Lenox vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Lenox

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Lenox vacation rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$72 - $1,224$1,224 - $2,376$2,376 - $3,528$3,528 - $4,679$4,679+ per night

Property Types

ApartmentChaletCondoCottageHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Lenox

Show all
Restored 1881 Farm House - Lenox - Kitchen
Restored 1881 Farm House
Lenox, MA
9.8Wonderful(17)
Free Wi-Fi
Pet friendly
$459+
Check availability
Heart of Lenox!! - renovated downtown apartment - Lenox - Kitchen
Heart of Lenox!! - renovated downtown apartment
Lenox, MA
9.8Wonderful(22)
$700+
Check availability
Renovated Downtown 1bedroom - Lenox - Living room
Renovated Downtown 1bedroom
Lenox, MA
10Wonderful(13)
$416+
Check availability
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys! - Lenox - Living room
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
Lenox, MA
9.3Wonderful(13)
$344+
Check availability
Historical Downtown 1bedroom - Lenox - Kitchen
Historical Downtown 1bedroom
Lenox, MA
9.4Wonderful(15)
$419+
Check availability
Urban Peak Escape - Lenox - Kitchen
Urban Peak Escape
Lenox, MA
10Wonderful(1)
Free Wi-Fi
$513+
Check availability
5 Star Casual Elegance For 5 Star Guests - Lenox - Bedroom
5 Star Casual Elegance For 5 Star Guests
Lenox, MA
10Wonderful(37)
Free Wi-Fi
$612+
Check availability
Perfect location in the heart of downtown Lenox - Lenox - Living room
Perfect location in the heart of downtown Lenox
Lenox, MA
10Wonderful(1)
Free Wi-Fi
$609+
Check availability
Huge Designer House on 2 acres property, minutes to restaurants, museums - Lenox - Building
Huge Designer House on 2 acres property, minutes to restaurants, museums
Lenox, MA
10Wonderful(1)
Pool
$401+
Check availability
Lovely Townhouse In Heart Of Lenox - Lenox - Dining room
Lovely Townhouse In Heart Of Lenox
Lenox, MA
10Wonderful(14)
$440+
Check availability
Beautiful Lenox Home, 3 Mi to Shakespeare and Co! - Lenox - Living room
Beautiful Lenox Home, 3 Mi to Shakespeare and Co!
Lenox, MA
9.3Wonderful(20)
Free Wi-Fi
$449+
Check availability
Imagine Being Lakeside This Summer! Book Now! - Lenox
Imagine Being Lakeside This Summer! Book Now!
Lenox, MA
10Wonderful(9)
$709+
Check availability
Luxury Berkshires Retreat in Lenox - Main House & Studio - Lenox - Bedroom
Luxury Berkshires Retreat in Lenox - Main House & Studio
Lenox, MA
9.8Wonderful(29)
Free Wi-Fi
$1,327+
Check availability
Renovated 1860's Farmhouse, across from the Miraval! Fenced in yard for dogs. - Lenox - Building
Renovated 1860's Farmhouse, across from the Miraval! Fenced in yard for dogs.
Lenox, MA
Pet friendly
$589+
Check availability
Charming Lenox cottage within walking distance to town - Lenox
Charming Lenox cottage within walking distance to town
Lenox, MA
Pet friendly
$426+
Check availability
Berkshires Getaway - Serene Lenox Hills Cottage - Lenox
Berkshires Getaway - Serene Lenox Hills Cottage
Lenox, MA
Free Wi-Fi
$370+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Lenox

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Lenox with confidence.

What is the cheapest day of the week to book a vacation rental in Lenox?

Wednesday offers the lowest rates in Lenox, with an average nightly price of $170. The highest prices are found on Thursday, with average rates at $456.
Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
November
$284
$347
Cheapest month to stay with an average 33% drop in price.
Most expensive month to stay with an average 71% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Lenox vacation rental deals

  • Vacation rentals in Lenox are around 52% more expensive than hotels on average. Search here to compare prices for all accommodation types in Lenox.
  • The best vacation rental properties in Lenox are 5 Star Casual Elegance For 5 Star Guests (10.0, 37 reviews), Main Street Delight 1bedroom (9.9, 22), and Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA (9.8, 24), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Lenox, you should consider visiting during the low season. The cheapest vacation homes in Lenox can be found in April and June.
  • The cheapest night for renting a vacation home in Lenox is Wednesday. In contrast, the most expensive is Thursday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Lenox for 5 days.
  • The cheapest Lenox vacation rental found on KAYAK in the last 2 weeks was $217, while the most expensive was $217.

FAQs when booking a vacation home in Lenox

  • How much is a vacation rental for a week in Lenox?

    The average price for a weekly Lenox vacation rental found by KAYAK users in the last 2 weeks is $1,294.

  • How much is a vacation rental for a month in Lenox?

    The average price for a monthly Lenox vacation rental found by KAYAK users in the last 2 weeks is $5,546.

  • What types of vacation rentals are available in Lenox?

    There are loads of different property types that you can make your vacation home in Lenox. You’ll find agritourism, apartments, caravan parks, chalets, condos, cottages, houses and villas.

  • Are there any pet-friendly vacation rentals in Lenox?

    There are a number of dog and pet-friendly Lenox vacation rentals, with around 8% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Lenox?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Lenox?

Our map will help you find the perfect place to stay in Lenox by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Lenox

Not what you’re looking for? Find thousands of other hotels, airline tickets, car rentals and package deals with KAYAK.