Sherwood Holiday Rentals from NZ$273: Search Short-Term Rentals

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Our top choices for Sherwood holiday 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

includes taxes & fees

15 Nov - 16 Nov

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

Sewanee

Ryan B.

includes taxes & fees

22 Oct - 23 Oct

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

includes taxes & fees

22 Oct - 23 Oct

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.

includes taxes & fees

3 Nov - 4 Nov

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

5. Story-time Stay at Our Rupert Cottage!

Monteagle

Taroub F.

includes taxes & fees

22 Oct - 23 Oct

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.

includes taxes & fees

11 Nov - 12 Nov

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

7. Winchester's Premier Downtown Loft!

Winchester

Gianmarco

includes taxes & fees

25 Oct - 26 Oct

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.

includes taxes & fees

26 Oct - 27 Oct

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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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sherwood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sherwood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Sherwood. Seeing all the best attractions is bound to make you fall in love with Sherwood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Sherwood short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Sherwood?

Yes, there are holiday rentals close to the most popular sights in Sherwood, or you can select a more secluded option if you're looking for a relaxing stay.

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

Secluded, amazing artesian home in beautiful Coppingers Cove - outdoor paradise : This holiday home rental outside of Sherwood is located on a river, and has a balcony, a garden and a BBQ 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 wider area, you’ll find University of the South and Sewanee Golf and Tennis Club.

What are holiday rentals like in Sherwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sherwood. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for small groups.

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Check prices for these dates

Our top choices for Sherwood holiday 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 holiday 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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