Winchester Hotels

    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

Check Winchester hotel prices

Tomorrow night
This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Winchester hotels

The Smokehouse Lodge and Cabins
3.0 star property
8.4 out of 10, Very good, (1017)
"We had a lovely, quintessential Tennessee stay here. Being from the UK, we absolutely loved it. The staff were great, the place is a great price and we had a great time at the restaurant with live music. Awesome stay!"
The price is €56
includes taxes & fees
25 Nov - 26 Nov
The Smokehouse Lodge and Cabins
The Sewanee Inn
4.0 star property
9.8 out of 10, Exceptional, (322)
"Loved it!"
The price is €183
includes taxes & fees
22 Dec - 23 Dec
The Sewanee Inn
Quality Inn
2.5 star property
8.8 out of 10, Excellent, (632)
"Elevator broke "
The price is €71
includes taxes & fees
15 Dec - 16 Dec
Quality Inn
Red Roof Inn Monteagle - I-24
2.0 star property
7.0 out of 10, Good, (526)
"It was altogether a nice experience. It's conveniently located by I-24."
The price is €76
includes taxes & fees
27 Nov - 28 Nov
Red Roof Inn Monteagle - I-24
Best Western Inn
2.5 star property
8.8 out of 10, Excellent, (571)
" Very friendly staff! Easy check in. Very clean rooms."
The price is €100
includes taxes & fees
8 Dec - 9 Dec
Best Western Inn
Quality Inn Decherd / Winchester
2.5 star property
7.0 out of 10, Good, (245)
"Friendly staff, comfy bed"
The price is €75
includes taxes & fees
15 Dec - 16 Dec
Quality Inn Decherd / Winchester
Snuggle Up in our Teddy Cottage! *New Listing*
10.0 out of 10, Exceptional, (3)
"Clean , place has some wear on it but overall clean and no problem with my deposit getting returned . I’ve heard friends have issues with other non Vrbo getting charged for damages they did not do . I will stay with VRBO!!"
The price is €168
includes taxes & fees
24 Nov - 25 Nov
Snuggle Up in our Teddy Cottage! *New Listing*
Luxe Nest at The Retreat at Sunset Bluff
10.0 out of 10, Exceptional, (10)
"This tiny home was gorgeous. The bed was luxurious and we loved the tiny kitchen. The side porch was great for reading and eating. I’d recommend for couples or for a girls trip. "
The price is €353
includes taxes & fees
26 Nov - 27 Nov
Luxe Nest at The Retreat at Sunset Bluff
Cozy Tiny House Cabin @ Trailhead Cabins. South Cumberland Plateau
10.0 out of 10, Exceptional, (21)
"We wanted to enjoy the fall beauty and take in a few hiked. Great spot to rest your head. "
The price is €181
includes taxes & fees
2 Dec - 3 Dec
Cozy Tiny House Cabin @ Trailhead Cabins. South Cumberland Plateau
Mountain Memories to provide a cozy retreat on your vacation!
10.0 out of 10, Exceptional, (11)
"This is the perfect place to spend a few days on the cumberland plateau for hiking and enjoying nature. The well kept place is located in a quiet neighborhood, clean and has a large kitchen/comon area as well as a fenced backyard with bbq, etc. Access to washer and dryer is a plus for families. Communication with the host was easy and fast. Highly recommended!"
The price is €205
includes taxes & fees
25 Nov - 26 Nov
Mountain Memories to provide a cozy retreat on your vacation!
Eagle's Escape at The Retreat at Sunset Bluff
10.0 out of 10, Exceptional, (3)
"Very clean, but it is brand new. Love the community, great spot for chilling."
The price is €256
includes taxes & fees
2 Dec - 3 Dec
Eagle's Escape at The Retreat at Sunset Bluff
Secluded Scandinavian Style Cabin/20 private acres/ View/Hot Tub/Game Room
9.8 out of 10, Exceptional, (41)
"This was an amazing little getaway!!!"
Secluded Scandinavian Style Cabin/20 private acres/ View/Hot Tub/Game Room
Newly Remodled Suite in Monteagle TN!
10.0 out of 10, Exceptional, (1)
"Very cozy and clean. Bed and couch were both very comfortable. Kitchen was also an added bonus. Nice rocking chairs and table outside of the room to enjoy nature and fresh mountain air. Will definitely come back again. Host were very awesome also ."
The price is €151
includes taxes & fees
24 Nov - 25 Nov
Newly Remodled Suite in Monteagle TN!
Mountain Point of View Cottage
9.8 out of 10, Exceptional, (13)
"We just loved our stay in the Mountain point of view cottage, the access and location are just beautiful. Everything we need has been provided for us. Nice and spacious for dinner guests and cooking. Fantasic job on fall decorations. We will be booking this place again next year. "
The price is €194
includes taxes & fees
22 Nov - 23 Nov
Mountain Point of View Cottage
Dove Treehouse Getaway w/ Hot Tub & Firepit!
10.0 out of 10, Exceptional, (271)
"The Dove more than met our expectations! It was well appointed and cozy. It had everything we needed for a weekend visiting our daughter at Sewanee. "
The price is €286
includes taxes & fees
2 Dec - 3 Dec
Dove Treehouse Getaway w/ Hot Tub & Firepit!
Cozy cabin in the mountains with hiking trails and gorgeous waterfalls close by!
The price is €122
includes taxes & fees
24 Nov - 25 Nov
Cozy cabin in the mountains with hiking trails and gorgeous waterfalls close by!
Shea's Chalet - Cozy home in Monteagle, TN
2.0 star property
10.0 out of 10, Exceptional, (3)
"My friends and I stayed here over the weekend for a girls hiking trip. Was a little hard to find house at first as it is behind another house. Super clean, plenty of room and the beds were comfortable. Good water pressure in front bath. Excellent check out process- thanks for not requiring us to strip beds and clean dishes, etc. "
The price is €299
includes taxes & fees
22 Nov - 23 Nov
Shea's Chalet - Cozy home in Monteagle, TN
Hidden forest campground in South Pittsburg
1.0 star property
Hidden forest campground in South Pittsburg
Hickory Creek Cottage: Monteagle @Trailhead Cabins
9.6 out of 10, Exceptional, (58)
"Cute and cozy little cottage. It was nice to have access to the Mountain Goat Trail from behind the cabin. "
The price is €158
includes taxes & fees
24 Nov - 25 Nov
Hickory Creek Cottage: Monteagle @Trailhead Cabins
Cabin with Fishing Pond and Gorgeous Bluff Views!
9.8 out of 10, Exceptional, (9)
"What a fantastic getaway! This charming cabin nestled in the woods was the perfect escape for our family. The stunning mountain view was a highlight, and our dogs absolutely loved exploring the wooded surroundings. The cabin was well-equipped and made us feel right at home. We can’t wait to return for another peaceful retreat! Highly recommend for anyone seeking relaxation and nature!"
The price is €433
includes taxes & fees
22 Nov - 23 Nov
Cabin with Fishing Pond and Gorgeous Bluff Views!
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Where is the best place for a stay in Winchester?

Best Western Inn is a favourite property for Expedia customers. This hotel offers free breakfast and an outdoor pool. See all available top hotels, or vacation rentals in Winchester.

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

Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc: This highly rated holiday home rental in Winchester is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with an arcade/games room and 1 hot tub. Some other homes for rent in Winchester include Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK and Awesome Home close to the Lake.. See all vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What's the best place to stay on a budget in Winchester?

Based on reviews, Best Western Inn is a popular 2.5-star hotel for our travellers looking for an economical choice, and features free full breakfast and free WiFi. View all budget hotels in Winchester.

What's the best accommodation option when travelling with children to Winchester?

Best Western Inn is a hotel with an outdoor pool and free parking, and it's a top choice on Expedia for families. Also, children of all ages will enjoy a visit to Tim's Ford Marina.

What's the best hotel for a romantic holiday to Winchester?

Best Western Inn is a favourite hotel for couples, and features deep-soaking baths and LCD TVs.

What's the best dog-friendly accommodation option in Winchester?

Best Western Inn is a top hotel for people travelling with their pets, and offers an outdoor pool and free wired Internet for its human guests. Spectacular views and location on Tim's Ford Lake! is another good option if you're bringing your pet along. See more pet-friendly hotel accommodations in Winchester.

What are some hotels with pools in Winchester?

Best Western Inn is a top hotel with a seasonal outdoor pool, free full breakfast and free Internet. View all hotels with pools in Winchester.

What's it like staying in Winchester?

Visitors can enjoy all that Winchester has to offer, including the theme park, lake views and university setting. Tourists can also enjoy the city's coffee shops and shopping. In Winchester, there are 163 hotels and other accommodation options to choose from. Find out more about Winchester.

What are the top places to visit in Winchester?

Families come for attractions such as Tim's Ford Marina, Hammers and Expressions. Natural beauty is on display at Tims Ford State Park, Tims Ford and Tims Ford Lake. A couple of additional sights to add to your itinerary are Twin Creeks Marina and Elk River. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Winchester is 1622 mm.