Lee vacation rentals

We found 839 vacation rentals — enter your dates for availability

Nestled in the heart of the Berkshires, Lee captivates with its charming historic architecture and vibrant art scene, inviting travelers to explore picturesque clapboard houses and local galleries. Outdoor enthusiasts can dive into adventure at nearby lakes and scenic reserves, while romantic getaways abound in cozy accommodations. With easy access to captivating destinations like Lenox and Great Barrington, Lee is perfect for groups seeking comfort and convenience, offering vacation rentals that provide the spaciousness and amenities of a true home away from home.

Holiday rentals with weekly discounts - Lee

Showing deals for:Dec 11 - Dec 18

Dining
The great room with wonderful water views and working fireplace
Open kitchen to great room, wonderful for cooking and entertaining
Hot tub overlooking the lake
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

9% off
$607
$4,250 for 7 nights
All fees included
Spectacular setting on your own private lake close to it all!
View of the lower deck from the sunroom
view from the 2nd bedroom
Open plan dining area with water views and access to the sunroom
Workstation with a view!
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
$642
$4,493 for 7 nights
All fees included
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
View of lake through window, table for 6 on right, 4 bar stools at counter
House facing lake with deck above, canoe and kayak stored on ground level.
Stairway to landing with one LR couch, barstools, kitchen in background
Terrace/patio
Exceptional
(169 reviews)

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

Otis

17% off
$251
$1,759 for 7 nights
All fees included
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
House 1- Mountain views from this open concept kitchen, dining, sitting room
Property grounds
3 season Sunroom
Welcome!
Exceptional
(6 reviews)

Grand Estate w/ Mountain Views by Evergreen Home

Ghent

12% off
$794
$5,557 for 7 nights
All fees included
Grand Estate w/ Mountain Views by Evergreen Home
Interior
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

12% off
$544
$3,810 for 7 nights
All fees included
Renovated Pittsfield Colonial by Evergreen Home
Private kitchen
Terrace/patio
Property grounds
Game room
Exceptional
(5 reviews)

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale

8% off
$747
$5,229 for 7 nights
All fees included
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Enclosed porch- view into back yard- dining/game table
Kitchen with counter seating for 4- door on the right to garage
View from entry into living room- perfect spot for relaxing!
Outdoor dining
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

12% off
$486
$3,405 for 7 nights
All fees included
Sophisticated Lenox Retreat by Evergreen Home
Living area
Private kitchen
Terrace/patio
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
$480
$3,361 for 7 nights
All fees included
Beautiful House in the Woods: Huge Yard, Hot Tub
Outdoor dining and grill on the 16' x 20' wooden deck.
You will love dining and working in this rich and colorful room
Staircase
The living room flows into the dining room.
Exceptional
(42 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
$456
$3,195 for 7 nights
All fees included
An In-Town Beauty with Late Checkout
Add a touch of warmth and charm to your dining experience!
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Welcome Home!
Back patio with Hot Tub
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

12% off
$723
$5,061 for 7 nights
All fees included
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Front Staircase
Fully screened porch!
Reading nook with natural lighting
Kitchen with stainless steel appliances
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

13% off
$395
$2,762 for 7 nights
All fees included
Berkshires Colonial on 2 Acres by Evergreen Home
Open floor plan, natural light in a stylish space
Ultimate Relaxation!  The hot tub will be warm and waiting for your arrival
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Welcome Home!
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

12% off
$362
$2,531 for 7 nights
All fees included
Best of the Berkshires + Hot Tub by Evergreen Home
Interior
Terrace/patio
Exterior
Dining
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington

9% off
$315
$2,208 for 7 nights
All fees included
Waterfront Cottage 10 Min From Great Barrington
Living Room

Great Barrington Castle house
Front view of home
Great Barrington Castle
Exceptional
(51 reviews)

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington

9% off
$453
$3,171 for 7 nights
All fees included
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Seamless entertaining with the wide open concept, living room -kitchen- patio
After a hard day on the trails or a long day on the town, relax in this oasis
Enjoy a beautiful crisp night under the lights
Never miss a thing with this expansive open concept kitchen and living room
Exceptional
(29 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

7% off
$506
$3,542 for 7 nights
All fees included
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Blue House side entry from driveway
River view from window
Great room river view
Alfresco dining
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
$332
$2,325 for 7 nights
All fees included
Renovated Colonial on the River! Fantastic Views
Dining
Interior
Exterior
Property grounds
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

9% off
$354
$2,478 for 7 nights
All fees included
Serene rustic cabin in the Berkshires!
Interior
Interior
Pool
Private kitchen
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
$402
$2,813 for 7 nights
All fees included
A Fun Farmhouse Near Ski Butternut
Living area
Private kitchen
Living area
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Southfield

9% off
$849
$5,943 for 7 nights
All fees included
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Kitchen
Interior
Property grounds
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

9% off
$505
$3,535 for 7 nights
All fees included
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Property grounds
Living Room
Back Porch
Front Gardens
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

South Lee

9% off
$414
$2,898 for 7 nights
All fees included
Secluded Family Home in Serene Stockbridge Woods
Private kitchen
Living area
Living area
Terrace/patio
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

8% off
$364
$2,549 for 7 nights
All fees included
Modern Log Chalet - 10 acres, views, and a pond!
2nd  bedroom
Kitchen
Cottage Entrance
Kitchen open to living room
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

Great Barrington

9% off
$215
$1,503 for 7 nights
All fees included
Charming Cottage, New Marlborough Village Green in the Berkshires
Property grounds
Property grounds
We highly recommend the Sauna
After a day in the snow
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

13% off
$322
$2,256 for 7 nights
All fees included
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
  • Peace of mind

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    Enjoy full kitchens, laundry, pools, yards and more
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    More space, more privacy, more amenities — more value
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    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Lee

Why visit Lee

  • Charming Historic Architecture: Explore picturesque clapboard houses that reflect Lee's rich history.
  • Vibrant Art Scene: Immerse yourself in local galleries and cultural events showcasing regional artists.
  • Outdoor Adventures: Enjoy scenic reserves, nearby lakes, and boat rentals for a day of fun on the water.
  • Romantic Getaways: Experience cozy accommodations perfect for couples seeking a peaceful retreat.
  • Proximity to Nearby Cities: Easily venture out for additional entertainment and attractions in surrounding areas.

Popular types of accommodation in Lee

If you're exploring vacation rentals in Lee, you're in for a treat. Our top accommodations include Houses, cozy Condos, and charming Cottages, perfect for any traveler. Looking for something different? Check out our boutique hotel rentals and other hotel options in Lee. No matter your preference, we ensure transparency, savings, and reassurance in every choice you make.

  • Houses: These spacious homes are the top choice for visitors seeking comfort and privacy, ideal for families or groups.
  • Condos: A popular option offering modern amenities and convenient locations, perfect for couples or small families.
  • Cottages: Quaint and charming, these cozy retreats provide a picturesque escape for those wanting a rustic feel.
  • Cabins: Ideal for nature lovers, these secluded spots offer a serene atmosphere and outdoor adventure.
  • Apartments: Great for solo travelers or couples, these rentals offer convenience and easy access to local attractions.**

Top attractions in and around Lee

Lee, Massachusetts, is perfect for a romantic or family getaway, offering a blend of culture, outdoor adventure, and entertainment. Explore historic houses, scenic reserves, and nearby lakes, or enjoy boat rentals for a day on the water. With various rental options available by neighborhood, you can find the ideal summer home to enhance your vacation experience in this charming town.

  • Animagic Museum of Animation: Immerse yourself in the whimsical world of animation at this unique museum in Lee. With a focus on the art and history of animated films, it offers interactive exhibits that will delight visitors of all ages.
  • National Shrine of the Divine Mercy: Located just 3 miles from Lee, this serene shrine is a place of reflection and worship. Experience its beautiful grounds and peaceful atmosphere, perfect for those seeking spiritual enrichment.
  • Norman Rockwell Museum: Situated 5 miles away, this museum showcases the iconic works of artist Norman Rockwell. Explore his captivating paintings and illustrations that depict American life and culture, making it a must-visit for art lovers.

Things to do recommended for couples

Lee, Massachusetts, offers a charming escape for couples. Enjoy a scenic hike at October Mountain State Forest, followed by a cozy dinner at a local bistro. Don't miss a romantic stroll through the picturesque downtown, where quaint shops and art galleries await to be explored together.

Things to do recommended for families

Families will love exploring the interactive exhibits at the Berkshire Museum, enjoying outdoor fun at the Lee State Forest, or visiting the nearby charming shops and eateries in downtown Lee. Don't miss the beautiful scenery at the picturesque Laurel Lake for a perfect picnic.

Things to do recommended for groups

Groups visiting Lee, Massachusetts, can enjoy a scenic hike at Kennedy Park, explore the local art scene at the Lee Art Gallery, and savor delicious meals at charming restaurants. Don't miss a visit to the nearby Berkshire Botanical Garden for a relaxing afternoon immersed in nature.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Lee

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, be sure to refine your search based on your top priorities. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Lee with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Lee with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering how close you are to family-friendly attractions is a smart move.
  • Taking your pets with you to Lee: For many families, a vacation isn't truly fulfilling without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer amenities like food bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Lee: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Lee

Lee, Massachusetts, offers a charming blend of romantic getaways and family-friendly adventures. Explore picturesque clapboard houses and immerse yourself in the local art scene. With its prime location, you can easily venture into nearby cities for more entertainment options. Enjoy the serene landscapes and vibrant atmosphere that make Lee a perfect destination for relaxation and exploration. Whether you’re an art lover or seeking a peaceful retreat, Lee promises an unforgettable experience.

  • Lenox: Located 4 miles from Lee, Lenox is a charming town known for its vibrant cultural scene and romantic ambiance. Visitors flock to Lenox for entertainment-themed experiences, including captivating music concerts and theater performances. Outdoor enthusiasts can enjoy the nearby mountains and lakes, perfect for hiking, picnicking, and water activities. The town also features notable venues for conferences and events, making it a hub for gatherings. Whether you’re indulging in fine dining or exploring local art galleries, Lenox offers a delightful blend of culture and leisure.
  • Great Barrington: Situated 9 miles from Lee, Great Barrington is a dynamic city that attracts adventure seekers and sports enthusiasts alike. Known for its ski resorts and fields, this destination is perfect for those looking to hit the slopes in winter or enjoy outdoor sports during warmer months. The stunning landscapes, including nearby lakes and mountains, provide a picturesque backdrop for hiking, biking, and exploring the breathtaking national state park. Great Barrington's charming downtown area is filled with unique shops, restaurants, and local art, making it a vibrant place to experience the Berkshires.
  • The Berkshires: Just 11 miles from Lee, The Berkshires is a renowned region celebrated for its stunning outdoor scenery and adventurous spirit. Ideal for nature lovers, visitors can partake in various activities such as skiing, hiking, and exploring the beautiful lakes and mountains. The area is home to several ski resorts and fields, catering to winter sports enthusiasts. With its picturesque landscapes and tranquil atmosphere, The Berkshires invites travelers to immerse themselves in the beauty of nature while enjoying arts and culture throughout the region.

Best time to go to Lee

If you're planning a trip to Lee, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1°C)Light RainMostly CloudySlightly LowAverage
February24.6°F (-4.1°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnySlightly HighSlightly High
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighAverage
August68.4°F (20.2°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyAverageAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.5°F (-1.4°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you eager to save on your upcoming journey? Being flexible with your travel dates can help, as prices do tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform to help you plan your trips, continue from where you paused, or manage your travel arrangements. You'll find your saved or booked properties neatly organized into categories: Potential, Upcoming, and Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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.

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.

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.

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.

Frequently asked questions

What is the best area to stay in Lee when booking a vacation rental?
One of the most in-demand areas to choose a vacation property in Lee is Tyringham. Spend your time here and enjoy some must-see attractions, such as Ashintully Gardens and Tyringham Cobble.
What is the most popular type of vacation rental accommodation in Lee?
The most popular types of vacation rentals in Lee are apartments. Hoping for something different? Vrbo offers a variety of options to match our guests' diverse needs, so you'll see properties in all sizes and shapes. The ideal fit is waiting for you — discover yours today.
How much does it cost to rent a vacation rental in Lee?
Season, property type and length of stay are some factors that can influence the price of a vacation home. Simply add your travel dates to find your perfect match. From comfy cottages to expansive luxury villas, all Vrbo vacation rentals provide amazing value.
How much does it cost to rent a beach house in Lee?
The average price for a vacation rental by the beach in Lee depends on when you'll be there and the type and size of property you want. Find prices quickly and easily on Vrbo by entering your preferred travel dates and destination. Then use the handy filters to pick the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.
Are there pet-friendly vacation rentals in Lee?
Good news. There are. You'll have your pick of 51 stays that welcome pets in Lee on Vrbo. Our furry companions also deserve a getaway, so simply use our search function for pet-friendly vacation rentals to find a perfect property where Spot can lap up the fun.
Can I rent a house with a pool in Lee?
Grab your swimsuit and inflatable flamingo, because there are eight houses with a private pool in Lee. Kick back at one of these terrific vacation rentals and every day will be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Lee?
When it comes to rental amenities that people prefer in Lee, a firepit, a lake view and a sauna rank the highest. With Vrbo vacation homes, you'll enjoy choices to suit your taste and style, whether you're going away with friends, relatives or even pets.
Are there large group vacation rentals in Lee?
You can pick from 15 properties in Lee that can accommodate 10 or more people. Whether you're planning a get-together with extended family or a celebration like a birthday, there's enough space to get your group together under the same roof.
Are there vacation rentals in Lee that welcome kids?
Bring the entire family together for an unforgettable adventure in Lee at one of our 51 family-friendly properties. Many of these stays provide amenities that are ideally suited to getaways with youngsters, such as kitchens, multiple bedrooms and patios. Simply click on the "Properties good for families" filter box and select your favorite.
What are the top attractions for families in Lee?
Keep the kids busy at these fabulous family-friendly attractions in Lee:
  • Goose Pond Reservation
  • Lee Premium Outlets
  • Ashintully Gardens
Are there one-bedroom vacation rentals in Lee?
Yes, you'll find five one-bedroom properties in Lee to choose from. A one-bedroom vacation rental is a wonderful option if it's just the two of you or if you're flying solo. Throw in more convenience, space and privacy compared to a hotel, and you've got the makings of a trip to remember.
Can I find two-bedroom vacation rentals in Lee?
Pick from 10 two-bedroom vacation rentals in Lee. Give the kids the second room or fill it with a couple of your best buddies. There's a spot for whoever's fortunate enough to be coming along for the ride.
Are there vacation rentals with WiFi in Lee?
Whether you'd like to stay in touch with the news, send some emails or update your social media, there are 27 vacation homes with WiFi in Lee. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Lee?
There are 47 Vrbo vacation rentals with air conditioning in Lee offering that gentle, cool breeze and extra level of comfort. Simply enter your preferred travel dates and then use our handy filters to look for stays with air conditioning.
How old do you have to be to rent a vacation rental in Lee?
It's advisable to check with the Lee vacation property you're considering on Vrbo as age restrictions vary. However, it's typically 16, 18 or 21.
How long can I rent a vacation rental in Lee for?
The length of time you can book a vacation rental in Lee varies according to the property. Simply enter your selected dates to look at a list of options offering extended stays. With a range of amenities such as kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to discover the perfect place to call your home away from home in Lee.
Does Vrbo offer discounts for vacation homes in Lee?
Short stay or a much-needed extended escape, Vrbo has some incredible bargains and discounts in Lee that'll suit your style and budget. Browse our weekly and monthly discounts on vacation rentals, or see what's just been added with one of our newly listed homes. Whatever kind of getaway you're after, you'll find the ideal place to stay — without spending a fortune.

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