Shenandoah Vacation Packages

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Your Shenandoah Vacation

Take the guesswork out of travel planning with a Shenandoah vacation package. One of the best neighborhoods to stay in this vibrant city is Spackenkill, which is good for golfing and lots more. You'll want to do some exploring during your trip to Shenandoah. Swing by major attractions such as East Fishkill Community Library, Beekman Golf Course and Canopus Beach. Your ideal Shenandoah vacation is just clicks away. Browse airfares, hotels and more on Expedia for a getaway that's tailored to suit your style.

Top Shenandoah Vacation Deals

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

Hotel St. James

2.5 out of 5
Manhattan
Price was CA $1,290, price is now CA $816 per person
CA $816
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (6,263 reviews)
Very pleasant stay! We'd stay again.

Reviewed on Aug. 24, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Price was CA $1,710, price is now CA $1,017 per person
CA $1,017
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (10 reviews)
Nice stay. Very low bed and little room to get in and out. Great location. If booking through Expedia, be careful to check for shared/private bathroom as the description is misleading.

Reviewed on Aug. 22, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,776, price is now CA $1,669 per person
CA $1,669
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $3,020, price is now CA $1,895 per person
CA $1,895
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (129 reviews)
Love the hotel especially the design and decor. Staff is so nice and professional. Room service food is excellent. The only negative is the lack of an in-house gym. Would stay again.

Reviewed on Aug. 22, 2025

The Mark

The Mark

5 out of 5
Manhattan
Price was CA $3,912, price is now CA $2,499 per person
CA $2,499
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (681 reviews)
This is a perfect location!

Reviewed on Aug. 17, 2025

Ready to book your vacation to Shenandoah?

 

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Shenandoah Hotel Deals

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
The price is CA $136 per night from Sep 2 to Sep 3
CA $136
CA $160 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (522 reviews)
"I enjoyed the location. The place was clean and employees were very pleasant"

Reviewed on Aug. 21, 2025

The Crossroads Hotel, Newburgh
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
The price is CA $181 per night from Aug 26 to Aug 27
CA $181
CA $205 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"The Overlook Lodge is a wonderful property nestled in the woods and yet close to the Inn for dining. Our room was spacious and the beds were very comfortable."

Reviewed on Aug. 23, 2025

Overlook Lodge at Bear Mountain
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
The price is CA $140 per night from Sep 21 to Sep 22
CA $140
CA $163 total
Sep 21 - Sep 22
includes taxes & fees
7.6/10 Good! (402 reviews)
"Overall good stay"

Reviewed on Aug. 24, 2025

Quality Inn Poughkeepsie
See all 650 properties in Shenandoah
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 Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Shenandoah vacation package cost?
You can pick up a vacation package to this top destination from CA $816 on Expedia. However, how much your vacation to Shenandoah costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Shenandoah?
You can typically find lower rates and greater availability in January, February and March. Take a look at our cheap Shenandoah vacation packages and you could land some excellent off-season deals.
How many days is enough for Shenandoah?
The ideal length of your Shenandoah vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to visit all the top attractions and explore some hidden gems along the way.
How to find the best Shenandoah package deals?
Begin your search for a Shenandoah package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Shenandoah package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Shenandoah adventure underway.
Is it cheaper to book a Shenandoah vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Shenandoah trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Shenandoah?
If you're considering a spontaneous Shenandoah getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Shenandoah?

  1. Choose your dates: The things you want to do in Shenandoah and your preferred season will help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to cover everything from food and transportation to flights and experiences. Your accommodations will likely be the biggest expense during your trip to Shenandoah.
  3. Decide how long to go for: Now that you're more familiar with Shenandoah, you can figure out the right length of your vacation. Pull together a rough plan and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Shenandoah vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.