Best Vacation Homes in Lenox
Condo
10.0(150 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Fireplace/Heating
Kitchen
Parking
Air Conditioner
CA $474/Night
7 Nights - CA $3,318
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
12916.69 ft²
- Parking
- Air Conditioner
Internet
Child Friendly
CA $554/Night
7 Nights - CA $3,881
Apartment
10.0(37 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $356/Night
7 Nights - CA $2,491
House
9.8(5 Reviews)
4 Bedrooms
2 Baths
4 Guests
1291.67 ft²
Skiing- Fireplace/Heating
Balcony/Terrace
Pet Friendly
CA $546/Night
7 Nights - CA $3,823
House
10.0(33 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $489/Night
7 Nights - CA $3,425
Apartment
10.0(28 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $516/Night
7 Nights - CA $3,612
Apartment
10.0(24 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $336/Night
7 Nights - CA $2,354
Lenox Luxury Rentals
Villa
10.0(2 Reviews)
12 Bedrooms
10 Baths
24 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $6,834/Night
7 Nights - CA $47,840
Villa
10.0(19 Reviews)
13 Bedrooms
13 Baths
35 Guests
15000 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $4,778/Night
7 Nights - CA $33,444
House
10 Bedrooms
9 Baths
17 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $3,167/Night
7 Nights - CA $22,171
House
9.8(52 Reviews)
5 Bedrooms
5 Baths
8 Guests
6000 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $2,381/Night
7 Nights - CA $16,665
House
10.0(55 Reviews)
8 Bedrooms
4 Baths
17 Guests
5600 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
CA $2,024/Night
7 Nights - CA $14,170
House
10.0(43 Reviews)
4 Bedrooms
3 Baths
8 Guests
4000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $1,871/Night
7 Nights - CA $13,096
House
10.0(61 Reviews)
6 Bedrooms
3 Baths
13 Guests
4400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $1,683/Night
7 Nights - CA $11,780
House
10.0(127 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $1,231/Night
7 Nights - CA $8,615
Lenox Pet Friendly Vacation Rentals
Apartment
10.0(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
CA $760/Night
7 Nights - CA $5,321
Hotel
8.9(10 Reviews)
3 Baths
208.1 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
CA $866/Night
7 Nights - CA $6,061
Hotel
9.6(25 Reviews)
1 Bath
- Fireplace/Heating
Pool- Balcony/Terrace
Breakfast
CA $320/Night
7 Nights - CA $2,237
House
9.8(57 Reviews)
2 Bedrooms
3 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $575/Night
7 Nights - CA $4,028
New
House
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Internet
- Child Friendly
CA $530/Night
7 Nights - CA $3,708
House
10.0(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
3024 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $1,197/Night
7 Nights - CA $8,377
House
9.8(9 Reviews)
4 Bedrooms
2 Baths
8 Guests
2560 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $771/Night
7 Nights - CA $5,397
Lenox Large Vacation Homes
House
10.0(77 Reviews)
5 Bedrooms
2 Baths
9 Guests
2600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $1,124/Night
7 Nights - CA $7,867
Bed & Breakfast
9.4(572 Reviews)
28 Bedrooms
8 Baths
17 Guests
256.99 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
CA $532/Night
7 Nights - CA $3,727
House
10.0(22 Reviews)
5 Bedrooms
3 Baths
8 Guests
2900 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $819/Night
7 Nights - CA $5,731
Bed & Breakfast
9.0(52 Reviews)
15 Bedrooms
15 Baths
37 Guests
334.45 ft²
- Skiing
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $709/Night
7 Nights - CA $4,963
House
10.0(125 Reviews)
5 Bedrooms
3 Baths
8 Guests
3500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $977/Night
7 Nights - CA $6,839
House
10.0(1 Review)
9 Bedrooms
8 Baths
15 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
CA $1,555/Night
7 Nights - CA $10,889
Villa
10.0(4 Reviews)
11 Bedrooms
11 Baths
24 Guests
11748 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $4,224/Night
7 Nights - CA $29,567
House
10.0(3 Reviews)
6 Bedrooms
5 Baths
10 Guests
4500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $858/Night
7 Nights - CA $6,008
Why Choose Rent By Owner for your Lenox Vacation Rental Homes?
What makes our Vacation Rentals 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 Vacation Rentals stay?
To make the most of your stay, consider visiting during the shoulder seasons when this destination offers a peaceful ambiance and pleasant weather, perfect for exploring the region's natural beauty and enjoying your chosen vacation rentals.
Peak Season Highlights
Summer (June to August)
During the warmest months, this destination becomes lively with outdoor activities and cultural events, making it an ideal time for a scenic getaway.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
The vibrant foliage attracts visitors seeking picturesque views and pleasant weather, perfect for exploring the area's natural beauty.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
This quieter period offers a peaceful retreat with opportunities for cozy stays and wintertime relaxation amidst the scenic landscape.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
Spring (March to May)
As the region awakens from winter, you can enjoy fewer crowds and discover the area's blooming scenery during this shoulder season.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Lenox
How to Book Your Lenox Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Lenox
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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 access to outdoor swimming pools for a refreshing dip during your stay.
- Relax in a private or shared outdoor hot tub, perfect for unwinding after exploring the area's attractions.
- Take advantage of spacious outdoor patios or decks that provide ideal spaces for dining and entertaining.
- Benefit from landscaped gardens or yards that offer peaceful spots for relaxation or outdoor activities.
- Make the most of scenic walking trails or nature paths surrounding your rental property.
- Utilize outdoor grilling facilities to host barbecues and enjoy meals al fresco with family or friends.
- Access to well-maintained tennis courts or other recreational sports amenities often available here.
Top Attractions Around Lenox
What attractions are nearby?
Within the area, you can enjoy a variety of outdoor activities, cultural experiences, and scenic excursions that showcase the best of what this destination has to offer for an unforgettable stay.
Family Activities
- Lenox Mountain Scenic Trails: Explore family-friendly hiking paths that offer breathtaking views and an engaging outdoor experience in the area’s natural beauty.
- Tanglewood Music Center: Enjoy outdoor concerts and performances suitable for all ages, making it a memorable cultural activity for families here.
- The Mount, Edith Wharton's Home: Discover the historic estate with guided tours and garden strolls that captivate visitors of every age in this destination’s literary heritage.
- Lenox Library and Community Events: Participate in seasonal programs and storytimes that foster learning and fun for children in the region’s charming town center.
Adult Activities
- Lenox Mountain Trail Hiking: Explore scenic paths that offer stunning views of the surrounding landscape, perfect for outdoor enthusiasts seeking adventure in the area.
- Tanglewood Music Center Tours: Experience world-class performances and attend guided tours at this renowned summer music venue, immersing yourself in the region’s rich cultural scene.
- Museums and Art Galleries: Discover local history and vibrant contemporary art by visiting several museums and galleries nestled within this charming destination.
- Skiing and Snowboarding: In winter months, enjoy the thrill of hitting the slopes at nearby ski resorts, ideal for adult visitors looking for seasonal excitement in the region.
Other Places to Stay in Lenox, MA
The Mount
Cranwell Golf Club
Frelinghuysen Morris House and Studio
Shakespeare and Company
Tanglewood Music Center
Ventfort Hall Mansion and Gilded Age Museum
Lenox Library
The Bookstore
B.J. Faulkner Gallery
Pleasant Valley Wilderness Sanctuary
Kennedy Park
Lenox Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Arts and Culture: Take advantage of the region’s vibrant arts scene by visiting galleries, theaters, and cultural events to enrich your stay in this charming destination.
- Plan Your Outdoor Adventures: Make the most of the area's natural beauty by scheduling outdoor activities such as hiking, biking, or leisurely walks through scenic parks and trails.
- Discover Unique Dining Options: Enjoy local cuisine at restaurants and cafes that highlight the region’s culinary charm, offering an authentic taste experience during your visit.
- Book in Advance for Popular Attractions: Secure reservations ahead of time to ensure access to sought-after attractions and experiences that showcase the best of this coveted destination.
Transportation Options
- Lenox Municipal Airport: This regional airport offers convenient first- and last-mile connectivity for travelers arriving or departing locally.
- Amtrak Train Service: The nearby train station provides accessible rail options, allowing you to enjoy scenic journeys through the region.
- Local Taxi Services and Rideshares: Reliable taxi and rideshare options are available for flexible transportation within and around the area.
- Public Bus Transit: Local bus routes connect key destinations in this part of Massachusetts, facilitating affordable travel for visitors staying in vacation rentals here.
Local Customs Options
- Reverend's Festival: Celebrated annually, this event reflects the area's deep-rooted religious traditions and community spirit.
- Lenox Art Walks: During certain times of the year, local galleries showcase regional artistry, highlighting the region’s thriving arts scene.
- Farmers’ Market Traditions: Visitors can experience the authentic local culture by exploring the region’s farmers’ markets, offering fresh, regional produce.
- Summer Music Festivals: The area hosts vibrant outdoor concerts that embody its lively cultural atmosphere and love for music.
Frequently Asked Questions About Lenox?
1. What are the top vacation rentals 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 Vacation Rentals in Lenox:
- Unique Condo, Quiet Neighborhood, Walk to Town.
- St Anne`s Manor | Walk to Downtown! Sleeps 8
- 5 STAR CASUAL ELEGANCE for 5 STAR GUESTS
- Enjoy comfortable elegance in this secluded grand home located in town
- 33 Main
- Luxury Berkshires Retreat in Lenox - Main House
- Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood
- Luxury Berkshires Retreat in Lenox - Main House & Studio
- Chic Modern Farmhouse 1 Mile to Downtown Lenox
- NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN.
2. How many vacation rentals have private pools in Lenox?
There are 7 vacation rentals with private pools near Lenox. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Lenox are best for families?
If you are looking for a family-friendly vacation home in Lenox, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Lenox:
4. How many Rentbyowner vacation rentals are available in Lenox?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 151 in the Lenox area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Lenox.
5. What is the cancellation policy for vacation rentals in Lenox, Massachusetts?
Cancellation policies vary depending on the property listing. It is recommended that you review the specific cancellation terms outlined in the rental details or contact the property owner directly for clarification.
6. Are there any additional fees I should be aware of when booking a rental in the area?
Additional fees such as cleaning charges, security deposits, or service fees may apply. These details are typically specified in the listing, so reviewing the rental description or reaching out to the owner will provide clarity.
7. How do I ensure my reservation is secure and verified?
Reservations are secured through trusted booking platforms that verify listings and owner credentials. For added confidence, always confirm your booking directly through the platform's official communication channels.
8. What amenities can I expect from vacation rentals here?
Amenities vary by property, but common features include Wi-Fi, kitchen facilities, parking, and outdoor spaces. Detailed amenities were listed in the property description—review these carefully to ensure they meet your needs.
9. Is it possible to make special requests or customize my stay in this region?
Many hosts are willing to accommodate special requests or personalized arrangements. Contact the property owner before booking to discuss any specific needs or preferences to ensure a comfortable stay.
Lenox Top Rated Vacation Rentals
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
2500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $804/Night
7 Nights - CA $5,627
Other
9.6(15 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $395/Night
7 Nights - CA $2,765
Bed & Breakfast
9.4(164 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
CA $291/Night
7 Nights - CA $2,040
Hotel
9.2(1007 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
CA $182/Night
7 Nights - CA $1,276
CA $151/Night
7 Nights - CA $1,059
Hotel
9.2(625 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
CA $259/Night
7 Nights - CA $1,811
CA $300/Night
7 Nights - CA $2,098
CA $335/Night
7 Nights - CA $2,343
