Sherwood Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Sherwood

our very rusticbarn converted-unique cozy cabin
9.8 out of 10, Exceptional, 108 reviews
"My wife and I really loved this spacious rustic cabin. Filled with lots of toys and appliances from bygone eras. You could stay there for days and still not see all of the unique little pieces that they’ve decorated with. Nearby market provides most of the necessities that you may need or you can travel to nearby Lynchburg, Tullahoma, or Winchester for restaurants. We found a beautiful, hiking trail just 30 minutes away with a waterfall we were able to walk and splash in To the Jack Daniels...
The price is AU$243
per night
20 June - 21 June
our very rusticbarn converted-unique cozy cabin
Luxurious Waterfront Oasis on Tims Ford Lake!
10.0 out of 10, Exceptional, 39 reviews
"The house was beautifully decorated, extremely clean and very comfortable. Linda, our host, was amazing! She was quick to respond the two times I had questions and added special touches to our stay. Sitting outside in the evening, right next to the lake was so peaceful and relaxing. Downtown Winchester is just up the street. I highly recommend this property and hope to go back."
Luxurious Waterfront Oasis on Tims Ford Lake!
Hickory Creek Cottage: Monteagle @Trailhead Cabins
9.8 out of 10, Exceptional, 44 reviews
"Excellent 👌👍"
The price is AU$246
per night
25 June - 26 June
Hickory Creek Cottage: Monteagle @Trailhead Cabins
Save an average of 15% on thousands of hotels when you're signed in
Calming Cabin: Relaxing | Peaceful Getaway | Close to Area Activities
10.0 out of 10, Exceptional, 48 reviews
"The cabin is conveniently located close to town and activities but is also in a quiet and private setting. The amenities include most everything you need for a cozy and relaxing getaway. The cabin is clean and convenient inside and out. It is truly a perfect place to relax and reset. The hosts were excellent with communication and made sure we had a great stay. We highly recommend and plan to come back to visit!"
The price is AU$346
per night
19 June - 20 June
Calming Cabin: Relaxing | Peaceful Getaway | Close to Area Activities
The Sewanee House: Serene Oasis 5 minutes from Campus
10.0 out of 10, Exceptional, 21 reviews
"10 of us headed to unknown terrirtory--stayed in Sewanee to attend a concert (Irish band "Altan") at The Caverns. We wanted a place we could all be together (ha, we travel in a herd) and wanted a place where we would not disturb anyone as we love our music, competitive games (ha). This place was PERFECT! Extra clean, plenty of room, clear on what we needed to do on arrival/departure. Kathryn, property manager, was an awesome communicator, and appreciated her efforts in finding places to eat--we...
The Sewanee House: Serene Oasis 5 minutes from Campus
Lakefront Home, With Hot Tub and Boat deck! Backyard is On the water!
10.0 out of 10, Exceptional, 24 reviews
"House was very warm and inviting. Very well appointed. Yard was well maintained and had plenty of space. Enjoyed the boat deck for fishing. Neighborhood was a little bit tight towing a 27’ boat"
Lakefront Home, With Hot Tub and Boat deck! Backyard is On the water!
Family friendly lake front home with private dock in a cove
9.8 out of 10, Exceptional, 17 reviews
"We had a short family vacation before my husband started chemo treatments. We had the best time! My brother in law brought his pontoon boat and having the dock at the house made it so convenient. We had plenty of room and enjoyed grilling and eating on the deck! The owner was great to respond to any needs that we had!"
Family friendly lake front home with private dock in a cove
Million Dollar Views: Lakefront, Dock, Kayaks+More
10.0 out of 10, Exceptional, 32 reviews
"Great property with a great location on the lake. Communication with the property managers was great. Would stay again."
The price is AU$1,242
per night
20 June - 21 June
Million Dollar Views: Lakefront, Dock, Kayaks+More
Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!
10.0 out of 10, Exceptional, 33 reviews
"Cute house! Perfect for 3 and wonderful location! Needs a good deep cleaning to clear spider webs, dust and scuff marks throughout. But those are very minor. Would definitely recommend and hope to rent it again!"
The price is AU$399
per night
19 June - 20 June
Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
10.0 out of 10, Exceptional, 17 reviews
"Tara's house was exactly as advertised. We all enjoyed a relaxing weekend away from the busy lives we have and plan on doing it again next year!"
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
Private Multi Family Retreat on 5 Acres!
10.0 out of 10, Exceptional, 3 reviews
"I wasn’t sure exactly what to expect. The online description is accurate but it does not describe how staying there makes you feel. Yes it is spacious, has a well equipped kitchen, a sauna, hot tub, plunge pool and is clean; but the thoughtful details given to create each space impart multiple surprise moments of joy and comfort. I will never forget the awe of waking up in the mornings, surrounded by lush green trees. A luxurious treehouse!"
The price is AU$1,434
per night
19 June - 20 June
Private Multi Family Retreat on 5 Acres!
Cozy Tiny House Cabin @ Trailhead Cabins. South Cumberland Plateau
9.8 out of 10, Exceptional, 18 reviews
"The cabin was very affordable and convenient for going to the Caverns for a concert. It was also convenient to the park and several hiking trails."
The price is AU$282
per night
25 June - 26 June
Cozy Tiny House Cabin @ Trailhead Cabins. South Cumberland Plateau
Hillside Haven at The Retreat at Water's Edge
10.0 out of 10, Exceptional, 12 reviews
"Hillside Haven was just what our souls needed: nature, comfort, relaxation and a quiet getaway. The property was just as pictured and described. I would absolutely vacation here again, and recommend it to friends and family."
The price is AU$536
per night
20 June - 21 June
Hillside Haven at The Retreat at Water's Edge
The Yellow Cottage by Tims Ford Lake
9.4 out of 10, Exceptional, 12 reviews
"It was just what we needed for a one night stop, as we traveled through the area. Very charming."
The price is AU$423
per night
26 June - 27 June
The Yellow Cottage by Tims Ford Lake
3 bedroom 1 bath vacation home, sleeps 6 people.
10.0 out of 10, Exceptional, 146 reviews
"Relaxing comfortable and peaceful"
The price is AU$489
per night
16 June - 17 June
3 bedroom 1 bath vacation home, sleeps 6 people.
Spacious Lakefront Retreat w/ Hot Tub + Dock!
10.0 out of 10, Exceptional, 10 reviews
"Super nice. Everything was great"
Spacious Lakefront Retreat w/ Hot Tub + Dock!
Cozy basecamp minutes from waterfalls, hiking and climbing
10.0 out of 10, Exceptional, 4 reviews
"Very wonderful!"
The price is AU$312
per night
1 July - 2 July
Cozy basecamp minutes from waterfalls, hiking and climbing
Eagle's Nest · NO SUNDAY CHECKIN hot tub-great view EAGLE'S NEST- Grant Summit Cabins
10.0 out of 10, Exceptional, 222 reviews
"What an amazing view. The pictures don’t do it justice. The cabin is beautiful! Would definitely go back."
Eagle's Nest · NO SUNDAY CHECKIN hot tub-great view EAGLE'S NEST- Grant Summit Cabins
Luxe Nest at The Retreat at Sunset Bluff
10.0 out of 10, Exceptional, 5 reviews
"We can’t say enough about our stay! It had all the comforts of home and was located near so many great places to hike. The house was so new and clean and the property manager was very responsive and friendly. We’ll definitely be back!"
The price is AU$565
per night
16 June - 17 June
Luxe Nest at The Retreat at Sunset Bluff
Exquisite Tranquil Lake View Prime Location, Community Dock, private boat slip
10.0 out of 10, Exceptional, 18 reviews
"I can't espouse enough about how great this stay was! The property was fantastic, very clean and laid out great for 2 families with young ones. (The little side bedroom off the 2 masters were the selling point!) We had the boat in the water all weekend, super short drive to the winchester boat ramp and local marina. We fished off the dock and the kids had a blast catching bluegills. Will be staying again!"
Exquisite Tranquil Lake View Prime Location, Community Dock, private boat slip
Don't see what you're looking for?
See all available properties in Sherwood
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.

Other types of properties in Sherwood you may be interested in

The Smokehouse Lodge and Cabins
3.0 star property
8.2 out of 10, Very good, 1,005 reviews
"We stayed for 2 nights and we had a very comfortable stay. The restaurant behind the motel also had delicious food."
The price is AU$87
per night
15 July - 16 July
The Smokehouse Lodge and Cabins
Quality Inn
2.5 star property
8.8 out of 10, Excellent, 575 reviews
"Friendly staff, clean comfortable room"
The price is AU$160
per night
14 July - 15 July
Quality Inn
Quality Inn & Suites
2.5 star property
8.0 out of 10, Very good, 398 reviews
"Great area for quick travel rest/sleep. Easily accessible. Restaurants within walking distance."
The price is AU$115
per night
1 July - 2 July
Quality Inn & Suites
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.

Everything you need to know about Sherwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sherwood holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sherwood holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sherwood holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherwood holiday rentals we have selected for you start as low as AU$243 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sherwood rentals

At Expedia, we put the best Sherwood holiday 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 holiday.

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 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?

Luxurious Waterfront Oasis on Tims Ford Lake!: This holiday home rental outside of Sherwood is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Sherwood?

While exploring the area, visit family-friendly sights like Cowan Railroad Museum, or get outside and enjoy nature at Walls of Jericho Hiking Trailhead. 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.

Recent reviews of Sherwood properties
Expedia verified reviews