Winchester vacation rentals

We found 106 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 5 homes and other vacation rentals in Winchester that are perfect for your trip. Vacation rentals provide the best amenities for you and your friends, family, or even pets, such as a fireplace and a washer and dryer. You're sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

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Find the perfect vacation rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a private vacation home. There's no shortage of things to see and do in the area.Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Winchester

Are you hoping to find attractions to see in the city? Venture out of your vacation home and check out everything that makes Winchester a fun spot to vacation. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Connecticut Valley Winery (8.3 mi / 13.4 km)
  • Ski Sundown (9.4 mi / 15.2 km)
  • Mohawk Mountain Ski Area (12.4 mi / 20 km)
  • Flamig Farm (13.5 mi / 21.7 km)
  • Talcott Mountain State Park (17.9 mi / 28.8 km)
  • Sunset Meadow Vineyards (11.1 mi / 17.9 km)

Exploring the natural landscape of Winchester

Whether you're an active traveler or just want to appreciate the scenery, Winchester is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Highland Lake (2.6 mi / 4.3 km)
  • Haystack Mountain State Park (6.9 mi / 11.1 km)
  • Satan's Kingdom State Recreation Area (9.5 mi / 15.4 km)
  • Woodridge Lake (11.5 mi / 18.6 km)
  • Mohawk Mountain State Forest (12.2 mi / 19.6 km)
  • Litchfield Town Green (13.6 mi / 22 km)

How to get to and around Winchester

Fly into Bradley Intl. Airport (BDL), the closest airport, located 21.9 mi (35.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Winchester?

Houses are the most popular kind of vacation rental in Winchester, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in a variety of sizes and shapes. Explore our options to find your ideal fit.

How much does it cost to rent a vacation rental in Winchester?

Several factors influence how much you'll pay for a vacation rental in Winchester, like the season, type of property and length of stay. But, all our vacation homes have something in common — amazing value. Simply enter your travel dates to find your perfect fit.

How much does it cost to rent a beach house in Winchester?

The average price for a vacation rental close to the beach in Winchester will depend on when you'll be there and the type and size of property you want. You can find prices easily and quickly on Vrbo by entering your dates of travel. Then use the handy filter tool to pick the number of bedrooms and amenities important to you, like a pool, air conditioning and WiFi.

Are there pet-friendly vacation rentals in Winchester?

Happily, yes. You'll find eight vacation rentals that welcome pets in Winchester on Vrbo. Our cuddly best friends also deserve a little time out, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where Rover can join the fun.

What are popular rental amenities in Winchester?

Some of the most popular rental amenities people are looking for in Winchester include a lake view, nearby museums and a nearby waterfront. Whether you're traveling with family, your besties or even pets, Vrbo vacation rentals have the best amenities for making new memories with the people who matter most.

Are there large group vacation rentals in Winchester?

With six Winchester properties that can accommodate five or more people, you can bring a few extra family members or pals along. Whether you're planning an informal get-together or a birthday party, we'll help you book the ideal space for the occasion.

Are there vacation rentals in Winchester that welcome kids?

With eight family-friendly vacation properties available in Winchester, now is a superb time to introduce the kids to the joys of travel. Simply click on our "Properties good for families" filter box to search for stays that come with conveniences ideal for vacationing families, such as living rooms, patios, hot tubs and bunk beds.

What are the top attractions for families in Winchester?

Keep the kids amused at these leading family-friendly attractions in Winchester:

  • Winchester Historical Society
  • Laurel Lanes
  • Highland Lake

Can I find two-bedroom vacation rentals in Winchester?

Gather your nearest and dearest and experience complete comfort and privacy in one of the three two-bedroom vacation homes Winchester has to offer.

Are there vacation rentals with WiFi in Winchester?

You can choose from six vacation rentals with WiFi in Winchester. If you'd like to disconnect from the world while on vacation, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Winchester?

Pick from eight Vrbo vacation rentals with air conditioning in Winchester offering that cool, cool breeze and extra touch of comfort. Simply enter your travel dates and then make use of our filters to look for stays with air conditioning.

How old do you have to be to rent a vacation rental in Winchester?

Age restrictions can differ between properties on Vrbo, so check the rules of the vacation home in Winchester you want. But in general, it's 16, 18 or 21.

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