Winchester Holiday Rentals : Search Short-Term Rentals

Q: 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 4 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 Spacious Lakefront Retreat w/ Hot Tub + Dock! and Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK .

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Holiday Rentals in Winchester

"We enjoyed spending special family time. The kitchen is perfect for a multi family gathering. Liked having multiple spaces to eat, play games, a do crafts. Having the kayaks (adult and kid size) was wonderful. Realized we were one kayak short late in the week and could have used all that were stated in the description. The kids loved fishing off the dock! Having kids fishing poles was a huge hit! We had to borrow another little kid life jacket from a friend. We rented a boat for the day and the...

"The house is clean, updated and the views are amazing! We were there in January, so we didn't use the dock, but the house was perfect. The living space and kitchen is large and open, the bedrooms are spacious, and the movie screen set up downstairs was perfect to watch a game and a movie. Will be back!"

"My girlfriends and I wanted to get a cabin for a couple of days for a book retreat, and this place did not disappoint! We took a walk around the neighborhood, both solo as well as in a group, and everyone felt very safe. We did end up bringing all of our own groceries, so I can’t comment on ease of finding food, but we had no problem preparing all of our meals, the hot tub was GREAT! A couple of girls took advantage of the fire pit that was also available, and had no issues. The sleeping...

"We stayed in this home with some childhood friends. It was a good house for just hanging out and the communication up to, during and after the stay was great!"

"Our stay was very nice overall. House was clean and host was very communicative. Great views from the kitchen and the porch. My only complaint is that the lake was drawn down when visited (January), so the dock was sitting on dirt. The only critters within casting distance of the dock were squirrels. Probably a lovely place in the Spring and Summer."

"The house's description met real life to perfection. There was plenty of space, plenty of cookware and plenty of fun things to do. But even better than the house may have been the communication with the property owner. When we had an issue, they responded with quickness and care. We'll definitely work with them again."

"This is a clean, comfortable and well-appointed cabin and a well-maintained property. It was perfectly simple and had everything we needed…even a flashlight, which we forgot. Our host generously accommodated our special request. Access to water with a kayak was easy. We would love to rent this again! Leslie November 2024"

includes taxes & fees

8 Feb - 9 Feb

"The home was beautiful - it looks just like the photos. We had a great time. When in the house, we spent most of our time in the sunroom - it was beautiful. The host went out of her way to make the place comfortable and inviting, ensuring we had a great time. She provided some snacks, coffee pods for the keurig, and the kitchen was stocked with pots, silverware, etc. She had a book with information about different restaurants in the area - was a great host and easy to work with. I would...

"Perfect"

includes taxes & fees

3 Feb - 4 Feb

"Beautiful and Quiet home. My family enjoyed the spacious home that had all the amenities that made our stay very enjoyable. Will return again"

"We just had a great week at this property. Ages 18-82 we all had so much fun. "

"Nice location, easy instructions in the binder to reference information about the stay. Prior guests left some lovely floats by the dock. Friendly neighbors as well."

"The place was lovely and the view of the lake was awesome. We caught some nice catfish off the dock. The fire pit made the night warm and romantic. The game room was just right for some friendly pool, shuffleboard, and ping-pong Anyone would love this lovely Cozy place for a fun getaway. Can’t wait till next trip. "

"Lovely stay and great communication with the hosts. "

"Amy was wonderful to deal with. The house is perfect for a larger group. The elevator allowed us to bring our 85 year old mom who loved watching us on the boat from the cover porch. Several age groups were part of this trip and everyone loved their experience (not always easy to pull this off). The fire pit out back was great for the evenings. The highlight is the boat dock. I even did the waterslide and jumping off second story and I'm 59. The boat rental recommendations were perfect. They...

"We gathered with our adult children at this beautiful home and property for an early Thanksgiving and let me say, we couldn’t have asked for better accommodations. The house is newly remodeled and is so warm and inviting. We especially loved the sunroom with the gas fireplace, it was the perfect spot for a cup of coffee on a cool fall morning, while watching the sunrise and again the perfect spot to sit and watch the sunset at the end of the day. Our adult children enjoyed the hot tub immensely...

"A get together for high school friends after many years and we all turned 60. "

"We booked this place for my grandmothers 80th birthday trip. The whole family came together. This place was truly awesome. So clean, so many things to do and fit all of us so nice. We will definitely be back. "

"Family of 11 ranging from grandparents to infants shared this wonderful home during the week of Thanksgiving. Lots of space for everyone to separate but also great living areas on the first floor and basement to stay together. The game room was a great hit with the kids and parents. The house has a great location on the lake and I can imagine this is a bustling spot in the summer to swim. The breeze off the lake was definitely brisk but that lended to the magic of the holiday. Great space to run...

includes taxes & fees

25 Feb - 26 Feb

"Six 76 year young high school teammates enjoyed a 3 day reunion at this very clean and comfortable house. The house was perfect for 6 old friends to sit in the large great room or large screened-in porch and reminisce and re-connect.. The lake view from the great room and screened-in porch is great. All the beds and furniture was very clean and comfortable. The neighborhood is quiet and uncontested. Be sure to have lunch at Ms Mary BoBos in Lynchburg. We highly recomend this property. "

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Other types of properties in Winchester you may be interested in

Suite, 1 King Bed, Non Smoking, Jetted Tub (Oversized Room)

"We arrived after 1:00 am and front desk was very kind and even offered us free water as everything was closed in town."

includes taxes & fees

9 Feb - 10 Feb

"We enjoyed spending special family time. The kitchen is perfect for a multi family gathering. Liked having multiple spaces to eat, play games, a do crafts. Having the kayaks (adult and kid size) was wonderful. Realized we were one kayak short late in the week and could have used all that were stated in the description. The kids loved fishing off the dock! Having kids fishing poles was a huge hit! We had to borrow another little kid life jacket from a friend. We rented a boat for the day and the...

"My girlfriends and I wanted to get a cabin for a couple of days for a book retreat, and this place did not disappoint! We took a walk around the neighborhood, both solo as well as in a group, and everyone felt very safe. We did end up bringing all of our own groceries, so I can’t comment on ease of finding food, but we had no problem preparing all of our meals, the hot tub was GREAT! A couple of girls took advantage of the fire pit that was also available, and had no issues. The sleeping...

Find out more about Winchester

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 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.

Recent reviews of Winchester properties

Million Dollar Views: Lakefront, Dock, Kayaks+More

5/5 Excellent

Perfect Weekend Getaway

"The house is clean, updated and the views are amazing! We were there in January, so we didn't use the dock, but the house was perfect. The living space and kitchen is large and open, the bedrooms are spacious, and the movie screen set up downstairs was perfect to watch a game and a movie. Will be back!"

A verified traveller stayed at Million Dollar Views: Lakefront, Dock, Kayaks+More

Posted 3 days ago

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

5/5 Excellent

Perfect Book Retreat

"My girlfriends and I wanted to get a cabin for a couple of days for a book retreat, and this place did not disappoint! We took a walk around the neighborhood, both solo as well as in a group, and everyone felt very safe. We did end up bringing all of our own groceries, so I can’t comment on ease of finding food, but we had no problem preparing all of our meals, the hot tub was GREAT! A couple of girls took advantage of the fire pit that was also available, and had no issues. The sleeping arrangements were great as well, no one felt cramped or on top of each other.A wonderful experience!"

A verified traveller from Memphis stayed at Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Posted 3 days ago

Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart

5/5 Excellent

Beautiful home

"Beautiful and Quiet home. My family enjoyed the spacious home that had all the amenities that made our stay very enjoyable. Will return again"

A verified traveller stayed at Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart

Posted 3 weeks ago

Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

5/5 Excellent

Christmas in the Mountains

"The house's description met real life to perfection. There was plenty of space, plenty of cookware and plenty of fun things to do. But even better than the house may have been the communication with the property owner. When we had an issue, they responded with quickness and care. We'll definitely work with them again."

A verified traveller stayed at Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

Posted 1 month ago

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

5/5 Excellent

Excellent property

"We booked this place for my grandmothers 80th birthday trip. The whole family came together. This place was truly awesome. So clean, so many things to do and fit all of us so nice. We will definitely be back. "

A verified traveller stayed at Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

Posted 2 months ago

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

5/5 Excellent

Exceeded expectations

"We gathered with our adult children at this beautiful home and property for an early Thanksgiving and let me say, we couldn’t have asked for better accommodations. The house is newly remodeled and is so warm and inviting. We especially loved the sunroom with the gas fireplace, it was the perfect spot for a cup of coffee on a cool fall morning, while watching the sunrise and again the perfect spot to sit and watch the sunset at the end of the day. Our adult children enjoyed the hot tub immensely and my husband was able to fish to his hearts content right off the dock. We appreciated all the little touches…the toiletries, the beach towels that were available to use for the hot tub and we were pleasantly surprised that they had firewood on the property for use with the outdoor fireplace! The kitchen is fully equipped with all the appliances, dishes, and utensils we needed to make meals for our family of 8. They even had a crockpot! Walmart and Kroger are only 10 minutes away as well as fast food and local restaurants. Downtown Winchester is quaint with little shops, a movie theater and what became our favorite place, Walnut Hill Coffee Company, you’ve got to try it! Justin and Derrick are quick to respond to text messages and so helpful, something we truly appreciated! We would definitely book this property again. "

A verified traveller stayed at Best Views on Lake, TIki Hut, Boat Rental + More

Posted 2 months ago

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

5/5 Excellent

Wonderful Place to Stay

"The home was beautiful - it looks just like the photos. We had a great time. When in the house, we spent most of our time in the sunroom - it was beautiful. The host went out of her way to make the place comfortable and inviting, ensuring we had a great time. She provided some snacks, coffee pods for the keurig, and the kitchen was stocked with pots, silverware, etc. She had a book with information about different restaurants in the area - was a great host and easy to work with. I would recommend staying here and would go back again. "

A verified traveller stayed at Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

Posted 3 months ago

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

5/5 Excellent

Great Communication

"We stayed in this home with some childhood friends. It was a good house for just hanging out and the communication up to, during and after the stay was great!"

A verified traveller stayed at New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

Posted 3 months ago

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?

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 4 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 Spacious Lakefront Retreat w/ Hot Tub + Dock! and Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK.

How many holiday rentals are there in Winchester?

Expedia has 119 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 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 Hammers.

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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Holiday Rentals in Winchester

Plan, book, stay with confidence

Check prices for these dates

Holiday Rentals in Winchester

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

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

Million Dollar Views: Lakefront, Dock, Kayaks+More

Million Dollar Views: Lakefront, Dock, Kayaks+More

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

Spacious Lakefront Retreat w/ Hot Tub + Dock!

Spacious Lakefront Retreat w/ Hot Tub + Dock!

Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

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

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

Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart

Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart

NewBuild Lakehouse 4BR4BA 2Kitchen DoubleDeck SwimPool BoatRamp Family Vacation

NewBuild Lakehouse 4BR4BA 2Kitchen DoubleDeck SwimPool BoatRamp Family Vacation

Family friendly lake front home with private dock in a cove

Family friendly lake front home with private dock in a cove

Gorgeous lakefront view in Hopkins Pt. Private dock, gazebo and swimming area

Gorgeous lakefront view in Hopkins Pt. Private dock, gazebo and swimming area

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

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

Luxury Estate Center of Tims Ford Lake with Unbeatable Lakefront Views, Dock

Luxury Estate Center of Tims Ford Lake with Unbeatable Lakefront Views, Dock

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

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

Lakeside Haven w/Dock/Slip, Fire Pit, Game Room, Kayaks,

Lakeside Haven w/Dock/Slip, Fire Pit, Game Room, Kayaks,

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

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

Gather at Tims Ford Lake

Gather at Tims Ford Lake

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

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

Other types of properties in Winchester you may be interested in

Best Western Inn

Best Western Inn

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

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

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Find out more about Winchester

Find out more about Winchester

Recent reviews of Winchester properties

Recent reviews of Winchester properties

Million Dollar Views: Lakefront, Dock, Kayaks+More

Frequently asked questions

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