Vacation rentals in Lee

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Top-rated vacation rentals in Lee

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

Guest favorite

Home in Lee

4.89 out of 5 average rating, 234 reviews

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)

Sep 13 – 20

$108 per night
Guest favorite

Home in Lee

4.9 out of 5 average rating, 202 reviews

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.

Sep 4 – 11

$221 per night
Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 222 reviews

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

May 13 – 20

$249 per night

Popular amenities for Lee vacation rentals

Stay near Lee's top sights

Lee Premium Outlets155 locals recommend
51 Park Restaurant & Tavern23 locals recommend
Big Y World Class Market99 locals recommend
Haven67 locals recommend
The Mount, Edith Wharton's Home167 locals recommend
Salmon Run Fish House23 locals recommend

Other great vacation rentals in Lee

Guest favorite

Guesthouse in Lenox

4.94 out of 5 average rating, 271 reviews

The Granary at House on Golden Hill

Jun 6 – 13

$180 per night
Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 346 reviews

Mid-Century Glass Octagon in the Berkshires

Jun 13 – 20

$327 per night
Guest favorite

Cabin in Lee

4.9 out of 5 average rating, 102 reviews

Cozy cabin with panoramic views in the Berkshires

Sep 10 – 17

$339 per night
Guest favorite

Home in Canaan

5.0 out of 5 average rating, 132 reviews

Country Cottage

Mar 12 – 19

$135 per night
Guest favorite

Cottage in Great Barrington

4.91 out of 5 average rating, 223 reviews

Cottage on Scenic Road

Mar 23 – 30

$117 per night
Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 178 reviews

Tiny House on 70 Private Acres in Hudson Valley

Sep 13 – 20

$133 per night
Guest favorite

Home in Lee

5.0 out of 5 average rating, 33 reviews

GreenHouse

Sep 1 – 8

$119 per night
Guest favorite

Apartment in Lee

4.91 out of 5 average rating, 56 reviews

Studio 208 at Garfield Annex on Main St

Oct 9 – 16

$120 per night
Guest favorite

Apartment in Lee

5.0 out of 5 average rating, 97 reviews

Lovely Berkshire apartment with beautiful views

May 1 – 8

$214 per night
Guest favorite

Home in Becket

4.94 out of 5 average rating, 36 reviews

Nerd Preservation Sanctuary

Oct 21 – 28

$82 per night
Guest favorite

Apartment in Pittsfield

4.92 out of 5 average rating, 24 reviews

Comfortable Pittsfield Loft

Feb 1 – 8

$65 per night
Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

Nov 18 – 25

$91 per night

Quick stats about vacation rentals in Lee

Total rentals

240 properties

Rentals with a pool

60 properties have a pool

Pet-friendly rentals

70 properties allow pets

Family-friendly rentals

140 properties are a good fit for families

Total number of reviews

8.4K reviews

Nightly prices starting at

$10 before taxes and fees

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Lee?

    Lee has more than 140 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Lee?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a gym, over 90 homes with wireless internet, over 90 homes with air conditioning, over 40 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly vacation rentals in Lee?

    Four-legged friends are welcome in Lee. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Do house rentals in Lee have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Lee. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Lee have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Lee. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Lee?

    Experience the best of Lee with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Lee?

    Yes! Work meets play with ease at over 80 vacation rentals in Lee featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do hotel rentals in Lee have wireless internet?

    Absolutely! We offer over 10 hotel rentals with wireless internet in Lee. Enjoy a tailored experience with all the comforts you desire.

  • Are there Lee vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Lee, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Lee have a bbq area?

    Absolutely! We offer over 40 house rentals with a bbq area in Lee. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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