Winchendon vacation rentals

We found 64 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in Winchendon that are perfect for your trip. Vacation rentals offer the amenities you expect for your family, friends, or furry companion, such as a garden and pool. You'll be able to choose a rental to meet everyone's needs, including places that are non-smoking or accessible.
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Choose a vacation rental for your Winchendon getaway

The parks and surrounding scenery provide a peaceful ambiance to your vacation home in Winchendon. There's no shortage of things to see and do in the area.Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Winchendon

Do you want to discover top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Winchendon has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Cathedral of the Pines (6.8 mi / 10.9 km)
  • Shattuck Golf Course (10.2 mi / 16.5 km)
  • Monadnock State Park (11.2 mi / 18.1 km)
  • 1761 Old Mill Gift Shop (11.4 mi / 18.4 km)
  • Game On Fitchburg (12.6 mi / 20.2 km)
  • Great Wolf Lodge Waterpark (13.6 mi / 21.9 km)

Exploring the natural features in Winchendon

Whether you're an active traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Winchendon. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Paradise Island (2.9 mi / 4.7 km)
  • Lake Dennison State Recreation Area (3.5 mi / 5.6 km)
  • Laurel Lake (6.6 mi / 10.6 km)
  • Contoocook Lake (7.3 mi / 11.7 km)
  • Royalston Falls (10.1 mi / 16.3 km)
  • Millers River (11.2 mi / 18 km)

How to get to and around Winchendon

Fly into Nashua, NH (ASH-Nashua Municipal), the closest airport, located 28 mi (45.1 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Worcester, MA (ORH-Worcester Regional), which is 30.1 mi (48.5 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Winchendon?
The most sought-after types of vacation rentals in Winchendon are cottages. After something a little different? Vrbo offers a variety of options to match the needs of our guests, so you’ll see vacation homes in lots of shapes and sizes. The ideal home away from home is waiting for you — snap up yours today.
How much does it cost to rent a vacation rental in Winchendon?
Several factors can determine how much you’ll pay for a vacation rental in Winchendon, including the time of year, length of stay and property type. But, all our vacation homes have one thing in common — unbeatable value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Winchendon?
Prices for beach houses in Winchendon vary depending on the style and size of the property and when you’re traveling. Simply enter your travel dates into Vrbo and how many guests to view vacation rental options and prices. From there you can use our filters to refine your search by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Winchendon?
Pack a tug toy and treats for the pup in your life because Winchendon has four properties that open their doors to pets. Let your four-legged buddy join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check the “Pets allowed” filter box.
What are popular rental amenities in Winchendon?
A firepit, a lake view and a barbecue grill rank as the most popular rental amenities in Winchendon. Whether you’re taking to the road alone, with a partner or a group of best friends, Vrbo will help you find a vacation rental that matches your tastes with a load of extras you’ll love.
Are there large group vacation rentals in Winchendon?
You’ll find four properties in Winchendon that can sleep five or more people. From family getaways to a special event, these stays have ample space to spend time with your favorite people.
Are there vacation rentals in Winchendon that welcome kids?
Winchendon has four family-friendly vacation homes to choose from. And booking a stay that welcomes little ones is simple with Vrbo’s “Properties good for families” filter. As well as having the entire place to yourselves, you’ll also get access to perks and amenities such as multiple bedrooms, yards and private pools.
What are the top attractions for families in Winchendon?
Enjoy a day out with the family at Lake Dennison State Recreation Area. This awesome attraction is within easy reach of the center of Winchendon.
Are there vacation rentals with WiFi in Winchendon?
Whether you’d like to stay in touch with the news, check emails or surf social networks, there are two vacation homes with WiFi in Winchendon. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Winchendon?
Select your dates and then use the filter tool to search for vacation rentals with ac in Winchendon on Vrbo. With four air-conditioned properties on offer here, you can look forward to a cool and comfortable trip.
How old do you have to be to rent a vacation rental in Winchendon?
The age limit can differ across properties on Vrbo, so double-check the rules of the vacation home in Winchendon you’re considering. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Winchendon for?
It really depends on the Winchendon property. To see all available options offering extended stays, just type your travel dates and guest number into Vrbo’s search page. You can enjoy having the entire place to yourself, along with comforts such as air conditioning, a fully-equipped kitchen and outdoor spaces where the kids can run and play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Winchendon?
Whether you’ve got your eye on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some fabulous bargains and discounts on Vrbo. From weekend retreats to extended vacations, we’ve got the ideal space for your next Winchendon escape.

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