Lenox vacation rentals

We found 510 vacation rentals — enter your dates for availability

Select from 45 houses, 11 condos, and other vacation rentals to find the perfect place for your stay in Lenox. Whether you’re staying in a vacation home with family or friends, you'll find the amenities you need and want, which might include WiFi and a pool. Whatever you're looking for, you're sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Lenox

Showing deals for:May 22 - May 29

Image gallery for Ski at Historic Stone Church in The Berkshires

Interior
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Ski at Historic Stone Church in The Berkshires

Lanesborough

9% off
Price is $353
$2,470 for 7 nights
All fees included
Ski at Historic Stone Church in The Berkshires

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Find out more about Lenox

Why visit Lenox

  • Cultural Experiences: Immerse yourself in the rich arts scene, including theaters and galleries that showcase local talent.
  • Outdoor Adventures: Enjoy hiking, biking, and exploring nature preserves and beautiful lakes in the Berkshires.
  • Historic Attractions: Visit charming historic houses that reflect the town's heritage and architectural beauty.
  • Family-Friendly Activities: Engage in fun, budget-friendly activities that cater to visitors of all ages.
  • Cozy Accommodations: Choose from a variety of vacation rentals, including cottages and modern condos, for a comfortable stay.

Popular types of accommodation in Lenox

Planning a getaway to Lenox? You're in for a treat. This charming destination offers a variety of vacation rentals, including houses, cozy cottages, and modern condos. Whether you're seeking spacious house rentals or comfortable vacation apartments, you'll find the perfect spot to unwind. With options available in various sizes, you're sure to enjoy a memorable stay in Lenox.

  • Houses: The top choice for visitors to Lenox, these spacious homes offer comfort and privacy for families and groups.
  • Condos: A popular selection, condos provide modern amenities and often feature stunning views, perfect for a relaxing stay.
  • Cottages: These quaint and cozy homes are ideal for a charming getaway, nestled in nature and full of character.
  • Apartments: A practical option for travelers, apartments offer convenience and accessibility in the heart of Lenox.
  • Cabins: For those seeking a rustic experience, cabins provide a serene escape surrounded by the beauty of the outdoors.**

Top attractions in and around Lenox

Lenox, Massachusetts, is perfect for entertainment, romantic getaways, and family vacations. Visitors can explore a variety of attractions, including historic houses, nature preserves, and beautiful lakes. Whether you're seeking cultural experiences, outdoor adventures, or family-friendly activities, Lenox offers something for everyone, ensuring a memorable trip filled with diverse experiences.

  • National Shrine of the Divine Mercy: A peaceful and spiritual oasis, this shrine offers serene gardens, beautiful chapels, and a unique opportunity for reflection and prayer, enhancing your cultural experience.
  • The Mount: Home of author Edith Wharton, this historic estate features stunning gardens and architecture, allowing visitors to immerse themselves in literary history and artistic inspiration.
  • Norman Rockwell Museum: Dedicated to the iconic American artist, this museum showcases his timeless artwork and provides insight into his creative process, making it a must-visit for art enthusiasts.

Things to do recommended for couples

Planning a romantic getaway in Lenox? Enjoy an enchanting evening at Tanglewood Music Center, hit the slopes at Bousquet Ski Area, or savor fine wines at Furnace Brook Winery. These experiences promise romance and adventure for an unforgettable couple's vacation.

Things to do recommended for families

Families visiting Lenox can unwind at Kennedy Park, a serene recreational area perfect for relaxation. Just a short drive away, Fairfield Brook WMA offers additional outdoor fun and tranquility, making it an ideal spot for a family day out in nature.

Things to do recommended for groups

Groups visiting Lenox can enjoy a captivating performance at Shakespeare and Company, play a round of golf at Wyndhurst Golf & Club, and browse the charming selections at The Bookstore, immersing themselves in the local culture and outdoor vibes of this beautiful area.

*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 Lenox

If you're traveling with a group, with family, bringing your pets, or planning an extended stay, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Lenox with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Lenox with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Lenox: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many 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 Lenox: If you're searching for vacation rentals with special offers 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 rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Lenox

Lenox, Massachusetts, offers a delightful blend of romantic getaways and family-friendly activities. Explore the charming local shops or unwind in scenic vacation rentals that capture the essence of this picturesque town. Nearby attractions provide a relaxing atmosphere perfect for a budget-friendly family vacation. Whether you're seeking a cozy retreat or an adventure-filled escape, Lenox is the ideal destination for a memorable experience in the Berkshires.

  • Pittsfield: Located 7 miles from Lenox, Pittsfield is a vibrant city known for its outdoor adventures and sports experiences. The area is a haven for skiing enthusiasts, with numerous ski fields and resorts nearby. Beyond the slopes, visitors can enjoy stunning landscapes featuring picturesque lakes and mountains. A local favorite is the waterpark, perfect for families looking for a day of fun. Pittsfield's blend of recreational activities and natural beauty makes it a must-visit for adventure-seekers.
  • Great Barrington: Situated 12 miles from Lenox, Great Barrington attracts travelers with its charming blend of outdoor activities and cultural experiences. This city is another hotspot for skiing, offering excellent ski fields and resorts for winter sports lovers. Nature enthusiasts will appreciate the proximity to breathtaking lakes and the renowned national state park, which offers hiking trails and scenic views. Great Barrington's vibrant arts scene, coupled with its outdoor attractions, provides a delightful escape for visitors.
  • Lee: Just 4 miles away from Lenox, Lee is a quaint city that offers a romantic and family-friendly atmosphere. Known for its entertainment options, Lee features a variety of theaters and music concert venues that cater to diverse tastes. For those seeking outdoor fun, the nearby ski fields provide winter activities for all ages. Visitors can also explore local landmarks, including scenic lakes, majestic mountains, and historical monuments, making Lee a delightful addition to your vacation itinerary.

Best time to go to Lenox

If you're planning a trip to Lenox, 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 CloudyModerately 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 SunnyModerately HighAverage
July70.3°F (21.3°C)Light RainMostly SunnyModerately HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnyModerately 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 SunnyModerately LowAverage
December29.5°F (-1.4°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of 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 earn OneKeyCash on the full booking amount. Being the organizer has its perks. Become a member of our One Key rewards program to unlock exclusive savings and accumulate OneKeyCash on eligible stays. Sign up today and start reaping the benefits.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform to help you plan new trips, continue from where you last stopped, or manage your travel arrangements effortlessly. You can easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The lively city of Lenox awaits you

Enjoy the area's museums, live music and art galleries and make a vacation rental your home during your stay in Lenox. Well known for its gardens, yoga and architecture, this scenic city won't disappoint. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Lenox

Are you looking for attractions to visit while you're in the area? Venture out of your vacation home and experience everything that makes Lenox a fun spot to vacation. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Wyndhurst Golf & Club (1.3 mi / 2.1 km)
  • Bousquet Ski Area (4 mi / 6.5 km)
  • Furnace Brook Winery at Hilltop Orchards (5.7 mi / 9.2 km)
  • Ski Butternut (12.2 mi / 19.6 km)
  • Jiminy Peak Mountain Resort (13.7 mi / 22.1 km)
  • Otis Ridge (14.6 mi / 23.5 km)

Exploring the natural features in Lenox

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Lenox is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • The Mount (1.5 mi / 2.4 km)
  • Berkshire Botanical Garden (4.7 mi / 7.5 km)
  • Naumkeag Museum (4.9 mi / 7.9 km)
  • Goose Pond Reservation (7.1 mi / 11.5 km)
  • Queechy Lake (7.5 mi / 12 km)
  • Housatonic River Walk (11.7 mi / 18.8 km)

Traveling to and around Lenox

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 4.7 mi (7.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.8 km) away.

Frequently asked questions

What is the best area to stay in Lenox, Massachusetts, United States of America when booking a vacation rental?
When booking a vacation rental in Lenox, Massachusetts, one of the best areas to consider is the neighborhood surrounding the historic downtown. This charming area offers a delightful mix of quaint shops, local eateries, and cultural attractions. Staying here puts you within walking distance of the renowned Tanglewood Music Center, where you can enjoy world-class performances in a stunning outdoor setting. Additionally, the nearby Shakespeare & Company provides a wonderful opportunity to experience captivating theatrical performances in a picturesque environment.

Another appealing option is the neighborhoods that border the scenic Laurel Lake. This area offers a serene backdrop, great for those who enjoy outdoor activities such as swimming, kayaking, and hiking. The lake itself is a popular spot for relaxation and enjoying nature. There are a variety of vacation rentals available in both of these areas, providing options that cater to different preferences and group sizes.
How much does it cost to rent a vacation home in Lenox?
Prices for vacation rentals in Lenox 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 Lenox 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 Lenox vacation house rentals?
You can find great discounts on house rentals in Lenox 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 Lenox ski resort rentals?
For renting ski accommodations near Lenox, Massachusetts, travelers should focus on the nearby Berkshires, particularly around the town of Pittsfield, which is about a 20-minute drive from the ski areas. The area features a range of vacation rentals, including cozy cabins and charming chalets that cater to both families and groups. Many of these properties come with amenities such as fireplaces, fully equipped kitchens, and hot tubs, superb for relaxing after a day on the slopes.

In Lenox itself, visitors can find lovely inns and bed-and-breakfasts that provide a warm, welcoming atmosphere and often include breakfast as part of the stay. These accommodations are close to cultural attractions like Tanglewood and the Norman Rockwell Museum, offering a great blend of outdoor activities and local arts.

Travelers can also look towards the nearby Jiminy Peak Mountain Resort in Hancock, where ski-in/ski-out condos and lodges can be found. These properties typically feature amenities such as ski storage, on-site dining options, and access to fitness facilities, making them convenient for ski enthusiasts.
What is the most popular type of vacation rental accomodation in Lenox?
In Lenox, vacation houses are the most prevalent type of rental, with about 36 available throughout the area. These homes provide ample space, featuring multiple bedrooms, fully equipped kitchens, and often outdoor patios or decks for enjoying the beautiful surroundings. Many are located in serene neighborhoods, close to cultural landmarks such as the Tanglewood Music Center and the Norman Rockwell Museum, making them ideal for travelers looking to explore the rich artistic heritage of the region.

Additionally, there are several apartments, condos, and cottages that offer a more compact yet comfortable option for visitors, often including amenities like cozy living areas and access to shared facilities.
Are there any family house rentals in Lenox?
In Lenox, Massachusetts, there are some family-friendly house rentals available, with approximately 37 options to choose from. The area is known for its charming New England atmosphere and proximity to various attractions. Many of these homes offer spacious living areas, full kitchens for preparing meals, and outdoor spaces superb for family activities.

Visitors can explore nearby points of interest such as Tanglewood, the renowned summer home of the Boston Symphony Orchestra, or the picturesque gardens at the Edith Wharton Estate. The quaint downtown area features shops and restaurants, adding to the convenience of a family stay.
Can I rent a vacation home with a pool or hot tub in Lenox?
In Lenox, Massachusetts, there are several vacation homes available for rent that feature pools and hot tubs, with around 11 options to choose from. This picturesque town, located in the heart of the Berkshires, is known for its beautiful landscapes and cultural attractions. Many of these properties come equipped with private pools and hot tubs, allowing travelers to unwind in a serene setting after a day of exploring the area.

Travelers can expect amenities such as spacious outdoor areas, fully equipped kitchens for dining in, and cozy living spaces superb for family gatherings. Some rentals may also offer additional features like fire pits and scenic views of the surrounding mountains.
Can I find long-stay vacation rentals in Lenox?
A long-stay vacation rental in Lenox 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 Lenox?
In Lenox, travelers can find a variety of pet-friendly house rentals that cater to both comfort and convenience. With around 13 available options, visitors can expect properties equipped with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces ideal for pets to roam. Many of these rentals are situated near beautiful parks and natural areas, providing ample opportunities for outdoor activities.

The neighborhood is known for its charming atmosphere and proximity to attractions like Tanglewood, a renowned music venue surrounded by scenic landscapes. This makes it a great choice for travelers who want to enjoy cultural events while ensuring their furry friends are welcome. Additionally, the area offers convenient access to walking trails and nature reserves, great for leisurely strolls or more adventurous hikes with pets. See all pet-friendly rentals in Lenox.
Are there any remote work vacation rentals in Lenox?
In Lenox, Massachusetts, there are numerous vacation rentals suitable for remote work, with approximately 55 options available. Travelers can expect properties equipped with essential amenities like high-speed internet, Wi-Fi, and dedicated workspaces, ensuring a comfortable and productive environment. Many rentals also offer cozy living areas, fully equipped kitchens, and outdoor spaces, allowing guests to enjoy the picturesque surroundings during breaks.

The town itself is rich in culture and history, with attractions such as the Tanglewood Music Center and the Edith Wharton Museum nearby, providing a superb balance of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lenox vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Lenox 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 Lenox?
In Lenox, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals and enjoy the convenience of home dining. Many rentals feature onsite parking, making it easy for guests to explore the beautiful surroundings without worrying about finding a spot. Outdoor spaces are also highly sought after; most properties come with decks or patios where visitors can relax and enjoy the fresh air. Cozy fireplaces are a common feature, providing warmth and a charming atmosphere, especially during the colder months. Additionally, coffee and tea makers are typically included, superb for those looking to start their day with a warm beverage while enjoying the scenic views of the Berkshires.
How early should I book a Lenox vacation rental?
Book your Lenox 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 Lenox, Massachusetts, United States of America?
In Lenox, Massachusetts, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural offerings. Tanglewood, located just outside of town, is the summer home of the Boston Symphony Orchestra and features beautiful grounds for outdoor concerts. Vacation rentals in this area often provide easy access to the performances and the scenic landscape.

The Lenox Village Center is charming and filled with quaint shops, galleries, and dining options, making it a delightful place to explore on foot. Nearby, the stunning Edith Wharton's The Mount offers a glimpse into the life of the famed author, set amidst gorgeous gardens and architecture.

For outdoor enthusiasts, the surrounding Berkshire Mountains provide ample opportunities for hiking, particularly in the nearby Kennedy Park, where trails wind through lush forests. Additionally, visitors can explore the picturesque landscapes of the Berkshire Botanical Garden, which showcases a variety of plant species and beautiful designs throughout its grounds.

Cultural attractions also include the Shakespeare & Company theater, renowned for its productions and workshops, which attracts visitors year-round.
Can I change or cancel my Lenox home rental booking on Vrbo?
To find Lenox 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 Lenox 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.

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