Lenox holiday lettings

We found 514 holiday rentals — enter your dates for availability

Select from 41 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:13 Feb - 20 Feb

Image gallery for Tranquil 3-BR Waterfront Retreat

Exterior
10 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)

Tranquil 3-BR Waterfront Retreat

Becket, MA

8% off
Price is £3,151
for 7 nights, 1 home
£450 per night
includes taxes & fees
Tranquil 3-BR Waterfront Retreat

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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)
  • 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 best area to stay in Lenox when booking a holiday rental?
When considering a holiday rental in Lenox, Massachusetts, the best area to stay in is the charming neighbourhood surrounding the historic downtown. This area not only boasts a delightful array of shops and restaurants but also places you in proximity to some of the town's most celebrated attractions. One such highlight is the renowned Tanglewood, the summer home of the Boston Symphony Orchestra, which draws music lovers from far and wide. Additionally, the picturesque Edith Wharton's The Mount offers a glimpse into the life of the celebrated author, complete with beautiful gardens and stunning views.
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.
Where are the best Lenox ski resort rentals?
For ski resort rentals in Lenox, Massachusetts, travellers should consider nearby areas such as Lee and Stockbridge, which provide convenient access to the slopes at Jiminy Peak, located approximately 30 minutes away. In Lee, visitors can find charming cabins and cottages that often feature amenities like wood-burning fireplaces, hot tubs, and fully equipped kitchens, great for relaxing after a day on the mountain.

In Stockbridge, there are options for elegant historic homes and modern lodges that cater to larger groups or families. Many of these properties come with outdoor spaces, some boasting stunning views of the surrounding Berkshires, and amenities such as game rooms, fire pits, and expansive living areas for social gatherings.

Additionally, those looking for a more rustic experience can explore properties in the nearby Otis area, where you'll find cosy chalets and cabins set amidst nature, often equipped with essential comforts like Wi-Fi, heating, and outdoor decks for enjoying the serene landscape.
What is the most popular type of holiday rental accomodation in Lenox?
In Lenox, holiday houses are the most popular type of accommodation, with around 37 available throughout the area. These houses typically feature multiple bedrooms, spacious living areas, fully equipped kitchens, and often come with outdoor spaces such as patios or gardens, allowing guests to enjoy the natural surroundings. Additionally, there are several apartments, condos, and cottages that provide a range of options for visitors. These smaller rooms generally include essential amenities like kitchen facilities and comfortable living spaces, making them suitable for couples or solo travellers.
Are there any family house rentals in Lenox?
In Lenox, Massachusetts, there are numerous family-friendly house rentals available, with around 39 options to choose from. This charming town is known for its cultural attractions and natural beauty, making it an excellent choice for families. Many of the properties boast spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.

Visitors can enjoy close proximity to local highlights such as the Berkshire Botanical Garden and Tanglewood, the summer home of the Boston Symphony Orchestra, which offers a variety of concerts and events. Additionally, the nearby Stockbridge area features picturesque landscapes and opportunities for hiking and exploring the delightful New England countryside.
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 feature pools or hot tubs, with approximately 11 options to choose from. This charming town, located in the picturesque Berkshires, offers a serene environment ideal for relaxation. Many of these properties come with private pools, hot tubs, and outdoor spaces where guests can unwind and enjoy the natural beauty surrounding them.
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, Massachusetts, there are several pet-friendly house rentals available for travellers seeking a comfortable getaway. The area is renowned for its beautiful natural surroundings and cultural attractions, making it an ideal destination for both pets and their owners. Many of these holiday rentals come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and private outdoor spaces, ensuring a relaxing stay.
Are there any remote work holiday rentals in Lenox?
In Lenox, Massachusetts, there are a variety of remote work holiday rentals available, with around 54 options to choose from. This charming town, known for its picturesque landscapes and cultural attractions, provides an excellent backdrop for those looking to combine work and leisure. Many properties come equipped with dedicated workspaces, including desks and comfortable office chairs, as well as amenities such as high-speed Wi-Fi, making it easier for guests to stay productive during their stay. 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 fully equipped kitchens, which are essential for those who prefer self-catering. Many rentals feature modern appliances such as dishwashers, stovetops, and microwaves, along with cookware, dishware, and utensils to make meal preparation easy. These amenities cater well to families and groups looking to enjoy home-cooked meals after a day of exploring local attractions like the Tanglewood Music Festival or the picturesque gardens of the Ventfort Hall Mansion.
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 summer months, particularly in July. This period falls within the peak season, where visitors flock to this charming town to enjoy its vibrant cultural scene and picturesque landscapes. With warm temperatures typically ranging from 20 to 30 degrees Celsius, you'll find ideal conditions for outdoor activities, from hiking in the nearby Berkshire Mountains to leisurely strolls through the lush gardens of Tanglewood.

The town buzzes with energy in July, as it hosts a variety of events and performances, making it a delightful choice for those looking to immerse themselves in the local arts and music scene. Whether you're attending a concert at the renowned Tanglewood Music Centre or exploring the charming galleries and shops, there's plenty to keep you entertained.

For those who prefer a quieter experience or are looking for more budget-friendly options, consider visiting Lenox in December. This month, while outside the peak tourist season, offers a magical winter atmosphere complete with festive decorations and opportunities for cosy indoor activities. You can enjoy the tranquillity of the town while experiencing its seasonal charm.
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 enjoy a range of attractions that highlight the area's natural beauty and cultural richness. The Tanglewood Music Centre, located just outside of town, is a premier venue for concerts during the summer, drawing music lovers from all over. The picturesque grounds provide a lovely setting for outdoor performances, making it a favourite spot for both locals and tourists.

In addition, the nearby Edith Wharton Estate, known as The Mount, offers guided tours of the author's home and beautiful gardens, allowing guests to immerse themselves in the literary history of the region.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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