Lee vacation rentals

We found 833 vacation rentals — enter your dates for availability

Discover a selection of 43 homes, 10 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:May 22 - May 29

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10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Best of the Berkshires & Hudson Valley

Canaan

9% off
Price is $506
$3,544 for 7 nights
All fees included
Best of the Berkshires & Hudson Valley

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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, Massachusetts, United States of America when booking a vacation rental?
When looking for a great area to stay in Lee, Massachusetts, you might consider the charming downtown neighborhood. This area boasts a delightful mix of historic architecture and modern amenities, making it a pleasant spot for visitors. Here, you'll find a variety of vacation rentals, ranging from cozy cottages to spacious homes, which cater to different preferences and group sizes.

One of the top attractions in downtown Lee is the picturesque Lee Premium Outlets, where shopping enthusiasts can explore a range of brand-name stores at discounted prices. Additionally, the nearby Laurel Lake offers opportunities for outdoor recreation, including swimming, fishing, and picnicking, making it a wonderful spot to relax and enjoy nature.

Another appealing area is the peaceful surrounding countryside, where you'll discover serene vacation rentals located among the trees. This location provides easy access to the scenic hiking trails of the nearby Berkshire Mountains and the cultural experiences offered by the renowned Tanglewood music venue.
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 ski resort rentals near Lee, Massachusetts, the best options are concentrated around the popular area of Butternut Ski Area, which is just a short drive away. Travelers can find a variety of cozy cabins and vacation homes in the surrounding towns of Great Barrington and Stockbridge. These accommodations often feature rustic charm, with amenities such as wood-burning fireplaces, fully equipped kitchens, and outdoor decks superb for relaxing after a day on the slopes.

In Great Barrington, you'll find properties that provide easy access to local shops and restaurants, enhancing the overall experience for visitors. Many rentals here come with added conveniences like ski storage, laundry facilities, and spacious living areas, suitable for families or groups.

Moreover, Stockbridge offers a more tranquil atmosphere, with options ranging from historic inns to modern lodges. Some properties may include access to hot tubs, fire pits, or even game rooms, making them ideal for unwinding in the evenings. With the scenic beauty of the Berkshires surrounding these areas, travelers can also enjoy year-round outdoor activities, such as hiking and exploring nearby cultural attractions.
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 throughout the area. These spacious homes are often located in serene settings, making them superb for families or groups looking to enjoy the natural beauty of the Berkshires. Most vacation houses come equipped with fully furnished kitchens, comfortable living areas, and outdoor spaces for relaxation and gatherings. Additionally, there are several apartments, cottages, chalets, and condos available, offering various options for travelers. These alternative accommodations typically feature similar amenities, such as kitchen facilities and cozy living spaces, suiting a range of preferences.
Are there any family house rentals in Lee?
In Lee, Massachusetts, families will find a variety of vacation rentals—about 36 suitable options throughout the area. This charming town is close to popular attractions such as the Berkshire Theatre Festival and the beautiful parks surrounding the nearby Stockbridge Bowl. Many of these homes feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces where children can play or families can enjoy barbecues.

Visitors can also expect amenities like Wi-Fi, air conditioning, and sometimes even game rooms or fireplaces, ensuring a comfortable stay. The locale is great for exploring the natural beauty of the Berkshires, with opportunities for hiking, biking, and enjoying local events.
Can I rent a vacation home with a pool or hot tub in Lee?
In Lee, Massachusetts, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing destination for travelers seeking relaxation. The area is known for its beautiful natural surroundings, including the scenic Berkshire Mountains, which provide a tranquil backdrop for your getaway. Many of these rentals come equipped with private pools and hot tubs, along with spacious outdoor areas superb for enjoying the fresh air. Inside, travelers can expect amenities such as fully equipped kitchens, cozy living spaces, and sometimes even game rooms for family entertainment.
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, making it a great destination for travelers who wish to bring their furry companions along. The vacation rentals in this area often feature comfortable amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, including patios or yards where pets can enjoy the fresh air.

Many of these rentals are conveniently located near local parks and outdoor recreational areas, providing opportunities for walks and playtime with pets. The serene landscapes of the Berkshires surround Lee, offering beautiful views and hiking trails that are pet-friendly, ensuring that both you and your pet can enjoy the natural surroundings.
Are there any remote work vacation rentals in Lee?
In Lee, Massachusetts, there are numerous options for remote work vacation rentals, with around 48 available in the area. Travelers can expect a variety of properties equipped with essential amenities for a productive stay, such as free Wi-Fi, dedicated workspaces, and comfortable chairs. Many rentals also provide additional conveniences like kitchens for preparing meals and spacious living areas for relaxation after work hours.

The town is situated in the beautiful Berkshires, offering access to outdoor activities and cultural attractions. Nearby points of interest include the picturesque Laurel Lake and the vibrant town center, where local shops and eateries can be explored during breaks. 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, Massachusetts, vacation rentals are favored for their variety of amenities that enhance the guest experience. Most properties include kitchens, allowing travelers to prepare their own meals and enjoy a home-cooked dining experience. Many rentals also feature decks or patios, providing outdoor spaces for relaxation or gatherings amidst the beautiful natural surroundings. Onsite parking is commonly available, making it convenient for guests traveling by car. Additionally, properties often come equipped with coffee and tea makers for a comforting morning routine, and fireplaces that add warmth and ambiance, especially during the cooler months.
When is the best time to visit Lee for a vacation rental?
The peak season for visiting Lee, Massachusetts, falls between June and August, with July being the most popular month. This vibrant period attracts travelers seeking to enjoy the beautiful summer weather and partake in outdoor activities such as hiking and exploring the picturesque local parks. With temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, visitors can comfortably engage in sightseeing and enjoy the natural beauty of the Berkshire region.

During the summer months, Lee transforms into a hub of activity, with numerous festivals and events that cater to various interests. From art shows to music festivals, there's something for everyone, making it an excellent time for travelers.

For those looking for more budget-friendly options, consider visiting in November. This quieter month allows for a more tranquil experience, with stunning fall foliage still visible early in the month. You can enjoy scenic walks and cozy evenings, all while benefiting from lower rental rates.

Ultimately, your choice of when to visit Lee will depend on whether you prefer the lively energy of summer activities or the peaceful charm of late fall.
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, Massachusetts, United States of America?
In Lee, Massachusetts, visitors can enjoy a mix of natural beauty and cultural attractions. The quaint downtown area offers charming shops and restaurants, providing a pleasant spot to explore local flavors. Just a short drive away, the picturesque Laurel Lake is superb for swimming, kayaking, and fishing, making it a popular destination for outdoor enthusiasts.

For those interested in history and art, the nearby Berkshire Museum in Pittsfield features a diverse collection of art, science exhibits, and local history, showcasing the region's rich heritage. The area is also known for its proximity to Tanglewood, the summer home of the Boston Symphony Orchestra, where visitors can enjoy world-class performances in a stunning outdoor setting during the warmer months.

Nature lovers will appreciate the scenic hiking trails and beautiful landscapes in the nearby October Mountain State Forest, offering ample opportunities for outdoor activities year-round.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

Frequently asked questions

Can I find a vacation rental in Lee?
Yes, you can find vacation rentals in Lee near Berkshire Scenic Railway Museum, or you can go with a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and museums in Lee. Leave plenty of time to check out the shops and lakeside during your trip.
How many vacation rentals are there in Lee?
Choose from 43 Expedia vacation rentals in Lee for a memorable vacation.
What can I see and do in Lee?
Cultural attractions include Berkshire Scenic Railway Museum and Animagic Museum of Animation, whereas Goose Pond Reservation and Tyringham Cobble are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Berkshire Mountain Country Store and Lee Premium Outlets.
What are vacation rentals like in Lee?
Vacation rentals are privately owned properties you can book for several days or longer in Lee. Vacation rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.

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