Winchester vacation rentals

We found 260 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Scroll through and select from vacation rentals in Winchester to find one that's perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for spending time at your vacation home, which might include a garden and WiFi. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

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Take in the lakeside beauty of Winchester

The lake and forests provide a pleasant backdrop to your vacation home in Winchester. This city is relaxing and scenic, recognized for its canoeing, boating and kayaking. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Winchester

Are you hoping to find attractions to see while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Winchester has to offer. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Monadnock State Park (15.8 mi / 25.4 km)
  • Cathedral of the Pines (20.1 mi / 32.3 km)
  • Northfield Mountain Recreation Center (12 mi / 19.3 km)
  • Brattleboro Country Club (12.2 mi / 19.6 km)
  • Brentwood Golf Course (14.9 mi / 23.9 km)
  • Granite Gorge (16 mi / 25.8 km)

Exploring the natural features in Winchester

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Winchester is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Madame Sherri Forest (9.3 mi / 15 km)
  • Madame Sherris Castle Ruins (9.4 mi / 15.1 km)
  • Spofford Lake (10 mi / 16.1 km)
  • Brattleboro Common (10.7 mi / 17.2 km)
  • Turner Falls (14.2 mi / 22.8 km)
  • Monadnock State Park (15.8 mi / 25.4 km)

Frequently asked questions

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

Based on our data, apartments are the most in-demand property type in Winchester. But as you know, everyone's idea of the perfect trip can vary. Vrbo has vacation homes with every shape, size and budget in mind, so you're sure to find the perfect fit.

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

Property type, length of stay and time of year are some of the conditions that can affect the price of a vacation home. Simply click on your dates of travel to find your dream escape. From cozy chalets to expansive villas, all Vrbo vacation rentals offer terrific value.

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

The average price for a vacation home near the beach in Winchester will depend on when you're going and the size and style of property you're searching for. Find prices easily and quickly on Vrbo by entering your preferred travel dates. Then use the handy filter tool to pick the number of bedrooms and amenities that you need, like WiFi, air conditioning and a hot tub.

Are there pet-friendly vacation rentals in Winchester?

Yes. There are. You'll have your pick of seven vacation rentals that allow pets in Winchester. Plenty of our pet-friendly vacation rentals even have space outdoors for your fur baby to run around in, special dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect digs on Vrbo.

What are popular rental amenities in Winchester?

The most popular rental amenities people look for in Winchester are a firepit, a water view and nearby museums. Whether you're going on vacation with family, friends or even pets, Vrbo vacation homes come with the best amenities for ultimate relaxation with the people you cherish the most.

Are there large group vacation rentals in Winchester?

With four Winchester properties that can sleep five or more people, you can bring a few extra buddies or family members along. Whether you're planning a casual get-together or a celebratory event, Vrbo will help you book a comfy space to match the occasion.

Are there vacation rentals in Winchester that welcome kids?

Winchester has seven family-friendly vacation rentals. And finding a stay that welcomes kids is easy with Vrbo's "Properties good for families" filter. On top of having the whole place to yourselves, you'll enjoy access to perks and amenities such as multiple bedrooms, kitchens and private pools.

What are the top attractions for families in Winchester?

There are plenty of cool things to see and do with the family in Winchester, such as:

  • Birch Point
  • Pisgah State Park
  • Little Monadnock Mountain

Are there one-bedroom vacation rentals in Winchester?

Winchester has two one-bedroom rentals on offer. Often positioned in prime areas thanks to their compact size, a one-bedroom vacation property is great if you're getting away with a friend or your partner. And with plenty of home comforts like kitchens and more privacy than a standard hotel, you'll be able to chill out while enjoying this amazing destination.

Can I find two-bedroom vacation rentals in Winchester?

Gather your family and enjoy total privacy and comfort in one of the five two-bedroom vacation homes Winchester has to offer.

Are there vacation rentals with WiFi in Winchester?

Whether you'd like to keep up to date with the news, check emails or post a pic to social media, there are five vacation homes with WiFi in Winchester. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

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

You'll have a choice of seven vacation homes with air conditioning in Winchester providing that gentle, cool breeze and extra touch of comfort. Just enter your chosen travel dates and then take advantage of our filters to help you locate properties with air conditioning.

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