Sherwood Vacations from $271

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The Latest Sherwood vacation packages

Price found within the past 48 hours. Click for updated prices.
The Mallard Hotel

The Mallard Hotel

2 out of 5
Price was $365, price is now $271 per person
$271
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Chattanooga (CHA)
15.2/10 Exceptional! (109 reviews)
Code did not work on assigned room. Had to call and they had to change our room. Very frustrating after a long day on the road.

Reviewed on Nov 14, 2025

Doubletree by Hilton Chattanooga Hamilton Place

Doubletree by Hilton Chattanooga Hamilton Place

4 out of 5
Hamilton Place
Save 100% on your flight
Price was $656, price is now $401 per person
$401
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Chattanooga (CHA)
16.8/10 Exceptional! (1,000 reviews)
Excellent hotel. Room was very clean. Had a comfortable stay.

Reviewed on Nov 21, 2025

Staybridge Suites Chattanooga Downtown - Convention Center by IHG

Staybridge Suites Chattanooga Downtown - Convention Center by IHG

3 out of 5
Downtown Chattanooga
Price was $666, price is now $478 per person
$478
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Chattanooga (CHA)
16/10 Exceptional! (1,002 reviews)
I saw a lot of bad reviews for this hotel but went ahead anyway. My room and my stay were very good, especially for the price compared to other downtown hotels.

Reviewed on Nov 24, 2025

Country Inn & Suites by Radisson, Chattanooga-Lookout Mountain

Country Inn & Suites by Radisson, Chattanooga-Lookout Mountain

2.5 out of 5
Lookout Valley
Price was $572, price is now $426 per person
$426
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Chattanooga (CHA)
15.2/10 Exceptional! (1,002 reviews)
Yes Breakfast was good and a very nice Hotel! Clean and Quiet

Reviewed on Nov 24, 2025

Hotel Bo, a Days Inn by Wyndham Chattanooga Downtown

Hotel Bo, a Days Inn by Wyndham Chattanooga Downtown

2 out of 5
Downtown Chattanooga
Price was $655, price is now $493 per person
$493
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Chattanooga (CHA)
18/10 Exceptional! (1,001 reviews)
Staff was very helpful .. Room was clean and perfect for the price .

Reviewed on Nov 20, 2025

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The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

3 out of 5
844 W Main Street Monteagle TN
Fully refundableReserve now, pay when you stay
$53 nightly
The price is $61 total per night from Dec 1 to Dec 2
$61 total
Dec 1 - Dec 2
Total with taxes and fees
8.4/10 Very Good! (1,140 reviews)
Great staff as always

Reviewed on Nov 19, 2025

The Smokehouse Lodge and Cabins
Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
1156 Highway 28 Jasper TN
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $78 total per night from Dec 6 to Dec 7
$78 total
Dec 6 - Dec 7
Total with taxes and fees
7.8/10 Good! (547 reviews)
Easy in and out

Reviewed on Nov 10, 2025

Quality Inn & Suites
Quality Inn Monteagle

Quality Inn Monteagle

2.5 out of 5
509 W Main St Pelham TN
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $93 total per night from Dec 1 to Dec 2
$93 total
Dec 1 - Dec 2
Total with taxes and fees
8.6/10 Excellent! (803 reviews)
Staff was very helpful and friendly.

Reviewed on Nov 18, 2025

Quality Inn Monteagle
See all 466 properties in Sherwood
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

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Frequently asked questions

How much does a Sherwood vacation package cost?
You can grab a vacation package to this destination from $271 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.