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Lenox holiday rentals

Q: 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.

Q: 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.

Q: 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.

Q: 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.

Q: 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.

Q: 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.

Q: 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.

Q: 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

Q: 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.

Q: 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.

We found 505 holiday rentals — enter your dates for availability

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July 2025

August 2025

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:10 Oct - 17 Oct

Exceptional

(110 reviews)

General Williams Estate House Lenox/Stockbridge

Stockbridge, MA

8% off

S$1,820 per night

includes taxes & fees

Exceptional

(6 reviews)

Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Stockbridge, MA

8% off

S$1,843 per night

includes taxes & fees

Exceptional

(18 reviews)

Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood

West Stockbridge, MA

8% off

S$520 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Lenox

Tanglewood Music Center

Find the best place to stay - Lenox

The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History

Sleeps 20 · 6 bedrooms · 5 bathrooms

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

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:

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)
Wyndhurst Golf & Club (1.3 mi / 2.1 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)
Lenox Mountain Reserve (2.9 mi / 4.7 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)
Housatonic River (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 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.