Sherwood Vacation Rentals from $162: Search Short-Term Rentals

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Our top choices for Sherwood vacation rentals

A cozy bedroom with a large bed, a window with a view of greenery, and wooden ceiling beams.

1. Sasquatch Farm

South Pittsburg

Kimberly

$150 nightly

Oct 22 - Oct 23

Total with taxes and fees

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

Sewanee

Ryan B.

$221 nightly

Oct 22 - Oct 23

Total with taxes and fees

A compact kitchen with wooden cabinets, a microwave, stove, and a dining area with a table and chairs.

3. Cozy Cottage in Monteagle!

Monteagle

Rebecca

$218 nightly

Oct 22 - Oct 23

Total with taxes and fees

A restaurant with a neon sign indicating it is a smokehouse and trading post.

4. The Woods at The Retreat at Deer Lick Falls

Monteagle

John S.

$279 nightly

Oct 26 - Oct 27

Total with taxes and fees

A log cabin with a deck, large windows, and a table with chairs.

5. Story-time Stay at Our Rupert Cottage!

Monteagle

Taroub F.

$218 nightly

Oct 22 - Oct 23

Total with taxes and fees

A rustic cabin with a green metal roof, wooden porch, and a small garden with pink flowers.

6. The Calming Cabin — Relaxing Getaway, Park-Like Setting, and Area Waterfalls

Tracy City

Marc N.

$253 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern living room with a built-in aquarium, a leather sofa, and a patterned rug.

7. Winchester's Premier Downtown Loft!

Winchester

Gianmarco

$185 nightly

Oct 25 - Oct 26

Total with taxes and fees

A hallway with a wooden floor, a welcome sign, a mirror, and a potted plant.

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

Monteagle

David C.

$178 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

9. Shea's Chalet - Cozy home in Monteagle, TN

Downtown Monteagle

Keith J.

$237 nightly

Oct 22 - Oct 23

Total with taxes and fees

A rustic log cabin with a wooden deck and a covered porch.

10. Martin Springs Cabin.

South Pittsburg

Alan D.

$232 nightly

Oct 26 - Oct 27

Total with taxes and fees

A wooden cabin interior with a dining area, kitchen, and a staircase leading to a loft.

11. Cabin with Fishing Pond and Gorgeous Bluff Views!

Sewanee

Dan M.

A spacious kitchen with granite countertops, white cabinetry, and a built-in dishwasher. There are multiple windows providing natural light and a view of the outdoors.

12. Tiny Home w/ RV Hookups

Winchester

Erica P.

$175 nightly

Oct 26 - Oct 27

Total with taxes and fees

A concrete planter with various succulents and cacti.

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

South Pittsburg

TJ S.

$264 nightly

Nov 3 - Nov 4

Total with taxes and fees

A spacious living room with a brown leather sofa, a dining table, and a kitchen area.

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

Monteagle

Scott

$188 nightly

Oct 26 - Oct 27

Total with taxes and fees

A white house with a covered porch, stone pathway, and outdoor seating.

15. Forest Retreat: Poolside Bliss Close to Campus

Sewanee

Denise M.

$472 nightly

Oct 25 - Oct 26

Total with taxes and fees

A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

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

Pelham

Antonio M.

$232 nightly

Oct 22 - Oct 23

Total with taxes and fees

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

17. Newly Remodled Suite in Monteagle TN!

Monteagle

Tina

$194 nightly

Oct 22 - Oct 23

Total with taxes and fees

A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

18. Tiny Haven at the Retreat

Monteagle

Todd

$170 nightly

Oct 22 - Oct 23

Total with taxes and fees

A modern kitchen with dark cabinetry, stainless steel appliances, and a light-colored backsplash.

19. Oasis on the Square

Winchester

possible Amanda H

$155 nightly

Oct 22 - Oct 23

Total with taxes and fees

A red mailbox with "McCormick Farmall" on it, a black barbecue grill, a red metal table and chairs, and a sign that says "Come In We're Open".

20. A very rustic converted pole barn unique cozy cabin

Estill Springs

Jacquelyne S.

$145 nightly

Oct 22 - Oct 23

Total with taxes and fees

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Top Sherwood Hotel Reviews

Best Western Inn

8/10 Good

"Good location. Friendly staff. Bed was comfortable with plenty of pillows. Bathroom shower would benefit from a little extra deep cleaning and that is my only issue. I would stay here again."

Clarion Pointe Kimball By Choice Hotels

10/10 Excellent

"The room was clean, and the staff was friendly and helpful. The hotel is conveniently located near Top of the Rock Restaurant and Brewery and just a short drive from Hales Bar Haunted House. It was a budget-friendly place to stay for a day trip, especially since it saved us from having to drive home afterward."

Moonshine Runners Cabin

10/10 Excellent

"We absolutely loved our stay at the Moonshine Runners Cabin! We felt right at home. Cynthia greeted us with some wonderful cinnamon rolls shortly after we arrived. The location was perfect for our weekend trip going to the Caverns for a concert. We enjoyed breakfast at Dutch Maid Bakery and lots of hiking nearby. The cabin had everything we needed and was very cozy. Loved all the antiques! Cynthia was very responsive to messages and check in/check out was super easy. We really hope to stay again!"

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

10/10 Excellent

"We had a wonderful stay! The place was extremely cute, clean (other than some to be expected spider webs here and there). Beds were comfy, porch and firepit were relaxing spaces to hang out. Some new skillets that lay flat on the stove top and a spatula/pancake flipper would be nice. Other than that we had everything we needed. Thanks again for a wonderful getaway!"

Red Roof Inn Monteagle - I-24

10/10 Excellent

"We ended up at the Red Roof Inn when Hurricane Isaias and a leaky tent made camping impossible. The host family answered our call at 4 AM and gave us a warm, dry room for which we were very grateful. We ended up staying the next two nights as well and we found the location to be convenient to The Caverns music venue (about 20 minutes of rural driving). The room was well-equipped with a microwave and refrigerator, the shower was hot with good water pressure, and the beds were comfy. Hard floors rather than carpet were helpful since everything we had was dripping wet. Parking was very convenient and the staff were helpful and friendly. A flyer in the lobby led us to The Lodge museum of cast iron just down the road in South Pittsburgh - a fun treat we would not have known of otherwise. Thanks for saving our vacation, Red Roof!"

Secluded, amazing artesian home in beautiful Coppingers Cove - outdoor paradise

8/10 Good

"Clean, very private, spacious but close to town for groceries, etc and a short drive to Chattanooga. Really enjoyed our 3 night stay. Very reasonable price. Outdoor grill was pretty old, dirty and couldn’t find a grill brush. Would b nice to have a gas grill. Owner provided a straight forward heads up for the possibility of a few insect guests that might show up!Overall a great place and would def return."

Magnolia Veil With view of the Lake

10/10 Excellent

"The home was lovely. Tucked back in a wooded neighborhood which wraps around the lake. Not a peep was heard except the occasional acorn on the roof or an insect in the surrounding woods. The lake is but a brief walk across the road, and the community fire pit, charming, was located in the cul-de-sac just past the house. Community common areas provided places to gather and relax outdoors. The screened in porch was an evening retreat, but the deck was beyond enough space to sit outside- grill and dine. Private, clean, classic exterior with a cozy interior. If you’re planning meals, pack your spices and any special equipment needed so you are fully prepared to present that memorable meal on the beautiful Sur la table dishes. Initial supplies are there and were good for about a two day stay. Bring more if you are there for more days or have more than two people. Full size washer dryer available. Beds! Well appointed, beautifully made (great job, Jason) quality linens and pillows. Zzzzzz!!! Layout: You enter through the screened in porch, next is the living area with kitchen just beyond. Large primary bedroom on the left of kitchen with king bed. Stairs to loft next to primary entrance in kitchen area. Two beds in loft that kids are going to love. Washer/dryer under the stairs on the left just before the bathroom. Across from washer/dryer on the right side is the second bedroom with single bed. Go, enjoy the retreat from life and create those special memories!"

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Sherwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $162 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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Check prices for these dates

Our top choices for Sherwood vacation rentals

1. Sasquatch Farm

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

3. Cozy Cottage in Monteagle!

4. The Woods at The Retreat at Deer Lick Falls

5. Story-time Stay at Our Rupert Cottage!

6. The Calming Cabin — Relaxing Getaway, Park-Like Setting, and Area Waterfalls

7. Winchester's Premier Downtown Loft!

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

9. Shea's Chalet - Cozy home in Monteagle, TN

10. Martin Springs Cabin.

11. Cabin with Fishing Pond and Gorgeous Bluff Views!

12. Tiny Home w/ RV Hookups

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

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

15. Forest Retreat: Poolside Bliss Close to Campus

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

17. Newly Remodled Suite in Monteagle TN!

18. Tiny Haven at the Retreat

19. Oasis on the Square

20. A very rustic converted pole barn unique cozy cabin

Find vacation rentals that suit your style

Top Sherwood Hotel Reviews

Best Western Inn

Quality Inn Monteagle

The Smokehouse Lodge and Cabins

Clarion Pointe Kimball By Choice Hotels

Moonshine Runners Cabin

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

Red Roof Inn Monteagle - I-24

Secluded, amazing artesian home in beautiful Coppingers Cove - outdoor paradise

Magnolia Veil With view of the Lake

Find out more about Sherwood

Frequently asked questions

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