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Holiday homes in Lenox

Enjoy your stay and find the best Holiday homes in Lenox at affordable prices

Searching for a holiday home in Lenox (Massachusetts)? Explore a great selection of vacation homes in Lenox to find the one that best fits to your needs, starting from $156.75 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Lenox and region (30 miles)
Restored 1881 Farm House in Lenox, USA

Restored 1881 Farm House

Holiday home in Lenox, Massachusetts , 76 East Dugway Road
Located in Lenox, 5.2 km from Tanglewood and 5.5 km from Cranwell Spa & Golf Club, Restored 1881 Farm House provides air-conditioned accommodation wit...
  • Pets allowed
  • Family rooms

no reviews

from $399.00 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 Lakefront Beach! is situated in Stockbridge, 3.9 km from Tanglewood, 5.7 km from Cranwell Spa & Golf Club, and 6.5 km from ...
  • Parking

no reviews

from $272.33 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
Located in Lenox, 5.6 km from Tanglewood and 5.9 km from Cranwell Spa & Golf Club, Beautiful Lenox Home, 3 Mi to Shakespeare and Co! provides accommod...
  • Parking
  • Internet facilities
  • Shower
  • Bath
  • TV

Superb 3 Reviews 9.0

from $346.67 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
Set in Stockbridge, 4.7 km from Tanglewood Musical Center and 5.1 km from Norman Rockwell Museum, Cozy Stockbridge Cabin - Walk to Beach and Lake! pro...
  • Parking

Superb 2 Reviews 9.5

from $341.00 Show details »

Charming Lenox Home View of October Mountain in Lenox, USA

Charming Lenox Home View of October Moun...

Holiday home in Lenox, Massachusetts
Located in Lenox, within 8.5 km of Tanglewood and 8.8 km of Cranwell Spa & Golf Club, Charming Lenox Home View of October Mountain offers accommodatio...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $364.00 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 centre, Berkshire Mountain Lodge is located in Pittsfield.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 497 Reviews 8.4

from $191.67 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 3BR Stockbridge House with Private Deck! is situated in Stockbridge, 8.5 km from Tanglewood Musical Center, 9.1 km from Tanglewood, and 14 km...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Iron

Superb 2 Reviews 9.5

from $416.00 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
Within 5.1 km of Norman Rockwell Museum and 10 km of Cranwell Spa & Golf Club, Too Good AKA 2 Goodrich St offers free WiFi and a garden.
  • Family rooms

no reviews

from $449.00 Show details »

Lakefront Berkshires Retreat with Deck, Dock and Boat! in Great Barrington, USA

Lakefront Berkshires Retreat with Deck,...

Holiday home in Great Barrington near Lenox, Massachusetts
Offering lake views, Lakefront Berkshires Retreat with Deck, Dock and Boat! is an accommodation set in Great Barrington, 8.3 km from Norman Rockwell M...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Iron

Good 4 Reviews 7.7

from $329.00 Show details »

Berkshires Cabin 2 Mi to Appalachian Trail! in Otis, USA

Berkshires Cabin 2 Mi to Appalachian Tra...

Holiday home in Otis near Lenox, Massachusetts
Berkshires Cabin 2 Mi to Appalachian Trail! is located in Otis, 21 km from Cranwell Spa & Golf Club, 25 km from Tanglewood, as well as 26 km from Tang...
  • Parking

no reviews

from $259.00 Show details »

Berkshires Home on 11 Acres with Pond and 2 Fire Pits! in Becket, USA

Berkshires Home on 11 Acres with Pond an...

Holiday home in Becket near Lenox, Massachusetts
Berkshires Home on 11 Acres with Pond and 2 Fire Pits! is located in Becket, 22 km from Cranwell Spa & Golf Club, and provides a patio, garden, and fr...
  • Parking
  • Internet facilities
  • Hairdryer
  • Iron
  • Refrigerator

no reviews

from $383.00 Show details »

Cozy Monterey Home with Porch Walk to Lake Garfield in Monterey, USA

Cozy Monterey Home with Porch Walk to La...

Holiday home in Monterey near Lenox, Massachusetts
Set 22 km from Norman Rockwell Museum, 24 km from Tanglewood and 25 km from Tanglewood Musical Center, Cozy Monterey Home with Porch Walk to Lake Garf...
  • Parking

no reviews

from $304.14 Show details »

Picturesque Cottage with Sunroom on Ashmere Lake! in Hinsdale, USA

Picturesque Cottage with Sunroom on Ashm...

Holiday home in Hinsdale near Lenox, Massachusetts
Located 32 km from Cranwell Spa & Golf Club, 32 km from Tanglewood Musical Center and 40 km from Norman Rockwell Museum, Picturesque Cottage with Sunr...
  • Parking

Exceptional 1 Reviews 10.0

from $208.00 Show details »

Cozy Great Barrington Home about 1 Mi to Ski Resort! in Great Barrington, USA

Cozy Great Barrington Home about 1 Mi to...

Holiday home in Great Barrington near Lenox, Massachusetts
Located in Great Barrington, 18 km from Norman Rockwell Museum, 22 km from Cranwell Spa & Golf Club and 23 km from Tanglewood Musical Center, Cozy Gre...
  • Parking

Very good 2 Reviews 8.5

from $488.67 Show details »

Waterfront Cottage 10 Min to Great Barrington! in New Marlborough, USA

Waterfront Cottage 10 Min to Great Barri...

Holiday home in New Marlborough near Lenox, Massachusetts
Waterfront Lake Buel Cottage 7 Mi to Monument Mtn is located in New Marlborough, 25 km from Cranwell Spa & Golf Club, 26 km from Tanglewood Musical Ce...
  • Parking
  • Internet facilities
  • Refrigerator
  • DVD player
  • Fan

Exceptional 1 Reviews 10.0

from $465.00 Show details »

Rustic Berkshires Cottage at Lake Buel with Kayaks! in New Marlborough, USA

Rustic Berkshires Cottage at Lake Buel w...

Holiday home in New Marlborough near Lenox, Massachusetts
Situated in New Marlborough, 21 km from Norman Rockwell Museum, 25 km from Cranwell Spa & Golf Club and 26 km from Tanglewood Musical Center, Rustic B...
  • Parking
  • Pets allowed

Superb 4 Reviews 9.3

from $262.67 Show details »

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 in Hancock, USA

Unique Yeti-Theme Ski On Off Suite Jimin...

Holiday home in Hancock near Lenox, Massachusetts , 37 Corey Road
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 features free WiFi and a fitness ...
  • Parking
  • Fitness centre
  • Indoor pool
  • Outdoor pool
  • Swimming pool

Superb 16 Reviews 9.2

from $162.77 Show details »

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak in Hancock, USA

Ski On Off 1BR Suite 1st Flr Sleeps 4 Ji...

Holiday home in Hancock near Lenox, Massachusetts , 37 Corey Road
Located about 33 km from Tanglewood, Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak offers accommodation with an outdoor pool and free WiFi.
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 4 Reviews 8.8

from $156.75 Show details »

Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn in Hancock, USA

Deluxe Ski On Off 1BR Suite Sleeps 4 on...

Holiday home in Hancock near Lenox, Massachusetts , 37 Corey Road
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn features free WiFi and a fitness ...
  • Parking
  • Fitness centre

Superb 12 Reviews 9.0

from $183.08 Show details »

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak in Hancock, USA

Mountain View Suite Sleeps 4 Ski OnOff J...

Holiday home in Hancock near Lenox, Massachusetts , Corey Road 37
Situated about 33 km from Tanglewood, Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak offers accommodation with an outdoor pool and free WiFi.
  • Parking
  • Fitness centre
  • Indoor pool
  • Outdoor pool
  • Swimming pool

Exceptional 6 Reviews 10.0

from $171.33 Show details »

Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy in Hancock, USA

Gorgeous New Zen Suite Sleeps 4-Ski On O...

Holiday home in Hancock near Lenox, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy provides free WiFi and a fitness c...
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 6 Reviews 9.0

from $162.77 Show details »

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk in Hancock, USA

WOW-New Ski OnOff Suite By Pool Sleeps 4...

Holiday home in Hancock near Lenox, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk features free WiFi and a fitness ...
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 11 Reviews 9.1

from $171.33 Show details »

Restored 1800s Home Half Mile to Ski Resort! in Otis, USA

Restored 1800s Home Half Mile to Ski Res...

Holiday home in Otis near Lenox, Massachusetts
Set 26 km from Cranwell Spa & Golf Club and 30 km from Tanglewood in Otis, Restored 1800s Home Half Mile to Ski Resort! offers accommodation with a ki...
  • Parking

no reviews

from $284.29 Show details »

Hancock Log Cabin Retreat 2 Miles to Jiminy Peak! in Hancock, USA

Hancock Log Cabin Retreat 2 Miles to Jim...

Holiday home in Hancock near Lenox, Massachusetts
Situated in Hancock, 34 km from Tanglewood and 34 km from Cranwell Spa & Golf Club, Hancock Log Cabin Retreat 2 Miles to Jiminy Peak! provides accommo...
  • Parking
  • Shower
  • Bath
  • TV
  • Hairdryer

Exceptional 1 Reviews 10.0

from $226.00 Show details »

Cabin with 3 Acres, Tennis Courts By 4 Ski Mtns in Sandisfield, USA

Cabin with 3 Acres, Tennis Courts By 4 S...

Holiday home in Sandisfield near Lenox, Massachusetts
Situated in Sandisfield, 25 km from Cranwell Spa & Golf Club, 28 km from Norman Rockwell Museum and 29 km from Tanglewood, Cabin with 3 Acres, Tennis ...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Refrigerator

Very good 1 Reviews 8.0

from $393.00 Show details »

Number of Holiday homes in Lenox 38
Number of guest ratings 4361
Average price per night $429.77
Lowest price per night $156.75
Highest price per night $995.00

Most popular Holiday-homes in Lenox

The most popular Holiday-homes in Lenox based on average guest rating (Top 10).

Cheapest Holiday-homes in Lenox

The cheapest Holiday-homes in Lenox based on room rate per night (Top 10).

Most booked Holiday-homes in Lenox

The most booked Holiday-homes in Lenox based on popularity with guests (Top 10).

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