Airbnb your place

Holiday rentals in Lee

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Lee

  • Total holiday rentals

    Explore 300 holiday rentals in Lee

  • Nightly prices starting at

    Lee holiday rentals start at ₹3,841 per night before taxes and fees

  • Verified guest reviews

    Over 9,790 verified reviews to help you choose

  • Family-friendly holiday rentals

    210 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Holiday rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wifi availability

    290 of Lee holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Lee rentals

  • 4.8 Average rating

    Lee stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Lee

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

1 of 1 pages1 / 1
Top guest favourite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

LocationFamilyHot tub

4.97 out of 5 average rating, 109 reviews
Top guest favourite
A charming outdoor seating area is situated under a spacious pergola, designed with warm lights. Comfortable seating is set on a stone patio, with a grill nearby, surrounded by a grassy yard. Soft clouds and a gentle twilight sky provide a serene backdrop.
Home in Lee

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

FamilyLocationBiking

4.98 out of 5 average rating, 253 reviews
Top guest favourite
A modern kitchen is equipped with stainless steel appliances and wooden cabinetry, complemented by light hardwood flooring. A rustic table with a fruit bowl is surrounded by four wooden chairs. A glass door provides access to the outdoor deck, allowing natural light to fill the space.
Cottage in Lee

Perfect Holiday Home Renovated & Fully Equipped

Welcome to Prospect Place! Our charming renovated home is set upon a hilltop overlooking downtown Lee, "The Gateway to the Berkshires." The house is in the heart of the Berkshires and central to just about everything. It is a a short drive to Tanglewood, the Berkshire Theater Festival, Jacobs Pillow and the Berkshire Outlet Mall. Golf, tennis, skiing, swimming, and spas are just minutes away. It is a perfect spot for relaxation, culture, sports, a girls weekend, and family gatherings.

LocationFamilyKitchen

4.99 out of 5 average rating, 116 reviews
Guest favourite
The living room features a spacious leather sectional sofa facing a TV, with a wooden coffee table placed in front. A wood stove is positioned nearby on a black hearth, and a large window allows natural light to illuminate the space, adorned with plants and decorative items.
Home in Lee

Cozy Berkshires Cottage

Stay in a cozy, newly remodeled Berkshires 1920's cottage! We've added bedrooms and a bathroom with a soaking tub upstairs, expanded the first floor bathroom and added a laundry room. The cottage is set back from the main road, easily accessible yet private. -Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. -Ideal for couples, adventurers, business travelers, and furry friends (pets). -Note: Stairs to the 2nd floor are steep: guests are responsible for child safety.

FamilyLocationOutdoor spaces

4.9 out of 5 average rating, 282 reviews
Guest favourite
Cabin in Stockbridge

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood walls & fantastic interior design. Unwind in the reading nook, relax in the en suite bedroom with skylight, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9 minute walk or 2 minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood minutes away.

FamilyLocationGetting around

4.89 out of 5 average rating, 254 reviews
Guest favourite
A spacious living area features a modern sectional sofa adorned with various cushions, positioned around a round coffee table. Exposed wooden beams and high ceilings create an open atmosphere. A staircase leads to an upper level, and natural light illuminates the well-equipped kitchen visible in the background.
Home in Lee

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

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 Berkshires, this cozy cabin is a perfect escape from everyday life. Enjoy the fully appointed trappings of modernity—high-speed internet, a beautifully updated and well-stocked kitchen, hot tub, brand new stylish and comfortable furnishings, TV room, and more! Find us on social media: @stonebridgecabin

ValueFamilyHiking

4.88 out of 5 average rating, 108 reviews
Top guest favourite
The exterior of a Craftsman-inspired home is showcased against a colorful sunset sky. Natural materials create a warm facade, with a prominent stone chimney and large windows enhancing the inviting atmosphere. Lush landscaping surrounds the property, highlighting its connection to nature.
Home in Lee

Lovely Berkshire Home

"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 filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring, Jerusalem stone and porcelain plank tiles. Inviting color and intriguing design elements make this an extraordinarily pleasing home. Every detail has been thoughtfully considered within. Dreamy!"

LocationFamilyLayout

4.98 out of 5 average rating, 138 reviews
Top guest favourite
Home in Pittsfield

Cozy cottage on peaceful pond

This little slice of heaven is located on the serene Richmond Pond. Right down the street from Balderdash winery and a 15 minute drive to charming downtown Lenox and Tanglewood. In Lenox you can find great dining, shopping, and there is plenty of hiking and biking around this area. This cozy cottage has everything you need for a Berkshire retreat. In the fall cozy up next to the fireplace inside or out take a break and unwind at this Peaceful oasis. 

FamilyLocationCondition

5.0 out of 5 average rating, 38 reviews
Guest favourite
A light and neutral living room showcases a comfortable sectional sofa with decorative pillows. A round marble coffee table is positioned in front, adorned with a small plant. Two framed art pieces hang above the sofa, and textured rugs lie across the wooden flooring.
Flat in Lenox

Historical Downtown 1 Bedroom Apartment

Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.

LocationFamilyParking

4.96 out of 5 average rating, 118 reviews
Guest favourite
A spacious bedroom features a large window with a view of the lush greenery outside. The bed is adorned with a mix of pillows and a colorful area rug rests on the floor, enhancing the room's serene atmosphere.
Cabin in Lee

Comfy cabin with scenic views in the Berkshires

The Beaver Dam is a sunlight-filled & recently renovated cabin tucked in the woods, overlooking the October Mountain State Park and steps away from Basin Pond. We are located close to a number of excellent ski slopes. Our cottage is the last house on a private road and right next to protected forest. You can't ask for more privacy, peace and quiet than you'll find at our little piece of paradise on the pond!

ValueLocationBeach

4.91 out of 5 average rating, 146 reviews
Top guest favourite
The exterior of the house features a classic design with white siding and green accents. Large windows line the front, providing ample natural light. A pathway leads up to the entrance, surrounded by a green lawn and views of the Berkshire Hills in the background.
Home in Lee

Berkshire Hills country retreat

Relax in the comfort of the Berkshire Hills adjacent to October Mountain. This complete house comes with a large kitchen fully stocked with appliances and utensils to prepare a gourmet meal. Sit back and enjoy the vintage decor and a movie on the large 55 inch Roku TV. Within a very 5 minute drive you will find the towns of Lee, Lenox, and Stockbridge for shopping, dining, and entertainment.

FamilyLocationIndoor spaces

4.96 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Lee

Eliza Suite

Recently redecorated, new bed & hybrid memory foam mattress. 😍 Charming 1-bedroom apartment in a beautifully maintained Victorian home, located in the heart of town. Enjoy high ceilings, period details, and modern comfort just steps from shops, cafes and local attractions. Ideal for anyone looking to enjoy the convenience and character in a vibrant, safe and walkable neighborhood.

LocationCheck-inBeach

4.97 out of 5 average rating, 36 reviews

Popular amenities for Lee holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Lee's top sights

Mount Edith Wharton's Home

255 locals recommend

Shakespeare & Company

167 locals recommend

Kennedy Park

88 locals recommend

October Mountain State Forest

50 locals recommend

Cranwell Resort

22 locals recommend

Goose Pond

6 locals recommend

Other great holiday rentals in Lee

Top guest favourite
A spacious kitchen area is presented with light-colored cabinetry and a modern countertop. A wooden table, designed to accommodate ten, is centered in the room. Open shelves display glassware, and stainless steel appliances are visible, enhancing the functional layout.
Home in Lenox

Home away from home: Minutes to Tanglewood.

ValueFamilyCleanliness

4.93 out of 5 average rating, 60 reviews
Guest favourite
Home in Lee

Pond House at Middle Way Farm • Sunset Views

LocationAmenitiesView

5.0 out of 5 average rating, 9 reviews
Superhost
Home in Lee

4BDR Elegant Berkshires Escape | Beaver Creek

FamilyLocationBathroom

5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Lenox

The Berkshire Quintessential Cape downtown Lenox

LocationFamilyHospitality

5.0 out of 5 average rating, 10 reviews
Top guest favourite
A charming two-story house with yellow siding and gray shutters is framed by lush greenery. Solar panels are installed on the roof, and a welcoming porch is accessible by brick steps. The surrounding foliage adds a natural touch to the inviting exterior.
Home in Lee

Charming 19th Century Farmhouse

FamilyLocationWalkability

4.98 out of 5 average rating, 44 reviews
Top guest favourite
A well-lit living area is furnished with two light-colored sofas and a round coffee table. Soft curtains frame large windows, allowing natural light to brighten the space. A bookshelf filled with books is visible, alongside a cozy area rug that enhances the inviting ambiance.
Home in Lee

Fairview Getaway

FamilyLocationSkiing

5.0 out of 5 average rating, 29 reviews
Top guest favourite
A tranquil lake reflects a charming red house set against a backdrop of lush green trees and blue sky. The surrounding nature provides a serene atmosphere, inviting peaceful contemplation and relaxation.
Home in Lee

Spectacular Berkshire Retreat on Private Lake

FamilyLocationSkiing

4.95 out of 5 average rating, 92 reviews
Top guest favourite
A newly renovated home is showcased amidst a wide expanse of lush green grass, surrounded by trees and open spaces. Bright blue skies feature soft, white clouds, creating a serene setting for relaxation.
Home in Lee

Meadowbrook Cottage

LocationFamilyGetting around

5.0 out of 5 average rating, 39 reviews

When is the best time to visit Lee?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price₹21,988₹20,931₹22,084₹23,716₹25,828₹26,020₹26,884₹24,676₹20,643₹24,004₹21,795₹23,428
Avg. temp-3°C-1°C3°C10°C16°C20°C24°C23°C18°C12°C6°C0°C

Frequently Asked Questions

  • What are the best places to stay in Lee?

    Many choose to stay in rentals near the historic town center, areas close to local parks, or neighborhoods with easy access to trails. Properties often feature porches, gardens, and flexible spaces for families or groups.

  • What are the best things to do in Lee with kids?

    Lee has fun things for families, such as visiting local parks, exploring playgrounds, and joining craft workshops at community spaces. Many children enjoy walking nature trails and taking part in seasonal outdoor events.

  • What are some of the best things to do in Lee?

    Explore the town’s vintage shops, art galleries, and coffee houses, or head outdoors for hikes and bike rides in the Berkshires. Lee is frequently suggested for its blend of small-town charm and access to nature.

  • How is the weather in Lee?

    Lee has cold winters from 19–35°F (-7–2°C) and warm, humid summers near 64–85°F (18–30°C). Spring and fall feature milder temperatures, with colorful foliage often attracting visitors.

  • When is the best time to visit Lee?

    Late spring through early fall is often recommended for milder weather and outdoor festivals, with temperatures ranging 48–85°F (9–30°C). Autumn brings colorful foliage, while winter appeals to those interested in quieter visits and seasonal traditions.

  • What are the best places to visit in Lee?

    Lee has charming downtown shops, historic churches, and local art galleries. Many visitors explore the Housatonic River area and the nearby Appalachian Trail for nature walks.

  • What are some hiking trails in Lee?

    Hiking enthusiasts in Lee often explore trails near the Appalachian Trail, local forests, and conservation land. Paths range from gentle walking routes to steeper woodland hikes.

  • What are some family activities we can do in Lee?

    Families can explore local parks, picnic areas, and art workshops in Lee. Seasonal events like outdoor movie nights and craft fairs are frequently suggested for visitors with children.

  • What are some of the best day trip ideas from Lee?

    From Lee, travelers frequently visit neighboring Berkshires towns with museums, nature reserves, and scenic lakes. Many enjoy exploring surrounding landscapes and regional cultural sites.

  • Are there any pet friendly accommodations available in Lee?

    Lee has pet friendly stays in neighborhoods around the town and near outdoor trails. Many hosts welcome travelers with pets and provide easy access to parks for walks.

  • What are some local tips for visiting Lee?

    Locals often suggest bringing comfortable shoes for walking, sampling seasonal produce from markets, and exploring antique shops. Early mornings in the town center and hikes in nearby woods reveal a quieter side of Lee.

  • What is Lee known for?

    Lee is known for its classic New England atmosphere, locally rooted arts, and historic architecture. The town is also recognized as a gateway to outdoor adventures in the Berkshires.

  • What are the best hidden gems to explore in Lee?

    Explore locally owned bookstores, garden spaces, and historic nooks of the town center for quieter discoveries. Lee’s community spaces and off-the-path outdoor spots often reveal unique experiences.

  • What are the best foods to try in Lee?

    Lee is frequently suggested for its locally sourced New England fare, including maple syrup, artisanal cheeses, and hearty breads. Visitors often find fresh farm-to-table options and classic diner comfort dishes around town.

  • What should I bring for a trip to Lee?

    Pack layers for changing temperatures, sturdy walking shoes, and a reusable water bottle. Guests often bring rain gear for spring and fall and warm clothing for winter visits.

  • What is the nightlife in Lee like?

    Lee’s nightlife centers around cozy pubs, music cafes, and community gathering spots. Evenings see live performances, trivia nights, and casual social spaces for locals and visitors.

  • What are the most popular events or festivals in Lee?

    Lee hosts festivals celebrating Berkshire culture, music, and art, often during summer and fall. Traditional events like summer concerts and fall harvest celebrations are frequently suggested by locals.

  • Are there family friendly vacation rentals in Lee?

    Lee has a variety of family friendly accommodations, including rentals near parks, spacious homes, and properties with kitchens for self-catering. Families often find it easy to settle in neighborhoods around the town center.

Destinations to explore