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Sherwood Vacation Rentals

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    Check prices for these dates, December 15–16, 2026

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    Our top choices for Sherwood vacation rentals

    1. Sasquatch Farm

    A cabin with a wooden exterior, a staircase leading to a deck, and a gravel driveway surrounded by trees.

    2. The Woods at The Retreat at Deer Lick Falls

    A wooden deck with a railing, a table, and chairs.

    3. Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24

    An outdoor patio area with a wooden deck, seating, and string lights.

    4. Smarter than the Average Stay at the Yogi Cottage!

    A log cabin with a large sliding glass door, a deck, and a wooden fence.

    5. Newly Remodled Suite in Monteagle TN!

    A wooden deck with outdoor seating and a covered area with large windows.

    6. Cozy Cottage in Monteagle!

    A covered porch with a table and chairs, a potted plant, and a view of the surrounding trees.

    7. The Cabin in Tracy City

    A stone building with a traditional architectural style, featuring a central entrance and multiple windows.

    8. Snuggle Up in our Teddy Cottage! *New Listing*

    A wooden cabin with a deck, large windows, and a sliding glass door.

    9. The Calming Cabin — A Peaceful Retreat, Park-Like Setting, and Area Adventures

    A wooden deck with a railing, surrounded by trees with autumn foliage.

    10. Tiny Haven at the Retreat

    A wooden deck with a railing, surrounded by trees, leading to a building with large windows.

    11. Chic 2BR Cabin D by MHM Luxury Properties

    A stone sign for 'Top of the Rock Restaurant & Brewery' with a rustic stone wall and greenery in the foreground.

    12. The Hummingbird Treehouse

    A wooden pathway leading to a black tent-like structure with a triangular roof, surrounded by trees.

    13. The Loft - Lounge with Grill and Hot Tub!

    An outdoor patio with a fire pit, seating area, and a grill.

    14. Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!

    A serene outdoor setting with a wooden deck, two Adirondack chairs, and a backdrop of blooming trees and a lake.

    15. Terralodge: Wild Luxury Cabin on Monteagle Mountain

    A wooden pathway leading to a black tent-like structure with a triangular roof, surrounded by trees.

    16. Mountain Top Mini Home at The Retreat at Deer Lick Falls

    A cabin with a fire pit, outdoor seating, and a view of the surrounding forest.

    17. Caverns•Sewanee•Waterfalls•Hikes• Basecamp Tiny

    A cabin with a large glass front, surrounded by a gravel path and rock border, set in a forested area with string lights.

    18. Mountain Memories to provide a cozy retreat on your vacation!

    Dining

    19. Oasis on the Square

    A row of brick buildings with storefronts, including a restaurant with a black awning and a shop with a striped awning.

    20. Eagle’s Escape to Sunset Bluff - With OHV Trailer Parking Space

    A circular stone fire pit with Adirondack chairs around it, set in a forest with autumn foliage.

    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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    Top Sherwood Hotel Reviews

    Quality Inn Monteagle

    A spacious room with a stone fireplace, a flat-screen TV mounted above it, and a green upholstered sofa.

    Best Western Inn

    A commercial kitchen with a coffee machine, a waffle maker, and a toaster.

    Holiday Inn Express & Suites Kimball by IHG

    A Holiday Inn Express building with a covered entrance and a clear sign.

    The Smokehouse Lodge and Cabins

    A lodge with a large wooden overhang, stone pillars, and a stone entrance.

    Quality Inn & Suites Jasper - Kimball

    A hotel lobby with a reception desk, a seating area with leather sofas, a vending machine, and large windows offering a view of the outside.

    Clarion Pointe Kimball By Choice Hotels

    A hotel room with two beds, a large painting of a waterfall, a window with curtains, and a bedside table with a lamp.

    Find out more about Sherwood

    Everything you need to know about Sherwood vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sherwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sherwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Sherwood vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Sherwood. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sherwood vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Sherwood vacation rentals we have selected for you start as low as CA $89 per night. Entering your travel dates in the search wizard you might find even better deals!

    How to find incredible deals on Sherwood rentals

    At Expedia, we put the best Sherwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Sherwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sherwood vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sherwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Are there vacation rentals in Sherwood?

    Yes, there are vacation rentals near popular points of interest in Sherwood, or you can select a more secluded option if you want a relaxing place to stay.

    What are some of the best vacation home rentals that Sherwood has to offer?

    Secluded, amazing artesian home in beautiful Coppingers Cove - outdoor paradise : Visitors like this Sherwood vacation home rental. It is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

    What can I see and do in Sherwood?

    While exploring the area, visit family-friendly sights like Twin Creeks Marina, or get outside and enjoy nature at Lake Cheston. In the larger area, you’ll find University of the South and Sewanee Golf and Tennis Club.

    What are vacation rentals like in Sherwood?

    Vacation rentals are private accommodations you can stay in for several days or longer in Sherwood. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for small groups.