Villas and Holiday homes in Lee, MA

48 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Lee, MA holiday homes
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

48 Villa rentals in Lee, MA

Best Lee, MA villas and holiday homes with a fireplace

Beautiful Lenox Home, 3 Mi To Shakespeare & Co! - Lee, MA
9.3 112 reviews

Beautiful Lenox Home, 3 Mi To Shakespeare & Co!

house, Lenox
This Lenox property is located just six kilometres from both Cranwell Spa & Golf Club and Tanglewood Musical Center, making it a convenient base for exploring the area's cultural and leisure attractions. The house has received excellent ratings for cleanliness and user experience, and a very good rating for its location.
The three-bedroom house offers 228 square metres of space and can comfortably accommodate up to six guests. The property features a fully equipped kitchen, air conditioning, a garden, a spa, parking, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
Modern Chalet Near Tanglewood & Downtown Lenox - Lee, MA
9.8 45 reviews

Modern Chalet Near Tanglewood & Downtown Lenox

chalet, Lenox
This modern A-frame cabin is located in Lenox, just a short walk from Tanglewood, Kennedy Park, and Kripalu, offering easy access to cultural events, outdoor recreation, and wellness activities. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The cabin features a split-level mezzanine design, offering a blend of modern and rustic charm, and can accommodate up to six guests. Enjoy stunning views of the Berkshires from the open living room with triple-height ceilings, relax on the sun porch or deck, or unwind in the garden hammocks. The cabin also includes a fully equipped kitchen, a private garden, a ping pong table, and BBQ facilities available upon request.
Enchanted Tiny Tower Nestled In The Berkshires - Lee, MA
9.9 407 reviews

Enchanted Tiny Tower Nestled In The Berkshires

cabin, Tyringham
The Enchanted Tiny Tower is situated on the Santarella Estate in Tyringham, Massachusetts, just a few kilometers from the charming town of Great Barrington and close to the Berkshires' scenic attractions. This unique accommodation has received excellent ratings for its location, cleanliness, and overall experience.
The tower offers a romantic and whimsical stay for two guests, with a fully equipped kitchenette, dining area, and comfortable living space. Guests can enjoy a stone bench seating area and a 'chiminea' for evenings by the fire, as well as the surrounding gardens, lily pond, stone bridges, babbling brook, and wooded area.
189 M² House ∙ 5 Bedrooms ∙ 12 Guests - Lee, MA
9.1 40 reviews

189 M² House ∙ 5 Bedrooms ∙ 12 Guests

house, Lee
This five-bedroom cottage in Lee, Massachusetts, is a short drive from attractions such as the Berkshire Botanical Garden and the Norman Rockwell Museum.
The 189-square-metre (2,033 sq ft) property sleeps twelve, boasts a country-style kitchen, a clawfoot bath, and offers AvantStay amenities including 24/7 support and optional extras.

Check Out Holiday Houses with a Jacuzzi in Lee, MA

Private hot tub access in your holiday home after an active day is a special detail that makes your trip to Lee, MA truly memorable.

Restored 1881 Farm House - Lee, MA
9.9 177 reviews

Restored 1881 Farm House

house, Lenox
This restored 1881 farmhouse is located in Lenox, just over 5 kilometres from both Tanglewood and Cranwell Spa & Golf Club, in a peaceful rural setting. It has received excellent ratings for location, cleanliness, and overall experience.
The house is a 2-bedroom property with a floor area of 120 square metres, comfortably accommodating up to 4 guests. It offers modern amenities like air conditioning, Wi-Fi, a fully equipped kitchen, a washing machine, and a bathroom with a bath, as well as a terrace and garden for enjoying the outdoors.

Frequently asked questions about villa rentals in Lee, MA

Popular destinations

Best Lee, MA villas and holiday homes with a kitchen

A Grand Property In Historic Stockbridge - Lee, MA
9.8 163 reviews

A Grand Property In Historic Stockbridge

apartment, Stockbridge
This beautiful six-bedroom house is located in Stockbridge, just a short distance from Mission House, a significant historical site, and within a 24-kilometre drive of Schantz Galleries and the Berkshire Theatre Festival. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious home provides ample room for a large family or group of friends, covering 836 square metres and comfortably accommodating up to 12 guests. The house offers a range of modern amenities, including a fully equipped kitchen, a spa, a tennis court, and a beautiful garden with a barbecue, perfect for enjoying the outdoors.

Best Lee, MA villas and holiday homes with a pool

Among the 48 accommodations in Lee, MA, here are the 1 best villas and holiday homes with a pool

Lakeside Estate 2 Homes For Family Gatherings - Lee, MA
No reviews

Lakeside Estate 2 Homes For Family Gatherings

house, Lenox
This detached house in Lenox is situated 2.7 kilometres from Cranwell Spa & Golf Club and 5.9 kilometres from Tanglewood Musical Center, with Great Falls and Canaan Village Historic District both 40.2 kilometres away.
This property accommodates up to 18 guests with 1 bedroom, 5 bathrooms, air conditioning, a kitchen, free Wi-Fi, private parking, and a garden, offering an ideal setting for family gatherings near the Norman Rockwell Museum.
©2026 cozycozy.com