec 30, 2025
25 OLD VINEYARD PLACE Hyde Park NY
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $163 total per night from Jan 25 to Jan 26
$163 total
Jan 25 - Jan 26
Total with taxes and fees
9.6/10 Exceptional! (449 reviews)
Great place. New. Terrific rooms beyond exceptional. Highly recommend
Reviewed on Jan 5, 2026
46 West Market St Rhinebeck NY
$462 nightly
The price is $522 total per night from Jan 14 to Jan 15
$522 total
Jan 14 - Jan 15
Total with taxes and fees
9.6/10 Exceptional! (310 reviews)
My wife and I have stayed there for 3 straight years during December. The rooms are always clean, the staff is extremely helpful, and the spa is always top notch. The town of Rhinebeck is beautiful, especially during the Christmas season, and the restaurants are incredible. We look forward to our ...
Reviewed on Jan 4, 2026
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Mill St Rhinebeck NY
9/10 Wonderful! (114 reviews)
Convenient to walking around town
Reviewed on Nov 6, 2025
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Feb 1 to Feb 2
$101 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Clean. Parking. Service of front desk!
Reviewed on Jan 8, 2026
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $203 total per night from Feb 8 to Feb 9
$203 total
Feb 8 - Feb 9
Total with taxes and fees
8.2/10 Very Good! (820 reviews)
Staff is amazing. Rooms are very clean. Historic building. Restaurant is outstanding.
Reviewed on Jan 4, 2026
4142 Albany Post Rd Hyde Park NY
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $87 total per night from Feb 8 to Feb 9
$87 total
Feb 8 - Feb 9
Total with taxes and fees
8/10 Very Good! (1,010 reviews)
Breakfast was packaged goods
Reviewed on Jan 10, 2026
74 Interlaken Road Lakeville CT
$195 nightly
The price is $225 total per night from Feb 11 to Feb 12
$225 total
Feb 11 - Feb 12
Total with taxes and fees
8/10 Very Good! (275 reviews)
The setting was beautiful in Lakeville, CT. The property was clean and very much updated and the staff was incredibly friendly. We attended a wedding and reception at the inn and it was beautiful. Highly recommend!
Reviewed on Jan 1, 2026
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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^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.