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

FlightsFlightsHotelsHotels

Rhinebeck

Rhinebeck

Top Dutchess County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Price was £2,440, price is now £1,322 per person
£1,322
per person
5 Jul - 8 Jul
found 22 hours ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (2,170 reviews)
A very busy location . None friendly staff

Reviewed on 20 May 2026

Casa Francesca 6BR Villa & Heated Pool

Casa Francesca 6BR Villa & Heated Pool

3.5 out of 5
Save 100% on your flight
Price was £6,799, price is now £4,056 per person
£4,056
per person
5 Aug - 12 Aug
found 1 day ago
Return direct flight included
London (LGW) to Newark Liberty Intl. Airport (EWR)
No reviews
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was £4,958, price is now £3,094 per person
£3,094
per person
23 Jul - 2 Aug
found 1 day ago
Return flight included
London (LON) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
Nice property great location

Reviewed on 21 May 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was £3,386, price is now £2,250 per person
£2,250
per person
23 Jul - 2 Aug
found 1 day ago
Return flight included
London (LON) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
This is the only hotel I stay in when I come to NYC. Everyone there is amazing!

Reviewed on 15 May 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was £2,359, price is now £1,605 per person
£1,605
per person
31 Jul - 12 Aug
found 1 day ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,520 reviews)
Very clean and staff was nice.

Reviewed on 20 May 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

Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

2.5 out of 5
25 Merritt Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is £69 per night from 1 Jun to 2 Jun
£69
1 Jun - 2 Jun
includes taxes & fees
6.6/10 (1,001 reviews)
"Was not able to stay there due to accommodations. It’s a good thing though. The place smelt like dog urine and looked run down. Still waiting on my refund and it’s been 5 days."

Reviewed on 19 May 2026

Studio 6 Extended Stay Fishkill Route 9 NY
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is £102 per night from 27 May to 28 May
£102
27 May - 28 May
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Good breakfast, clean hotel, and great staff."

Reviewed on 22 May 2026

Hyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is £80 per night from 9 Jun to 10 Jun
£80
9 Jun - 10 Jun
includes taxes & fees
8.2/10 Very Good! (101 reviews)
"The room was nice. The bathroom could use some updates as the tub had chips and the tub spout was practically sideways as opposed to facing down. The breakfast was minimal (hard boiled eggs, cereals, bagels, muffins) not the most nutritious. The gym was very small and doesn't open until 7am which ..."

Reviewed on 21 May 2026

Spark by Hilton Fishkill
See all 404 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
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 £1,322, 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.