Winchester holiday lettings

We found 124 holiday rentals — enter your dates for availability

Discover a selection of 7 homes and other holiday rentals in Winchester that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as parking and a hot tub. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Winchester

Showing deals for:6 Mar - 13 Mar

Image gallery for Cozy Cabin in the Berkshires

Exterior
10 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)

Cozy Cabin in the Berkshires

Sandisfield, MA

12% off
Price is £1,467
for 7 nights, 1 cabin
£210 per night
includes taxes & fees
Cozy Cabin in the Berkshires

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Winchester

Do you want to discover top things to see and do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Winchester a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Connecticut Valley Winery (8.3 mi / 13.4 km)
  • Ski Sundown (9.4 mi / 15.2 km)
  • Sunset Meadow Vineyards (11.1 mi / 17.9 km)
  • Land of Nod Vineyard and Winery (11.1 mi / 17.9 km)
  • Mohawk Mountain Ski Area (12.4 mi / 19.9 km)
  • Flamig Farm (13.5 mi / 21.7 km)

Exploring the natural landscape of Winchester

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Winchester is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Highland Lake (2.6 mi / 4.3 km)
  • Satan's Kingdom State Recreation Area (9.5 mi / 15.4 km)
  • Woodridge Lake (11.5 mi / 18.6 km)
  • Harwinton Conservation and Recreation Area (11.7 mi / 18.8 km)
  • Mohawk Mountain State Forest (12.2 mi / 19.6 km)
  • Great Falls (13.6 mi / 21.8 km)

How to get to and around Winchester

Fly into Hartford, CT (BDL-Bradley Intl.), the closest airport, located 21.9 mi (35.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away.

Frequently asked questions

What is the best area to stay in Winchester when booking a holiday rental?
When considering a holiday rental in Winchester, Connecticut, a popular area to stay is the quaint community of Winsted. This charming neighbourhood offers a delightful blend of history and natural beauty, making it an appealing choice for visitors. Winsted is known for its picturesque landscapes, with the serene Highland Lake providing opportunities for swimming, fishing, and boating during the warmer months.

Additionally, Winsted boasts a rich historical backdrop, highlighted by the intriguing Warner Theatre, which hosts a variety of performances and events throughout the year. The area features a selection of holiday rentals, providing plenty of options for visitors seeking a comfortable and convenient stay.

Another wonderful option is the surrounding rural areas, which offer a peaceful retreat while still being close to Winsted's amenities. Here, you can immerse yourself in the natural surroundings, with numerous hiking trails and scenic vistas to explore. This area generally has a good number of properties available, suiting different tastes and budgets.
How much does it cost to rent a holiday home in Winchester?
Prices for holiday rentals in Winchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winchester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winchester holiday house rentals?
You can find great discounts on house rentals in Winchester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay holiday rentals in Winchester?
A long-stay holiday rental in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Winchester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winchester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Winchester for a holiday rental?
July is the most popular time to visit Winchester, Connecticut, when the town comes alive with summer activities and vibrant community events. This peak season, which spans from July to September, offers visitors a delightful mix of outdoor adventures, local festivals, and opportunities for relaxation in the warm sunshine.

During these months, the weather typically hovers around the mid to high 20s Celsius, creating great conditions for hiking, exploring scenic parks, and enjoying the natural beauty of the surrounding areas. Whether you're wandering through the picturesque downtown or taking part in seasonal events, there's plenty to keep you entertained.

For those who prefer a quieter experience, consider visiting in December. This month, while less busy, presents a unique charm with winter festivities and the chance to enjoy the serene beauty of Winchester's snowy landscapes. It's a great time for cosy gatherings and exploring the area's historical sites without the crowds.
How early should I book a Winchester holiday rental?
Book your Winchester holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winchester?
In Winchester, Connecticut, visitors can enjoy a range of attractions that highlight the area's natural beauty and historical significance. The picturesque Lake Wononskopomuc is a popular spot for outdoor activities such as swimming and boating, with several rental properties available nearby offering serene views of the water.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winchester holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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