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Latest Vacation Rentals in Lee MA (25)

5 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Experience the beauty of the Berkshires from Cordelia, your charming Massachusetts home with a chic cottage style and romantic outdoor spaces. Head to the backyard to find a brick patio and...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

This is the perfect Berkshire home to swim, hike, leaf-peep, ski, sled, engage in the cultural attractions of the neighborhood (Tanglwood, Jacobs Pillow, Shakespeare and Co etc.), RELAX and get...

Created Jul 20, 2026

2 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Cozy Townhouse on Main St in Lee , the entrance to the Berkshires. The townhouse is two stories with 2 Bedrooms, 1 1/2 Bathroom, kitchen, dining room, TV, family room, back yard with private porch...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Stylish, fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires! Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco...

Created Jul 20, 2026

1 Br Apartment Vacation Rental In Lee, Massachusetts

Completely renovated downtown second floor apartment with open floor plan, located in historical downtown Lee. This apartment is equipped with everything you need for a get away in the Berkshires....

Created Jul 20, 2026

6 Br Private Vacation Home Vacation Rental In Stockbridge, Massachusetts

The General Williams house is located 2 miles from Stockbridge Center and 5 miles from Lenox Center. Only 7 miles from the Mass Pike it is an easy commute from Boston or New York City. The house...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Summary:Our quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort of a home away from home. Only 5 minutes from town and in the heart of the...

Created Jul 20, 2026

5 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Welcome to our 5BR/5BA Berkshire vacation home, just 5 minutes to Stockbridge and 10 minutes to Tanglewood. Enjoy a walk to downtown Lee restaurants and shops from our perfectly located family...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

This meticulously cared for home is just ideal for year-round or vacation living. Enjoy the private screen porch on summer nights or soak in the sun on the wrap around deck. Take a leisurely boat...

Created Jul 20, 2026

1 Br Apartment Vacation Rental In Lee, Massachusetts

This 1-bedroom apartment is perfect for your peaceful escape in the Berkshires. Inside, guests find a soothing space featuring a full bed and a superb bathroom with a relaxing bathtub. The...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Lee, Massachusetts

Your Berkshires getaway starts at this sweet 1-bedroom, 1-den condo. The picture windows in the front sitting area look out onto Heron Pond. Sunlight streams in through the skylight in the...

Created Jul 20, 2026

2 Br Apartment Vacation Rental In Lee, Massachusetts

Experience the beauty of the Berkshires. Newly renovated two bedroom retreat in downtown, Lee. Steps from all the restaurants & shops. Equipped with a brand-new eat in kitchen with an array of...

Created Jul 20, 2026

2 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Stay comfortably in Lee at this 2-bedroom house. The space features two queen beds, offering plenty of room for a restful night. Guests can enjoy a welcoming atmosphere with heating and window air...

Created Jul 20, 2026

3 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

A modern 3-bedroom, 2-bathroom idyllic getaway surrounded by the Berkshires lush forests, mountain vistas and culture. Less than a mile hike to the Appalachian Trail. Drive 10-15 minutes to...

Created Jul 20, 2026

3 Br Condo Vacation Rental In Lee, Massachusetts

Sunny three bedroom condo available for summer rental , with two full baths. Shaded front porch and sunny rear deck with BBQ. Rental is fully furnished with linens. Well stocked kitchen- includes...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Escape to Hillside Haven, a cozy Berkshire retreat perfect for families. This spacious 4BR, 2.5BA home features an open floor plan on the lower level, a kids` room with two twin beds, and a fun...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Stockbridge, Massachusetts

Welcome to Beaver Creek by AvantStay!Tucked amid the rolling hills and vibrant forests of Stockbridge, Beaver Creek is a storybook escape where New England charm meets modern comfort. This...

Created Jul 20, 2026

3 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

This newly renovated house in the woods on a private road in Lee is an ideal summer or fall retreat. Our little community (30 homes) has a beach and a dock on Goose Pond, community kayaks and other...

Created Jul 20, 2026

2 Br Cabin Vacation Rental In Lee, Massachusetts

Lake Access On-Site | Kayak Provided | Cozy Interior w/ Big-Screen TVExperience the ultimate remote escape at this Lee vacation rental on Goose Pond! You may find its not easy to get to, but it's...

Created Jul 20, 2026

2 Br Apartment Vacation Rental In Lee, Massachusetts

High-Speed WiFi | Upgraded Kitchen | Private Forest-View Balcony | 2010 Addition to 1738 PropertyKick off your next Berkshire getaway at this Lee vacation rental, where historic soul meets modern...

Created Jul 20, 2026

3 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Experience the Berkshires like a local in this adorable 3-bedroom house. With two queen beds and twin trundle beds, it comfortably welcomes guests of all kinds. The house features two bathrooms,...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Our completely renovated farmhouse is set upon a hilltop overlooking downtown Lee. It is a perfect spot for culture, sports, relaxation, holidays and gatherings with family and friends. Take in the...

Created Jul 20, 2026

3 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Three bedroom, one bath, fully furnished home located on a tree-lined cul-de-sac in a quiet Lee neighborhood. Bright home is newly renovated, hardwood and tile floors, kitchen has floor to ceiling...

Created Jul 20, 2026

2 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Garfield House Vacation living for short or longer stays in a newly renovated townhouse is in close proximity to all Berkshire and town amenities. It has 2 levels, 1 and1/2 baths, 2 bedrooms, full...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Lee, Massachusetts

Summary:We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the Gatehouse to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is...

Created Jul 20, 2026

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