Discover a selection of 490 vacation rentals in Lee, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $75 per night, and houses and cottages are popular options for a stay in Lee. Either way, you'll find a rental for everyone's needs.
Destination guide

Lee is Queen Bee of the Berkshires

If it's charm you want, the quaint town of Lee has it in spades. Nestled in the foothills of Massachusetts' Berkshire Mountains, it's crammed with charming clapboard houses and tall church steeples and is a popular spot to witness the fall foliage. Book a Lee vacation rental and you'll have the best of the Berkshires right on your doorstep. Enjoy a concert at the Tanglewood Music Festival in nearby Lenox, the summer home of the Boston Symphony Orchestra, or visit the Norman Rockwell Museum, the largest collection of Rockwell art in the world.

Things to do

You'd be Berking mad to miss Berkshire's main attractions

A popular family destination, keep the kids occupied with an afternoon at AniMagic, a hands-on museum about animation and special effects. The museum and workshops are run by Oscar-winning visual effects guy Eugene Mamut, and appeals to all ages. For more classical art lovers, visit the Norman Rockwell Museum in the next town of Stockbridge. The Berkshire's are also a big draw for music fans. Visit between June and September, when the Tanglewood Music Festival hits town, and see a concert by the Boston Symphony Orchestra in their summer home.


Lee is Lee-ding the way when it comes to relaxing

If it's a relaxing vacation you want, then make Lee your first stop. Known as the Gateway to the Berkshires, the clutch of rural towns and villages in western Massachusetts, life rolls at a slower pace here. Potter around the antiques shops on Main Street, or catch a concert by the Boston Symphony Orchestra in their summer home in nearby Lenox. If you're more into action than classics, then rent a canoe or go fishing on Laurel Lake. But for a classic experience, see the blazing fall foliage along the Mohawk Trail.


For fabulous fall foliage, visit Lee

There's no bad time to visit Lee, and every season brings something different. Peak season is June, July, and August, when Lee's top vacation rentals are in most demand. The temperatures can reach highs of mid-70s in July and August, which brings plenty of sunshine. Fall is also a popular time to visit, when much of New England bursts into color during the fall foliage. But don't strike out a winter vacation, because when the Berkshires experience a blanket of snow, it turns the charming towns and villages, including Lee, into a dazzling Christmas card scene.

Natural features

Join the hunt for the red October (Forest)

Part of the Berkshires, a clutch of pretty New England towns, Lee is surrounded by the eponymous Berkshire Mountains in Western Massachusetts. The region is dominated by the lush green October Mountain State Forest, where the world-famous Appalachian Trail draws hikers and adventurers from all over the world. One of the forest's most scenic trails is through the Schermerhorn Gorge, where you'll find waterfalls, wildflowers, and rare flora. And come winter, the forest trails become the perfect foil for some brilliant cross-country skiing.

How to get there

Transportation to and around Lee

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 8.5 mi (13.7 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Hudson, NY (HCC-Columbia County), which is 23.7 mi (38.1 km) away.

How many vacation rentals are available around Lee, MA?

Our 2020 property listings offer a large selection of 490 vacation rentals around Lee. From 318 house rentals to 62 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a mountain-view property in Lee?

Would you check out that view?! That's what you'll find yourself saying when you travel out to the hills and indulge in a tranquil high-altitude getaway. Vrbo has 136 mountain vacation rentals available. Of course, that might not be everyone's style. Fortunately, Vrbo has loads more options, including:

  • 129 rural vacation rentals.
  • 68 village vacation rentals.
  • 57 lake-view vacation rentals.

Can I rent a house in Lee?

Instead of booking a cookie-cutter, chain hotel room this vacation, you could just go for a whole house. You'll feel like part of the neighborhood before you know it! There are 275 options currently listed on Vrbo. Prices start from $85 per night. Or perhaps you'd rather go for one of the area's other property types, like:

  • Cottage: 32 vacation homes. Prices start from $100 per night.
  • Apartment: 22 vacation homes. Prices start from $93 per night.
  • Hotel: 19 vacation homes. Prices start from $45 per night.

Can I stay in Lee in a large group?

There's nothing better than being somewhere completely new with your family and loved ones. And the best news is Vrbo has options suitable for large groups. 65 house vacation homes are listed. Presently, they're the top choice here for large groups. Properties in this area that can cater for large groups include:

  • If yours is a party of 6, we offer 172 vacation homes perfect for that size. Spend a night for as little as $85.
  • After a vacation property for 8 guests? We have 147 that will suit. Prices start from $93 a night.
  • Hunting down properties for rent to suit 10 people? You'll be happy to learn we have 71 that will fit the bill. You can book one from just $200 per night.

So don't fear! When you travel with us you can bring your mom, your brother and all your mates to Lee.

Where are the cheapest rentals in Lee?

Teeny tiny hotel rooms are no place to spend your precious vacation moments! Explore our budget-friendly rentals now and make sure everyone in your crew has room to spread out. When it comes to seeking out a great deal, the first place you look should be Taconic. Here, Vrbo has 4 rentals at an average price of $148 a night. Another 11 Vrbo rentals are available in or around Sherwood Forest. With an average price of $253 per night, you're sure to snatch a deal worth boasting about.