Sherwood Vacations from $411
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Sherwood vacation packages
Price found within the past 48 hours. Click for updated prices.
WoodSpring Suites Cleveland North
$411
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chattanooga (CHA)
7.6/10 Good! (58 reviews)
This place is excellent. It’s brand new. It’s squeaky clean. It was very quiet. There’s a normal size refrigerator with a freezer. There’s a kitchen sink.
There’s a hot plate you can cook with. I would bring your own utensils and stuff like that.
It’s just a really good quiet place at a great price.
Reviewed on Oct 21, 2026
Candlewood Suites Chattanooga East Ridge by IHG
East Ridge
$626
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
9/10 Wonderful! (436 reviews)
I will start by saying the staff was helpful. We got there and the first room had people in it. We went back to the front and got another room, which was the wrong beds. I booked two queens and they gave us a king. (We had 2 adults and 2 kids). So we went back to the front. Finally after about 30ish minutes we got into our room. It was an ok experience but for the price we paid.... it wasn't worth it.
Reviewed on Oct 18, 2026
Sherwood Hotel Deals
The Smokehouse Lodge and Cabins
844 W Main Street Monteagle TN
Fully refundableReserve now, pay when you stay
$56 nightly
$64 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (1,307 reviews)
"The website makes the property look nicer than it is."
Reviewed on Oct 21, 2026
Quality Inn Monteagle
509 W Main St Monteagle TN
Fully refundableReserve now, pay when you stay
$79 nightly
$94 total
Oct 27 - Oct 28
Total with taxes and fees
8.8/10 Excellent! (969 reviews)
"The staff, rooms, breakfast, etc were fine but there is NO ELEVATOR so be sure to request a room on the first floor is you have a lot of luggage."
Reviewed on Oct 21, 2026
The Sewanee Inn
1235 University Ave Sewanee TN
$359 nightly
$417 total
Oct 25 - Oct 26
Total with taxes and fees
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.
Find the Best Sherwood Vacation Packages
Sherwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | University of the South, Monteagle Sunday School Assembly and Sewanee Golf and Tennis Club |
More vacations you might like
Frequently asked questions
How much does a Sherwood vacation package cost?
You can grab a vacation package to this destination from $411 on Expedia. However, how much your vacation to Sherwood costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Sherwood?
October, November and December are the best times to search for cheap Sherwood vacation packages. Opting to travel in quieter periods means you can typically find lower prices on hotels and flights.
How many days is enough for Sherwood?
Usually, a handful of days is enough to visit the major sights during your Sherwood vacation. However, if you prefer to have more time to relax or take day trips, think about extending your itinerary.
How to find the best Sherwood package deals?
Begin your search for a Sherwood package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Sherwood package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Sherwood escape underway.
Is it cheaper to book a Sherwood vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations separately. Better still, you can customize your Sherwood getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Sherwood?
If you're considering a spontaneous Sherwood vacation, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Sherwood vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Sherwood trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
