Default HTG hotel image

Sherwood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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

Sasquatch Farm
3.0 star property
South Pittsburg
9.0 out of 10, Wonderful, (9 reviews)
"Omgoodness this place is absolutely amazing!!! We went for a spiritual journey and it was perfect!! The lake & water fall creek with seats sitting in the water was perfect for my reading and meditating. It is absolutely beautiful!!! They had a concert Saturday night, we didn't go to the actual concert but was right beside it and they were fabulous!! Great place to stay! We will definitely return. Thank you so much for everything!"
United States
Tina
The price is CA $192
CA $221 total
includes taxes & fees
Oct 4 - Oct 5
Sasquatch Farm
A log cabin with a deck, large windows, and a table with chairs.

2. Story-time Stay at Our Rupert Cottage!

Story-time Stay at Our Rupert Cottage!
Monteagle
8.8 out of 10, Excellent, (6 reviews)
"Pet friendly, host communication was excellent. The cottage was tidy and clean. "
United States
Taroub F.
The price is CA $114
CA $330 total
includes taxes & fees
Oct 4 - Oct 5
Story-time Stay at Our Rupert Cottage!
Living area

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

Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
Sewanee
9.8 out of 10, Exceptional, (27 reviews)
"A great deal and a great location- nice and secluded and close to the caverns where we did a couple shows while visiting. Comfortable spot and wonderful hosts. "
United States
Ryan B.
The price is CA $127
CA $327 total
includes taxes & fees
Oct 11 - Oct 12
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
A building with a sign reading 'THE LEMON FAIR' and a yellow door.

4. The Woods at The Retreat at Deer Lick Falls

The Woods at The Retreat at Deer Lick Falls
Monteagle
9.8 out of 10, Exceptional, (41 reviews)
"Fit the needs for a golf trip away from home. Very charming community in the woods. Place was clean with no issues. Nice loft if you have kids. Would recommend!"
United States
John S.
The price is CA $120
CA $437 total
includes taxes & fees
Oct 5 - Oct 6
The Woods at The Retreat at Deer Lick Falls
A concrete planter with various succulents and cacti.

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

The Loft - Lounge with Grill and Hot Tub!
South Pittsburg
10.0 out of 10, Exceptional, (14 reviews)
"Clean and quiet. Everything we needed for a quiet little getaway was provided."
United States
TJ S.
The price is CA $145
CA $415 total
includes taxes & fees
Oct 7 - Oct 8
The Loft - Lounge with Grill and Hot Tub!
A compact kitchen with wooden cabinets, a microwave, stove, and a dining area with a table and chairs.

6. Cozy Cottage in Monteagle!

Cozy Cottage in Monteagle!
Monteagle
9.0 out of 10, Wonderful, (2 reviews)
"Very nice cabin. It was convenient to our activities and had everything that we needed."
United States
Rebecca
The price is CA $114
CA $308 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Cottage in Monteagle!
A wooden deck with outdoor seating and a covered area with large windows.

7. Newly Remodled Suite in Monteagle TN!

Newly Remodled Suite in Monteagle TN!
Monteagle
9.4 out of 10, Exceptional, (13 reviews)
"Everything about this place was wonderful!"
United States
Mary Dabney G.
The price is CA $99
CA $277 total
includes taxes & fees
Oct 5 - Oct 6
Newly Remodled Suite in Monteagle TN!
A spacious living room with a brown leather sofa, a dining table, and a kitchen area.

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

Eagle’s Escape to Sunset Bluff - With OHV Trailer Parking Space
Monteagle
9.4 out of 10, Exceptional, (10 reviews)
"Perfect little cottage with all the necessities. Backyard firepit was great!"
United States
Scott
The price is CA $93
CA $272 total
includes taxes & fees
Oct 4 - Oct 5
Eagle’s Escape to Sunset Bluff - With OHV Trailer Parking Space
A cozy room with a fireplace, a dining area, and a kitchen.

9. The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.8 out of 10, Exceptional, (32 reviews)
"Great place, clean and quiet!!"
United States
Jose
The price is CA $80
CA $258 total
includes taxes & fees
Oct 5 - Oct 6
The Cabin in Tracy City
A rustic cabin with a green metal roof, wooden porch, and a small garden with pink flowers.

10. The Calming Cabin — Indulge in Peace, Relaxation and Area Excursions

The Calming Cabin — Indulge in Peace, Relaxation and Area Excursions
Tracy City
10.0 out of 10, Exceptional, (66 reviews)
"We loved our stay!"
United States
Marc N.
The price is CA $157
CA $338 total
includes taxes & fees
Oct 20 - Oct 21
The Calming Cabin — Indulge in Peace, Relaxation and Area Excursions
A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

11. Tiny Haven at the Retreat

Tiny Haven at the Retreat
Monteagle
9.4 out of 10, Exceptional, (21 reviews)
"Tiny Haven was exactly as it was described and was a perfect spot for my family to relax after long days hiking and swimming. The beds are super comfortable and we had everything we needed to make the stay perfect. We enjoyed all the deer that stopped through to check us out. We would definitely stay here again if in the area. Highly recommend!"
United States
Kathleen
The price is CA $93
CA $274 total
includes taxes & fees
Oct 7 - Oct 8
Tiny Haven at the Retreat
A hallway with a wooden floor, a welcome sign, a mirror, and a potted plant.

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

Mountain Memories to provide a cozy retreat on your vacation!
Monteagle
9.4 out of 10, Exceptional, (52 reviews)
"Good host and property."
United States
David C.
The price is CA $115
CA $296 total
includes taxes & fees
Oct 5 - Oct 6
Mountain Memories to provide a cozy retreat on your vacation!
A rustic log cabin with a wooden deck and a covered porch.

13. Martin Springs Cabin.

Martin Springs Cabin.
South Pittsburg
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay will definitely stay here again !!!!! "
United States
Alan D.
The price is CA $177
CA $375 total
includes taxes & fees
Oct 5 - Oct 6
Martin Springs Cabin.
A cozy interior with a wooden ceiling, a kitchen area, a leather sofa, and a staircase leading to an upper level.

14. Deciduous Dreams in Deer Lick Falls

Deciduous Dreams in Deer Lick Falls
Monteagle
9.2 out of 10, Wonderful, (19 reviews)
"Very nice"
United States
Joseph
The price is CA $93
CA $274 total
includes taxes & fees
Oct 5 - Oct 6
Deciduous Dreams in Deer Lick Falls
A bedroom with a bed, ceiling fan, large windows, and a view of the outdoors.

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

Snuggle Up in our Teddy Cottage! *New Listing*
Monteagle
10.0 out of 10, Exceptional, (8 reviews)
"I really enjoyed my stay here with my girlfriend and our two dogs. The cottage & surrounding area is super cute and cozy. There is also a nice walking trail right outside the entrance of the lodging area that we got to use. This is for sure a place I would stay at again!"
United States
Samantha B.
The price is CA $107
CA $302 total
includes taxes & fees
Oct 6 - Oct 7
Snuggle Up in our Teddy Cottage! *New Listing*
A stone building with a traditional architectural style, featuring a central entrance and multiple windows.

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

Shea's Chalet - Cozy home in Monteagle, TN
Downtown Monteagle
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay"
United States
Keith J.
The price is CA $85
CA $388 total
includes taxes & fees
Oct 4 - Oct 5
Shea's Chalet - Cozy home in Monteagle, TN
A kitchen with copper cookware hanging on the wall, a framed picture, and a variety of fresh vegetables on the counter.

17. Sleepy Hollow at The Retreat at Sunset Bluff

Sleepy Hollow at The Retreat at Sunset Bluff
Monteagle
9.6 out of 10, Exceptional, (18 reviews)
"Had a great time at this beautiful tiny home. Thanks!"
United States
Spencer D.
The price is CA $158
CA $554 total
includes taxes & fees
Oct 4 - Oct 5
Sleepy Hollow at The Retreat at Sunset Bluff
A cabin with a large glass front, surrounded by a gravel path and rock border, set in a forested area with string lights.

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

Sewanee•Caverns•Waterfalls•Hikes • Basecamp Tiny
Monteagle
10.0 out of 10, Exceptional, (87 reviews)
"We enjoyed our stay at Tiny Mojo. It was conveniently located to the Caverns, Sewanee, and lots of hiking. The host was very helpful and the house was very clean and comfortable."
United States
Kelley P.
The price is CA $141
CA $289 total
includes taxes & fees
Oct 7 - Oct 8
Sewanee•Caverns•Waterfalls•Hikes • Basecamp Tiny
A hallway with wooden doors labeled 'The Cove' and 'The Overlook,' leading to a room with a view.

19. Boutique Suite in Historic Tracy City!

Boutique Suite in Historic Tracy City!
Tracy City
10.0 out of 10, Exceptional, (5 reviews)
"Great stay, host was very accommodating. Would stay again! Clean accommodations, great location, and very comfortable."
United States
Eric S.
The price is CA $85
CA $198 total
includes taxes & fees
Oct 6 - Oct 7
Boutique Suite in Historic Tracy City!
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

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

Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Pelham
9.6 out of 10, Exceptional, (39 reviews)
"House is kept in great condition, beautiful location, and perfect stay when attending the caverns (12 minutes away)"
United States
Antonio M.
The price is CA $100
CA $373 total
includes taxes & fees
Oct 4 - Oct 5
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sherwood Hotel Reviews

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

10/10 Excellent
"Amazing little gem! This place was great and the staff was so kind. Will definitely be back!"
Michael 1-night trip
Posted 2 hours ago
The Smokehouse Lodge and Cabins

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 $221 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.