Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

Ambassador Inn And Suites

Ambassador Inn And Suites
3.5 star property
Manchester
6.4 out of 10, (287)
"The rooms are very nice and clean. The staff here is more then awesome and makes you feel like your home. Everyone goes out of their way to make sure you have everything you need. There is always a person at the front desk 24/7 to help or get whatever you need. Thank you for going above and beyond to make me and my husband feel like we are at home with family. "
United States
Bridget
The price is €59
includes taxes & fees
10 Jan - 11 Jan
Ambassador Inn And Suites

Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
8.0 out of 10, Very good, (2)
"loved the place and area, only issue was it did seem like it wasn’t properly cleaned before we arrived and found someone’s socks under the pull out couch. But overall everything else was great! "
United States
Mayumi
The price is €129
includes taxes & fees
11 Jan - 12 Jan
Sasquatch Farm
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

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 €59 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?

Beautiful Lake Views at Twin Creeks!: This highly rated holiday home rental in Winchester is located on a lake, and has an outdoor pool, a fireplace 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. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. Some other top choices in Winchester are Modern Charm with Rare Flat Lot, Dock, Game Area and Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp.

How many holiday rentals are there in Winchester?

Expedia has 113 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.