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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
per person
Oct 20 - Oct 23
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,004 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul. 18, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (8 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on Jun. 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on Aug. 3, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,273 reviews)
Right across from the subway entrance, a Starbucks, and next to a Walgreens. Down the street, McD’s, Subway, Panda, CVS. Blocks away from Rockefeller Center. A block away from police and fire, felt safe the whole time. The property was modern and clean. We used the microwave in the lobby, our room had a fridge. Normal room size and not NY size, bed was comfortable and room was quiet! Definitely want to stay here again on the next trip.

Reviewed on Aug. 3, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,897 reviews)
Great location - courteous staff.

Reviewed on Aug. 1, 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 $124 per night from Sep 3 to Sep 4
CA $124
CA $147 total
Sep 3 - Sep 4
includes taxes & fees
7.4/10 Good! (493 reviews)
"Pretty good"

Reviewed on Jul. 28, 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
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Aug 25 to Aug 26
CA $188
CA $213 total
Aug 25 - Aug 26
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Great price. Wonderful location. Will be back!"

Reviewed on Jul. 31, 2025

Overlook Lodge at Bear Mountain
Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

3 out of 5
20 Schuyler Blvd, Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Aug 17 to Aug 18
CA $143
CA $162 total
Aug 17 - Aug 18
includes taxes & fees
7.4/10 Good! (458 reviews)
"Would go back"

Reviewed on Jul. 30, 2025

Wingate by Wyndham Fishkill
See all 658 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.
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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 $768 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.