Lenox holiday rentals

We found 520 holiday rentals — enter your dates for availability
Select from 42 houses, 12 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:8 Jan - 15 Jan

Interior
Private kitchen
Interior
Exterior
Exceptional
(21 reviews)

Historic Stockbridge Villa on 25 acres

Stockbridge

16% off
AU$6,361
for 7 nights, 1 villa
AU$909 per night
includes taxes & fees
Historic Stockbridge Villa on 25 acres
Sunroom has Queen pull out sofa bed
The great room with wonderful water views and working fireplace
Dining
Hot tub overlooking the lake
Exceptional
(87 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
AU$6,709
for 7 nights, 1 home
AU$958 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Dining
Interior
Exterior
Living area
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,928
for 7 nights, 1 cabin
AU$561 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Kitchen with stainless steel appliances
Fully screened porch!
Front Staircase
Reading nook with natural lighting
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield

12% off
AU$5,589
for 7 nights, 1 home
AU$798 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Interior
Private kitchen
Room
Living area
Exceptional
(14 reviews)

Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

New Lebanon

17% off
AU$9,751
for 7 nights, 1 home
AU$1,393 per night
includes taxes & fees
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires
Laundry room with washer, dryer, storage, and a convenient garage entry area.
Main living room with soaring windows overlooking the lake and wooded grounds.
Snow-covered house surrounded by evergreens and winter woods.
Main-level queen bedroom with four-poster bed and views of the surrounding woods
Exceptional
(32 reviews)

Lake View Berkshire Retreat – Private Setting Near Lenox

Lee

15% off
AU$5,656
for 7 nights, 1 home
AU$808 per night
includes taxes & fees
Lake View Berkshire Retreat – Private Setting Near Lenox
Outdoor spa tub
Exterior
Living area
Interior
Exceptional
(22 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
AU$6,588
for 7 nights, 1 home
AU$941 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Living area
Private kitchen
Property grounds
Exterior
Exceptional
(11 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$5,963
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Exterior detail
Living area
Interior
Interior
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,125
for 7 nights, 1 home
AU$875 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Kitchen
Living Room
Property grounds
Back Porch
Exceptional
(29 reviews)

Secluded Family Home in Serene Stockbridge Woods

Stockbridge

8% off
AU$4,483
for 7 nights, 1 home
AU$640 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Property grounds
Kitchen with counter seating for 4- door on the right to garage
View from entry into living room- perfect spot for relaxing!
Outdoor dining
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
AU$5,514
for 7 nights, 1 home
AU$788 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
The spacious kitchen island is complete with a wine fridge, inviting relaxation and entertainment into your stay.
Outdoor dining
Plenty of natural light fills the kitchen.
Natural light fills the living room.
Exceptional
(5 reviews)

Richmond Ranch w/ Hot Tub by Evergreen Home

Richmond

12% off
AU$4,808
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
Richmond Ranch w/ Hot Tub by Evergreen Home
kitchen and laundry room area
new backyard table
Beaver Pond Pool/clubhouse
another view of kitchen
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Hancock

23% off
AU$5,171
for 7 nights, 1 apartment
AU$739 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Exterior
Exterior
Property grounds
Interior
Exceptional
(81 reviews)

Bershire Home Rental: Enjoy Berkshire Fall Foliage

Washington

20% off
AU$3,136
for 7 nights, 1 home
AU$448 per night
includes taxes & fees
Bershire Home Rental: Enjoy Berkshire Fall Foliage
View from the lawn by the water
view from the 2nd bedroom
Open plan dining area with water views and access to the sunroom
View of the lower deck from the sunroom
Exceptional
(66 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$6,982
for 7 nights, 1 home
AU$997 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
The living room flows into the dining room.
You will love dining and working in this rich and colorful room
Outdoor dining and grill on the 16' x 20' wooden deck.
Staircase
Exceptional
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

12% off
AU$4,328
for 7 nights, 1 home
AU$618 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Interior
Property grounds
Exterior
Room
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

5% off
AU$2,535
for 7 nights, 1 apartment
AU$362 per night
includes taxes & fees
The Serendipity Spot
Backyard
Living Room - Queen Sleep Sofa (First Floor)
Front Porch
Dining Room - table expands to seat 10
Exceptional
(11 reviews)

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

9% off
AU$4,189
for 7 nights, 1 home
AU$598 per night
includes taxes & fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Queen bedroom
Terrace/patio
Screened in porch
Dining room with butcher block table
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,938
for 7 nights, 1 home
AU$563 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Unwind and cherish moments together in the inviting warmth of the cozy living room.
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Back patio with Hot Tub
Add a touch of warmth and charm to your dining experience!
Exceptional
(8 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
AU$8,416
for 7 nights, 1 home
AU$1,202 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
50 inch TV for family movie night!
BBQ dinner not included :)
Interior
Exterior
Exceptional
(11 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Pittsfield

8% off
AU$5,268
for 7 nights, 1 home
AU$753 per night
includes taxes & fees
Family Fun in The Berkshires at Beautiful Hygge House
Kitchen
Interior
Kitchen
Property grounds
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,511
for 7 nights, 1 home
AU$787 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Interior
Interior
Property grounds
Bathroom
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
AU$3,929
for 7 nights, 1 home
AU$561 per night
includes taxes & fees
Historic Stone Church in The Berkshires
Interior
Dining
view into large bathroom
Living Room, wow!
Exceptional
(17 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
AU$3,624
for 7 nights, 1 apartment
AU$518 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

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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)
  • Otis Ridge (14.6 mi / 23.5 km)
  • Catamount Ski Area (16.5 mi / 26.5 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)
  • Stockbridge Bowl (2.3 mi / 3.7 km)
  • Lenox Mountain (3.3 mi / 5.3 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)

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.
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.
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 Stayz.
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.
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.
Are all fees included in the Lenox holiday homes prices shown on Stayz?
Stayz 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.
Are there any Lenox holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Lenox holiday homes?
You can find great discounts on holiday homes in Lenox on Stayz, 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.
Can I change or cancel my Lenox holiday home booking on Stayz?
To find Lenox holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Lenox?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Lenox holiday home?
Book your Lenox holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Lenox?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Lenox to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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