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Wellesley holiday lettings

We found 2,171 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 7 homes and other holiday rentals in Wellesley that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and parking. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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  • Peace of mind
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  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
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    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Wellesley getaway

The gardens and other outdoor surroundings create an inviting atmosphere in Wellesley. Renowned for its university setting, basketball games and ice skating, this city welcomes all visitors. Fenway Park and TD Garden are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Wellesley

Do you want to discover attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that Wellesley has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • New England Aquarium (13.1 mi / 21.1 km)
  • Encore Boston Harbor (13.4 mi / 21.5 km)
  • Massachusetts Horticultural Society's Gardens at Elm Bank (1.6 mi / 2.6 km)
  • Samuel Adams Brewery (9.8 mi / 15.7 km)
  • Franklin Park Zoo (10.4 mi / 16.7 km)
  • Blue Hills Ski Area (10.6 mi / 17.1 km)

Exploring the natural features in Wellesley

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Wellesley is a great place to get outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Copley Square (11.6 mi / 18.7 km)
  • Boston Common (12.2 mi / 19.7 km)
  • Cochituate State Park (4.4 mi / 7.1 km)
  • Walden Pond (10.1 mi / 16.3 km)
  • Back Bay Fens (10.7 mi / 17.2 km)
  • Minute Man National Historical Park (10.9 mi / 17.6 km)

Transport options to and around Wellesley

Fly into Norwood, MA (OWD-Norwood Memorial), the closest airport, located 9.6 mi (15.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Bedford, MA (BED-Laurence G. Hanscom Field), which is 11.5 mi (18.6 km) away.

If you're travelling by train, Wellesley Square Station, Wellesley Hills Station and Wellesley Farms Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in Wellesley when booking a holiday rental?

Babson Park is among the more sought-after locations for a holiday property in Wellesley. Stay here to enjoy the comfort and privacy that comes with having an entire place to yourself.

What is the most popular type of holiday rental accommodation in Wellesley?

Houses are the most popular style of holiday rental in Wellesley, according to our data. Even if you've got something else in mind, Vrbo has holiday homes in many shapes and sizes. Take a look at our options to find your ideal match.

How much does it cost to rent a holiday rental in Wellesley?

Different things determine what you'll pay for a holiday rental in Wellesley, including the time of year, length of stay and property type. However, all of our holiday homes have one thing in common — unbeatable value. Just enter your travel dates to find your ideal fit.

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

Prices for beach houses in Wellesley may differ depending on the size and type of the property and when you plan to travel. Just enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use our filter tool to tailor your search by ratings, amenities, nearby activities and more.

Are there pet-friendly holiday rentals in Wellesley?

With 10 properties that welcome pets, your furry friend can join in on your Wellesley getaway. Use our filter tool to browse our pet-friendly holiday rentals and find a stay that's pawfect on Vrbo.

What are popular rental amenities in Wellesley?

A barbecue grill, tennis and nearby museums rank as the most popular rental amenities in Wellesley. Whether you plan to go by yourself, with your better half or a group of friends, Vrbo can help you find a holiday rental that matches your style with all the features you're looking for.

Are there large group holiday rentals in Wellesley?

You'll find three properties in Wellesley that can host a group of five or more guests. From family getaways to events like a friend's birthday, these stays have enough space to chill out with your favourite people.

Are there holiday rentals in Wellesley that welcome kids?

Wellesley has 10 family-friendly holiday homes to pick from. And securing a stay that welcomes kiddos is a cinch with Vrbo's "Properties good for families" filter. Besides having the entire place to yourselves, you'll enjoy access to perks and amenities such as multiple bedrooms, full kitchens and private pools.

What are the top attractions for families in Wellesley?

Keep the kids amused at these popular family-friendly attractions in Wellesley:

  • Legacy Place
  • Fun and Games Family Entertainment Centre
  • Larz Anderson Auto Museum

Can I find two-bedroom holiday rentals in Wellesley?

Wellesley has two two-bedroom holiday properties for you to select from. Find a holiday home with all the privacy and comfort you want at a price that won't break the bank on Vrbo.

Are there holiday rentals with WiFi in Wellesley?

You can pick from three holiday rentals with WiFi in Wellesley. If you'd like to disconnect from the world during your escape, but still want to be connected to the internet, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find holiday rentals with air conditioning in Wellesley?

Select your travel dates and then use our filter tool to find holiday rentals with ac in Wellesley on Vrbo. With eight air-conditioned properties available, you can enjoy a cool and comfortable break.

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