Discover a selection of 500 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 WiFi. Prices start at $76 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.
Top rated rentals — Lee
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.

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 Albany Intl. Airport (ALB), located 41.8 mi (67.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Bradley Intl. Airport (BDL), which is 38.7 mi (62.3 km) away.

What are the top vacation rentals in or near Lee?

Whatever vacation experience you're seeking, you'll find a rental in or around Lee that's a match made in heaven. Why not try these on for size?:

  • "Close To Skiing Beautiful +family Friendly" is a favorite with guests. Around 17 miles from Lee, it has 4 bedrooms and lots of handy amenities, including cable/satellite TV services and a washing machine.
  • Alternatively, make your home away from home at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". Located around 15 miles from the heart of Lee, it has 4 bedrooms and features a bicycle and a separate dining area.

For even more great options, use the search bar at the top of the page to find the perfect Lee vacation rental for you.

Can I find log cabins to rent in or near Lee?

You can. From simple hideaways to high-end escapes, we've got an impressive range of log cabins to rent in or near Lee. If the great outdoors is calling, look no further:

  • "Water Front Log Cabin Next To Tanglewood": At this cabin, you'll be perfectly placed to experience the exciting outdoor activities offered in this region, including windsurfing and snowboarding.
  • "Cozy Log Cabin Adjacent To Beartown Forest": Spend your time enjoying all the conveniences of this unique property. When it's time to get active, skiing and snowmobiling will get your blood flowing.

What are the top-rated vacation rentals for weekend getaways in or near Lee?

Clock out on Friday afternoon and then pack your carry-on bag. If it's time for some relaxation and fun, these properties in and around Lee promise an awesome weekend getaway:

  • Spend your whirlwind escape at "Elterwater - - Your Lakefront Oasis", which is around 14 miles to the southwest of central Lee. There's plenty of nature and adventure to keep you happy here. Go mountain biking and sledding or simply explore the sights of Housatonic River Walk and McLennan Reservation.
  • "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" is another great property to consider. Around 14 miles northeast of Lee, use it as a base to do a little golf or hiking and biking. Historic Summit House and Umpachene Falls Park should also be on your itinerary if you stay here.

Can I find studio apartments for rent in and around Lee?

Enjoy the culture and vibe of Lee from the privacy and comfort of a studio apartment. Whether you'd like to kick back on your own or have some fun with pals, we'll help you find the perfect studio apartment in or near Lee:

  • Get out and explore from the comfort of "The Clearing - Quiet - Close To Nature". This vacation rental is a popular base for sightseeing and offers amenities including a living room and a fridge.
  • "Cabin - A - Frame In Sherwood Forest" is another awesome option. Get cozy and enjoy the use of a kitchen, coffee and tea making facilities and more.

There are plenty of sights around Lee to add to your itinerary. Nourish your inner culture vulture by visiting Merrimack Repertory Theater and Peabody Essex Museum.

Can I find short term rentals in or near Lee?

Just because you only have a couple of days off work doesn't mean you have to spend it in a bland hotel. Head off on vacation but still have the home comforts you love at one of these short-term rentals in or around Lee:

  • "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" is close to the heart of Lee, which means you'll have lots of things to entertain you. Make your way to unique attractions like Walden Pond and Louisa May Alcott's Orchard House when you're not kicking back in your cozy digs.
  • Leap out of bed, make some breakfast and then begin planning what to see around "Unique People And Pet - Welcoming Country Haven". Old Manse and Concord Visitors Center should be on your itinerary if you choose to stay at this top-rated rental.

What are the best romantic weekend getaways in or near Lee?

Nothing says "I love you" quite like a romantic weekend rendezvous. If you're eager to spend a couple of nights away with your sweetie, we've got some romantic getaways in and around Lee that will set your hearts aflutter:

  • Put on some soft music and kick back together at "Close To Skiing Beautiful +family Friendly". Around 17 miles from Lee, this property has everything you could want for a romantic weekend away, including a fireplace and skiing facilities.
  • Alternatively, spend your break sipping wine and canoodling at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", around 15 miles from Lee. A restaurant dining guide and shopping facilities will help set the mood for romance.

What are the best houses for rent with a pool in or near Lee?

Of all the conveniences a vacation rental can offer, a pool is hands down the most fun. Take a peek at these houses for rent with a pool in or near Lee and spend your days splashing about. Just remember to take your flamingo floatie:

  • Pack your swimsuit and take a break at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". There are also lots of other great amenities here, including childrens activities and a microwave oven.
  • Spend leisurely days splashing about or finding some peaceful moments beside the water at "General Williams Estate House Lenox". This vacation home is also a firm favorite and offers a toaster, on-site watersports and more.

Wondering what the weather's like in Lee? It has a humid continental climate, with average summertime temperatures ranging from 55 ºF to 75 ºF. If you're searching for more inspiration on places to stay in this popular destination, use the search bar at the top of the page and adjust the filters to look through our entire range of Lee vacation rentals.

What are the best large family vacation rentals in or near Lee?

A family get-together should be memorable. Whether you're organizing a fun escape with the kids or that long-overdue family reunion, these large family vacation rentals in or near Lee offer a home away from home with plenty of space for everyone:

  • Get everyone together at "88 Acres Of Beauty In The Berkshires", which has 4 bedrooms that sleep up to 9 guests. This retreat is around 17 miles to the southwest of Lee and comes with amenities such as coffee and tea making facilities and a garden.
  • "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi" also has the space you need to connect with the ones you love. This option is around 15 miles to the southeast of Lee, and accommodates 10 guests in its 4 bedrooms. A balcony and cable/satellite TV services will help keep everyone content and comfortable.

When you want to step outside your front door, there are loads of family-friendly attractions in the area to keep everyone entertained. New England Aquarium, Newbury Street and CoCo Key Water Resort - Boston should be on your agenda.

Can I find family cabin rentals in or near Lee?

Nothing is more important than family, which is why we'll help you find a space where you can truly connect. Rent one of these family cabin rentals in or near Lee and make memories with your loved ones:

  • "Cabin - A - Frame In Sherwood Forest" - Located around 9 miles east of the center of Lee, this family-friendly retreat offers amenities like a fridge and pet-friendly facilities.
  • "Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating" - Another fabulous choice, this vacation rental comes with a fridge, a toaster and more. You'll find it around 11 miles to the southeast of Lee.

For more options, use the search bar at the top of the page and adjust the filters to find the Lee vacation rental that's perfect for your needs.

What are the best large houses to rent with indoor pools in or near Lee?

Add a splash of indulgence to your vacation by booking someplace with a private indoor pool. These large houses in or near Lee have a swimming space to call your own, as well as plenty of room for whoever you're inviting along:

  • With 3 bedrooms that can fit up to 8 people, "Equipped Villa With Access To Pools" is the perfect place to escape to with your family or friends. Make use of this property's many amenities, such as a swimming pool and a sauna.
  • Alternatively, treat your gang to a stay at "Private, Mountain Retreat With Indoor Pool And Fantastic Westward Mountain Views", which has 5 bedrooms and accommodates up to 10 guests. Along with that chic pool at your beck and call inside, a sauna and a kitchen will keep everyone comfortable and content.

Eager for more options? Find the perfect pad among these the search bar at the top of the page. Simply adjust the filters to find the Lee vacation rental that's perfect for you.