For a town with a population of only 8,467 people, Winchester offers more activities and impressive attractions than you can imagine. Named after a soldier of the American Revolution General James Winchester, the lakeshore city has a long history and culture to share. Take your time to dig into architectural history about the American Indians, civil wars, and world wars. Make sure to allocate a few days to embrace the beauty of Tim’s Ford Lake and let the clock tick slower as you stroll around downtown Winchester. See our picks of best Vrbo rentals in this article below to secure a pleasant stay in this charming neighborhood. Scroll below for the best Vrbo vacation rentals in Winchester, Tennessee.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.
1. Family-friendly retreat with countryside views (from USD 290)
Roomy and well-appointed, this vacation rental provides a true country getaway ideal for a family. It offers a kitchen, dining area, three bedrooms as well as two full baths that are equipped with a hairdryer and towels. Other amenities include air conditioning, a garage, and on-site horse stables that are accessible if needed.
Families can use the ping-pong table, pool table, and the darts in the playroom for some quality family time. They can also play lawn games or just sit around the fire pit in the backyard and take in beautiful sunset views. Tims Ford Lake is, Cowan Railroad Museum, and Elk River Dam are just 2.1 mi (3.4 km), 4.6 mi (7.4 km) away, and 10 mi (16 km) away, respectively.
Top guest reviews
Amenities & Room:
very comfortable and well maintained propertyCleanliness:
very clean and quiteRead more reviewsHost:
host was super to communicate withchantel was an amazing host and we loved everything about her beautiful home
2. Spacious townhome with communal pool access (from USD 275)
This spacious townhome has 4 bedrooms and 3 full baths, making it an ideal place to stay for up to 12 guests. The bathrooms are complete with toiletries, towels, and bath essentials. There is also a well-equipped kitchen that boasts a stainless Saber infrared grill. Other areas include the garage, family room, and outdoor patio. Amenities like an air-conditioning system, a fireplace, and laundry essentials are available as well.
Guests can hop on the golf cart that comes with the rental and head down to the clubhouse to take a dip in the seasonal communal pool. It is also an ideal ride to cruise around the neighborhood or go to the marina, where a bar and eatery are located. Tims Ford Marina and Tims Ford Lake are just 6.8 mi (10.9 km) and 0.2 mi (0.3 km) away, respectively.
Top guest reviews
Amenities & Room:
the mattresses were also very comfortablethe property offered us plenty of comfortable sleeping space and gathering spacewe had a lovely stay with very comfortable accommodationsCleanliness:
the condo was very clean and had everything we neededvery clean house very easy processgreat set up modern clean and perfect for a familyeverything was very clean and ben was very easy to contact for anything i neededthe property was clean and attractive and worked out very well for our familyHost:
easy process and owners very helpful with any questions i hadthanks to the owners for providing christmas decorwe appreciated that the owners had decorated for christmasben was very responsive to any questions or issues we had and resolved them quicklyRead more reviewsLocation:
thank you for offering this locationgood location for tn history visitsgreat location lots of fungreat location; close to the marina and an easy day trip to lynchburg for a distillery tourconvenient location clean well appointed home
3. Lakefront oasis with large yard (from USD 338)
Situated in the gated community of Barefoot Bay, this lakefront rental can easily accommodate up to eight guests. The bedrooms are spacious and the bathrooms are equipped with towels, toiletries, and a hairdryer. The fireplace makes it a cozy home away from home. Amenities such as strong Wi-Fi, TV, washing machine, and home safety features are also available. Guests can enjoy full access of the property as well, including a well-equipped kitchen, sunroom, garage, and yard.
While the clubhouse pool is easily accessible, guests can always opt for more adventures at the lake. They can go swimming, boating, kayaking, and trying out other water sports. Beach towels and kayak floats come with the rental. Just less than a mile away is Historic Winchester, where restaurants, distilleries, gift shops, and museums can be found.
Top guest reviews
Cleanliness:
the house is new beautifully decorated and immaculately cleanthe property was very clean and well appointed with special touches throughoutthe property was clean and well appointed with special touches (fresh flowers) and a welcoming giftRead more reviewsHost:
linda the owner is so kind and lovingour host was easy to contact and quick to respond to all questions about our stayour host was easy to contact and quick to respond when we had questions regarding our staythe owner linda was very responsive and informative about the areathe owner was very responsible accessible and well organized
4. Fully furnished abode best for families (from USD 228)
Stunning lake views are only one of the many great things about this rental. It is also well-furnished and packed with family-friendly amenities such as a baby gate, a travel crib, children’s dining ware, and several games. With three bedrooms and three bathrooms, this lovely retreat can comfortably sleep up to eight guests. Guests can also enjoy access to a well-equipped kitchen, game room, living room, and dining room.
Other amenities included in this rental are strong Wi-Fi, home safety features, toiletries, laundry essentials, heating and air-conditioning, and fireplace. To make family time at Tims Ford Lake even more fun, the host provides lake towels, kayaks, beach bicycles, sports gear, and water toys. The spacious garage can fit two cars as well as a double stroller for kids.
Top guest reviews
Amenities & Room:
one of the most complete and comfortable homes we've ever rentedwe also love the twin creeks pool and marina areaCleanliness:
beautiful house very clean and upto datethe house is clean warm and welcomingeverything was great the house was well clean well furnishedwe had a great time and everything was nice clean and well keptwe like for things to be very cleanHost:
owner very helpful and friendlyowners have done a great job making sure you have everything you needowners very helpful and quick to answerbeautiful property and owners are very responsivethe communication with the owner is the best i’ve ever hadRead more reviewsLocation:
loved the location and propertyhouse is nice perfect locationlocation of house to lake and marina was perfectyou won't be disappointed if you choose this placethe property owners were very responsive and helpful and the location is great
5. Well-equipped home with lake views (from USD 500)
Nestled in the gated community of Twin Creeks Village, this four-bedroom home delivers stunning views of Tim Fords Lake. It also features 8 beds, making it an ideal accommodation for a group of up to 12 guests. Its five bathrooms are well-equipped with bath essentials and toiletries. Laundry essentials are readily available as well. The kitchen is complete with cooking basics and a coffee maker. For entertainment, guests are provided games, a strong Wi-Fi connection, a DVD player, and Roku Smart TVs. The cherry on top is an indoor fireplace to make the evenings cozier.
The clubhouse offers kayak and pontoon rentals so guests can have more fun in the lake. There is also a seasonal pool available. Guests can end the day huddling around the fire pit located just outside of this vacation rental.
Top guest reviews
Amenities & Room:
the couch in the front room folds to make a bed which was very helpfulCleanliness:
beautiful home clean with all necessitiesthe stay was great the pictures were exactly the same and it was so cleanHost:
super nice and responsive property managerRead more reviewsLocation:
i would recommend this location to anyone
6. Lakeside accommodation with sauna (from USD 270)
Perched on a quiet slough of Tims Ford Lake is this spacious paradise that gives plenty of room for up to 12 guests. It offers two full baths and three bedrooms, one of which is a kid’s room with a nautical theme. Other areas include a well-equipped kitchen, a dining area, and a living room with a stone fireplace. This rental also boasts a pub table overlooking the dock and lake.
After enjoying water sports at Tims Ford Lake, guests can pamper themselves with the small dry sauna. Guests can also explore nearby attractions like Cowan Railroad Museum and Northgate Mall Tullahoma just 9.4 mi (15.1 km) and 11.5 mi (18.5 km) away, respectively.
Top guest reviews
Amenities & Room:
the top deck of the dock was comfortable for laying outthe rooms were very nice and the bunk beds are super funthe ac had been left on so the house was a comfortable oasis from the summer heatwe liked how cozy the cabin was and the dock is unbelievableit has a fantastic pool with diving boardsCleanliness:
the cabin was extremely clean and had everything we neededit was spacious and cleanthe property was clean had everything we needed and moreHost:
the owner was helpful and responded to our questions in a timely mannergreat escape before the new school year owner was wonderful and responding quicklyjon the manager was very helpful and easy to contact & answer questions quickly via emailthe owner john was very helpful in preparing for the stayRead more reviewsLocation:
great location and access to local storesclose proximity to town was greatwe loved the location of this adorable lake cottageto start the location was perfectit was a great location and enjoyed having access to the lake
7. Pet-friendly 1950s lake house (from USD 237)
If a gated community facility is not your thing, then consider this vacation rental as an alternative. Located near the new Twin Creeks marina, this classic American-style house gives astonishing lake views as the private resort. Enjoy Tims Ford Lake right at the back of your door, walk to the downtown, and explore all that historic Winchester can offer during your stay. Rent a boat or bike along the lake before enjoying a casual dinner with dramatic sunset views by the dock.
Top guest reviews
Amenities & Room:
The kids had the downstairs and it was a perfect spot for them with their own bed and bathroomThe house was perfect for our group - 4 adults and 3 kidsThe beds were comfortable and there was more than enough towels and linensThe house itself was well stocked presentable and cleanWas in town for a conference and really enjoyed my stay hereCleanliness:
bathrooms clean and functional plenty of clean bedsBeautiful place Very clean and has everything you need Spacious andThe place was fantastic Easy to access cleanHost:
The owner Christy was great with communicating with us with any questions we had about the propertyOwner is always available and helpful if anything is needed Highly recommendedThe dock was big enough for all of us to enjoyWe had fast friendly service at Twin creeks MarinaWe had a wonderful timeRead more reviewsLocation:
My Labrador enjoyed jumping off the dock and swimmingmy Yellow Labrador loves it tooEnjoyed grilling out everyday Nothing but positive reviews for this propertya great dock for swimmingVery clean and well maintained Lots of activities nearby and
8. Scenic three-bedroom getaway (from USD 290)
The three-bedroom lake house is a perfect getaway for families, with an open floorplan design and a sunken great room connecting to a large multilevel deck overlooking the lake. Let the kids play on the vast backyard that leads to the floating boat dock where you can take a ride and explore the neighborhood. Whether you want to venture to downtown Winchester or simply relax by the covered patio, it’s your choice!
Top guest reviews
Amenities & Room:
Comfortable cozy lake home on a beautiful treeroomy and clean great view of the lake the door facing in the pink bedroom was an eye sore but other than that was quite niceThe stairs to the dock (like most on Tims) can be tricky in partsThis place beats staying in a hotel for over a month and it was cheaper View of the lake from Master living room and kitchenThe house was spacious and made living arrangements comfortable for the weekendCleanliness:
Place was clean neat and the owner respected my privacyHouse had everything we needed andHost:
Lana was very helpful and a wonderful hostGood covered dock for boat and relaxationOwner was easy to deal with and had recommendations for restaurantsDock is huge and convenientWell stocked great location beautiful views very comfortableRead more reviewsLocation:
First started renting this lake house around 2007 Have rented others around Tim's Ford Lake along the way but this location is the best Older place butGreat location Convenient to dock and gasTims Ford Note - there are about 50 plus steps to the dock and also some steps down from the circle drive to front doorVery clean Lots of space Overlooking lakemake it a joy to wake up eat and just sit
9. Historic studio with outdoor hot tub (from USD 246)
A Nashville painter offers this historic studio to a group of up to four. It features two bedrooms as well as two full baths that are equipped with toiletries and bathroom essentials. For entertainment, guests can use the strong Wi-Fi for free, as well as the stereo, TV, and video games that come with the rental. Other amenities include a functioning air-conditioning system, cooking basics, and beach towels. An outdoor hot tub, the highlight of this rental, is ideal for a rejuvenating soak to end the day.
This rental is also conveniently located just less than a mile away from Tims Ford Lake and Tims Ford State Park. Guests are welcome to bring their boats or kayaks and use the public boat ramp for a fun adventure in the waters.
Top guest reviews
Host:
excellent response time from the owner grateful for our time therewe enjoyed staying in this beautifully restored historic vacation home of artist/ownerwill be staying again next year host is quick to reply and very helpfulRead more reviewsLocation:
really enjoyed this rental great location only a short drive away from everythingsuperb location close to the square and swim beach/boat ramp/dock
10. Resort-style home with access to seasonal pool
Enjoy resort-style accommodation in this luxurious home located inside Twin Creek Marina Resort. It features 4 spacious bedrooms, 2 full bathrooms, and a half bathroom that are ideal for a group of up to 13 guests. The bathrooms are equipped with towels and a hairdryer. Games and books are available as well, making this rental a family-friendly place to stay.
Guests are given access to the seasonal pool at the clubhouse. They can also enjoy time at the lake by renting kayaks, paddleboards, and boats that are available for rent at the community dock. For a fee, guests can also use the host’s six-seater golf cart to tour around the neighborhood and visit places like Tims Ford State Park and Tims Ford Lake just less than a mile away.
12.34 km (7.7 mi) from Tims Ford State ParkAccommodates: 13
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Read more reviewsLocation:
had 3 families meet up and enjoyed the location and the house worked well
A place where history meets nature
While downtown Winchester has a long history to narrate, the surrounding areas boast of charming picturesque views. Its convenient location on the shores of beautiful Tims Ford Lake, make the area a magnet for those seeking tranquility and peace. These vacation rentals that we have picked above guarantee the best stay that this historic town can offer. So, better be quick and make the reservation before they’re all booked!
History
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