Winchester Holiday Rentals from €458: Search Short-Term Rentals

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

Reflection Bay-Dock, Hot Tub, Kayaks : This highly rated holiday home rental in Winchester is located on a lake, and has a balcony, a garden 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. You can relax into your holiday with a pool table and 1 hot tub. Some other top choices in Winchester are Spacious Lakefront Retreat w/ Hot Tub + Dock! and New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks .

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Holiday Rentals in Winchester

"Place was great"

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

"Golf cart is a plus"

"We absolutely loved staying here. The owner was very communicative with us.The view and peacefulness was amazing. Close to Winchester if you want to go into town. We truly enjoyed our stay! "

includes taxes & fees

6 Sept - 7 Sept

"What a fantastic experience. We've stayed at a lot of VRBOs and Deah's attention to detail with this home was outstanding. Thank you for thinking about what special touches would make the guest experience a great one. Beautiful home, wonderfully appointed, lovely lakefront location!"

"The location was great"

"This place was just what i needed in a getaway. And it was an excellent choice the location to the lake private dock and for relaxing a jacuzzi. I love this place and will be returning."

"The house has it all, we had a guys fishing trip and loved the house and location to the boat ramp at the dam. Recommend this property highly. "

"Great time was had, place was clean and just what we needed."

"Beautiful house so convenient to everything. Lake out back shopping minutes away. We had a great family vacation "

"The house was very comfortable and clean and the views were beautiful. Eddie communicated with us often and was available whenever we needed him. "

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

"Great location, easy in and out. Thanks John!"

"Great stay!! Plenty of space. Clean. Great location. "

"Spacious and comfortable! Perfect place to stay (even in the off-season) for family and friends! "

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

"We couldn't have been more happy with this home for our girls getaway trip! The place is spectacular with comfy beds and more than enough room for us all. The manager of this property was the best - responding quickly to every inquiry and being wonderful. A"

"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."

Smart TV, fireplace, video games, DVD player

"What a wonderful home and neighborhood! Everyone we met was friendly and welcoming. We had a great weekend and hope to call Winchester home one day."

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Top Winchester Hotel Reviews

The Smokehouse Lodge and Cabins

10/10 Excellent

"Wonderful "

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

10/10 Excellent

"Great property that is clean and well maintained. The kitchen is well stocked with all the basics you might need during your stay. Highly recommended adding the golf cart rental to get down to the dock! All of the activities on the dock and at the house kept our crew ranging from 9-50 years old entertained the entire time! We will be back!"

Reflection Bay-Dock, Hot Tub, Kayaks

10/10 Excellent

"We loved everything about our stay. The place was clean and well stocked. The dock was perfect for fishing (we brought our own gear). The Kayaks and floating Lilly Pad provided hours of entertainment. The hot tub was clean. A large dining table for meals and games. Living room had lots of comfortable seating. The deck was perfect sitting and playing board games when a storm rolled through. The view was great! Property management was very responsive. We will come back! "

Family friendly lake front home with private dock in a cove

10/10 Excellent

"Property was as described . Very spacious. Kitchen was well stocked with utensils, pans, 1 med crock pot and a med size air fryer . Large frig upstairs and a 2nd frig in basement ! We had 7 adults and 5 kids from age 6-10. Large main floor master with shower and toilet. 2 smaller bedrooms on main floor as well with a full bath in hallway. The deck off the main floor was awesome ! Great view of dock and could watch kids swimming from it. There was several kayaks at the house . The downstairs was so spacious had a 3rd bathroom with shower and washer dryer. The space was much bigger than the pics. We had to contact our host about one minor thing and she was so responsive and helpful. The steps to the dock were more of a challenge the first few days but by the end of our week we were all better for it ! We rented a pontoon several days from the nearby marina the location made it easy for pick up and return and there is a wonderful sand beach close by. We all said we would love to go back for another stay. Great week went way too fast . Convenient to town and1 hour from the space center in Huntsville. We totally enjoyed the puzzles and games. Great stay. Peaceful and private."

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

10/10 Excellent

"We just returned from our family vacation on Tims Ford Lake and this home was plenty spacious enough for our family of 14. Very well furnished and in a great location!Would definitely recommend it! "

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 €458 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 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?

Reflection Bay-Dock, Hot Tub, Kayaks: This highly rated holiday home rental in Winchester is located on a lake, and has a balcony, a garden 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. You can relax into your holiday with a pool table and 1 hot tub. Some other top choices in Winchester are Spacious Lakefront Retreat w/ Hot Tub + Dock! and New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks.

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 Twin Creeks Marina and Tim's Ford Marina, whereas Harvey's Garden and Tims Ford are a couple of great spots to enjoy the outdoors. Other places in town to visit include Tims Ford State Park and Tims Ford Lake.

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

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Holiday Rentals in Winchester

Reflection Bay-Dock, Hot Tub, Kayaks

Spacious Lakefront Retreat w/ Hot Tub + Dock!

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

"The Hawk Nest" cabin on Tims Ford Lake

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Family friendly lake front home with private dock in a cove

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

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

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

Barefoot Bliss w/Stunning Waterfront Lot & Pool

Private dock/gazebo on quiet cove. Tims Ford Lake!

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

Dockside Dreams-**Best Game/Movie Room at the Lake

Best Day Yet! Spacious 5-bedroom house in Twin Creeks Village

Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

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

Lakefront Luxury on Tims Ford Lake

Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK

Gorgeous Renovated Home with Open Floor Plan and Large Lot

Beautiful Lake Views at Twin Creeks!

Top Winchester Hotel Reviews

The Smokehouse Lodge and Cabins

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

Microtel Inn & Suites by Wyndham Manchester

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

Barefoot Bliss w/Stunning Waterfront Lot & Pool

Reflection Bay-Dock, Hot Tub, Kayaks

Family friendly lake front home with private dock in a cove

Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

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

Find out more about Winchester

Frequently asked questions