Fitness-friendly vacation rentals in Hancock

4.9 out of 5 average rating, 168 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 with Hot Tub & Pools –15 mins to Mt Snow

Unwind in this cozy 4BR, 2BA retreat featuring a private hot tub, fire pit, game room, and access to indoor/outdoor pools, gym, and clubhouse amenities. Comfortably sleeps 8 (King, Queen, Full + trundle, bunk room) and includes a Pack ’n Play for little ones, perfect for families and groups. Whether you’re here for skiing, hiking, lake days, or fall foliage, enjoy the perfect blend of mountain charm, modern comfort, and unbeatable location near Wilmington’s shops, dining, and outdoor adventures.

5 out of 5 average rating, 114 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: Pool+Sauna, 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.

4.92 out of 5 average rating, 108 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, 123 reviews

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, 334 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/ deck, fire pit, by Hudson & hiking

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.

4.97 out of 5 average rating, 147 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

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

4.96 out of 5 average rating, 52 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

Corey Road Condo | @ Jiminy Peak • Pool • Hot Tub

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, 136 reviews

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.

Apartment in Mechanicville

A warm living area features an orange leather sofa paired with a dark ottoman. A modern light fixture hangs from the ceiling, while an open kitchen with stainless steel appliances is visible in the background. Wooden flooring contributes to the cozy atmosphere.

4.91 out of 5 average rating, 294 reviews

Boho hipster penthouse - Artsy City vibes upstate!

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, 279 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.

4.96 out of 5 average rating, 163 reviews

The living area features a spacious arrangement of comfortable brown couches, positioned around a wooden coffee table. A large, framed landscape photograph adorns the wall above, while natural light filters through large glass doors leading to a small outdoor deck.

Townhouse in Dover

Bear's Den - Mt Snow Townhome w/ Heated Pool!

Renovated 3-level, 2 bedroom+ twin sleep loft, 2.5 bathroom townhouse on Mt Snow. For the non-snowy months, enjoy the outdoor heated pool, gas fire pit, grill, tennis courts & hiking trails up the mountain as well as other great local activities, lakes and festivals near by. In the winter, take the shuttle 1 mile to the mountain and take the private ski trail back home. NOTE: Pool is Open between Memorial Day & Labor Day

5 out of 5 average rating, 9 reviews

Townhouse in Hancock

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure ★☆ ABOUT THIS SPACE ☆★ Welcome to Jiminy Peak Slopeside Getaway, your all-season mountain retreat. Enjoy scenic views and a true ski-in/ski-out experience—just a 3-minute walk to the chair lift at Jiminy Peak. This 2-bedroom, 2-bath home sleeps up to 7 guests and offers private parking, a porch, and a deck, plus access to a heated pool, indoor/outdoor hot tub, and clubhouse.

Popular amenities for Hancock fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

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

5 out of 5 average rating, 3 reviews

Apartment in Wilmington

Luxury 2 Bedroom 202B

4.84 out of 5 average rating, 44 reviews

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.

Apartment in Hancock

Mountainside Condo Ski on/off

4.96 out of 5 average rating, 54 reviews

A view from the condo showcases snow-covered slopes leading up to the mountain, with ski lifts operating in the distance. The landscape is framed by the rustic stone chimney of the adjacent building, creating a serene winter scene.

Apartment in Hancock

Ski-In Ski-Out Loft Lift & MT. Views

A bright bedroom features a spacious bed covered in a vibrant red comforter. Two large windows allow natural light to fill the room, complemented by neutral walls and dark curtains. A small bedside table is positioned next to the bed, adding to the cozy atmosphere.

Apartment in Albany

4.84 out of 5 average rating, 38 reviews

Limited Time Listing

Apartment in Hancock

4.74 out of 5 average rating, 31 reviews

Central Berkshires Artsy Loft with Pool & Hot Tub

4.73 out of 5 average rating, 11 reviews

Apartment in Schenectady

It’s Good To Be Home

4.96 out of 5 average rating, 89 reviews

An outdoor recreational area is illuminated at night, featuring a billiard table under a gazebo. Guests are seated around picnic tables, enjoying their time. Soft lighting enhances the ambiance, while the yard displays green grass and surrounding structures.

Apartment in Watervliet

Uptown Watervliet

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.

4.94 out of 5 average rating, 71 reviews

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

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.

Condo in Dover

5 out of 5 average rating, 4 reviews

Cozy Townhome by Mt Snow with Ski Home Trail

A comfortable living area is presented with a plaid chair and a sofa, complemented by a coffee table. Natural light fills the space through a large window with elegant drapery. A flat-screen television is positioned nearby, enhancing the relaxation setting.

4.86 out of 5 average rating, 37 reviews

Jiminy Peak Apartment

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, 162 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

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.

Condo in Dover

4.9 out of 5 average rating, 10 reviews

SKI HOME Trail Bears Crossing Mount Snow

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, 81 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.

4.79 out of 5 average rating, 14 reviews

Ski-in/Ski-Out on Jiminy Peak

Fitness-friendly house rentals

4.83 out of 5 average rating, 6 reviews

The backyard features a well-maintained heated pool surrounded by a stone patio. Lounge chairs with striped cushions are arranged under blue umbrellas, providing shaded seating options. The house, with a screened porch, is visible in the background, complemented by lush greenery and blooming plants.

Home in Egremont

Big Views, Heated Pool, Mini-Gym, Sun Porch!

5 out of 5 average rating, 29 reviews

A bright dining area features a rustic wooden table surrounded by white chairs. A large pool table with a playful cat painting above adds a fun element to the space. Natural light streams in through a window, highlighting the warm tones of the wooden floor.

Home in Hudson

End-of-Spring discount! Sleeps 12! In town!

4.83 out of 5 average rating, 18 reviews

Home in Becket

Secluded Berkshires Cabin | Deck, BBQ & Town Beach

4.76 out of 5 average rating, 67 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

5 out of 5 average rating, 84 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

VT Outdoor Retreat-Fire Pit-Yard Games-Sleeps 11

5 out of 5 average rating, 24 reviews

An aerial view captures a large log home nestled among tall trees near a lake. The structure features a gabled roof and multiple chimneys. Surrounding greenery adds to the natural setting, while a neatly maintained lawn showcases the home’s spacious footprint.

Home in Goshen

Waterfront Wonderland | Luxe Log Cabin (Sauna/Gym)

5 out of 5 average rating, 17 reviews

An aerial view of a spacious Hudson farmhouse is presented, surrounded by lush greenery and a manicured lawn. The property features a large patio area with outdoor seating, and the landscaped grounds provide a serene setting. The home showcases a charming roof and ample outdoor space.

Home in Hudson

Stylish farmhouse w/fireplace by downtown & nature