Vacation rentals with a patio near Jiminy Peak Mountain Resort

Shipping container in Whitingham

A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.

4.93 out of 5 average rating, 105 reviews

The House of Pi

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

4.93 out of 5 average rating, 128 reviews

A cottage with a white exterior is set amidst trees with bare branches, indicating a winter landscape. A gravel path leads to the entrance, and a small porch is visible at the front. Snow lightly dusts the roof, enhancing the serene ambiance.

Cabin in Hinsdale

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere

Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a loft with two full size beds, cathedral ceilings, a year-round six person hot tub and a large working kitchen stocked with everything you need. The living space is bright and airy. WiFi in the cottage is over 500 mbps, making it ideal for longer stays. The spectacular lake is just a three-minute walk from the cottage and has a kayak and inner tubes available to our guests.

5 out of 5 average rating, 199 reviews

A cozy sleeping area is highlighted by a spacious bed dressed in neutral linens. An inviting cushion rests on the bed, while warm light emanates from two bedside lamps. A wooden bench sits at the foot of the bed, and decorative greenery adorns the walls.

Guesthouse in Cummington

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Apartment in Great Barrington

A spacious room features a plush king-sized bed centered on a decorative area rug. Dark-colored walls provide contrast to the light wooden flooring. A functional desk and chair are positioned by the window, with a small kitchenette area visible. A bathroom door is seen in the background.

4.87 out of 5 average rating, 211 reviews

King Bed|Wi-Fi|2m Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58" Tv with Hulu Live

4.91 out of 5 average rating, 132 reviews

A view from a framed window reveals a cozy living space featuring a vintage wood-burning stove. A green sectional sofa provides seating, complemented by a light wood coffee table. Natural light fills the room, highlighting the open layout connecting to the kitchen area.

Cottage in Becket

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

4.94 out of 5 average rating, 181 reviews

A spacious mountain lodge is depicted, featuring a striking stone chimney and expansive decks. Large windows frame the scenic landscape, while lush green grass surrounds the building. The warm tones of the log exterior harmonize with the natural setting, inviting outdoor relaxation.

Apartment in North Adams

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

4.95 out of 5 average rating, 212 reviews

A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.

Home in Pittsfield

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

5 out of 5 average rating, 121 reviews

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

The Vermont Farmhouse|Hiking|Dog Trails|Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Treehouse in New Marlborough

The treehouse is nestled among tall trees, surrounded by a gravel area. A cozy seating arrangement with several chairs is positioned near a fire pit, offering an inviting outdoor space. A shaded canopy provides shelter, enhancing the serene forest setting.

4.9 out of 5 average rating, 154 reviews

Berkshire Treehouse Retreat

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

4.99 out of 5 average rating, 107 reviews

Apartment in North Adams

The MoCA-Cabana: 2 bd + Sauna

Welcome to the MoCA-Cabana, our newest listing at Chase Hill Estate—the historic home of the owners of the factory that became MASS MoCA. More than just a house, Chase Hill is an experience: gardens, fire pits, sauna, massages, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

4.99 out of 5 average rating, 356 reviews

Tiny home in Chatham

Boutique TINY home+private HOT TUB-walk to Main St

Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries & great dining. @artparkhomes

4.94 out of 5 average rating, 133 reviews

A vintage black rotary phone sits atop a white marble-topped table. The table holds a collection of stacked books in various colors. Two elegant white candles are placed in gold holders alongside a minimalist white vase, which is decorated with a leafy plant. The background features a patterned wall in earthy tones.

Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

A cozy, charming retreat just minutes from downtown Hudson—perfect for couples, families, or small groups looking to relax, unwind, and explore the Hudson Valley. + Hot tub, firepit & BBQ + Mini movie theater w/ projector + Dedicated workspace w/ views + Fast WiFi + Smart TV + Stocked kitchen + Coffee setup + Professionally designed interiors + Quick drive to Warren Street + Nature trail to Oakdale Lake

Popular amenities for patio rentals near Jiminy Peak Mountain Resort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.97 out of 5 average rating, 222 reviews

Apartment in Hudson

Studio Oasis nr Warren St w porch & yard

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

4.98 out of 5 average rating, 135 reviews

A balcony deck is depicted with two blue Adirondack chairs facing a small round table. A floral centerpiece is placed on the table, which is accompanied by two glasses. The area is surrounded by lush green trees, creating a serene atmosphere.

Apartment in North Adams

Historic Victorian - Entire 3rd floor

4.61 out of 5 average rating, 31 reviews

A spacious sleeping area features a large bed with a soft white duvet, complemented by two windows providing natural light. A modern sofa is positioned against one wall, and a small nightstand is beside the bed, creating a comfortable, inviting space.

Apartment in Adams

Guestrooms on the Bike Trail

4.93 out of 5 average rating, 157 reviews

A historic Greek Revival house is seen from the front yard, featuring a white facade complemented by green trees. A red door serves as a focal point, with several windows allowing natural light. The yard is bordered by a wooden fence and includes well-maintained grass.

Apartment in Coxsackie

Lovely 1 bedroom suite in historical house

4.99 out of 5 average rating, 186 reviews

A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.

Apartment in Charlemont

Suite 23 - Spacious Sunny 2-BR with Mountain view

4.92 out of 5 average rating, 235 reviews

A comfortable living area features a gray sofa adjacent to a wooden table and two chairs. Natural light filters through sheer curtains on the windows, highlighting the rustic wood flooring and a statement brick wall with a vintage-style light fixture above.

Apartment in Catskill

Catskill Village House - Garden Studio

4.99 out of 5 average rating, 153 reviews

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

Hudson River Beach House

House rentals with a patio

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

5 out of 5 average rating, 22 reviews

A serene outdoor setting captures a vibrant sunset over expansive green hills. The scene features a stone outdoor kitchen area with a grill, and several white lounge chairs positioned towards the view, inviting relaxation amid nature.

Home in Lanesborough

Berkshires Home Closed to Williams College

4.82 out of 5 average rating, 11 reviews

2 BR 2BA Condo Jiminy Peak Retreat w Mtn Views

5 out of 5 average rating, 36 reviews

A charming two-story home is set amidst lush greenery, featuring a spacious front porch with seating. The house is flanked by trees, and a large lawn is visible in front, complemented by a gravel driveway leading towards an attached garage.

Home in Lanesborough

Berkshire Mountain House

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, 53 reviews

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

An outdoor deck features a pair of unique swinging chairs and a dining set under a large umbrella. Lush greenery surrounds the area, with a backdrop of tall trees and a manicured lawn. Colorful lawn furniture is visible in the distance, inviting relaxation.

4.96 out of 5 average rating, 51 reviews

Grand 6BR Home by Jiminy | Hike • Hot Tub • Games

4.97 out of 5 average rating, 79 reviews

The historic stone church exterior is framed by lush greenery and a manicured lawn. Towering above, the bell tower features intricate architectural details. A wooden fence surrounds the property, leading to a pathway that invites exploration of the beautiful grounds.

Home in Lanesborough

Historic Stone Church in The Berkshires

4.97 out of 5 average rating, 211 reviews

A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.

Home in Catskill

Cheerful Catskill Village Cottage

Condo rentals with a patio

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.

Condo in Hancock

5 out of 5 average rating, 4 reviews

Vacation Village in the Berkshires-1 BD

A view of a downtown street, featuring a sidewalk lined with chairs and tables outside a café. Red accents can be seen on the café's exterior. Buildings of varying heights line the street, with greenery visible in the background under a cloudy sky.

Condo in Adams

4.73 out of 5 average rating, 60 reviews

Downtown Adams Vintage Getaway

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.

Condo in Hancock

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

4.91 out of 5 average rating, 47 reviews

A dining area features a light-colored table with four wooden chairs, complemented by a decorative fruit bowl. Exposed brick walls add character, while soft lighting from nearby lamps creates a bright and inviting atmosphere. A comfortable living space is also visible in the background.

Condo in Lenox

Spacious 3 bedroom apt in Lenox historic downtown

Other vacation rentals with a patio

4.87 out of 5 average rating, 23 reviews

Cabin in Windsor

Stone cabin in the Berkshires

4.94 out of 5 average rating, 36 reviews

A well-maintained two-car garage showcases a classic design with white paneled garage doors. A single window is positioned above the doors, providing a glimpse of the sky. The surrounding area is open, featuring a paved driveway and a diverse landscape of trees in the background.

Barn in Troy

The Barn@31, Quite/Private, 5min to RPI/Hospital

4.97 out of 5 average rating, 37 reviews

Cottage in East Otis

The lake house

4.94 out of 5 average rating, 160 reviews

A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.

Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

4.98 out of 5 average rating, 92 reviews

Cabin in East Nassau

Summer Mountain Retreat + Views, Fire Pit, Hot Tub

4.94 out of 5 average rating, 93 reviews

A mid-century A-frame house is set within a lush landscape, surrounded by trees displaying autumn colors. A spacious driveway leads to the entrance, and a large deck with railings extends along the front, offering an inviting outdoor space.

Chalet in Averill Park

A Hidden Sparrow

4.97 out of 5 average rating, 31 reviews

A bright entryway is enhanced by a yellow accent wall and rich wooden details. A stylish wooden chair is positioned against a wall, complemented by a decorative table featuring a vase with flowers. A staircase with a wooden banister leads to the upper floor.

Home in Hudson

Charming and spacious home in the heart of Hudson.

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.