Fitness-friendly holiday rentals in Pittsfield

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

A panoramic view captures the snowy landscape from the condo, showcasing ski trails on the mountains in the background. The foreground features a plaza with chairs arranged around a fire pit, with skiers and snowboards visible along the paths.

4.98 out of 5 average rating, 50 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

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.

5 out of 5 average rating, 108 reviews

The image displays a serene winter scene of a dark-green chalet nestled among snow-covered trees. Two sections of the interior show a cozy living space with modern leather furniture and a spacious dining area, both featuring large windows that bring in natural light.

Cabin in Wilmington

Mid-mod VT Dream Chalet near skiing, lake & forest

Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

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.

4.9 out of 5 average rating, 161 reviews

A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.

Home in Wilmington

4BR Cabin w/ Hot Tub & Pools –15 mins to Mt Snow

Family-friendly cabin in Chimney Hill, just 15 min to Mount Snow & 35 to Stratton! Relax in our 4BR, 2BA home with a hot tub, indoor and outdoor pools, fire pit, clubhouse gym, fully equipped kitchen & cozy living spaces. Sleeps 8 comfortably (King, Queen, Full + trundle, 2 Twins) with a Pack ’n Play for little ones. Perfect for skiing, hiking, or unwinding year-round. Enjoy mountain charm, modern comfort, and easy access to trails, lakes, and Wilmington’s shops & dining.

4.95 out of 5 average rating, 41 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

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

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

Enjoy a spacious yet cozy home in a quiet neighborhood with off-street parking. Minutes from restaurants, shopping, universities (UAlbany, Sage, St. Rose), parks, museums, hospitals(Albany Med, St.Peters) and State Capital Offices for those traveling for business. We’re right off the main highway leading to the World Famous Saratoga Race Track (30 min) and Adirondack Mountains/Lake George (50 min)! From this Air Force Family to yours, welcome to our home.

4.92 out of 5 average rating, 288 reviews

A small workspace is set against a textured wall showcasing exposed brick and plaster. A wooden desk features a task lamp and decorative items, including a plant and flowers. Nearby, an orange accent chair complements the blue upholstered stool.

Flat in Mechanicville

Winter Fun - Elegance & Charming!

You are going to love this place!!! It extremely unique and charming!!! 100 Year old school building converted into luxury apartments! The unit you’re viewing is on the MEZZANINE LEVEL, it’s exclusive to you! The unit overlooks the old gymnasium which Has been converted - It’s One of a kind!! A covered roof top terrace, a outdoor patio with fire pit & bbq. Theres a fitness area (Actual registered FALLOUT shelter of the 60’s) to name a few.

4.82 out of 5 average rating, 257 reviews

A charming country home is presented with a welcoming red front door. A pergola covers the entryway, surrounded by well-maintained landscaping that includes shrubs and a stone path. The exterior features light yellow siding, providing a warm, inviting appearance.

Home in Hudson

Bright, Airy Home in Hudson w/ TONS of Character!

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

4.98 out of 5 average rating, 136 reviews

A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.

Home in Pittsfield

Hidden Oasis in the Mountains by Evergreen Home

7 MINUTES TO BOUSQUET MOUNTAIN Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens, unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.

Popular amenities for fitness-friendly rentals in Pittsfield

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

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.

4.82 out of 5 average rating, 39 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.

Flat in Lenox

Peaceful 2 BR apartment minutes from Tanglewood

4.92 out of 5 average rating, 25 reviews

Flat in Wilmington

Luxury 2 Bedroom Suite 202B

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.

Flat in Lee

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

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

A bright studio apartment features a gray sofa with orange cushions and a wooden coffee table. A cozy blue bed is positioned nearby, and large windows allow natural light to fill the room. A flat-screen TV is mounted on the wall, enhancing the functional layout.

Flat in Center Square

4.76 out of 5 average rating, 33 reviews

Albany Business Class Apartment

A serene view of the resort features multiple two-story buildings surrounded by lush green grass and tall trees. A small pond reflects the surroundings, with large stone steps leading toward the water, creating a peaceful atmosphere for guests.

Flat in Lenox

Lovely Condo w/ Resort Amenities

Fitness-friendly apartment 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

A spacious living area is furnished with a large green sectional sofa adorned with red throw pillows. Natural wood paneling lines the walls, with a cozy fireplace set in the corner. A wooden coffee table is centrally located, positioned on a decorative area rug.

Apartment in Dover

5 out of 5 average rating, 4 reviews

Cozy Townhome by Mt Snow with Ski Home Trail

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

5 out of 5 average rating, 9 reviews

A spacious sectional sofa with intricate fabric patterns is positioned in a cozy living area. An accompanying ottoman sits in front, complementing the seating arrangement. Wooden paneling enhances the rustic ambiance, and a plaid curtain frames a nearby window.

Apartment in Dover

SKI HOME Trail Bears Crossing Mount Snow MLK+Pres

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.

Apartment in Lenox

4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

Apartment in Williamstown

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

Fitness-friendly house rentals

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

4.92 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

4.85 out of 5 average rating, 54 reviews

A serene view of the surrounding mountains is captured during sunset, with soft sunlight illuminating the landscape. A grassy area is visible, framed by trees, and a wooden deck extends into the view, creating a peaceful outdoor space.

Home in Hancock

Jiminy Peak Peaceful Home in Berkshires

5 out of 5 average rating, 78 reviews

A spacious two-story home is nestled among lush greenery, featuring a light pink exterior complemented by maroon shutters. A paved driveway leads to a double garage, while a well-maintained lawn and garden enhance the inviting atmosphere of the property.

Home in Whitingham

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

5 out of 5 average rating, 21 reviews

Home in Albany

Quiet & Cozy Near UAlbany | Parking & Fast WiFi

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