Dutchess County Holidays

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Your Dutchess County Holiday

Choose a holiday package to Dutchess County and make planning your adventure easy. With the logistics arranged before you leave, you can focus on enjoying every minute in this exciting destination. With so much to see on a trip to Dutchess County, it can be hard to know where to begin. Kick off your journey in Poughkeepsie at Vanderbilt Mansion National Historic Site and Hyde Park Station — two much-loved attractions here. Another great city worthy of a spot on your itinerary is Pawling. Be sure not to miss Candlewood Lake and Stormville Airport Antique Show & Flea Market. Find some travel buddies and start packing, because your Dutchess County holiday is only clicks away with Expedia.

Top destinations in Dutchess County

Poughkeepsie which includes autumn colours and a river or creek
FlightsFlightsHotelsHotels

Poughkeepsie

Poughkeepsie

Top Dutchess County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Five44

Hotel Five44

3 out of 5
Manhattan
Price was £1,220, price is now £777 per person
£777
per person
4 May - 7 May
found 1 day ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (715 reviews)
Loved the location and self check in if staff were unavailable. No key cards needed for front door or room made access easy. I would definitely stay here again.

Reviewed on 11 Oct 2025

Comfort Inn Manhattan - Midtown West

Comfort Inn Manhattan - Midtown West

2.5 out of 5
Manhattan
Price was £1,762, price is now £791 per person
£791
per person
16 Mar - 19 Mar
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
7.8/10 Good! (1,746 reviews)
We booked three rooms for our group for an overnight stay due to a fight cancellation. We were so impressed with the hotel location the facility considering the price is so affordable. The staff was really courageous, letting us store our luggage prior to checking in time and also help us with directions to the local area. We will definitely stay here again when we visit New York.

Reviewed on 31 Jan 2026

Hampton Inn Manhattan/Times Square Central

Hampton Inn Manhattan/Times Square Central

3.5 out of 5
Manhattan
Price was £1,977, price is now £962 per person
£962
per person
24 Mar - 27 Mar
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9.2/10 Wonderful! (2,329 reviews)
Staff was extremely friendly and helpful. Loved our stay.

Reviewed on 8 Feb 2026

The Sherry Netherland

The Sherry Netherland

4.5 out of 5
Manhattan
Price was £2,677, price is now £1,497 per person
£1,497
per person
11 Mar - 14 Mar
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9.6/10 Exceptional! (595 reviews)
The Sherry is a wonderful property.

Reviewed on 12 Jan 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £2,399, price is now £1,454 per person
£1,454
per person
25 Mar - 29 Mar
found 17 hours ago
Return flight included
London (LHR) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
The entire stay was exceptional! From the point of entry to departure 10/10

Reviewed on 29 Jan 2026

Dutchess County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Top Sights
Innisfree Garden, Bowdoin Park and Harlem Valley Rail Trail

Top hotels in Dutchess County

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is £87 per night from 17 Feb to 18 Feb
£87
17 Feb - 18 Feb
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
Room was nice. Staff was friendly

Reviewed on 7 Feb 2026

Courtyard by Marriott Poughkeepsie
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is £84 per night from 1 Mar to 2 Mar
£84
1 Mar - 2 Mar
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Room was clean and comfortable. Staff was so friendly. Would definitely stay here again

Reviewed on 29 Jan 2026

DoubleTree by Hilton Poughkeepsie Convention Center
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is £76 per night from 20 Feb to 21 Feb
£76
20 Feb - 21 Feb
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Best staff ever great location.

Reviewed on 1 Feb 2026

Hampton Inn & Suites Poughkeepsie
See all 3,882 properties in Dutchess County
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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All Inclusive Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Dutchess County travel package cost?
Our Dutchess County travel packages, which start from as low as £777, are an awesome way to save big. Handpick your favourite hotels, flights and rental car to create your perfect itinerary.
If I'm not able to travel, can I cancel my Dutchess County travel package?
If your travel plans in Dutchess County have been upended, it's comforting to know that you can cancel your booking. If your booking was made in the last 24 hours, you may be eligible to receive a refund. If your booking is older than that, your hotel, airline or car rental company may charge a cancellation fee. To learn more, visit our Customer Service Portal.
How do I get a cheap travel package to Dutchess County?
Combine your bookings with Expedia to save on your next getaway. With over 550 partner airlines and 1,000,000 properties throughout the world, your Dutchess County holiday package can be tailored exactly to suit your travel style. With all that extra cash, why not include one or more awesome tours and experiences? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Dutchess County is closer than you thought!
Does Expedia offer Book Now, Pay Later Dutchess County holidays?
Expedia has joined forces with online lender Klarna to make your next getaway easier on your bank balance. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Consider these flexible payment options:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all types of budgets, so you can book that well-earned holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday over multiple transactions.
  • Low deposit holidays: Clicking the "book now" button is much easier with this option. Just put down a small deposit on your holiday and then start working on your travel plans.

What are the top hotels in Dutchess County?
When it comes to properties in Rhinebeck, HYATT house Fishkill/Poughkeepsie and Hyatt Place Poughkeepsie are among the favourites. If you're also visiting Red Hook, HYATT house Fishkill/Poughkeepsie and Hyatt Place Poughkeepsie look forward to welcoming you.
How far in advance should I book my Dutchess County holiday?
It's hard to pick the ideal time for airfares, but we generally suggest the earlier, the better. Most international flights on Expedia become available up to a year in advance. If you can't book ahead, don't stress. Cheap prices appear from time to time just weeks before departure dates.
What does an Expedia Dutchess County travel package include?
Hotels, flights and a shiny set of wheels for your road trip adventures. Simply choose your favourite bundle and gain access to great discounts. Once you've made your booking, add on a couple of experiences and tours and watch your savings stack up. When it comes to organising your Dutchess County break, you're the boss!
What should I know before booking a Dutchess County travel package?
Bundling your bookings into a Dutchess County travel package is the easiest way to organise your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Dutchess County Expedia travel package?
Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have access to more than 550 partner airlines throughout the world, so you have options galore when creating your Dutchess County escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.