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Holiday homes in Lenox You’ll Love

Top-Rated Lenox Holiday homes for Every Budget and Style!

Looking for a holiday home in Lenox (Massachusetts)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Lenox.

We found 22 Holiday-homes in Lenox and the surrounding area (within 30 miles)

Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires in Stockbridge, USA

Berkshire Vacation Rental: Stockbridge H...

Holiday home in Stockbridge near Lenox, Massachusetts , Goodrich Street 22
Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires offers accommodations in Stockbridge, 3.7 miles from Norman Rockwell Museum...
  • Parking
  • Pets allowed

Exceptional 3 Reviews 10.0

from $462.25 Show details »

Stockbridge Retreat with Pool and Hot Tub! in Stockbridge, USA

Stockbridge Retreat with Pool and Hot Tu...

Holiday home in Stockbridge near Lenox, Massachusetts
Stockbridge Retreat with Pool and Hot Tub! is located in Stockbridge, just 3.8 miles from Norman Rockwell Museum and 6.8 miles from Cranwell Spa & Gol...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $1.677.89 Show details »

Holiday Inn Oak n Spruce Resort -1BD Sleep up to 4 in Lee, USA

Holiday Inn Oak n Spruce Resort -1BD Sle...

Holiday home in Lee near Lenox, Massachusetts , 190 Meadow St, Lee, MA 01238, USA
Holiday Inn Oak n Spruce Resort -1BD Sleep up to 4 is located in Lee, just 6.9 miles from Cranwell Spa & Golf Club and 8.4 miles from Tanglewood Music...
  • Fitness centre
  • Indoor pool
  • Swimming Pool

no reviews

from $99.00 Show details »

Too Good AKA 2 Goodrich St in Stockbridge, USA

Too Good AKA 2 Goodrich St

Holiday home in Stockbridge near Lenox, Massachusetts , 2 Goodrich Street
Too Good AKA 2 Goodrich St offers accommodations in Stockbridge, 6.9 miles from Tanglewood and 19 miles from Great Falls.
  • Family rooms

Exceptional 2 Reviews 10.0

from $403.19 Show details »

Classic Stockbridge Cottage in Stockbridge, USA

Classic Stockbridge Cottage

Holiday home in Stockbridge near Lenox, Massachusetts , Christian Hill Road 15
Classic Stockbridge Cottage is located in Stockbridge, just a 19-minute walk from Norman Rockwell Museum and 5.6 miles from Tanglewood Musical Center.
  • Parking
  • Pets allowed

no reviews

from $473.45 Show details »

Tranquil 3 BR Stockbridge House with Private Deck! in Stockbridge, USA

Tranquil 3 BR Stockbridge House with Pri...

Holiday home in Stockbridge near Lenox, Massachusetts
Tranquil 3 BR Stockbridge House with Private Deck! offers accommodations in Stockbridge, 5.7 miles from Tanglewood and 8.7 miles from Cranwell Spa & G...
  • Parking
  • Pets allowed
  • Spa and wellness centre

Exceptional 2 Reviews 9.5

from $354.41 Show details »

Cordelia by AvantStay Amazing Backyard 10mins from Stockbridge in Lee, USA

Cordelia by AvantStay Amazing Backyard 1...

Holiday home in Lee near Lenox, Massachusetts
Cordelia by AvantStay Amazing Backyard 10mins from Stockbridge is located in Lee, just 3.2 miles from Cranwell Spa & Golf Club and 5.7 miles from Tang...
  • Parking
  • Pets allowed

Very good 3 Reviews 8.3

from $307.34 Show details »

Berkshire Vacation Home in Lee - Pool is Open! in Lee, USA

Berkshire Vacation Home in Lee - Pool is...

Holiday home in Lee near Lenox, Massachusetts , 150 Theresa Terrace
Berkshire Vacation Home in Lee - Pool is Open! is located in Lee, just 2.4 miles from Cranwell Spa & Golf Club and 4.7 miles from Tanglewood.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming Pool

no reviews

from $76.00 Show details »

Cozy Stockbridge Cabin - Walk to Beach and Lake! in Stockbridge, USA

Cozy Stockbridge Cabin - Walk to Beach a...

Holiday home in Stockbridge near Lenox, Massachusetts
Cozy Stockbridge Cabin - Walk to Beach and Lake! is located in Stockbridge, just 3.2 miles from Norman Rockwell Museum and 3.3 miles from Tanglewood.
  • Parking
  • Spa and wellness centre

Fabulous 2 Reviews 9.0

from $288.51 Show details »

The Gatehouse on Golden Hill in Lee, USA

The Gatehouse on Golden Hill

Holiday home in Lee near Lenox, Massachusetts , 117 Golden Hill Road
The Gatehouse on Golden Hill is located in Lee, just 7.9 miles from Norman Rockwell Museum and 25 miles from Great Falls.
  • Family rooms

no reviews

from $467.41 Show details »

Stockbridge Home Walk to Town Beach! in Stockbridge, USA

Stockbridge Home Walk to Town Beach!

Holiday home in Stockbridge near Lenox, Massachusetts
Stockbridge Home Walk to Town Beach! is located in Stockbridge, just 2.4 miles from Tanglewood and 3.6 miles from Cranwell Spa & Golf Club.
  • Parking
  • Spa and wellness centre

Very good 4 Reviews 8.5

from $245.26 Show details »

Wellspring by AvantStay Indoor Pool Views in Richmond, USA

Wellspring by AvantStay Indoor Pool View...

Holiday home in Richmond near Lenox, Massachusetts
Wellspring by AvantStay Indoor Pool Views offers accommodations in Richmond, 2.4 miles from Tanglewood Musical Center and 2.8 miles from Tanglewood.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $1.101.83 Show details »

Private Guest House in Dtwn Lenox, Walk to Dining! in Lenox, USA

Private Guest House in Dtwn Lenox, Walk...

Holiday home in Lenox, Massachusetts
Private Guest House in Dtwn Lenox, Walk to Dining! offers accommodations in Lenox, 1.6 miles from Cranwell Spa & Golf Club and 1.6 miles from Tanglewo...
  • Parking

Exceptional 11 Reviews 9.5

from $331.27 Show details »

Restored 1881 Farm House in Lenox, USA

Restored 1881 Farm House

Holiday home in Lenox, Massachusetts , 76 East Dugway Road
Restored 1881 Farm House offers accommodations in Lenox, 8.6 miles from Norman Rockwell Museum and 26 miles from The Clark Art Institute.
  • Pets allowed
  • Family rooms

Exceptional 5 Reviews 9.8

from $326.15 Show details »

Beautiful Lenox Home, 3 Mi to Shakespeare and Co! in Lenox, USA

Beautiful Lenox Home, 3 Mi to Shakespear...

Holiday home in Lenox, Massachusetts
Beautiful Lenox Home, 3 Mi to Shakespeare and Co! offers accommodations in Lenox, 3.7 miles from Cranwell Spa & Golf Club and 3.7 miles from Tanglewoo...
  • Parking
  • Spa and wellness centre

Very good 4 Reviews 8.0

from $409.57 Show details »

Lenox House with Screened Patio and Mountain View in Lenox, USA

Lenox House with Screened Patio and Moun...

Holiday home in Lenox, Massachusetts
Lenox House with Screened Patio and Mountain View offers accommodations in Lenox, 5.3 miles from Tanglewood and 5.5 miles from Cranwell Spa & Golf Clu...
  • Parking
  • Pets allowed
  • Spa and wellness centre
  • Outdoor pool
  • Swimming pool

no reviews

from $236.17 Show details »

Richmond Cottage with Fire Pit and Furnished Deck! in Richmond, USA

Richmond Cottage with Fire Pit and Furni...

Holiday home in Richmond near Lenox, Massachusetts
Richmond Cottage with Fire Pit and Furnished Deck! is located in Richmond, just 6.8 miles from Tanglewood and 10 miles from Norman Rockwell Museum.
  • Parking

no reviews

from $82.00 Show details »

Family-Friendly Richmond Cottage with Private Yard in Pittsfield, USA

Family-Friendly Richmond Cottage with Pr...

Holiday home in Pittsfield near Lenox, Massachusetts
Family-Friendly Richmond Cottage with Private Yard is located in Pittsfield, just 6.7 miles from Tanglewood Musical Center and 7.1 miles from Tanglewo...
  • Parking
  • Pets allowed

Fabulous 1 Reviews 9.0

from $88.00 Show details »

6 Mi to Skiing Pet-Friendly Home in Pittsfield! in Pittsfield, USA

6 Mi to Skiing Pet-Friendly Home in Pitt...

Holiday home in Pittsfield near Lenox, Massachusetts
6 Mi to Skiing Pet-Friendly Home in Pittsfield! is located in Pittsfield, just 9.3 miles from Tanglewood and 9.4 miles from Cranwell Spa & Golf Club.
  • Parking
  • Pets allowed

no reviews

from $240.16 Show details »

Berkshire Vacation Rentals: Chic Pittsfield Home With A View in Pittsfield, USA

Berkshire Vacation Rentals: Chic Pittsfi...

Holiday home in Pittsfield near Lenox, Massachusetts , Tamarack Road 35
Berkshire Vacation Rentals: Chic Pittsfield Home With A View is located in Pittsfield, just 7.1 miles from Tanglewood and 7.3 miles from Cranwell Spa ...
  • Parking
  • Pets allowed

Good 2 Reviews 7.5

from $344.78 Show details »

Econo Lodge Lee - Great Barrington in Lee, USA

Econo Lodge Lee - Great Barrington

Lodge in Lee near Lenox, Massachusetts , 980 Pleasant Street
Located in Lee, Econo Lodge Lee - Great Barrington has mountain views and free WiFi, 5.4 miles from Norman Rockwell Museum and 5.7 miles from Cranwell...
  • Parking
  • Pets allowed

Pleasant 235 Reviews 6.5

from $56.97 Show details »

Berkshire Mountain Lodge in Pittsfield, USA

Berkshire Mountain Lodge

Lodge in Pittsfield near Lenox, Massachusetts , 8 Dan Fox Drive
Featuring an indoor swimming pool and a fitness center, Berkshire Mountain Lodge is located in Pittsfield.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 668 Reviews 8.5

from $95.40 Show details »

Number of Holiday homes in Lenox 22
Number of guest ratings 3,716
Average price per night $362.00
Lowest price per night $51,00
Highest price per night $4.626,94

Top 10 Cheapest Holiday-homes in Lenox

Discover the Cheapest Holiday-homes in Lenox – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Lenox

Check out the Most Booked Holiday-homes in Lenox – Based on Guest Popularity.

Holiday homes in Lenox (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Lenox can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Lenox for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Lenox should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com