Vacation rentals in Winchester

4.93 out of 5 average rating, 167 reviews

Cabin in Monteagle

Monteagle Mountain Serenity Nashville Chattanooga

"FAMILY CABIN" WITH VIEWS EVENTS OR LOUD PARTIES ARE NOT ALLOWED. NEAR MUSIC CITY USA AND CHATTANOOGA MILES HIKING TRAILS AND NINE NEARBY WATERFALLS After a day of exploring relax on the OVER SIZED Deck PANORAMIC MOUNTAIN VISTA'S GAS FIRE PLACE , FIRE PIT & GRILL FULLY STOCKED KITCHEN KING SUITE w/CUSTOM SHOWER QUEEN BEDROOM & 3 bed BUNK ROOM ADDITIONAL FULL CUSTOM BATH 4 TV's INTERNET & cable All the beauty of The SMOKEY'S without the crowds.

5 out of 5 average rating, 91 reviews

Home in Tullahoma

Lakeside Retreat at The Reserve w/ Golf Cart

Beautiful lakeside home on Tim's Ford Lake! Short Walk or Golf Cart ride to Blue Gill Grill & Holiday Landing Marina. Boat Parking on the Driveway during your stay! First Floor: Master Bed with Full Bath, Dining Room, Living Room, Kitchen (Fully stocked with basic spices and cooking utensils). Outside Patio with Fire Place and seating. Second Floor: BR 2- King Bed. BR 3 Queen Bed, Loft Space, Sectional Couch, Pull out Queen. *No Smoking *Max 10 Guest *Front Door Security Cam*

4.9 out of 5 average rating, 101 reviews

Tiny home in Monteagle

Sweet Dee's Tiny Home

FEATURES A HOT TUB! Relax in style at Sweet Dee's (formerly listed as The Alexander), a luxury tiny home in the Retreat at Deer Lick Falls. Serene, tranquil, rustic, wooded setting with relaxation stations throughout the community. The Retreat at Deer Lick Falls is a gated luxury tiny home community in southeast Tennessee. The community is only 15 minutes from the University of the South in Sewanee. Guests of the Retreat also have access to Retreat at Waters Edge and it's lake.

4.81 out of 5 average rating, 16 reviews

Tiny home in Tracy City

Pushin' Time Hideaway at The Retreat at Water's Ed

Please reach out prior to bringing your pet. A fee of $100 + tax will be applied to your reservation if approved. Experience superior comfort and charm at Pushin' Time Hideaway, a spacious two-bedroom, two-bathroom home with a loft. Special exterior features include two decks with a fireplace and lake views, outdoor seating and dining, plus a private firepit area in the back yard. The interior offers two king-sized beds in the downstairs bedrooms plus a queen in the l

5 out of 5 average rating, 20 reviews

Home in Winchester

The Modern Mainstay at Barefoot Bay

Welcome to The Modern Mainstay, your stylish retreat by the shores of Tims Ford Lake! This pet friendly contemporary home is just 1/2 mile from the historic downtown square where you can enjoy doing a bit of shopping or dining. Or sit on the front porch with lake views, and take in the serene surroundings. Take a dip in our lakefront community pool. Enjoy access to the lakefront common area for fishing, swimming in the lake, and relaxing by the fire pit with a glass of wine.

4.82 out of 5 average rating, 157 reviews

Cabin in Winchester

VACATION CABIN - Sunday Morning Rentals

We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

4.86 out of 5 average rating, 14 reviews

Home in Winchester

TC Easy Breeezee

Your home away from home a place to enjoy friends and family together under one roof, relax and enjoy, kick back and forget all your worries! We have you covered, awning for protection of sun and rain! Warm cozy beds and sofas! New furnishing throughout entire house!! Sip coffee, on our cozy outdoor furniture while listening to the pool bubblers take all your daily worries away!! Unplug, sit back and find your happy place Close to shopping, marina, dining and much more

5 out of 5 average rating, 9 reviews

Tiny home in Monteagle

Twin Pines - Large Porch w/ Fireplace, Hot Tub

NEW! Come relax & unwind at this beautiful property. Each space has been thoughtfully designed for your comfort with luxurious styling. Enjoy an open layout w/ vaulted ceilings, rustic - but modern - features, a large screened in porch as part of a 1000 sqft deck, and multiple outdoor amenities - hot tub, fireplace, secluded fire pit, and grill. Designer furniture styling throughout - no stone has been left unturned with the setup of this property.

4.67 out of 5 average rating, 3 reviews

Tiny home in Tracy City

Quaint lakeside escape w/hot tub & fire pit/5 beds

The Fallen Acorn + Casita is an adorable little retreat that boasts a breathtaking view of the lake! Relax in the hot tub on the deck, where you can gaze out at the lake or admire the starry sky above! Nestled right by the water, this enchanting gem provides a serene atmosphere with stunning vistas and convenient access to a public dock located just two houses away. Unwind, recharge, and let the beautiful surroundings envelop you.

4.6 out of 5 average rating, 5 reviews

Home in Winchester

The Mimosa @ Twin Creeks Resort w/ FREE BOAT*

*FREE BOAT - Any 2 or more nights booked and staying through May 31st, 2025 qualifies for one full day complimentary pontoon rental of your choosing, subject to terms & availability! This stylish place to stay is perfect for group trips, family reunions, or family vacations. With plenty of bedrooms, everyone will have plenty of space during their stay as well as large family rooms to get together for activities and fun!

4.91 out of 5 average rating, 206 reviews

Cabin in Bryant

Big Time Hill Cabin with an indoor pool, hot tub,

SUNDAY check in ALLOWED. BIG TIME HILL CABIN is located inside Paradise Pointe is gated & on a mountain at tristate corner of AL/TN/GA. Walk our HIKING TRAIL to tristate corner & be in 3 states at once. Paradise Pointe has 1 HuGe INDOOR POOL HOUSE with outdoor deck. 19 rentals has access to pool house. Cabin has hot tub, WIFI, fireplace, charcoal grill & fire pit!

4.96 out of 5 average rating, 193 reviews

Cabin in Dunlap

Spectacular Mountain Top Cabin Getaway

Overlooking four mountain ranges, with a private lake,this executive cabin offers serenity and privacy like none other. If you enjoy cooking, friends and family...this is the place! Enjoy a huge deck with a hot tub and outdoor fireplace. Inside and outside dining with spectacular sunrise and sunsets. Fifteen minutes from Dunlap and an hour from Chattanooga Tn

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What guests are saying

"Dock Holiday" Retreat on Tim's Ford Lake.

4.98 out of 5 average rating, 51 reviews4 days ago

We loved the house and will definitely be back. Lots of room in the house for catching up with friends. The golf cart was down for battery issues during our stay but Kyle was upfront about that the day I booked so we appreciated the notice he gave. Even without that, the home was great and well worth the stay.

Home in Tullahoma

What guests are saying

New Cottage on Tims Ford Lake/Marina/Restaurant

5 out of 5 average rating, 35 reviews2 months ago

We loved our quick Valentine's Weekend stay at Kelly's property. The house was immaculate with all the needed amenities you'd expect. The large TVs in the bedrooms, den, and on the deck were amazing. Kelly responded quickly and was very helpful and friendly. I would recommend this house to anyone looking to get away for the weekend, or for longer stays with family. There is a cute Winchester, TN square with several quaint shops and restaurants only 16 minutes away. Then of course there is the lake for fun as well. We'll be back!

Home in Tullahoma

What guests are saying

Mountain Retreat

4.92 out of 5 average rating, 48 reviews1 week ago

Tina’s place was perfect for our family! The pictures do not do it justice. Everything was just as described but even better than we expected! We brought 4 dogs along with us. The fenced gates on the front and back porches along with the fenced yard were perfect for them to run around and play. Even though we have vacationed in Monteagle at least 10 times, we used her book of recommendations to try out different activities and places to visit. This vacation away from everything is just what our family needed. Not listed in the description was that the TVs can be used to log into your streaming services. This made our stay extra comfortable! We will definitely be back!

Cottage in Monteagle

What guests are saying

Luxurious Lakefront Cabin w/Hot Tub~ Amazing Grace

5 out of 5 average rating, 16 reviews3 weeks ago

Our family of 5 loved staying at Amazing Grace! The location on the water was absolutely perfect and peaceful. My kids, 9, 6, and 4, spent hours skipping rocks as we watched from the deck. The king and queen beds were some of the most comfy we've ever slept in on a trip. The kids loved the loft area. The nearby hikes were gorgeous and we loved coming back to grill out and have some hot tub time! We will be back!

Cabin in Tracy City

What guests are saying

Beautiful Tims Ford Lake, boat dock, rental boat

4.94 out of 5 average rating, 31 reviews8 months ago

My kids and I went for the weekend and honestly wished we had a couple days longer to stay. The house was welcoming and the host made sure to leave lights on and doors open for us to get in with ease. Randy was extremely easy to work with. The lake was nice and the boat rental process was quite convenient…there was even a tube for a fantastic tubing experience! I’d recommend staying here!

Home in Winchester

What guests are saying

The Bluebird Cabin

4.98 out of 5 average rating, 42 reviews1 week ago

We couldn’t have loved Erin’s tiny home more! It doesn’t feel that tiny, more like a cottage. The beds were super comfortable, the decor was gorgeous, the outdoor area stunning with a grill, bags and fire pit. The fire pit chairs were so comfy too! The showers powerful. Great Sonos music system, fantastic hot tub, we have one at home so are picky about hot tubs and this one had great jets throughout! It really couldn’t have been any better and Erin was so nice to communicate with. The only warning I will issue is the stairs to the upstairs bedroom is very steep (just the way it is to fit into the footprint of the house). We had a good laugh watching our friends descend the steps it became part of the fun but reserve this room for able bodied people not elderly or young kids. The friends that shared the bunk beds loved the mattresses so much so any kid would be more than happy in that room anyway! Thanks Erin!

Tiny home in Monteagle

What guests are saying

Mountain cabin NPrTh

5 out of 5 average rating, 4 reviews12 months ago

If you’re coming for the caverns and need a place to say Shelia’s home is a perfect spot. It’s not to far and it’s an amazing home. Even if you’re not coming for the caverns this is a great spot to just bring the family or even just a great relaxation spot but her home is 100% worth it so I would stop searching and book this place!

Cabin in Altamont

What guests are saying

Mossy Falls Cabin | Outdoor Hot Tub & Fire Pit!

4.89 out of 5 average rating, 27 reviews1 week ago

We loved our stay here! The house is remote, but the views and amenities were well worth it. Be sure to pack in your groceries as there isn’t anything close. If you are looking for a relaxing and peaceful place to spend with family and friends, this is it! We had our two kids with us and hiked waterfall trails in the area during the day, then came back and cooked dinner and relaxed in the hot tub in the evening. Definitely a wonderful place to relax and unplug.

Cabin in Altamont

What guests are saying

Lakefront Tiny Home/Pet Friendly

4.97 out of 5 average rating, 30 reviews1 week ago

This was the best pet friendly placed we have stayed. We didn’t have to worry about her running away or getting g lost. The place was nice that we could sit outside in the screened porch and looked at the lake which was very peaceful. It was nice to hear the birds and see God’s creation.

Tiny home in Tracy City

What guests are saying

Deerpath Cabin

4.96 out of 5 average rating, 95 reviews1 week ago

I had a wonderful stay at this beautiful mini home. Tucked away in a peaceful, remote area, it offered the perfect escape. The space was thoughtfully designed and had everything I needed for a comfortable stay. The hosts were kind, responsive, and made me feel right at home. Highly recommend this spot if you’re looking for a quiet retreat with great hospitality!

Tiny home in Hillsboro

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Popular amenities for Winchester vacation rentals

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BBQ grill

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Stay near Winchester's top sights

Twin Creeks Marina44 locals recommend

Piezan Pizzeria Italiano25 locals recommend

Walnut Hill Coffee Company19 locals recommend

Drafts & Watercrafts19 locals recommend

The Oldham16 locals recommend

SUNRISE (The Breakfast Place)16 locals recommend

Other great vacation rentals in Winchester

4.78 out of 5 average rating, 86 reviews

Cabin in Monteagle

Cabin Nestled in the Trees. Firepit and Hot Tub!

4.97 out of 5 average rating, 36 reviews

Home in Tracy City

*Sommarstuga* Modern cozy lakeview retreat for 6

4.92 out of 5 average rating, 12 reviews

Home in Estill Springs

Spacious 4 bedroom 2 bath house

4.98 out of 5 average rating, 89 reviews

Cabin in Bryant

WILDFLOWER CABIN, NO SUNDAY CHECK INS, HOT TUB

Townhouse in Lookout Valley

5 out of 5 average rating, 4 reviews

The Juniper - a PMI Scenic City Vacation Rental

4.98 out of 5 average rating, 55 reviews

Cottage in Tracy City

Swordfish Suite - Pup Shed Retreat

Home in Village of Pelham

4.92 out of 5 average rating, 26 reviews

3 Bedroom Apartment by the Caverns!