Lenox vacation rentals

We found 513 vacation rentals — enter your dates for availability

Select from 42 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:Mar 27 - Apr 3

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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 $511
$3,575 for 7 nights
All fees included
Best of the Berkshires & Hudson Valley

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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)
  • Kennedy Park (1.6 mi / 2.6 km)
  • Bousquet Ski Area (4 mi / 6.5 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)
  • Kennedy Park (1.6 mi / 2.6 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)

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 when booking a vacation rental?
When planning a vacation in Lenox, Massachusetts, one of the best areas to consider for a rental is the neighborhood surrounding the picturesque Kennedy Park. This area is ideal for those who appreciate nature and outdoor activities, as Kennedy Park offers a network of trails great for hiking and biking. Additionally, the nearby Tanglewood, the summer home of the Boston Symphony Orchestra, is a must-visit for music lovers and cultural enthusiasts, providing a great experience in a stunning outdoor setting.

Another great option is the area around downtown Lenox, which boasts a charming small-town atmosphere with a variety of shops, restaurants, and art galleries. Staying here allows you to immerse yourself in the local culture and enjoy attractions like the Lenox Library and the Ventfort Hall Mansion and Gilded Age Museum, both of which are rich in history and offer captivating tours.

In terms of vacation rentals, both neighborhoods offer a diverse range of properties, ensuring you'll find something that suits your needs and preferences.
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 skiing near Lenox, Massachusetts, the closest resort is Jiminy Peak, located just a short drive away in Hancock. Travelers looking for rentals in this area should consider properties in both Lenox and nearby towns like Hancock and Pittsfield. In Lenox, you can find charming vacation homes and cozy cabins that often feature amenities such as fireplaces, fully equipped kitchens, and outdoor spaces for enjoying the beautiful Berkshire scenery.

In Hancock, options may include ski-in/ski-out lodges or condos that provide direct access to the slopes, making them ideal for avid skiers. These accommodations typically offer conveniences like ski storage, hot tubs, and community recreation areas. Additionally, many properties have easy access to local dining and shopping, enhancing the overall experience for travelers.

Pittsfield also offers various rental options, ranging from modern apartments to historic properties, which are superb for larger groups or families. Many of these rentals include amenities like laundry facilities, spacious living areas, and proximity to local attractions such as parks and cultural sites.
What is the most popular type of vacation rental accomodation in Lenox?
In Lenox, vacation houses are the most popular type of rental, with about 37 available in the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens where guests can relax and enjoy the natural beauty of the Berkshires. Additionally, there are several apartments, condos, cottages, and villas available, providing travelers with a variety of options to suit different preferences and group sizes.
Are there any family house rentals in Lenox?
In Lenox, Massachusetts, visitors can find a variety of family-friendly house rentals, with around 36 options available throughout the area. The town is known for its beautiful landscapes and cultural attractions, making it a great destination for families. Many of these properties feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can play and explore. Amenities such as Wi-Fi, air conditioning, and laundry facilities are often included, ensuring a comfortable stay for guests.

Parents and children alike can enjoy nearby attractions, including the stunning grounds of Tanglewood, where the Boston Symphony Orchestra performs during the summer months, and the picturesque hiking trails in the surrounding Berkshire Mountains. Additionally, the town's quaint atmosphere includes charming shops, art galleries, and family-friendly dining options. See all family-friendly rentals in Lenox.
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, making it an appealing destination for travelers seeking relaxation and recreation. This charming town, known for its beautiful landscapes and cultural attractions, offers a variety of properties in neighborhoods such as the historic district, where visitors can enjoy easy access to local theaters, art galleries, and the picturesque gardens of Tanglewood.

Travelers can expect a range of amenities in these rentals, including private pools for leisurely swims, hot tubs great for unwinding after a day of exploring, and spacious outdoor areas for barbecues or family gatherings. Many homes also come equipped with modern kitchens, cozy living spaces, and comfortable bedrooms, ensuring a convenient and enjoyable stay. Find your rental in Lenox with a pool or a hot tub.
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, there are several pet-friendly house rentals available, with a total of 16 options for travelers. Many of these homes come equipped with amenities that enhance the stay, including spacious backyards for pets to roam, fully equipped kitchens, and cozy living areas superb for relaxation.

The area is known for its beautiful natural surroundings, with easy access to outdoor activities. Nearby, the stunning Kennedy Park offers walking trails that are superb for pet owners looking to enjoy the outdoors with their furry friends. Additionally, the picturesque Tanglewood, famous for its music festival, is also pet-friendly and provides ample space for walking and enjoying the scenery. 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 around 49 options available. This picturesque town, located in the Berkshires, is known for its scenic beauty and cultural attractions, making it an ideal backdrop for both productivity and leisure. Many of these rentals come equipped with essential remote work amenities, including dedicated desks, high-speed Wi-Fi, and comfortable office chairs, ensuring a conducive work environment.

Travelers can expect properties that feature spacious living areas and tranquil settings, often surrounded by nature, which can provide a refreshing escape from the typical office environment. Some rentals may also include additional amenities like laptop workspaces and computer monitors, catering specifically to the needs of remote workers.

Lenox is not only a great place to work but also to relax, with nearby attractions like Tanglewood, the summer home of the Boston Symphony Orchestra, and the beautiful gardens of the Edith Wharton Estate. 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 WiFi, kitchens equipped with essential appliances such as blenders and coffee/tea makers, and outdoor patios for enjoying the scenic surroundings. These features cater to travelers looking for convenience and comfort, allowing them to prepare meals and relax in a pleasant atmosphere.
When is the best time to visit Lenox for a vacation rental?
The best time to visit Lenox for a vacation rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts those seeking a mix of outdoor adventures, cultural experiences, and relaxation amid the beautiful Berkshire Mountains. Visitors can indulge in various activities such as hiking, exploring charming downtown shops, and attending world-class performances at Tanglewood, the summer home of the Boston Symphony Orchestra.

During the summer months, Lenox enjoys warm temperatures ranging from the mid-60s to the low 80s Fahrenheit, creating an inviting environment for outdoor activities and sightseeing. The area's lush landscapes and vibrant gardens are in full bloom, providing a picturesque setting for leisurely strolls and picnics.

If you're looking for a more budget-friendly option, consider visiting in December. While this month is less crowded, it offers a unique charm with holiday festivities, cozy winter settings, and opportunities for winter sports in the surrounding areas.

Ultimately, your choice will depend on whether you prefer the lively summer atmosphere filled with events and activities or the tranquil beauty of Lenox in the winter months.
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?
In Lenox, travelers can enjoy a variety of attractions located in the scenic Berkshires. The Tanglewood Music Center, located nearby, is a renowned summer venue for music lovers, offering concerts in a beautiful outdoor setting. The historic Shakespeare & Company is another cultural gem, providing performances and workshops in a picturesque setting that often draws visitors.

For those interested in nature, the nearby Kennedy Park features hiking trails and stunning views, ideal for outdoor enthusiasts. The Norman Rockwell Museum, located in Stockbridge just a short drive away, showcases the works of the beloved American illustrator and is a must-visit for art lovers.
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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