Lenox holiday lettings

We found 511 holiday rentals — enter your dates for availability

Select from 45 houses, 10 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:5 Dec - 12 Dec
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Find out more about Lenox

Find out more about Lenox

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)
  • Ski Butternut (12.2 mi / 19.6 km)
  • Jiminy Peak Mountain Resort (13.7 mi / 22.1 km)
  • Catamount Ski Area (16.5 mi / 26.5 km)
  • The Bookstore (0.1 mi / 0.1 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)
  • Lake Mansfield Park (11.3 mi / 18.2 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 most popular type of holiday rental accommodation in Lenox?
Houses are the most popular kind of holiday rental in Lenox, according to our data. Even if you have a different vision in mind, Vrbo has holiday homes in all shapes and sizes. Compare our options to find your perfect match.
How much does it cost to rent a holiday rental in Lenox?
Length of stay, property type and time of year are some factors that can affect the price of a holiday home. Simply click on your travel dates to find your ideal match. From comfy cabins to sprawling luxury villas, all Vrbo holiday rentals offer amazing value.
How much does it cost to rent a beach house in Lenox?
Prices for beach houses in Lenox can differ depending on the size and style of the property and when you're travelling. All you need to do is enter your travel dates into Vrbo and how many guests to see available options and prices. From there you can use the filters to tailor your search results by amenities, ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Lenox?
With 17 holiday rentals that welcome pets, your furry buddy can join in the fun on your Lenox holiday. Use our filter tool to browse our pet-friendly holiday rentals and find a holiday home that'll set tails wagging on Vrbo.
What are popular rental amenities in Lenox?
When it comes to rental amenities that people look for in Lenox, a fireplace, a sauna and a firepit are at the top of the list. With Vrbo holiday homes, there are options to match your taste and style, whether you're on a trip with your partner, family members or even pets.
Are there large group holiday rentals in Lenox?
With seven Lenox holiday rentals that can host five or more people, you can invite a few extra friends or family members along. Whether you're planning a casual gathering or a celebratory event, we'll help you find the perfect space to match the occasion.
Are there holiday rentals in Lenox that welcome kids?
Gather the whole crew for a memorable adventure in Lenox at one of our 17 family-friendly holiday homes. Many of these stays come with conveniences that are suitable for getaways with youngsters, such as kitchens, bunk beds and swimming pools. Simply check the "Properties good for families" filter box and book your favourite.
What are the top attractions for families in Lenox?
You'll find loads of fun things to do and see with the family in Lenox, including:

  • Berkshire Museum
  • Berkshire Scenic Railway Museum
  • Arrowhead Museum

Are there one-bedroom holiday rentals in Lenox?
You can choose from four one-bedroom rentals in Lenox. Whether you're looking for a cosy chalet or a condo, our one-bedroom rentals are ideal if you don't need loads of space. One of the best parts about having your own place? You won't need to share your getaway with strangers.
Can I find two-bedroom holiday rentals in Lenox?
You can pick from four two-bedroom holiday rentals in Lenox. Put your little ones in the second room or fill it with a couple of your best buddies. There's enough space for whoever's lucky enough to come along for the ride.
Are there holiday rentals with WiFi in Lenox?
Lenox has five holiday rentals with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to updating your social media, these Vrbo homes make it easy to get online.
How can I find holiday rentals with air conditioning in Lenox?
Select your travel dates and then use our filters to search for holiday rentals with air conditioning in Lenox on Vrbo. With 16 air-conditioned properties on offer here, you can look forward to a cool and comfy break.
How old do you have to be to rent a holiday rental in Lenox?
The minimum age can differ across properties on Vrbo, so double-check the rules of the holiday rental in Lenox you want. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Lenox for?
The length of time you can rent a holiday rental in Lenox varies according to the property. Simply enter your selected dates to view a list of options offering extended stays. With many amenities such as air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you're sure to get somewhere perfect to call your home away from home in Lenox.

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