Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Family friendly lake front home with private dock in a cove
9.8 out of 10, Exceptional, (17)
"Plenty of room for our family get together. Way larger than pictures show. Would definitely book again next time!!!"
Family friendly lake front home with private dock in a cove
Luxurious Waterfront Oasis on Tims Ford Lake!
10.0 out of 10, Exceptional, (38)
"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!
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
10.0 out of 10, Exceptional, (16)
"We stayed here for a staff retreat and comfortably had 10 people stay. It's spacious, beautiful, and clean, and the layout is awesome. There's a grocery store nearby for quick runs and close to pickleball courts and hiking. It's right on the lake with an awesome back yard and deck to make mornings and evenings extra great."
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
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Million Dollar Views: Lakefront, Dock, Kayaks+More
10.0 out of 10, Exceptional, (31)
"Communication w/mgnt company reps was top notch! Accomodations was great! Tims Ford Lake water is so clean compared to where we are from (Tenn. River area). We especially liked the home theater in evenings...picture and sound was awesome! Foosball, ping pong, shuffleboard games were in great shape and fun. The view was awesome! Just a heads up...there are a lot of steps down to dock etc.so if anyone has "mobility" issues that might be a problem.It appears most homes in that area, have lots of...
The price is €773
per night
30 Jun - 1 Jul
Million Dollar Views: Lakefront, Dock, Kayaks+More
Exquisite Tranquil Lake View Prime Location, Community Dock, private boat slip
10.0 out of 10, Exceptional, (18)
"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
Lakefront Home, With Hot Tub and Boat deck! Backyard is On the water!
10.0 out of 10, Exceptional, (24)
"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!
Hawk's Nest · Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc
9.6 out of 10, Exceptional, (5)
"Couldn’t be more pleased with communication prior to and after our stay. Very friendly host that wanted to ensure things went smoothly. We needed a last minute place to stay while out of town family was in after a remodel issue and it worked great for our 11 year old son and 2 adult couples. Plenty of room for everyone to enjoy without feeling crowded and bedrooms were a nice size."
The price is €575
per night
9 Jun - 10 Jun
Hawk's Nest · Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc
NewBuild Lakehouse 4BR4BA 2Kitchen DoubleDeck SwimPool BoatRamp Family Vacation
9.2 out of 10, Wonderful, (17)
"We loved the house. Great location and everyone was nice we met while there."
NewBuild Lakehouse 4BR4BA 2Kitchen DoubleDeck SwimPool BoatRamp Family Vacation
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks
10.0 out of 10, Exceptional, (22)
"We loved our spring break stay at this beautiful property. We had plenty of room to spread out with 2 couples and 5 children, ages 6-9. Our kids adored the game room, and we all loved utilizing the fire pit and hot tub in the evenings. We would love to come back in the summer to get to experience all the lake has to offer!"
The price is €735
per night
12 Jun - 13 Jun
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks
The Yellow Cottage by Tims Ford Lake
9.4 out of 10, Exceptional, (12)
"It was just what we needed for a one night stop, as we traveled through the area. Very charming."
The price is €259
per night
10 Jun - 11 Jun
The Yellow Cottage by Tims Ford Lake
Awesome Home close to the Lake.
8.6 out of 10, Excellent, (14)
"What we liked about the property was the three bedrooms. The beds were very comfortable. The house inside was very clean. There was plenty of supplies. There was dish soap, paper plates paper cups. Kitchen was fully stocked with dishes pots and pans silverware. Really the only complaint that we had is that there was a chair in living room that was broken. We had one of the children sit in it and it started to sink so we actually turned it to the wall and wouldn't let anyone sit in it for the...
Awesome Home close to the Lake.
Spacious Lakefront Retreat w/ Hot Tub + Dock!
10.0 out of 10, Exceptional, (10)
"Super nice. Everything was great"
Spacious Lakefront Retreat w/ Hot Tub + Dock!
NEW 2021 Tims Ford Lake Home - Private covered dock - Hot Tub
10.0 out of 10, Exceptional, (55)
"We LOVED the house! It had big bedrooms and bathrooms. We used both living room spaces to watch TV. We brought life jackets and used the kayaks and paddle board. We went to the Winchester park and played pickleball. The big dining tables were perfect for our group of 7. We got to meet Andy and Laura the owners and they are delightful! We had a fire outside and roasted marshmallows. We will be back!"
NEW 2021 Tims Ford Lake Home - Private covered dock - Hot Tub
Gather at Tims Ford Lake
9.2 out of 10, Wonderful, (9)
"Great hosts with great communication. Beautiful property and home! Unfortunately, we had to cut our stay short but the hosts were very understanding, were quick to respond and graciously accommodating."
The price is €856
per night
5 Jun - 6 Jun
Gather at Tims Ford Lake
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
10.0 out of 10, Exceptional, (10)
"We had a great time at this house. Loved the log cabin feel, it was very cozy and with great amenities. Great communication from the owner. Visited 3 local distilleries, what a fun trip! Would absolutely come back."
The price is €464
per night
6 Jun - 7 Jun
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
Kayak Kove* DOCK* Lake front Tim's Ford Lake NEW- 2 kayaks
10.0 out of 10, Exceptional, (14)
"I had the time of my life celebrating my 40th birthday with friends near and far. We took advantage of the open living space and back porch to congregate over coffee while enjoying the birds and waves of the water. I couldn't have asked for a more relaxing yet sophisticated escape! Will definitely be back!"
Kayak Kove* DOCK* Lake front Tim's Ford Lake NEW- 2 kayaks
Lakeshore Modern Brand new for 2023! Lake front with platform dock and 2 kayaks
10.0 out of 10, Exceptional, (8)
"What a great weekend! This group of 6 girls, work together and live 30 mins or less to Winchester. We wanted to spend time with each other and have fun! That’s exactly what we did! AMAZING HOUSE!!!! Everything you need!!!! I won’t lie….snow storm headed to Tennessee….I wish I could’ve stayed all week and watch the snow. Absolutely breathtaking house! A+. Tara is an amazing host….we communicated about several things. She was always on it!!! Thank you Tara for a wonderful experience. People...
Lakeshore Modern Brand new for 2023! Lake front with platform dock and 2 kayaks
Dock, Water Views, Kayaks, Fire Pit, Game Room
10.0 out of 10, Exceptional, (6)
"We were looking for a short getaway with friends to enjoy memorial weekend. This house was perfect for two families with kids ranged from 8-12. Adults had their own bedroom and kids had their own bed. Kids loved the backyard to play soccer and bocce ball along with the indoor foosball and pac man game. We grilled out, hiked at Tim Fords State Park and swam at the lake on their private dock. The dock was perfect for kids to swim, float and kayak. Quiet neighborhood with a great view of the lake."
The price is €872
per night
16 Jun - 17 Jun
Dock, Water Views, Kayaks, Fire Pit, Game Room
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK
10.0 out of 10, Exceptional, (21)
"Lovely location and wonderful host, highly recommend!"
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK
Basecamp Retreat TimsFordLake
10.0 out of 10, Exceptional, (5)
"The house is actually even nicer than the pictures, which is a rare thing. Beauty lake house, clean very new and priced right. Should we return to Winchester this will be the place we stay. Seven minutes from the downtown area, only ten minutes from Walmart. Next place exceeded our expectations."
Basecamp Retreat TimsFordLake
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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 Winchester you may be interested in

Best Western Inn
2.5 star property
8.8 out of 10, Excellent, (546)
"Fine"
The price is €116
per night
23 Jun - 24 Jun
Best Western Inn
Family friendly lake front home with private dock in a cove
9.8 out of 10, Exceptional, (17)
"Plenty of room for our family get together. Way larger than pictures show. Would definitely book again next time!!!"
Family friendly lake front home with private dock in a cove
Luxurious Waterfront Oasis on Tims Ford Lake!
10.0 out of 10, Exceptional, (38)
"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!
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 Winchester 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 Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. 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 Winchester 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 Winchester holiday rentals we have selected for you start as low as €260 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester 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 Winchester 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 Winchester 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 Winchester. 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

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Tim's Ford Marina, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its theme park and lake views. Make sure you have time to check out the university setting and coffee shops during your trip.

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

Million Dollar Views: Lakefront, Dock, Kayaks+More: This highly rated holiday home rental in Winchester is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Winchester are Luxurious Waterfront Oasis on Tims Ford Lake! and Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK.

How many holiday rentals are there in Winchester?

Expedia has 115 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

Family-friendly attractions include Tim's Ford Marina and Hammers, whereas Tims Ford State Park and Tims Ford Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Elk River and Expressions.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.

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