Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Winchester vacation rentals

Private kitchen
Ambassador Inn And Suites

Aparthotel in Manchester

Ambassador Inn And Suites
3.5 star property
6.4 out of 10, (286)
"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 ￥8,758
￥10,357 total
includes taxes & fees
Dec 30 - Dec 31
Ambassador Inn And Suites
Couples treatment rooms, hot stone massages, deep-tissue massages
Sasquatch Farm

Cabin in South Pittsburg

Sasquatch Farm
3.0 star property
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 ￥27,290
￥31,315 total
includes taxes & fees
Dec 28 - Dec 29
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

Comfort Suites Manchester near Arnold AFB

Comfort Suites Manchester near Arnold AFB

10/10 Excellent
"This hotel was the best we stayed in during our trip. The place was spotless. Front desk staff was MARVELOUS!!!! Quiet rooms. Nothing could have been better. "
Anita 1-night trip
Posted 2 days ago
Comfort Suites Manchester near Arnold AFB

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:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

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

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we have vacation rentals in Winchester close to Twin Creeks Marina, or you can select a secluded option if you're looking for extra privacy while you relax. Winchester is known for its theme park and lake views. Make sure you have time to check out the university setting and coffeehouses during your trip.

What are some of the best vacation home rentals in Winchester?

Beautiful Lake Views at Twin Creeks!: Visitors like this Winchester vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation. Our travelers also rate Modern Charm with Rare Flat Lot, Dock, Game Area as a favorite home for rent in Winchester.

How many vacation rentals are there in Winchester?

Expedia has 112 vacation 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 vacation rentals like in Winchester?

Vacation rentals are private accommodations you can reserve for a short or long stay in Winchester. Vacation rentals feature extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family gatherings.