Holiday Rentals in Winchester

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Holiday Rentals in Winchester

"The Hawk Nest" cabin on Tims Ford Lake

9.6 out of 10, Exceptional, (18)
"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! "
The price is €453
includes taxes & fees
7 Oct - 8 Oct
"The Hawk Nest" cabin on Tims Ford Lake

Reflection Bay-Dock, Hot Tub, Kayaks

10.0 out of 10, Exceptional, (11)
"Great communication and great location "
Reflection Bay-Dock, Hot Tub, Kayaks

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

10.0 out of 10, Exceptional, (49)
"Our granddaughters loved the dock! Peaceful beautiful setting."
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great stay!! Plenty of space. Clean. Great location. "
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

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

10.0 out of 10, Exceptional, (38)
"The house was very comfortable and clean and the views were beautiful. Eddie communicated with us often and was available whenever we needed him. "
Private dock/gazebo on quiet cove. Tims Ford Lake!

Beautiful Lake Views at Twin Creeks!

10.0 out of 10, Exceptional, (56)
"This house has everything! We enjoyed the screened porch each morning with coffee and the lake view. The neighborhood was great for walking the dog. We enjoyed the Bodega close by and the live music at the marina. The town of Winchester is adorable! "
Beautiful Lake Views at Twin Creeks!

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

2.0 star property
10.0 out of 10, Exceptional, (15)
"Everything was perfect. We really enjoyed our stay. "
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

9.6 out of 10, Exceptional, (35)
"We had a wonderful Memorial Day holiday weekend at the lake. The house and location were superb. We will definitely book again. "
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

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

10.0 out of 10, Exceptional, (29)
"We had a wonderful stay. We all loved your place. It was very accommodating and we loved the convenience of being in town."
Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

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

10.0 out of 10, Exceptional, (1)
"Great layout for fun family time at the lake!"
Dockside Dreams-**Best Game/Movie Room at the Lake

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

10.0 out of 10, Exceptional, (25)
"We had a wonderful time and will definitely be back!!!"
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Ambassador Inn And Suites

3.5 star property
6.4 out of 10, (276)
"Other then their being cockroach’s on everything. It was an ok stay. "
The price is €57
includes taxes & fees
6 Oct - 7 Oct
Ambassador Inn And Suites

Scandinavian Treetop Bliss @ Terralodge

9.6 out of 10, Exceptional, (10)
"Very impressed with the amenities. Everything needed for a wonderfully cozy stay. Hottub was very clean and perfect temp. Loved the attic sleeping area - very comfy bed. Perfect stay!"
The price is €216
includes taxes & fees
16 Oct - 17 Oct
Scandinavian Treetop Bliss @ Terralodge

Hummingbird Treehouse w/ Hot Tub & Firepit

10.0 out of 10, Exceptional, (363)
"Property was as described. Easy to access and close to hiking and two towns. Would stay here again. "
The price is €258
includes taxes & fees
27 Oct - 28 Oct
Hummingbird Treehouse w/ Hot Tub & Firepit

Private Off-Grid Cabin on a Bluff

The price is €142
includes taxes & fees
14 Oct - 15 Oct
Private Off-Grid Cabin on a Bluff

The Cabin in Tracy City

10.0 out of 10, Exceptional, (11)
"The cabin is quaint and well-accommodated. It is close to many trail heads. "
The price is €150
includes taxes & fees
3 Nov - 4 Nov
The Cabin in Tracy City

Shea's Chalet - Cozy home in Monteagle, TN

2.0 star property
9.8 out of 10, Exceptional, (12)
"Good location "
The price is €242
includes taxes & fees
2 Nov - 3 Nov
Shea's Chalet - Cozy home in Monteagle, TN

Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

10.0 out of 10, Exceptional, (19)
"The stay was amazing. The house was exactly as described. 100% recommend couldn’t have been happier and we will be back. "
The price is €205
includes taxes & fees
7 Oct - 8 Oct
Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

Eagle Treehouse: Hot Tub, Fireplace, and Outdoor Firepit!

10.0 out of 10, Exceptional, (265)
"Close, quite family getaway. "
The price is €252
includes taxes & fees
14 Oct - 15 Oct
Eagle Treehouse: Hot Tub, Fireplace, and Outdoor Firepit!

Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres

9.6 out of 10, Exceptional, (130)
"Everything was great! The house, the swimming, the bonfires, the view . . . We couldn't have asked for a nicer long weekend. "
Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres
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.
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Top Winchester Hotel Reviews

Find out more about Winchester

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 €57 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 Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs and Beautiful Lake Views at Twin Creeks!.

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 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.