Lenox, MA Villa Rentals | Rent By Owner

Name: Lenox
Address: Massachusetts, US

Lenox Villa

The Kemble- Built by a US Secretary of State in Lenox

Price Dropped

Villa

The Kemble- Built by a US Secretary of State in Lenox

10.0

Exceptional

(20 Reviews)

13 Bedrooms 13 Baths 35 Guests 15000 ft²

US $3,625/Night 7 Nights - US $25,376

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Villa

Winthrop Estate – An Elegant Home

10.0

Exceptional

(2 Reviews)

12 Bedrooms 10 Baths 24 Guests

US $5,472/Night 7 Nights - US $38,305

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Villa

The Winthrop Estate - 12K SF 32 Acres

10.0

Exceptional

(4 Reviews)

11 Bedrooms 11 Baths 24 Guests 11748 ft²

US $3,086/Night 7 Nights - US $21,600

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Apartment

51 Church Street, Lenox MA - One Bedroom Unit

10.0

Exceptional

(40 Reviews)

1 Bedroom 1 Bath 4 Guests

US $418/Night 7 Nights - US $2,927

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House

Walk to Dining: Downtown Lenox Guest House!

9.6

Exceptional

(9 Reviews)

3 Bedrooms 3 Baths 6 Guests 1905.21 ft²

US $217/Night 7 Nights - US $1,519

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Highly Rated

Bed & Breakfast

33 Main

10.0

Exceptional

(74 Reviews)

1 Bedroom 1 Bath

US $769/Night 7 Nights - US $5,382

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House

Lovely Townhouse In Heart Of Lenox, 2 Bedroom, 2 Bath

10.0

Exceptional

(35 Reviews)

2 Bedrooms 2 Baths 4 Guests

US $384/Night 7 Nights - US $2,689

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Bed & Breakfast

Eastgate Inn B&B

9.5

Exceptional

(23 Reviews)

3 Bedrooms 3 Baths 6 Guests

US $320/Night 7 Nights - US $2,240

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Price Dropped

Apartment

Main Street Delight 1bedroom

10.0

Exceptional

(28 Reviews)

1 Bedroom 1 Bath 4 Guests

US $363/Night 7 Nights - US $2,541

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Highly Rated

Bed & Breakfast

The Cornell Inn, Lenox & The Berkshires

9.4

Exceptional

(572 Reviews)

28 Bedrooms 8 Baths 17 Guests 256.99 ft²

US $389/Night 7 Nights - US $2,723

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Price Dropped

Apartment

Renovated Downtown 1bedroom

10.0

Exceptional

(26 Reviews)

1 Bedroom 1 Bath 4 Guests

US $326/Night 7 Nights - US $2,279

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Bed & Breakfast

Gateways Inn

9.3

Exceptional

(19 Reviews)

10 Bedrooms 4 Baths 8 Guests 18.84 ft²

US $350/Night 7 Nights - US $2,450

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More Top-Rated Villa in Lenox Area

Why Choose Rent By Owner for your Lenox Villa?

What makes our Villa special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Lenox

When should you plan your Villa stay?

To make the most of your stay, consider visiting this charming area during its shoulder seasons when the weather is mild and the crowds are fewer, ensuring a more relaxed experience in your chosen villa here in Lenox, Massachusetts, USA.

Peak Season Highlights

Summer (June to August)

During the summer months, this destination experiences warm and pleasant weather, making it an ideal time for outdoor activities and exploring the scenic surroundings.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: approximately 60°F (16°C)

Fall (September to October)

Autumn brings vibrant foliage and cooler temperatures, perfect for enjoying the region’s natural beauty and seasonal events.

Average Temperature Daytime: about 70°F (21°C) - Nighttime: roughly 50°F (10°C)

Off-Season Highlights

Winter (December to February)

With colder weather and quieter surroundings, winter offers a peaceful retreat with opportunities for cozy indoor gatherings.

Average Temperature Daytime: around 35°F (2°C) - Nighttime: close to 20°F (-6°C)

Spring (March to May)

Early spring sees the region awakening with budding flora and mild temperatures, providing a tranquil environment for relaxation.

Average Temperature Daytime: approximately 55°F (13°C) - Nighttime: around 35°F (2°C)

Weekly Weather Forecast for Lenox

How to Book Your Lenox Villa

What's our booking process?

Our platform allows you to browse a curated selection of villa. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Lenox

More Top-Rated Villa in Lenox Area

Common Villa Amenities

What amenities can you expect?

Our Villa are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy a private outdoor swimming pool to relax and unwind during your stay.
Take advantage of spacious patios or decks ideal for outdoor dining and entertaining.
Explore beautifully landscaped gardens surrounding your rental for peaceful walks.
Make use of outdoor barbecues or grilling areas perfect for family cookouts.
Benefit from furnished outdoor seating areas where you can enjoy the fresh air and scenic views.
Revel in outdoor fire pits for evening gatherings under the stars.
Discover access to well-maintained hiking trails nearby, allowing you to explore the area's natural beauty.

Top Attractions Around Lenox

What attractions are nearby?

Within this charming region, you can enjoy a variety of activities nearby, from exploring scenic parks and cultural attractions to indulging in local dining experiences-perfect for creating memorable moments during your stay in this destination’s welcoming surroundings.

Family Activities

Lenox Art Museum Tour: Explore the local art scene with a family-friendly visit to this area’s renowned museum, offering engaging exhibits and educational programs for all ages.
Lenox Greenway Trails: Enjoy outdoor adventures along scenic trails perfect for walking, biking, or picnicking, providing a peaceful escape within the region’s natural beauty.
Family Fun at Tanglewood: Attend seasonal concerts and outdoor performances at this iconic venue, creating memorable experiences for both kids and adults alike.
Historic Lenox Village: Discover charming shops, cafes, and historical sites in the heart of the town, ideal for leisurely strolls that showcase the area's rich heritage.

Adult Activities

Wine Tasting Tours: Experience the region's renowned wineries, offering guided tastings and scenic vineyard views that make for an elegant day out.
Golfing Adventures: Tee off at premier golf courses in the area, where lush fairways and beautiful landscapes provide a perfect setting for relaxation and sport.
Cultural Events and Performances: Engage with local arts through theaters, concerts, and festivals that showcase the creative spirit of this destination.
Spa and Wellness Centers: Indulge in rejuvenating treatments and massage therapies designed to enhance your stay in this picturesque region.

Other Places to Stay in Lenox, MA

Lenox Travel Tips

How Can You Make the Most of Your Stay?

Plan your activities ahead of time: Take advantage of the region's cultural calendar and outdoor opportunities to make the most of your stay here, ensuring you don’t miss any must-see events or scenic spots.
Choose a centrally located villa: Opt for accommodations that are near key attractions and amenities to minimize travel time and maximize your relaxation and exploration.
Explore local dining options: Dive into the area's culinary scene by visiting local eateries, giving you an authentic taste of this destination’s regional flavors.
Utilize local transportation services: Use convenient transit options or car rentals to easily access the surrounding countryside and hidden gems in the area.

Transportation Options

Car Rentals: Convenient car rental services are widely available in the area, offering you the flexibility to explore Lenox and its surroundings at your own pace.
Public Transit: Local bus services provide an affordable way to navigate here without the need for private transportation, ideal for short trips within the region.
Taxi and Ride-Sharing: Taxis and ride-sharing options like Uber or Lyft ensure quick and reliable transportation when you prefer door-to-door service during your stay.
Airport Transfers: Dedicated shuttle and transfer services connect the nearby airports with this destination, making your arrival and departure seamless and stress-free.

Local Customs Options

Maiden No More Day: Celebrated annually, this local custom honors the area's history by encouraging community members to embrace change and renewal in their personal and collective lives.
Lenox Artisans Fair: During this event, residents and visitors alike showcase handmade crafts reflecting the region's rich artistic traditions, emphasizing the importance of supporting local artisans.
Harvest Festival: Marking the bountiful season, this festival features traditional music, food, and communal activities that celebrate the region’s agricultural roots and seasonal abundance.
Summer Music Series: Enjoyed throughout warm months, this customs involves outdoor performances where locals gather to appreciate both classical and contemporary music in a relaxed setting.

Lenox Villa Frequently Asked Questions

1. What are the top Villas in Lenox?

There are a lot of options in Lenox. If you plan on staying in the Lenox area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Villas in Lenox:

2. How many Villas are available in Lenox?

Currently, the total number of properties listed by RBO in 2026 is over 3 in the Lenox area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Lenox. 

3. What is the cancellation policy for villas in this area?

Cancellation policies vary depending on the individual villa listing. You should review the specific terms and conditions outlined on the property’s page before booking, or contact the owner directly for detailed information.

4. Are there any specific amenities included with the villas here?

Amenities differ between properties, so it’s best to check the listing details for each villa. Typical features may include kitchens, outdoor spaces, or Wi-Fi, but availability varies.

5. How do I ensure my reservation is secure when booking a villa in this destination?

Booking through a reputable platform ensures your reservation is protected. Always verify that the listing has verified reviews and clear contact information, and communicate directly with the owner if needed.

6. Can I request special arrangements or accommodations during my stay?

Many villa owners are open to special requests. Contact the host prior to booking to discuss any specific needs or arrangements you seek for your stay.

7. What is the check-in and check-out process for villas in this region?

Check-in and check-out times vary by property. Details will be provided in your confirmation email or on the listing itself; reach out to the owner if you need clarification or have specific scheduling requests.