Holiday rentals in Lenox

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Top-rated holiday rentals in Lenox

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
*Close to ski resorts & tubing! We are nestled at the foot of October Mountain State Forest, yet close to the centers of Lee, Lenox, & Pittsfield. Our charming house was built in 1817- original wood beams, wood floors, and quite a history. Whether you enjoy skiing, exploring local restaurants & downtowns, venturing outdoors or experiencing the local art scene, the Berkshires has something for everyone. Our little farmhouse serves as the perfect "home base" for all of your Berkshire adventures.
6–13 JunIndividual Host,
€ 285 per night
4.9 out of 5 average rating, 202 reviews
Guest favourite
Home in Lee
Cozy Berkshires Cottage
Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)
5–12 SepIndividual Host,
€ 150 per night
4.89 out of 5 average rating, 234 reviews
Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon
13–20 AugIndividual Host,
€ 410 per night
4.94 out of 5 average rating, 345 reviews

Popular amenities for Lenox holiday rentals

Stay near Lenox's top sights

Kripalu Center For Yoga & Health122 locals recommend
Haven67 locals recommend
The Mount, Edith Wharton's Home167 locals recommend
Ventfort Hall Mansion and Gilded Age Museum19 locals recommend
Chocolate Springs Cafe23 locals recommend
Kennedy Park66 locals recommend

Other great holiday rentals in Lenox

Guest favourite
Flat in Lenox
The Penthouse, Downtown Lenox by Evergreen Home
19–24 MayProfessional Host,
€ 464 per night
4.93 out of 5 average rating, 30 reviews
Guest favourite
Guest house in Lenox
Guest House at Stonover Estate
2–9 SepIndividual Host,
€ 289 per night
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Lenox
Main Street Delight - One Bedroom Apartment
23–30 AprProfessional Host,
€ 272 per night
4.96 out of 5 average rating, 49 reviews
Guest favourite
Home in Lee
GreenHouse
20–25 MarIndividual Host,
€ 182 per night
5.0 out of 5 average rating, 31 reviews
Guest favourite
Flat in Lenox
All New-Heart of Lenox 2 Bedroom Apartment
30 Sep – 7 OctIndividual Host,
€ 297 per night
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Stockbridge
Relaxing Berkshire Retreat with Lake Access
11–18 MayIndividual Host,
€ 568 per night
5.0 out of 5 average rating, 31 reviews
Guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
25 Sep – 2 OctIndividual Host,
€ 317 per night
5.0 out of 5 average rating, 21 reviews
Guest favourite
Apartment in Lenox
Spacious 3 bedroom apt in Lenox historic downtown
10–17 JanIndividual Host,
€ 416 per night
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in Canaan
Mountain View Getaway
8–15 NovIndividual Host,
€ 106 per night
5.0 out of 5 average rating, 81 reviews
Guest favourite
Home in Richmond
LUXURY BERKSHIRES BARN! GRAND! VIEWS! 2/2
15–22 NovIndividual Host,
€ 267 per night
5.0 out of 5 average rating, 55 reviews
Guest favourite
Flat in Lenox
Peaceful 2 BR apartment minutes from Tanglewood
23–30 JunIndividual Host,
€ 326 per night
5.0 out of 5 average rating, 65 reviews
Guest favourite
Cabin in West Stockbridge
Modern Cabin near Tanglewood
21–28 FebIndividual Host,
€ 451 per night
4.98 out of 5 average rating, 41 reviews

Quick stats about holiday rentals in Lenox

Total rentals

250 properties

Rentals with a pool

60 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

100 properties are a good fit for families

Total number of reviews

6.5K reviews

Nightly prices starting at

€ 9 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Berkshire County
  5. Lenox