Book 5 Star Hotels in New Windsor
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Featured New Windsor 5 Stars Hotels
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave New Windsor NY
Free Cancellation
Reserve now, pay when you stay
2.89 mi from city center
$101 nightly
The price is $114 total per night
$114 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
At Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point, guests enjoy an indoor pool, a gym, and free WiFi in public areas. There's free parking, and an airport shuttle (available on request) for USD 15 per room one-way. The 24-hour front desk has multilingual staff ready to assist with securing valuables and luggage storage. Additional amenities include a business center, coffee/tea in a common area, and a meeting room.
Pool
Pet friendly
Homewood Suites Stewart Airport
180 Breunig Rd New Windsor NY
Free Cancellation
Reserve now, pay when you stay
3.85 mi from city center
$130 nightly
The price is $147 total per night
$147 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at Homewood Suites Stewart Airport enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking, as well as a free airport shuttle (available on request). The front desk is staffed 24/7 to help with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub
Hampton Inn Harriman Woodbury
60 Centre Dr Central Valley NY
Free Cancellation
Reserve now, pay when you stay
12.38 mi from city center
$98 nightly
The price is $120 total per night
$120 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
At Hampton Inn Harriman Woodbury, guests enjoy an indoor pool, a gym, and free WiFi in public areas. You can take advantage of free parking, along with a free train station shuttle. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include conference space, coffee/tea in a common area, and a computer station.
Pool
Breakfast included
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Free Cancellation
Reserve now, pay when you stay
10.98 mi from city center
$100 nightly
The price is $114 total per night
$114 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
Guests of Overlook Lodge at Bear Mountain enjoy features like a full-service spa, free WiFi in public areas, and conference space. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with concierge services, and answer any questions about the accommodations. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this spa hotel include a business center, a seasonal outdoor pool, and wedding services.
Pool
Spa
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Free Cancellation
15.87 mi from city center
$84 nightly
The price is $99 total per night
$99 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Holiday Inn Express Hotel & Suites Chester by IHG enjoy an indoor pool, free WiFi in public areas, and a 24-hour business center. A stay here includes free parking. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a meeting room, express check-out, and a gift shop.
Pool
Breakfast included
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
12.29 mi from city center
$118 nightly
The price is $137 total per night
$137 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Hyatt Place Poughkeepsie / Hudson Valley have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, take advantage of free parking. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Pet friendly
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
12.93 mi from city center
$98 nightly
The price is $113 total per night
$113 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Guests of Hampton Inn & Suites Poughkeepsie have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, take advantage of free parking. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and luggage storage. Other amenities at this golf hotel include meeting rooms, conference space, and a 24-hour business center.
Pool
Breakfast included
Hampton Inn by Hilton Middletown
20 Crystal Run Crossing Middletown NY
Free Cancellation
Reserve now, pay when you stay
17.77 mi from city center
$80 nightly
The price is $94 total per night
$94 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Guests of Hampton Inn by Hilton Middletown enjoy a gym, free WiFi in public areas, and conference space. If you drive, put free parking to good use. The front desk has multilingual staff standing by 24 hours a day to assist with dry cleaning/laundry and securing valuables. Additional amenities include a 24-hour business center, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Breakfast included
Courtyard by Marriott Poughkeepsie
2641 South Road/Route 9 Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
14.19 mi from city center
$95 nightly
The price is $107 total per night
$107 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
At Courtyard by Marriott Poughkeepsie, guests have access to a 24-hour gym, free WiFi in public areas, and conference space. Self parking is available for USD 10 per stay. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a 24-hour business center, a computer station, and express check-out.
Free WiFi
Restaurant
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.
Best 5 star hotels in New Windsor
Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in New Windsor. After all, treating yourself to the finer things is what vacations are about.
What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These New Windsor hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.
What amenities can I expect at a 5 star hotel?
New Windsor 5 star hotels and resorts typically offer luxury amenities such as:
- Gourmet restaurant
- Full-service fitness center with pool
- Luxury spa
- Welcome gifts upon arrival
- Top-of-the-line beds and linens
- Designer personal care products
- Premium cable, free Wi-Fi and device docking stations
How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in New Windsor with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place:
- Search hotels by price, ranging from $94 to $147
- Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
- Choose from 1,014 5 star hotels in New Windsor!
New Windsor hotels essential information
Accommodation | 1,014 hotels |
|---|---|
Lowest Price | $94 |
Highest Price | $147 |
Popular hotels | Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point, Homewood Suites Stewart Airport, Hampton Inn Harriman Woodbury, Overlook Lodge at Bear Mountain, Hampton Inn & Suites Poughkeepsie, Hyatt Place Poughkeepsie / Hudson Valley, Hampton Inn by Hilton Middletown, Courtyard by Marriott Poughkeepsie, Holiday Inn Express Hotel & Suites Chester by IHG |
Recent Reviews
Overlook Lodge at Bear Mountain
5/5 Excellent
"The staff were wonderful. Everyone (maintenance, front desk, restaurant, spa) was very helpful and welcoming. I throughly enjoyed my staff and look forward to visiting again."
A verified traveler stayed at Overlook Lodge at Bear Mountain
Posted 4 days ago
