Vacation rentals in Lee

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Top-rated vacation rentals in Lee

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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.

Apr 24 – May 1

G$32,383 GYD per night

Guest favorite

Home in Lee

4.89 out of 5 average rating, 235 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)

Oct 6 – 13

G$26,043 GYD per night

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 347 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Jul 17 – 24

G$84,374 GYD per night

Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 225 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.

Jul 19 – 26

G$64,722 GYD per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 255 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Oct 14 – 21

G$20,654 GYD per night

Superhost

Apartment in Lee

4.78 out of 5 average rating, 106 reviews

Cozy Berkshire Cottage Style Apartment

Stay in a cozy Berkshires apartment! All windows allow views to the peaceful surrounding state forest and yard. Watch humming birds, oriols, deer, squirrels, opossums, racoons, woodchucks, and many more... The house is set back from the road, easily accessible, yet private. The cottage is a duplex: the Airbnb apartment is on the left side of the cottage. • Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Stockbridge, Lenox, MA Turnpike • Ideal for lovers of nature & the Berkshires

Sep 9 – 16

G$23,354 GYD per night

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 257 reviews

Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Dec 31 – Jan 7

G$25,438 GYD per night

Guest favorite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Feb 7 – 14

G$26,888 GYD per night

Guest favorite

Home in Lee

5.0 out of 5 average rating, 228 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

G$63,742 GYD per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 275 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Sep 6 – 13

G$30,673 GYD per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

Jul 17 – 24

G$31,759 GYD per night

Guest favorite

Guesthouse in Stockbridge

4.96 out of 5 average rating, 175 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a brand new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Jun 17 – 24

G$36,384 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Lee vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Lee's top sights

Lee Premium Outlets155 locals recommend

51 Park Restaurant & Tavern23 locals recommend

Big Y World Class Market99 locals recommend

The Mount, Edith Wharton's Home167 locals recommend

Salmon Run Fish House23 locals recommend

Starving Artist Creperie and Cafe40 locals recommend

Other great vacation rentals in Lee

Superhost

Apartment in Lenox Dale

4.93 out of 5 average rating, 116 reviews

Charming 2BD apartment.

Apr 30 – May 7

G$31,874 GYD per night

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 237 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

Mar 12 – 19

G$39,498 GYD per night

Guest favorite

Home in New Lebanon

4.99 out of 5 average rating, 348 reviews

The old sawmill from 1771

Dec 25 – Jan 1

G$30,107 GYD per night

Guest favorite

Guesthouse in Canaan

4.93 out of 5 average rating, 166 reviews

Airy cottage with meadow views in The Berkshires

May 14 – 21

G$34,554 GYD per night

Superhost

Home in Dalton

4.88 out of 5 average rating, 113 reviews

The Yellow House

May 31 – Jun 7

G$23,663 GYD per night

Guest favorite

Home in Lee

5.0 out of 5 average rating, 35 reviews

GreenHouse

Sep 5 – 12

G$29,995 GYD per night

Guest favorite

Guesthouse in Lenox

4.9 out of 5 average rating, 51 reviews

Lenox - Sunny cottage nestled in the garden

Jan 4 – 11

G$26,234 GYD per night

Guest favorite

Home in Becket

4.94 out of 5 average rating, 36 reviews

Nerd Preservation Sanctuary

Nov 5 – 12

G$19,320 GYD per night

Show all

Quick stats about vacation rentals in Lee

Total rentals
250 properties
Rentals with a pool
70 properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
150 properties are a good fit for families
Total number of reviews
8.8K reviews
Nightly prices starting at
G$2,090 GYD before taxes and fees

Frequently Asked Questions

Are there family-friendly vacation rentals in Lee?
Lee has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Boutique Hotel Rentals in Lee?
Enhance your stay in our Boutique Hotel Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with air conditioning, 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 aparthotel rentals in Lee have a gym?
Absolutely! We offer over 20 aparthotel 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 bed and breakfast rentals in Lee?
Experience the best of Lee with our bed and breakfast rentals, starting at about $70 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 100 vacation rentals in Lee featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do bed and breakfast rentals in Lee have wireless internet?
Absolutely! We offer over 10 bed and breakfast 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 70 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 50 house rentals with a bbq area in Lee. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Lee

Top-rated vacation rentals in Lee

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Lee vacation rentals

Stay near Lee's top sights

Other great vacation rentals in Lee

Apartment in Lenox Dale

Cottage in Becket

Home in New Lebanon

Guesthouse in Canaan

Home in Dalton

Home in Lee

Guesthouse in Lenox

Home in Becket

Quick stats about vacation rentals in Lee

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there family-friendly vacation rentals in Lee?

What are the most popular amenities for Boutique Hotel Rentals in Lee?

Are there pet-friendly vacation rentals in Lee?

Do aparthotel rentals in Lee have a gym?

Do hotel rentals in Lee have air conditioning?

How much does it cost to stay in bed and breakfast rentals in Lee?

Are there vacation rentals with a dedicated workspace in Lee?

Do bed and breakfast rentals in Lee have wireless internet?

Are there Lee vacation rentals on Airbnb with pools?

Do house rentals in Lee have a bbq area?

Destinations to explore