Fitness-friendly holiday rentals in Lanesborough

4.86 out of 5 average rating, 177 reviews

A rustic two-story home is surrounded by lush greenery, featuring a wooden porch with seating areas. Stone pathways lead to a grill and an outdoor dining space, while a gentle slope of grass complements the natural setting.

Cabin in Wardsboro

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

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, 115 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, 336 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, 148 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!

4.93 out of 5 average rating, 159 reviews

A cozy living area is visible, featuring a comfortable seating arrangement with a guitar prominently displayed. A television is placed on a cabinet opposite a modern fireplace. Natural light fills the space through large windows, complemented by decorative plants and artwork on the walls.

Flat in Saratoga Springs

Modern Apartment - Close to Everything

Saratoga Springs is a beautiful horse racing town rich in history nestled on the edge of the Adirondack State park. Easy access from NYC and Boston. Saratoga claims “more restaurants per resident than NYC” This New Modern Apartment has all the amenities.... including rooftop and feee access to Victorian pool (ask about getting reimbursed)z Whether you are in town for a romantic getaway or to enjoy the Race track season. Minutes away from the race track, downtown and great cuisine.

4.95 out of 5 average rating, 138 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.

4.91 out of 5 average rating, 298 reviews

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.

Flat in Mechanicville

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.

4.97 out of 5 average rating, 171 reviews

Barn in Hillsdale

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

4.82 out of 5 average rating, 280 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.

Popular amenities for fitness-friendly rentals in Lanesborough

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

5 out of 5 average rating, 3 reviews

Flat 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.

Flat in Hancock

Mountainside Condo Ski on/off

5 out of 5 average rating, 27 reviews

The entryway features a covered porch with a wooden deck. Two blue chairs adorned with floral cushions are positioned beside the door. A welcome sign is displayed on the wall, and colorful flowers flourish around the steps, enhancing the inviting exterior.

Flat in Stillwater

Saratoga Getaway 2

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.

Flat in Hancock

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

4.89 out of 5 average rating, 19 reviews

The exterior of the Snow Tree Condo is depicted, featuring a two-level building nestled among trees. A sign for 'Snow Tree' is visible, along with a gravel parking area accommodating several vehicles. The backdrop showcases a mountainous landscape under a partly cloudy sky.

Flat in Dover

SnowTree Chalet- Walk to lifts! 1 bedroom + Loft

4.94 out of 5 average rating, 78 reviews

A cozy living area features a wood-burning fireplace with a flat-screen TV above. A foldout queen murphy bed is neatly tucked against the wall. A sectional sofa, dark wood coffee table, and a patterned area rug complete the inviting space, with large windows offering views of the outdoors.

Flat in Dover

Walk to main lift! The Handle Studio @ Mt. Snow!

Flat in Hancock

Ski-In Jiminy Peak 2 Bed/2 bath Condo

4.94 out of 5 average rating, 16 reviews

Flat in Dover

MtSnow Base/View/Fireplace/Balcony/Amenities

Fitness-friendly apartment rentals

4.94 out of 5 average rating, 71 reviews

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.

Apartment in Hancock

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

4.9 out of 5 average rating, 103 reviews

A spacious living area is highlighted by large windows that provide a panoramic view of the surrounding hills. The room features a comfortable sofa, a wooden coffee table, and a dining set. A fireplace and a fully equipped kitchen are situated in the background.

Apartment in Stratton

~10% OFF~Walk To Mountain~Amenities

4.95 out of 5 average rating, 120 reviews

The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.

Apartment in Stratton

Great 2 bedroom condo at Stratton Mountain

5 out of 5 average rating, 72 reviews

A tranquil lake reflects the vibrant colors of autumn foliage, showcasing a mix of red, orange, and yellow trees. A small island featuring a cluster of trees and shrubs emerges in the foreground, surrounded by calm waters and a gentle green grass shoreline.

Apartment in Dover

Four Seasons Slope-side Getaway at Mount Snow

4.61 out of 5 average rating, 162 reviews

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.

Apartment in Hancock

Jiminy Peak Country Inn 1 Bedroom Suite

4.94 out of 5 average rating, 106 reviews

A spacious living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in front, with a lamp beside it. A dining area is visible, accompanied by a window allowing ample natural light and a view of the surrounding trees.

Apartment in Dover

Cozy Mt Snow Ski In / Out

4.85 out of 5 average rating, 144 reviews

A comfortable living area showcases a gas fireplace beneath a large television mounted on the wall. A dark sofa sits beside a small coffee table, and light flows in through a glass door, which is accented by sheer curtains. Decorative elements enhance the space.

Apartment in Dover

Walk to Mt. Snow-Spa-Summer Pool

4.91 out of 5 average rating, 81 reviews

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.

Apartment in Hancock

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

Fitness-friendly house rentals

4.98 out of 5 average rating, 50 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 Stylish Hudson House w Fenced Backyard

4.83 out of 5 average rating, 18 reviews

Home in Becket

Secluded Berkshires Cabin | Deck, BBQ & Town Beach

4.77 out of 5 average rating, 69 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, 85 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, 49 reviews

A theater room features reclining seats with red throws, ideal for cozy movie nights. A spacious game room showcases a billiard table, enhancing entertainment options with bright natural light flooding in from large windows.

Home in Dover

Alpine Chalet: HotTub, Theatre, Game Rm, Gym & Spa

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

4.57 out of 5 average rating, 7 reviews

A modern lakefront home is presented at dusk, showcasing large glass windows and a spacious deck. Soft lighting from the interior adds warmth, highlighting the contemporary architecture. The surrounding lush greenery and open lawn create a serene environment, with a vibrant sunset visible in the background.

Home in Hillsdale

Hillsdale Lakeside | Lake Access, Balcony & BBQ