Woods Vacations from $570

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Your Woods Vacation

The adventure-packed city of Woods is calling. Uncover both its hidden gems and highlights with a Woods vacation package that's tailored to you. Every good trip to Woods should include a bit of sightseeing. Where to check out first? Jenny Wiley State Resort Park and StoneCrest Golf Course are leading attractions. A couple of clicks is all it takes to craft a tailor-made Woods vacation on Expedia.

The Latest Woods vacation packages

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

Hotel Thoroughbred

2 out of 5
Price was $775, price is now $570 per person
$570
per person
Jul 13 - Jul 18
found 12 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Lexington (LEX)
10/10 Exceptional! (4 reviews)
Beautiful, renovated historic building! The horse theme runs throughout. Bed was very comfortable. Location is central on Main Street, walking distance to restaurants, boutiques and shops. Would definitely recommend.

Reviewed on Jun 9, 2026

Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $1,017, price is now $794 per person
$794
per person
Jul 13 - Jul 18
found 12 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Lexington (LEX)
9.4/10 Exceptional! (107 reviews)
We were doing a cross country trip in our airstream. We stayed one night at the BnB and absolutely loved the grounds, our room, and our host. She went above and beyond accommodating our airstream and our dogs.

Reviewed on May 11, 2026

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
Price was $1,161, price is now $957 per person
$957
per person
Jul 13 - Jul 18
found 4 hours ago
Roundtrip non-stop flight included
Hartford (HFD) to Lexington (LEX)
9.4/10 Exceptional! (888 reviews)
Really nice stay. Staff was very nice and helpful. Highly recommend

Reviewed on May 25, 2026

Springhill Suites by Marriott Lexington Fritz Farm

Springhill Suites by Marriott Lexington Fritz Farm

3 out of 5
Price was $770, price is now $661 per person
$661
per person
Jul 13 - Jul 18
found 4 hours ago
Roundtrip non-stop flight included
Hartford (HFD) to Lexington (LEX)
9.2/10 Wonderful! (366 reviews)
I stood here with the family of three. The amenities were great option for anyone who is active the gym was just the right amount of equipment. The location was surrounded by a lot of shopping centers and supermarkets. The breakfast was a simple breakfast with decent options for the kids and adults weekdays till 9 AM weekends 10AM

Reviewed on May 25, 2026

Clarion Hotel Conference Center Lexington North

Clarion Hotel Conference Center Lexington North

3 out of 5
Price was $707, price is now $607 per person
$607
per person
Jul 13 - Jul 18
found 4 hours ago
Roundtrip non-stop flight included
Hartford (HFD) to Lexington (LEX)
7.6/10 Good! (1,003 reviews)
Stay was overall good. Room did have a weird smell to it and couldn’t check in early. We had a luggage cart full and was heading to room when a nice gentlemen older employee asked if he could help which was appreciated. Really good breakfast as well.

Reviewed on Jun 11, 2026

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Woods Hotel Deals

The Landmark Hotel

The Landmark Hotel

3.5 out of 5
190 S Mayo Trail Pikeville KY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Jun 13 to Jun 14
$102 total
Jun 13 - Jun 14
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Clean room"

Reviewed on Jun 6, 2026

The Landmark Hotel
Days Inn by Wyndham Paintsville

Days Inn by Wyndham Paintsville

2 out of 5
512 S Mayo Trail Paintsville KY
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Jun 15 to Jun 16
$80 total
Jun 15 - Jun 16
Total with taxes and fees
7.6/10 Good! (550 reviews)
"All and all a good place."

Reviewed on Jun 8, 2026

Days Inn by Wyndham Paintsville
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

Langley KY
9.8/10 Exceptional! (17 reviews)
"This was a unique and fun experience! It was cool to explore and find new things each time. The beds were extremely comfortable and the project manager was very responsive and helpful!"

Reviewed on Apr 28, 2026

Get rates
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
See all 61 properties in Woods
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 Woods Vacation Packages

Woods Essential Information

Language
English
Currency
U.S dollars
Top Sights
East Kentucky Science Center and Planetarium, StoneCrest Golf Course and Archer Park

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Frequently asked questions

How much does a Woods vacation package cost?
You'll find cheap prices from $570 on Expedia for your Woods escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Woods costs.
What are the cheapest months to go to Woods?
You can typically find reduced prices and better availability in January, September and October. Explore our cheap Woods vacation packages and you could land some great off-season discounts.
How many days is enough for Woods?
The ideal duration for your Woods vacation depends on what you'd like to see and do. Usually, a few days to a week will give you time to check out all the leading attractions and discover some hidden gems along the way.
How to find the best Woods package deals?
Landing a cheap Woods package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Woods package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Woods vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights individually. Better still, you can tailor your Woods trip to fit your exact style. Choose 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 Woods?
Score incredible discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Woods escape.
How to plan a trip to Woods?

  1. Pick your dates: The things you plan to do in Woods and your favorite season can help you decide when to get away.
  2. Set a budget: Factor in costs such as flights, meals and transportation when calculating how much to set aside for your trip to Woods. Then, choose a property that matches your budget, whether that's a wallet-friendly option or a deluxe getaway.
  3. Use our trip planning tool to explore Woods: Research every part of your trip to Woods with this handy planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're more familiar with Woods, you can work out the perfect length of your break. Pull together a rough plan and give yourself enough time to get through everything on your must-do list.
  5. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Woods vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Read our dedicated travel guide to find some awesome things to do in Woods. Book tickets or make reservations as soon as you can to save time and avoid the stress of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Woods vacation packages?
If you're like us, you love discovering new places but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Woods trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure 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.