Lee vacation rentals

We found 824 vacation rentals — enter your dates for availability

Discover a selection of 44 homes, 11 apartments, and other vacation rentals in Lee that are perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. No matter what you're looking for, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Lee

Showing deals for:Dec 5 - Dec 12

Image gallery for Spacious Luxury Berkshire's Estate on 21 acres

Exterior
10 out of 10 rating
Exceptional
(7 reviews)

Spacious Luxury Berkshire's Estate on 21 acres

Pittsfield, MA

9% off
Price is $1,290
$9,027 for 7 nights
All fees included
Spacious Luxury Berkshire's Estate on 21 acres

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Find out more about Lee

Find out more about Lee

Why visit Lee

  • Scenic Natural Beauty: Lee is surrounded by stunning landscapes, including serene lakes and beautiful state parks, perfect for outdoor activities.
  • Charming Neighborhoods: Explore vibrant neighborhoods filled with unique shops, restaurants, and historic homes that showcase local culture.
  • McLennan Reservation: Enjoy a peaceful retreat at this tranquil preserve, ideal for relaxation and nature walks.
  • Diverse Accommodation Options: Choose from cozy cottages to spacious vacation rentals, ensuring a comfortable stay.
  • Family-Friendly Activities: Lee offers a variety of fun experiences for families, making it a great vacation destination for all ages.

Popular types of accommodation in Lee

When it comes to vacation rentals in Lee, you'll find an array of options to suit your needs, including houses, cozy cottages, and modern condos. Whether you're seeking spacious house rentals or charming vacation homes, our platform offers transparency and reassurance to help you choose the best amenities for a memorable stay. Explore the variety of Lee vacation rentals and discover the perfect place for your getaway.

  • Houses: The top choice for travelers in Lee, offering spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Condos: A popular option that combines home-like amenities with resort-style facilities, ideal for those wanting modern conveniences.
  • Cottages: Quaint and charming, these cozy retreats are perfect for a romantic getaway or a peaceful solo escape.
  • Cabins: Rustic and nestled in nature, cabins provide a serene atmosphere for outdoor enthusiasts.
  • Apartments: Convenient and often centrally located, apartments are great for travelers looking for flexibility and easy access to local attractions.**

Top attractions near Lee

Lee, Massachusetts, is a fantastic destination for romantic getaways, family vacations, and entertainment-themed trips. Visitors can explore a variety of attractions, including historic houses, scenic lakes, and beautiful preserves. With options for culture, outdoor activities, and adventure experiences, Lee offers something for everyone, making it an ideal spot for travelers seeking a memorable experience in the heart of the Berkshires.

  • National Shrine of the Divine Mercy: Located just 3 miles from Lee, this serene shrine offers a unique spiritual experience with beautiful grounds and a peaceful atmosphere, perfect for reflection and prayer.
  • The Mount: Also 3 miles away, this historic house was once the home of author Edith Wharton. Visitors can explore its stunning gardens and architecture, capturing the essence of early 20th-century elegance.
  • Norman Rockwell Museum: Situated 5 miles from Lee, this art museum showcases the iconic works of Norman Rockwell, featuring captivating exhibitions that celebrate American culture and storytelling through art.

Things to do recommended for couples

For a romantic getaway in Lee, enjoy a concert at Tanglewood Music Center, just 5 miles away, or hit the slopes at Ski Butternut, 9 miles from town. Don’t miss a visit to Furnace Brook Winery at Hilltop Orchards for a delightful wine tasting experience, also 9 miles away.

Things to do recommended for families

Families will love exploring Goose Pond Reservation and Tyringham Cobble, both offering serene environments perfect for relaxation and wellness. Enjoy outdoor activities like hiking and picnicking while immersing yourselves in the natural beauty of Lee, Massachusetts.

Things to do recommended for groups

Experience a delightful shopping spree at Lee Premium Outlets, explore the cultural charm of Shakespeare and Company, and visit the Berkshire Mountain Country Store for unique finds—all perfect for creating memorable moments with your group in Lee, Massachusetts.

*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

If you're traveling with friends, family, bringing pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Lee with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search for all of 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 finding suitable amenities like a private swimming pool. Additionally, considering how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Lee: For many families, a vacation wouldn't be complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Lee: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Lee

Lee, Massachusetts, offers a delightful blend of romantic getaways, family-friendly activities, and entertainment options. Explore charming neighborhoods and vibrant city life while enjoying the scenic beauty of nearby state parks. Don't miss the serene McLennan Reservation for a relaxing escape. Whether you're seeking adventure or a peaceful retreat, Lee provides the perfect atmosphere to create unforgettable memories on your vacation.

  • Lenox: Located 4 miles from Lee, Lenox is a charming city known for its rich cultural scene and romantic ambiance. It’s an ideal destination for those seeking entertainment, family fun, or a couples’ getaway. Visitors can enjoy a variety of activities, including music concerts and theatrical performances, which are abundant in this artistic town. Outdoor enthusiasts will appreciate the nearby lakes and mountains, perfect for hiking and relaxing. Notable venues include event conference spaces that host seasonal festivals and community events throughout the year.
  • The Berkshires: Situated 11 miles from Lee, The Berkshires offers a stunning landscape that attracts outdoor adventurers and nature lovers alike. With its picturesque lakes and majestic mountains, this region is a haven for skiing and other outdoor activities. The numerous ski fields and resorts in the area cater to all levels of experience, making it a perfect spot for families and thrill-seekers. The breathtaking scenery provides a backdrop for hiking, biking, and exploring, ensuring a memorable experience for every visitor.
  • Great Barrington: Just 9 miles from Lee, Great Barrington is a vibrant city that draws sports enthusiasts and adventure seekers. Known for its excellent skiing opportunities, the area boasts several ski fields and resorts that promise exciting winter sports experiences. Beyond skiing, visitors can explore the nearby national state park, offering trails for hiking and stunning views of the surrounding wilderness. The combination of recreational activities and natural beauty makes Great Barrington a must-visit destination for those looking to embrace the great outdoors.

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 HighAverage
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
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

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash on the full booking amount. Being the organizer certainly has its perks. Enroll in our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash on eligible stays. Sign up today and begin enjoying your rewards.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up right where you left off, or keep track of your travel arrangements. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore the features of 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?
When planning a vacation in Lee, Massachusetts, one of the best areas to consider for your stay is the charming downtown area. This vibrant neighborhood boasts a variety of vacation rentals, offering visitors a blend of convenience and local culture. Staying here puts you within walking distance of delightful shops, art galleries, and a selection of restaurants that highlight the region's culinary scene.

One of the top attractions nearby is the Lee Premium Outlets, great for those looking to enjoy some retail therapy with a range of brand-name stores. Additionally, the picturesque Laurel Lake offers opportunities for outdoor activities like swimming, kayaking, and picnicking, making it a great spot for families or anyone looking to enjoy nature.
How much does it cost to rent a vacation home in Lee?
Prices for vacation rentals in Lee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Lee to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Lee vacation house rentals?
You can find great discounts on house rentals in Lee on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Lee ski resort rentals?
For the best ski resort rentals near Lee, Massachusetts, travelers should focus on the nearby area of Berkshire County, particularly around the town of Great Barrington. This region is home to several ski areas, with Butternut Ski Area being a popular choice for winter sports enthusiasts, located just a short drive from Lee.

In Great Barrington, visitors can find a variety of accommodations, including cozy cabins and modern condos that cater to families and groups. Many of these properties offer amenities such as fully equipped kitchens, spacious living areas, and outdoor decks, great for enjoying the snowy landscape. Some rentals may also provide hot tubs or fireplaces, ideal for unwinding after a day on the slopes.

Additionally, the nearby town of Stockbridge features charming inns and boutique hotels, some of which have easy access to ski areas and offer amenities like complimentary breakfast, ski storage, and comfortable lounge areas. Proximity to local dining and shopping adds to the convenience for travelers looking to explore the vibrant cultural scene in the Berkshires.

For those looking to combine skiing with other outdoor activities, the surrounding areas provide excellent opportunities for snowshoeing and cross-country skiing, enhancing the winter experience.
What is the most popular type of vacation rental accomodation in Lee?
In Lee, vacation houses are the most popular type of rental, with about 38 available in the area. These homes typically offer spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many houses also feature outdoor areas such as decks or patios, superb for enjoying the scenic views of the Berkshires. Additionally, there are around 10 apartments available, providing a more compact option for travelers who prefer a cozy feel. For those seeking a quaint experience, several cottages and chalets can be found, offering cozy settings close to local attractions like the Norman Rockwell Museum and the picturesque downtown area.
Are there any family house rentals in Lee?
In Lee, Massachusetts, there are numerous family-friendly house rentals available, with about 35 options to choose from. This charming town offers a great base for families looking to explore the beautiful Berkshires. Many homes come with spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for children to play. Visitors can often find amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay.

The surrounding area is rich in outdoor activities, with nearby attractions like Tanglewood, where you can enjoy live music in the summer, and the scenic trails of the Appalachian Trail for hiking enthusiasts.
Can I rent a vacation home with a pool or hot tub in Lee?
In Lee, Massachusetts, travelers can find several vacation homes available for rent that come equipped with pools and hot tubs. This charming town, located in the Berkshires, offers a serene escape with beautiful natural surroundings. Many of these properties feature private pools, outdoor decks, and hot tubs, providing the superb setting for relaxation after a day of exploring the area. Amenities commonly found in these rentals include fully equipped kitchens, spacious living areas, and outdoor spaces ideal for barbecues or family gatherings. Additionally, Lee's proximity to outdoor activities such as hiking, biking, and lakes adds to the appeal of vacationing in this area.
Can I find long-stay vacation rentals in Lee?
A long-stay vacation rental in Lee is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Lee?
In Lee, Massachusetts, there are several pet-friendly house rentals available, providing a great option for travelers who want to bring their furry friends along. Many of these rentals are situated in close proximity to scenic areas and outdoor activities, making it a superb spot for pet owners. Properties often feature amenities such as fenced yards, pet-friendly furnishings, and spacious living areas, allowing for a comfortable stay for both pets and their owners.

The town is conveniently located near the Berkshire Mountains, offering access to numerous hiking trails where pets are welcome. Additionally, there are local parks and open spaces that provide opportunities for leisurely walks and outdoor play. See all pet-friendly rentals in Lee.
Are there any remote work vacation rentals in Lee?
In Lee, Massachusetts, there are numerous vacation rentals that cater to remote work needs, with around 47 options available. The picturesque town, located in the Berkshires, provides a serene environment ideal for those looking to blend work and leisure. Many of these properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated workspaces with desks and chairs, and even computer monitors in some cases.

Travelers can expect cozy accommodations that often feature comfortable living areas, fully equipped kitchens, and outdoor spaces to enjoy the beautiful surroundings during breaks. The town offers easy access to local attractions such as the Norman Rockwell Museum and the scenic hiking trails of the nearby October Mountain State Forest, making it a great destination for both productivity and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lee vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Lee with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Lee?
In Lee, popular vacation rental amenities include WiFi, kitchens, blenders, coffee and tea makers, and patios. Travelers can expect to find comfortable accommodations equipped for cooking and dining, allowing for a home-like experience during their stay.
When is the best time to visit Lee for a vacation rental?
The best time to visit Lee, Massachusetts, is during the peak summer months of June through August, with July being particularly popular among travelers. This season is ideal for those looking to enjoy outdoor activities, as the warm temperatures (ranging from the mid-60s to mid-80s Fahrenheit) invite exploration of the beautiful Berkshire countryside. Visitors can partake in hiking, biking, and scenic drives, all while soaking in the stunning natural beauty and vibrant local culture.

July brings a bustling atmosphere, attracting travelers who come to enjoy festivals, art events, and the array of outdoor concerts that the region has to offer. Whether you're wandering through the charming downtown or visiting nearby attractions, there are plenty of opportunities to engage with the local community and experience the best of what Lee has to offer.

For those considering a visit on a budget, November presents a wonderful opportunity to experience the enchanting fall scenery while avoiding the crowds.
How early should I book a Lee vacation rental?
Book your Lee vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Lee?
In Lee, Massachusetts, visitors can enjoy a variety of attractions located in the picturesque Berkshire Mountains. The town is known for its beautiful outdoor spaces, including the nearby October Mountain State Forest, which offers hiking trails and opportunities for birdwatching. Vacation rentals in this area often provide easy access to nature and stunning views of the surrounding landscape.

Additionally, Lee is conveniently located near the charming town of Stockbridge, home to the Norman Rockwell Museum, which showcases the works of the famous American artist. The historic downtown area of Lee features quaint shops and local dining options, allowing travelers to immerse themselves in the local culture. For those interested in winter sports, the nearby ski resorts in the Berkshires, such as Butternut Basin, provide easy access for skiing and snowboarding enthusiasts during the colder months.
Can I change or cancel my Lee home rental booking on Vrbo?
To find Lee vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Lee vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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