Fitness-friendly holiday rentals in Lee

A cozy living area features a comfortable couch adorned with soft pillows, complemented by a wooden coffee table. An adjacent kitchen area with modern bar stools offers ample space. Natural light flows through the open layout, and a staircase leads to an upper level.

5 out of 5 average rating, 4 reviews

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Stylish 1BR, 1BA suite with an additional Pull Out Queen sleeps 4 comfortably. It sits RIGHT in the Thatcher Building in front of the MAIN ski lift in Village Center. You can not get better than that! All the convenience without the bustle. This large 650 sq ft condo features brand new decor meticulously maintained, and includes a full kitchen with all the amenities. As a guest, you will

4.98 out of 5 average rating, 45 reviews

A modern home with a dark exterior features large windows and a welcoming entrance. The surrounding landscape includes lush greenery and well-maintained plants, complemented by a gravel pathway leading to the front door, set against a backdrop of a clear blue sky.

Home in Great Barrington

Berkshires Family Oasis with Hot Tub, Patio, Gym

All seasons family retreat in PRIME Berkshires location. Located adjacent to the famous Appalachian trail, 5 minutes from downtown Great Barrington, 2 minutes from Ski Butternut and 15 minutes from Tanglewood in Lenox. Easy access to sensational hiking, dining, lakes and museums. The home is spacious and open with 4 BR, 7 beds, a large finished basement TV & game room space and backyard patio and hot tub. A perfect spot to enjoy the spectacular beauty and unlimited activities of the Berkshires.

4.94 out of 5 average rating, 32 reviews

Home in Becket

Serene 3-BR Berkshires Log Cabin

This spacious and comfortable 3- BR log cabin is the perfect refuge to gather with family and friends. Set on a private 60 acre lot in Becket, MA, the lodge is an inviting retreat; secluded and private in the woods, but close to all the Berkshires has to offer. There are 3 bedrooms, 1 of which has an attached full bath while the other 2 have attached half baths. There is another separate full bath on the main floor and additional half bath with infrared sauna lower level. The main floor feature

5 out of 5 average rating, 110 reviews

A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.

Home in Taghkanic

Sunbeam Lodge: Sauna+Hot Tub, 50 Acres, ‘70s Oasis

Our peaceful, skylit, 3-bed 2-bath lodge is a totally private woodland paradise on a quiet country lane. Part secluded retreat, part rustic resort, part '70s-style cottage, it's only 2 hours from NYC & 20 minutes from Hudson. Unwind in 50 acres of untouched forest & grounds, a seasonal saltwater pool & cabana bar, a Finnish sauna & 7-person hot tub (open year-round), an open chef's kitchen & living room, & a sunny deck overlooking endless natural splendor. See more @sunbeamlodge on Instagram.

Townhouse in Washington Park

A spacious living area is furnished with a large teal sofa adorned with decorative pillows. A wall-mounted TV is positioned across from the seating area. Two metallic tables and a stylish rug complement the space, while artwork adds a touch of color to the walls.

4.98 out of 5 average rating, 271 reviews

Modern & Cozy Cntr Square Townhouse Gem from 1854

This amazing Airbnb will give you all the comforts of home! Tastefully decorated with everything you need and then some!! -> Grab-N-Go items (Coffee, Tea, Light Snacks) -> Smart LED Tvs in (2) Livingrooms & (2) Bedrooms -> NordicTrack & Peloton bicycles -> Smart locks with keyless entry -> Fast wireless WiFi -> Queen beds with premium mattresses & pillow covers -> Fully equipped + utensil stocked kitchen + Keurig Coffee -> Full size washer/dryer And much more so come and enjoy your stay!

4.92 out of 5 average rating, 100 reviews

A peaceful scene reveals a winding road leading through a residential area with well-maintained homes. Snow-covered mountain slopes are visible in the background, flanked by trees that display early signs of changing seasons.

Townhouse in Hancock

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

4.99 out of 5 average rating, 304 reviews

A bright and inviting living area features large windows that offer views of the surrounding greenery. A comfortable sofa and chairs surround a coffee table, while a desk with a chair is positioned near the window for a productive workspace.

Cabin in Ghent

Cozy chalet w/ fireplace near Hudson & skiing

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, skiing, and year-round getaways.

4.75 out of 5 average rating, 16 reviews

A three-story building is set amidst a grassy area with scattered rocks. A small pond reflects the clear sky and nearby greenery, enhancing the serene landscape that surrounds the resort.

Hotel room in Lee

Beautiful place|2 BD|Kitchen| Pool

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge .

4.78 out of 5 average rating, 63 reviews

A spacious living area showcases a blue sectional sofa with decorative pillows, paired with an orange armchair. A central coffee table holds magazines and snacks, while large windows invite natural light. A brick fireplace and an open steel staircase add character to the room.

Home in Otis

Serene Berkshires Home On 5+ Acres, Rustic & Chic

Enjoy the beauty of the Berkshires in our tranquil retreat! The home, with rustic charm and modern touches, features artwork and furnishings from local Berkshires artists. An expansive, secluded yard located within protected forestland provides the ideal combination of privacy & natural outdoor space. Large enough for your entire family, your home away from home has dedicated spaces for everyone: game room, play area, office, home gym, screened porch, backyard seating, and more!

4.91 out of 5 average rating, 43 reviews

The resort area showcases a multi-story building, surrounded by green grass and landscaping. A small pond reflects the structure, while rocks line the water's edge. Trees provide additional greenery, creating a serene outdoor setting.

Hotel room in Lee

Great Place |2 BD|Kitchen| Pool 

4.95 out of 5 average rating, 58 reviews

Two glasses of red wine are placed beside a lit candle on a window sill. A plate filled with green grapes and assorted chocolates sits in the foreground. Outside, a vibrant garden of yellow flowers and greenery is visible through the window.

Apartment in Sandisfield

Sweet Dreams Retreat

Romantic weekend getaway, featuring fireplaces, hot tub, swimmingpool, and outdoor decks . The Berkshire's, a popular vacation location. This is the perfect spot to unwind and recharge. Sweet Dreams Retreat is kept spotlessly clean and generiously stocked with everything you might need, including a full kitchen, washer and dryer, luggage racks and much more. Enjoy hiking, skiing, and a great selection of resturaunts and unique shops and more.

5 out of 5 average rating, 14 reviews

An inviting kitchen features a central island with barstools and warm wood accents. Large windows allow natural light to fill the space, highlighting the modern appliances and tasteful decor. A dining area with additional seating is visible in the background, promoting a sense of openness.

Home in Lenox

Spacious Lenox Farmhouse | Perfect Winter Getaway

Welcome to Green Garden! This charming 3 bedroom, 2.5 bathroom New England farmhouse is your cozy winter retreat in the Berkshires. After a day of skiing, exploring Lenox, or walking snowy trails, warm up by the fire pit or relax inside. Minutes from Tanglewood and downtown Lenox, you’ll enjoy winter markets, great dining, and peaceful star filled nights. Kid friendly with a Pack ’n Play, Tripp Trapp high chair, and Inglesina Fast Table chair.

Popular amenities for Lee fitness-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Fitness-Friendly apartment accommodation

A modern kitchen with dark wood cabinetry is paired with stainless steel appliances, including a large refrigerator and oven. A cozy living area features a brown sofa and coffee table with a rug underneath. A staircase leads to a lofted den, enhancing the open layout.

Apartment in Downtown Albany

3.8 out of 5 average rating, 10 reviews

Walk to Everything Downtown Albany! Luxury Apt!

Apartment in Center Square

610E) Very Comfortable Studio Downtown

An outdoor pool area is surrounded by several lounge chairs and umbrellas, offering a view of vibrant autumn foliage on the hills. The pool is partially covered, and a building is visible in the background, enhancing the resort-like atmosphere.

4.83 out of 5 average rating, 40 reviews

Mountainside Condo Ski on/off

5 out of 5 average rating, 77 reviews

A charming entrance is framed by blooming pink shrubs and lush greenery, standing in front of a dark-colored home. The wooden fence complements the natural setting, with a soft pathway leading to the welcoming door. Sunlight filters through the trees, enhancing the peaceful ambiance.

Apartment in Lenox

Peaceful 2 BR apartment minutes from Tanglewood

An outdoor pool is featured at the resort, surrounded by lounge chairs and umbrellas for shade. Views of the well-maintained grounds and pool area are available, with trees and hills in the background. Nearby buildings provide accommodations for guests.

Apartment in Lee

4.92 out of 5 average rating, 25 reviews

Dream Vacation

A cozy living area showcases a combination of comfortable seating, including a sectional sofa with decorative pillows and a patterned armchair. A wooden table complements the space, while a mounted television is visible on the wall. Natural light enters through the window, enhancing the inviting atmosphere.

4.83 out of 5 average rating, 6 reviews

Cozy Ski Retreat

The living room features two reclining sofas positioned around a coffee table. A soft area rug adds comfort underfoot. A floor lamp provides ambient lighting, and wall art adds character to the neutral-toned space.

Apartment in Latham

Track Season Ready! Saratoga!

A cozy living area features a tall Christmas tree adorned with lights and ornaments next to a glass-top coffee table. A fireplace with built-in decor sits beneath a mounted television. Velvety blue chairs complement an orange accent pillow on the nearby couch, surrounded by large windows with sheer curtains.

4.78 out of 5 average rating, 18 reviews

Jiminy Peak Ski Loft with Hot Tub

Fitness-friendly condo rentals

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

4.95 out of 5 average rating, 63 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

A comfortable living room is presented with two sofas adorned with festive cushions. A coffee table is centered on a cozy area rug, while a television sits atop a media console. Large windows framed by dark curtains allow natural light to fill the space.

4.89 out of 5 average rating, 35 reviews

Unique - Country suite @ Jiminy Peak

The exterior of a large, two-story building is showcased against a snowy backdrop, with tall trees partially visible in the foreground. The building features arched entryways and multiple windows, while the sloped ski hill rises in the background, indicating proximity to winter sports.

4.61 out of 5 average rating, 157 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

An inviting indoor pool area is surrounded by large windows that provide a view of the outdoors. Lounge chairs line the poolside, and natural light fills the space, highlighting the tiled flooring and gently rippling water.

5 out of 5 average rating, 4 reviews

Ski Jiminy Peak - 1BD

A lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.

Condo in Lenox

4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.

4.91 out of 5 average rating, 74 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Condo in Williamstown

Vacation Village in Berkshires 12/28/25-1/4/26

A cozy living area features a comfortable sofa grouped with an armchair and a coffee table. A large window allows natural light to illuminate the space, while curtains frame the view. A television is positioned nearby, enhancing the room's functionality.

4.77 out of 5 average rating, 13 reviews

Ski-in/Ski-Out on Jiminy Peak

Fitness-Friendly Holiday House

4.81 out of 5 average rating, 70 reviews

Home in Troy

Warm Cozy 3 Queen Home in Troy- Full Kitchen

4.92 out of 5 average rating, 13 reviews

A comfortable living room is highlighted by two light-colored sofas, accented with colorful throw pillows and blankets. A central coffee table offers board games. A fireplace is visible, alongside a television mounted on the wall above a small work area with a chair. Decorative snowshoes are displayed on the wall.

Home in Hancock

Snowdrop Lodge: Beautiful Condo at Jiminy Peak

4.95 out of 5 average rating, 19 reviews

The home's exterior is framed by vibrant red foliage, creating a striking entryway. A path made of stone leads to the entrance, while steps adorned with leaves provide access. Surrounding greenery enhances the natural setting, offering a serene and inviting atmosphere.

Home in Richmond

"Hemlock Shadow" near Tanglewood on Six Acres

4.98 out of 5 average rating, 41 reviews

A bright bedroom features a four-poster bed draped with crisp white bedding. A patterned rug lies beneath the bed. Artwork adorns the walls, complemented by a sleek black lamp and wooden furniture. Natural light streams through a shuttered window, with a radiator adding warmth.

Home in Hudson

3BR Hudson House w backyard - skiing 20 min away

4.95 out of 5 average rating, 42 reviews

The open living area showcases a modern curved sectional sofa in dark leather, adorned with cream and patterned pillows. A sleek chandelier hangs from the high ceiling, complemented by a wall-mounted TV and a wooden fireplace. Large sliding doors lead to the outdoor patio.

Home in Hancock

Bougie B’s Mountainside Getaway

5 out of 5 average rating, 24 reviews

A clear set of wooden stairs leads up to the entrance of the cottage, adorned with colorful potted flowers. The side of the house features a soft green hue and a welcoming light fixture above the door. A small fenced yard and landscaped area can be seen in the background.

Home in Southwick

Peaceful, Modern Cottage, 20 min to BDL, 2BR/1BA

4.95 out of 5 average rating, 123 reviews

The exterior of the home features a well-maintained brick facade and a welcoming front entrance. A paved pathway leads to the door, flanked by vibrant flowering shrubs and manicured green lawns. Large windows provide natural light to the interior, enhancing the inviting appearance.

Home in Albany

Boho-Chic Cape Conveniently Located