Fitness-friendly holiday rentals near Jiminy Peak Mountain Resort

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.

4.88 out of 5 average rating, 17 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 snowy landscape is presented, showcasing ski slopes and a bustling scene below. A quaint building serves as a backdrop, surrounded by skiers and snowboarders. Tables and chairs are visible, along with ski equipment neatly arranged, highlighting the active atmosphere accessible from the condo.

4.95 out of 5 average rating, 96 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

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.

4.9 out of 5 average rating, 166 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.

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.

4.93 out of 5 average rating, 107 reviews

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.

The exterior of a townhome is shown covered in fresh snow, with a covered porch and white railing. Flanked by evergreen trees, the structure features a gabled roof and a single round window above the front entrance, adding character to the picturesque winter scene.

5 out of 5 average rating, 33 reviews

Serene+Stylish Mountain Retreat

Our beautifully-designed, comfortable, much-loved townhome is great for families or friends wanting an escape to the Berkshire mountains. Located up the hill from Jiminy Peak Village Center, the home has 4 bedrooms over 3 floors, an open plan living space, updated kitchen, family room, and new deck. A short walk to the slopes in winter and use of Jiminy Peak resort pools in the summer make it a year-round destination. Book your stay and find out why once you are here, it’s so hard to leave!

5 out of 5 average rating, 121 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, 326 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 & 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, 145 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!

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.

4.96 out of 5 average rating, 50 reviews

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!

4.82 out of 5 average rating, 272 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.

5 out of 5 average rating, 8 reviews

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.

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

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.

Popular amenities for fitness-friendly rentals near Jiminy Peak Mountain Resort

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.

Flat in Lenox

Peaceful 2 BR apartment minutes from Tanglewood

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.

4.84 out of 5 average rating, 44 reviews

Mountainside Condo Ski on/off

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

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.

4.89 out of 5 average rating, 9 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.

Flat in Latham

Track Season Ready! Saratoga!

4.77 out of 5 average rating, 30 reviews

Jiminy Peak Ski Loft with Hot Tub

Flat in Albany

Large 1 bedroom downtown!

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.

4.94 out of 5 average rating, 71 reviews

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

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, 161 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

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

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

A spacious living area features a light-colored sofa and an accent chair, with a coffee table centered on a patterned rug. Shelves display decorative items, while a television is mounted above a stone fireplace. Natural light enters through windows accented with blue curtains.

4.71 out of 5 average rating, 28 reviews

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

A serene view of well-maintained landscaping surrounding a tranquil pond is presented. The image captures multiple condo buildings set against a clear blue sky with scattered clouds. Lush green grass leads to the water's edge, framed by several mature trees.

Apartment in Lenox

4.58 out of 5 average rating, 19 reviews

Tranquil Lakeside Escape in the Berkshires

Fitness-friendly house rentals

4.98 out of 5 average rating, 49 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

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.

4.92 out of 5 average rating, 13 reviews

Snowdrop Lodge: Beautiful Condo at Jiminy Peak

4.94 out of 5 average rating, 17 reviews

Home in Becket

Cabin Retreat in the Berkshire Woods

4.93 out of 5 average rating, 41 reviews

A spacious mountain house is presented, surrounded by vibrant fall foliage. The exterior features a light-colored facade with multiple balconies, a large driveway, and a garage. Leaves cover the ground, creating a natural, seasonal carpet leading up to the inviting entrance.

Home in Wilmington

Family/Dog Friendly Mountain Home w/ Amenities

4.81 out of 5 average rating, 64 reviews

A spacious recreational area is showcased, featuring a billiards table with several balls arranged on it. Comfortable seating and a dining table are visible, while a cozy fireplace is seen in the background. Natural light filters in through the windows, illuminating the warm decor.

Home in Wilmington

Chimney Hill Home w/ New Hot Tub & Amenity Center!

4.97 out of 5 average rating, 92 reviews

A bright living area features large windows allowing natural light to fill the space. Comfortable seating arrangements include two armchairs and a vintage-style sofa. A small bookshelf displays assorted books, while a decorative mirror and plants add touches of character to the room.

Home in Brunswick

Eclectic Troy Retreat w/ Hot Tub & Sauna!

4.98 out of 5 average rating, 46 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

The exterior of a cozy mountain cabin is shown, featuring a mix of wooden and siding materials. A grassy front yard is bordered by a wooden fence, and trees are visible in the background. The sky is bright with clouds, creating a welcoming ambiance.

4.98 out of 5 average rating, 40 reviews

Cozy Ski Cabin in Berkshires Resort

Other fitness-friendly holiday rentals

A well-lit living area features large windows allowing natural light, with a cozy plaid sofa and two armchairs positioned around a modern fireplace. A rustic wooden coffee table is placed in the center, complementing the warm tones of the room.

4.79 out of 5 average rating, 14 reviews

Beautiful 4 Bedroom Townhouse in the Berkshires

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

An outdoor deck is furnished with a gas grill, fire pit, and comfortable seating. A hot tub is positioned nearby, surrounded by lush greenery, creating a serene setting for relaxation. Large windows provide natural light and connect the space to the inviting landscape.

4.94 out of 5 average rating, 49 reviews

Family-Friendly Hancock Home: Walk to Slopes!

4.99 out of 5 average rating, 86 reviews

A modern chalet sits surrounded by lush greenery, featuring a stunning wrap-around deck adorned with string lights. An inviting fire pit area with seating complements the spacious backyard, highlighting the connection between indoor comfort and natural beauty.

Cabin in Wilmington

Modern Chalet-private deck/firepit/ clubhouse pool

5 out of 5 average rating, 55 reviews

A wrap-around porch is displayed, featuring wooden flooring and a combination of rocking chairs and potted plants. A ceiling fan hangs above, and gentle lighting enhances the outdoor space. The entryway reveals a glimpse of the cozy interior through a glass door.

Cabin in East Nassau

Into the Woods- Berkshire Cabin Retreat!

4.91 out of 5 average rating, 70 reviews

A warm living area is highlighted by wooden walls and ceiling beams, featuring a stone fireplace with flames visible. A comfortable seating arrangement includes a dark sofa and rustic coffee table. Natural light filters through the large window, complemented by soft curtains.

Cabin in Wilmington

Bear Tracks Cabin - VT Escape

4.92 out of 5 average rating, 89 reviews

An open living space shows a cozy seating area with a dark sectional sofa and illuminated fireplace beneath a wall-mounted TV. A modern kitchen island with seating is visible, along with light cabinetry and a dining area that leads to a separate bedroom.

Loft in Cohoes

Luxury Studio Apt, walk to restaurants and bars.