Winchester Holiday Rentals: Short-Term Accommodations for Rent

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

Gorgeous Renovated Home with Open Floor Plan and Large Lot : This highly rated holiday home rental in Winchester is located on a lake, and has a patio, a selection of games 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. Some other top choices in Winchester are Spacious Lakefront Retreat w/ Hot Tub + Dock! and Dock, Water Views, Kayaks, Fire Pit, Game Room .

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Holiday Rentals in Winchester

"Great location, great host, lots of upgrades. Planning on coming back"

"Wonderful "

"We enjoyed the cottages roomie interior and comfortable beds. We saw a deer enjoyed walking the dog around the property and had a peaceful night sleep."

HK$2,693 total

includes taxes & fees

4 Aug - 5 Aug

"Beautiful home with everything we needed for our stay! The kids loved the game/bunk room and golf cart rides to the awesome dock. We enjoyed it so much and felt right at home!"

"The location was great"

"Private, comfortable, plenty of amenities. Kids are a little older so no problem with the ladder. Will stay again!"

HK$3,321 total

includes taxes & fees

8 Jul - 9 Jul

"Great place! We will definitely stay again!"

"Wonderfully maintained property by the lake. So much privacy and great amenities. We will definitely be back."

"Owners of this property are great, gave us extra days without cost due to bad weather during our stay. We will be back."

"Property was clean and well maintained. The Twin Creeks neighborhood had everything you could need and easy access to the lake. Downtown Winchester and great food options are a very short drive away."

"We didn’t go for the lake or anything other than simply to get away from our regular area. There weekend bad storms on our side of the map. I really just loved the home and the feel in general and absolutely hated having to leave"

"Place was great"

"Great Place to stay"

"Very relaxing stay in a quiet neighborhood on the lake. The house is very nice and as advertised. Owner is very communicative and helpful."

HK$10,281 total

includes taxes & fees

10 Jul - 11 Jul

"Great location and views!"

"The property was clean in a gated community slight6smaller 5gsn expected but served us well."

"Amazing property and location by the water. Really enjoyed our stay!!"

"Beautiful and convenient location! It's a great place to gather with family and to enjoy some down time. The home is nicely appointed and designed for guests' comfort. We especially loved the game room and the outdoor spaces I'd definitely choose to visit again."

"Was a great time, area is quiet and peaceful."

"Perfect property for a quick get away. Clean, good location, quiet. Highly recommended."

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Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winchester!

Recent reviews of Winchester properties

Microtel Inn & Suites by Wyndham Manchester

5/5 Excellent

"Clean rooms, friendly staff. It sounds odd but wide parking spaces; easy to park without having to squeeze in between other cars "

A verified traveller stayed at Microtel Inn & Suites by Wyndham Manchester

Posted 5 days ago

Dock, Water Views, Kayaks, Fire Pit, Game Room

5/5 Excellent

What a great house!

"We had a fantastic weekend at this lake house with two families—four parents and six college-age kids. The house was spotless, beautifully furnished, and thoughtfully laid out for a group our size. The setup worked perfectly: a king master suite, two queen bedrooms, and a spacious bunk room in the lower-level hangout area.We spent a lot of time on the screened-in porch enjoying the view—it was one of our favorite spots. The walk down to the lake is manageable, and having the golf cart made it easy to shuttle people and gear back and forth to the dock.The property management team was excellent—very responsive and helpful whenever we had a question.The location on the lake is ideal. It’s close to Tims Ford Marina and just a short ride to the state park, which was perfect for grabbing ice cream. The dock had plenty of space to relax, and we were able to tie up our boat along the side with no issues.Highly recommend this property—we’d absolutely stay here again."

A verified traveller from Atlanta, Georgia stayed at Dock, Water Views, Kayaks, Fire Pit, Game Room

Posted 7 days ago

Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

5/5 Excellent

Property management awesome!

"Property management of this house was fantastic to work with! Communication was easy, timely, & helpful. The house was clean and had plenty of bedrooms & bathrooms for us 6 adults to stay in comfortably. We had a few issues w/remote batteries needing to be changed out, & the refrigerator consistently beeping due to air & water filters needing to be changed, but a quick text to the property mngr had these issues resolved in a timely manner. They even brought more paper towels & without interruption delivered! The only negatives I would add (that don’t affect my rating, but fyi), is that the kitchen left a little to be desired, as far as dish & cup availability. We made due with what was there, but typically you’d see more matching plates & cups, platters & serving bowls in a rental. It was fine, though! They were stocked with aluminum foil, plastic wrap, laundry soap, shower & dish soaps, beach towels, but we brought our own ziplock baggies & extra dw tabs. Plenty of dish soap, but not enough dishwasher tabs for our stay. At checkout, we weren’t able to run the dishwasher for this reason, but in speaking with property mgmt about it, he was able to resolve it- no problem! We moved a couple of chairs from bedrooms out to kitchen table for us 6 to sit & have meals & play games. For a 4 BR house, I feel like they should have a bigger table & chairs/more seating, but again- we made due:) Rec: charcoal for grill & bug control. Beautiful view, quiet neighborhood. 5 stars! Thank you!!"

A verified traveller stayed at Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

Posted 10 days ago

Lakeside Comfort with Private Dock! Close to local marinas!!

5/5 Excellent

Great location

"We loved our stay at the house! Great view, loved the dock, & great central location to multiple marinas. The screened in porch was lovely to watch the rain. Upstairs was a little warm but overall the house was spacious. "

A verified traveller from Murfreesboro, TN stayed at Lakeside Comfort with Private Dock! Close to local marinas!!

Posted 2 weeks ago

5/5 Excellent

Great place to stay

"We loved staying here. Our boat is now on a lift at the marina and this house was a very clean and comfortable place to breakfast, get out of the rain, and to end our day comfortably. The wifi is also strong enough where I could do some pressing work that hit mid vacation. We plan to stay here again. "

A verified traveller stayed at Lake Life Getaway!

Posted 2 weeks ago

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All accommodation types in Winchester

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Twin Creeks 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?

Gorgeous Renovated Home with Open Floor Plan and Large Lot: This highly rated holiday home rental in Winchester is located on a lake, and has a patio, a selection of games 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. Some other top choices in Winchester are Spacious Lakefront Retreat w/ Hot Tub + Dock! and Dock, Water Views, Kayaks, Fire Pit, Game Room.

How many holiday rentals are there in Winchester?

Expedia has 114 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

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

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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Winchester Holiday Rentals

Check prices for these dates

Holiday Rentals in Winchester

Spacious Lakefront Retreat w/ Hot Tub + Dock!

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

Gorgeous Renovated Home with Open Floor Plan and Large Lot

Dock, Water Views, Kayaks, Fire Pit, Game Room

Family friendly lake front home with private dock in a cove

"The Hawk Nest" cabin on Tims Ford Lake

Lakeside Comfort with Private Dock! Close to local marinas!!

Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

NEW 2021 Tims Ford Lake Home - Private covered dock - Hot Tub

Lakin It Easy-Pool, Twin Creeks Marina, & Dry Creek Beach

Lake Life Getaway!

Reflection Bay-Dock, Hot Tub, Kayaks

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

Lakefront Luxury on Tims Ford Lake

Best Views on Lake, TIki Hut, Boat Rental + More

Cozy Lake Cottage W/Pool, Hot Tub,Kayaks, SUPs

Luxury Tim’s Ford Lake front -boat available pls inquire- 3 suites

Modern Charm with Rare Flat Lot, Dock, Game Area

Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

NEW! Tim's Ford Lakefront Home

Find out more about Winchester

Recent reviews of Winchester properties

Microtel Inn & Suites by Wyndham Manchester

The Smokehouse Lodge and Cabins

Dock, Water Views, Kayaks, Fire Pit, Game Room

Best Views on Lake, TIki Hut, Boat Rental + More

Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

Spacious Lakefront Retreat w/ Hot Tub + Dock!

Lakeside Comfort with Private Dock! Close to local marinas!!

Lake Life Getaway!

Explore a world of travel with Expedia

Frequently asked questions