Stroudsburg Vacations from $338

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Your Stroudsburg Vacation

Experience the unique personality of Stroudsburg with a tailor-made Stroudsburg vacation package. From its rich history to its spectacular views, you'll never have a boring moment in this city. Any trip to Stroudsburg needs a well-designed itinerary. Fill yours with major attractions like Sherman Theater, East Stroudsburg University and Shawnee Golf Resort. A few clicks is all it takes to craft your ideal Stroudsburg vacation on Expedia.

The Latest Stroudsburg vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Save 100% on your flight
Price was $538, price is now $338 per person
$338
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,450 reviews)
The food is really good, the view is amazing...

Reviewed on Aug 18, 2025

Paradise Stream Resort

Paradise Stream Resort

3.5 out of 5
Save 100% on your flight
Price was $1,045, price is now $665 per person
$665
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (1,005 reviews)
food options and bed comfort

Reviewed on Aug 18, 2025

The George

The George

4 out of 5
Save 100% on your flight
Price was $834, price is now $548 per person
$548
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (404 reviews)
Meticulous and comfortable; a winning combination.

Reviewed on Aug 20, 2025

La Posada

La Posada

2.5 out of 5
Save 100% on your flight
Price was $686, price is now $454 per person
$454
per person
Oct 30 - Nov 3
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (79 reviews)
I always stay at La Posada Hotel when you am in Milford, PA.

Reviewed on Jul 20, 2025

Hilton Short Hills

Hilton Short Hills

4 out of 5
Save 100% on your flight
Price was $640, price is now $425 per person
$425
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,004 reviews)
The room was fine. But the service was very unfriendly, uncooperative, just not what you would expect from a Hilton. We accidentally left a cell phone in the room and staff would not let us retrieve it, just 10 minutes after checking out. We waited almost 45 minutes to get the phone. Staff were generally not helpful. Parking garage is immense with Very poor signage. Many other guests having problems with the parking. And they charge $24 for this. Altogether Disappointing.

Reviewed on Aug 15, 2025

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Discover the most popular places to visit in Stroudsburg

Pocono Mountains Visitors Bureau

Pocono Mountains Visitors Bureau

After visiting Pocono Mountains Visitors Bureau, make a plan to see the other sights and activities in Stroudsburg. Wander the riverfront or discover the area's mountain views.

Pocono Mountains Visitors Bureau

Sherman Theater

You can get tickets for a performance at Sherman Theater during your trip to Stroudsburg. Discover the area's mountain views, or seek out its hiking trails.

Sherman Theater

Mountain View Vineyard

You can enjoy a tasting or tour at Mountain View Vineyard during your travels to Stroudsburg. Discover the mountain views in this family-friendly area, or enjoy its hiking trails.

Mountain View Vineyard

What to do in Stroudsburg

10 Mile Stock Car Drive Experience at Pocono Raceway

10 Mile Stock Car Drive Experience at Pocono Raceway

$399
per adult
10 Mile Stock Car Drive Experience at Pocono Raceway
20 Mile Stock Car Drive Experience at Pocono Raceway

20 Mile Stock Car Drive Experience at Pocono Raceway

$599
per adult
20 Mile Stock Car Drive Experience at Pocono Raceway
80 Mile Stock Car Drive Experience at Pocono Raceway

80 Mile Stock Car Drive Experience at Pocono Raceway

$2,299
per adult
80 Mile Stock Car Drive Experience at Pocono Raceway
See all activities in Stroudsburg

Stroudsburg Hotel Deals

Hampton Inn & Suites Stroudsburg Pocono Mountains

Hampton Inn & Suites Stroudsburg Pocono Mountains

3 out of 5
700 Commerce Blvd, Stroudsburg, PA
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $149 total per night from Sep 1 to Sep 2
$149 total
Sep 1 - Sep 2
Total includes taxes and fees
9/10 Wonderful! (1,004 reviews)
"Rooms were clean. Staff was very polite"

Reviewed on Aug 16, 2025

Hampton Inn & Suites Stroudsburg Pocono Mountains
The Penn Stroud, Stroudsburg - Poconos, Ascend Hotel Collection

The Penn Stroud, Stroudsburg - Poconos, Ascend Hotel Collection

3.5 out of 5
700 Main St, Stroudsburg, PA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $130 total per night from Sep 1 to Sep 2
$130 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (1,005 reviews)
"Stay was just fine I will say that I feel it is overpriced I stayed Thursday and Friday night asked about extending an extra night they quoted me $340 for the extra night. Were talking about stroudsburg, pa folks."

Reviewed on Aug 17, 2025

The Penn Stroud, Stroudsburg - Poconos, Ascend Hotel Collection
Red Roof Inn Stroudsburg

Red Roof Inn Stroudsburg

2 out of 5
100 Park Avenue, Stroudsburg, PA
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $84 total per night from Aug 24 to Aug 25
$84 total
Aug 24 - Aug 25
Total includes taxes and fees
6.6/10 (888 reviews)
"Great desk personnel and perfect location off the highway and very close to downtown main Street!"

Reviewed on Aug 11, 2025

Red Roof Inn Stroudsburg
See all 5,217 properties in Stroudsburg
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 Stroudsburg vacation package cost?
You can pick up a vacation package to this popular destination from $338 on Expedia. However, how much your vacation to Stroudsburg costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Stroudsburg?
You're likely to find lower prices and greater availability in March, October and December. Check out our cheap Stroudsburg vacation packages and you could land some excellent off-season deals.
How many days is enough for Stroudsburg?
Typically, a handful of days is great for a Stroudsburg vacation. With a detailed itinerary, you can check out all the popular attractions such as Stroud Mansion, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Stroudsburg?
Stroudsburg is a good vacation destination with attractions like Sherman Theater among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Stroudsburg vacation promises a good time for everyone.
How to find the best Stroudsburg package deals?
Begin your search for a Stroudsburg package deal by entering your destination and travel dates 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 discover offers that come with big savings. If you don't find the perfect Stroudsburg package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Stroudsburg adventure underway.
Is it cheaper to book a Stroudsburg vacation as a package?
You can enjoy significant savings on your Stroudsburg escape by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Stroudsburg?
If you've got your Stroudsburg vacation dates confirmed, book early to bag some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Stroudsburg?

  1. Choose when to go: Check your calendar and get your bags packed. Your preferred season and the activities on offer will also help you decide when to visit Stroudsburg.
  2. Set your budget: Factor in costs such as flights, meals and transportation when working out how much to save for your trip to Stroudsburg. Then, select a hotel that matches your budget, whether that's a low-cost stay or a lavish retreat.
  3. Explore Stroudsburg using our trip planning tool: Gain insights into the top attractions and best properties for your trip to Stroudsburg. You can also save your favorite locations, collaborate with friends and family and manage your plans in one place.
  4. Decide how many days away: Start by listing all the activities and attractions you want to get to in Stroudsburg. Then, estimate how long you'll need at each, including any travel time.
  5. Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the right Stroudsburg vacation package for you.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a day trip in nature, you won't have to worry about missing out on Stroudsburg's highlights. Find all the incredible things to do in Stroudsburg in Stroudsburg with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Stroudsburg vacation packages?
Your Stroudsburg break should be a relaxing escape from your daily routine, not a source of money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.