Lenox holiday lettings

We found 513 holiday rentals — enter your dates for availability

Select from 45 houses, 11 flats and other holiday rentals to find the perfect place for your stay in Lenox. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Lenox

Showing deals for:29 May - 5 Jun

Image gallery for Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Property grounds
10 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
Price is £4,235
for 7 nights, 1 home
£605 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

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Why visit Lenox

  • Cultural rich experiences: Discover historic houses and local attractions that showcase Lenox's vibrant heritage and artistic community.
  • Stunning natural beauty: Enjoy picturesque lakes and serene nature reserves, perfect for outdoor activities and relaxation.
  • Charming local shops: Stroll through delightful boutiques and shops that offer unique local goods and souvenirs.
  • Romantic getaways: Experience the intimate atmosphere ideal for couples seeking a romantic escape amidst natural beauty.
  • Family-friendly activities: Engage in a variety of attractions suitable for visitors of all ages, ensuring a fun-filled holiday.

Popular types of accommodation in Lenox

You've chosen Lenox for your getaway, and now it's time to find the perfect accommodation. From charming houses and inviting cottages to modern condos, there’s something for everyone. Many holiday rentals boast a second bedroom and ground floor options, ensuring comfort and convenience during your stay. Explore the ideal holiday apartments and accommodation that suit your needs and make your visit to Lenox truly memorable.

  • Houses: The top choice for visitors in Lenox, these homes offer a spacious and comfortable setting, ideal for families or groups.
  • Condos: A popular option for many, these self-contained units provide modern amenities and convenient locations.
  • Cottages: Charming and quaint, cottages in Lenox offer a picturesque retreat, perfect for a relaxing getaway.
  • Cabins: These rustic accommodations provide a cosy atmosphere, ideal for nature lovers seeking a peaceful escape.
  • Apartments: A practical choice for couples or solo travellers, offering a home-from-home feel in the heart of Lenox.**

Top attractions in and around Lenox

Lenox is ideal for entertainment, romantic getaways, and family holidays. Visitors can explore a range of attractions, including historic houses, picturesque lakes, and serene nature reserves. The local points of interest promise a rich blend of culture and outdoor experiences, ensuring a delightful holiday for families and couples alike. With its charming atmosphere, Lenox offers something for everyone.

  • The Mount: This historic house, once the home of author Edith Wharton, offers visitors a glimpse into the past with its stunning architecture and beautiful gardens, reflecting Wharton's literary legacy.
  • National Shrine of the Divine Mercy: A serene and spiritual site, this shrine features beautiful grounds and a peaceful atmosphere, perfect for reflection and contemplation.
  • Norman Rockwell Museum: Dedicated to the iconic American artist, this museum showcases a vast collection of Rockwell's illustrations and paintings, celebrating his contributions to American culture.

Things to do recommended for couples

For a romantic getaway in Lenox, indulge in a concert at Tanglewood Music Center for enchanting melodies. Experience skiing at Bousquet Ski Area, just 2.5km away, or relish exquisite wines at Furnace Brook Winery, 3.7km from town, perfect for a cosy evening together.

Things to do recommended for families

Families can unwind at Kennedy Park, a lovely recreational area in Lenox, or explore the serene Goose Pond Reservation, located 4.3km away. For a closer adventure, Fairfield Brook WMA, just 1.9km from Lenox, offers a peaceful retreat amidst nature.

Things to do recommended for groups

Groups visiting Lenox can enjoy a captivating performance at Shakespeare and Company, indulge in a round of golf at Wyndhurst Golf & Club, and browse the charming selection at The Bookstore, all while soaking in the local culture and vibrant atmosphere.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to filter your options according to your key priorities. Here are some helpful tips for booking on Vrbo.

  • Traveling to Lenox with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Lenox with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, alongside 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 holiday isn’t truly complete without their four-legged companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at ease.
  • Planning for a long term stay visiting Lenox: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Lenox

Lenox, Massachusetts, offers a delightful blend of entertainment, romance, and family-friendly activities. Explore charming local shops and enjoy scenic drives through picturesque landscapes. Just a short distance away, discover hidden gems that provide stunning views and a relaxing atmosphere. Whether you're seeking a vibrant community vibe or a tranquil retreat, Lenox and its surrounding areas promise an unforgettable holiday experience infused with natural beauty and warmth.

  • Pittsfield: Situated a mere 4.3km from Lenox, Pittsfield is a vibrant city renowned for its outdoor adventures and sporting events. The area is a haven for skiing enthusiasts, with several ski fields and resorts within easy reach. Beyond the slopes, visitors can enjoy the scenic beauty of local lakes and mountains that provide a picturesque backdrop for various recreational activities. Families and thrill-seekers alike will find a range of attractions, including an exciting waterpark, making Pittsfield a great choice for a fun-filled day trip.
  • Stockbridge: Located just 3.1km from Lenox, Stockbridge is a charming town steeped in culture and romance. It offers a delightful array of entertainment options, including music concerts and theatrical performances that attract visitors year-round. The town is home to notable landmarks such as serene lakes and significant monuments, as well as the famous Norman Rockwell Museum, which showcases the works of the iconic artist. Strolling through Stockbridge’s quaint streets, you’ll feel the town’s artistic spirit and inviting atmosphere, perfect for a leisurely afternoon.
  • Lee: Only 2.5km from Lenox, Lee is a delightful city that appeals to families and couples alike. With its emphasis on entertainment, visitors can enjoy live theatre and music concerts throughout the year. Surrounded by stunning lakes and mountains, Lee also boasts historical monuments that enrich the local landscape. Whether you're seeking a romantic getaway or a family adventure, Lee provides a warm, welcoming setting combined with engaging activities to make your visit memorable.

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 simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay frequently results in substantial savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to refine your search by price, location, and type of accommodation.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform to help you plan new trips, resume where you last stopped, or manage your existing arrangements. You can easily find properties you've saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The lively city of Lenox awaits you

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

Activities and attractions in and around Lenox

Do you want to find attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Lenox a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 exciting outdoor activities or just want to take in the scenery, Lenox is a great place to get outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling to and around Lenox

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 4.7 mi (7.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to 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 holiday rental?
When considering a holiday rental in Lenox, Massachusetts, a popular area to stay is the charming neighbourhood surrounding the Tanglewood Music Centre. This area not only offers a selection of delightful properties, including quaint cottages and elegant homes, but it also places you in close proximity to one of the region's top attractions. Tanglewood is renowned for its summer music festival, attracting visitors with its stunning outdoor performances.

Another great area to explore is the vicinity of the historic Lenox village. Here, you'll find a variety of holiday rentals that provide easy access to local shops, cafes, and art galleries. The village itself is a lovely place to wander, and you can visit the nearby Edith Wharton's The Mount, a beautiful estate that reflects the author's life and work, making it a great spot for literature enthusiasts.

Overall, Lenox offers a range of properties that cater to different tastes, and each neighbourhood provides a great experience that highlights the town's natural beauty and cultural richness.
How much does it cost to rent a holiday home in Lenox?
Prices for holiday 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 holiday 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.
What is the most popular type of holiday rental accomodation in Lenox?
In Lenox, holiday houses are the most popular type of holiday rental, with approximately 144 available throughout the area. These homes often provide spacious living areas, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or larger groups. Many are situated close to points of interest such as Tanglewood and the Norman Rockwell Museum, allowing easy access to local attractions. Additionally, there are around 36 apartments and 24 condos, which offer a more compact and convenient living option, typically featuring amenities like kitchenettes and shared facilities. Cottages and a few villas also add to the selection, suiting those seeking a quaint or luxurious stay.
Are there any family house rentals in Lenox?
In Lenox, Massachusetts, there is a solid selection of family-friendly holiday rentals, with around 37 options available. This charming town is located in the beautiful Berkshires and offers a variety of properties great for families. Many homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.

Visitors can enjoy easy access to nearby attractions such as Tanglewood, the summer home of the Boston Symphony Orchestra, and the picturesque grounds of the Edith Wharton Estate. Additionally, the town is close to several hiking trails and nature parks, ideal for outdoor adventures. The properties in Lenox often come with amenities like Wi-Fi, air conditioning, and comfortable furnishings, ensuring a pleasant stay for families seeking both relaxation and exploration.
Can I rent a holiday home with a pool or hot tub in Lenox?
In Lenox, Massachusetts, there are several holiday homes available for rent that come with pools or hot tubs, with around 11 options to choose from. This picturesque town, located in the Berkshires, is known for its vibrant cultural scene and stunning natural surroundings, making it an excellent choice for a relaxing getaway.

Travellers can expect a range of amenities in these properties, including private swimming pools, outdoor hot tubs, spacious patios, and well-equipped kitchens, superb for both relaxation and entertaining. Many rentals also offer beautiful views of the surrounding landscape, contributing to a tranquil atmosphere.
Can I find long-stay holiday rentals in Lenox?
A long-stay holiday rental in Lenox is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Lenox?
In Lenox, there are several pet-friendly house rentals available, providing a friendly setting for travellers with furry companions. Many of these properties come with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, allowing guests to enjoy a home-like environment during their stay.

The town is known for its picturesque landscapes and proximity to outdoor activities, making it an ideal destination for those looking to explore nature with their pets. Nearby attractions include the beautiful Kennedy Park, which offers walking trails and open spaces superb for leisurely strolls. Additionally, the charming streets of Lenox feature pet-friendly cafes and shops, enhancing the overall experience for pet owners.
Are there any remote work holiday rentals in Lenox?
In Lenox, Massachusetts, there are numerous holiday rentals suitable for remote work, with around 220 options available. This picturesque town, known for its cultural offerings and natural beauty, provides a conducive environment for working remotely. Many properties come equipped with high-speed internet and Wi-Fi, ensuring seamless connectivity for work-related tasks.

Travellers can expect amenities such as dedicated office spaces or desks, as well as comfortable living areas ideal for balancing work and relaxation. Additionally, some rentals may offer tranquil outdoor settings, allowing for enjoyable breaks amidst the beautiful landscapes. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lenox holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Lenox with parking available—perfect for families or travellers 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 holiday rental amenities include kitchens, which allow guests to prepare their own meals, and onsite parking for convenience. Many rentals also feature decks or patios, providing outdoor space to relax and enjoy the natural surroundings. A fireplace is a common amenity, adding a touch of warmth and comfort, particularly during the cooler months. Additionally, travellers can expect a coffee and tea maker in most properties, great for starting the day with a warm beverage.
When is the best time to visit Lenox for a holiday rental?
The best time to visit Lenox for a holiday rental is during the peak summer months of June to August, with July being particularly popular. This bustling season attracts visitors eager to explore the cultural gems of the Berkshires, including the renowned Tanglewood Music Festival, where you can enjoy world-class performances in a stunning outdoor setting.

During this vibrant period, the weather is typically warm, with temperatures ranging from the mid-teens to low 30s Celsius, making it superb for outdoor activities like hiking, exploring the picturesque gardens of the Edith Wharton estate, or simply relaxing at one of the many local parks. The atmosphere is lively, filled with fellow travellers and a variety of events to suit every taste.

For those looking to experience Lenox at a more relaxed pace, consider visiting in December. While this month falls into the low season, it offers a unique charm with fewer crowds and the opportunity to enjoy the festive spirit of the holidays. The serene beauty of the winter landscape and the chance to experience local winter festivities can make for a memorable getaway.

Ultimately, your choice of when to visit Lenox will depend on your preference for a vibrant summer experience filled with cultural events or a quieter, more intimate experience during the winter months.
How early should I book a Lenox holiday rental?
Book your Lenox holiday 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 holiday 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, Massachusetts, visitors can take part in a variety of attractions that showcase the area's rich cultural and natural heritage. One of the most prominent sites is Tanglewood, the summer home of the Boston Symphony Orchestra, where guests can enjoy world-class performances in a stunning outdoor setting. The surrounding countryside offers beautiful walking trails and scenic views, making it a superb spot for nature enthusiasts.

Another top attraction is the Ventfort Hall Mansion and Gilded Age Museum, which provides insight into the opulent lifestyle of the early 20th century, featuring period architecture and beautifully restored interiors. Additionally, the nearby Edith Wharton Home allows visitors to explore the life and works of the famous author in the very house she designed.

For those interested in outdoor activities, the area's beautiful parks, such as the Kennedy Park, offer hiking trails and picnic spots amidst picturesque landscapes. The town is also close to the picturesque Stockbridge, which features the Norman Rockwell Museum, celebrating the iconic American painter's work.
Can I change or cancel my Lenox home rental booking on Vrbo?
To find Lenox holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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