Holiday rentals with outdoor seating in Pittsfield

4.92 out of 5 average rating, 406 reviews

The exterior of the Granary is highlighted, featuring a mix of red barn siding and natural stone. The two upper windows allow natural light inside, while a mint green double door adds a pop of color. Lush greenery and colorful flowers surround the entrance.

Guest house in Lenox

Restored 1735 Granary I King Bed + Views & Pool

Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 15-ft vaulted ceilings, original wide-plank floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub + standing shower. Centrally located in the Berkshires and just minutes to Lenox and Tanglewood. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

A large Victorian house is framed by vibrant autumn foliage, with colorful orange, yellow, and red leaves. The home features a spacious porch and multiple gabled roofs, blending harmoniously with the surrounding nature and the peaceful landscape.

4.97 out of 5 average rating, 630 reviews

Steps to MoCA: 2bd + SAUNA!

A spacious, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Just a 5 minute-walk to MASS MoCA, 10 mins to downtown restaurants, 10 mins drive to Williams College & Clark. Closest ⛷️ SKI resorts are Jiminy Peak and Berkshire East Mountain. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates often available beyond what the calendar shows—contact us!

4.95 out of 5 average rating, 248 reviews

An open living space with a high wood-beam ceiling is displayed. A large stone fireplace serves as a focal point, surrounded by comfortable seating. A kitchen island with stools offers additional space. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

4.94 out of 5 average rating, 112 reviews

An open kitchen and dining area feature a wooden dining table surrounded by black chairs. The space is illuminated by natural light from large windows, with a breakfast bar visible in the background. A neutral color palette adds warmth to the inviting layout.

Home in Pittsfield

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

4.97 out of 5 average rating, 603 reviews

The bright studio features a cozy sleeping area with a spacious bed, a comfortable yellow armchair, and two plush couches. A coffee table sits in the center, with large windows allowing natural light and views of greenery. A television is mounted on the wall.

Flat in Shelburne Falls

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

4.94 out of 5 average rating, 206 reviews

A wooden rocking chair sits on a quaint porch, next to vibrant flower pots filled with blooming plants. Green grasses and a hint of autumn foliage create a serene outdoor setting, inviting relaxation and peaceful moments.

Cottage in New Lebanon

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

4.95 out of 5 average rating, 201 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!

4.89 out of 5 average rating, 206 reviews

A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.

Flat in Petersburgh

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Guest suite in Pittsfield

The entrance features a red door framed by light-colored siding. A small roof provides shelter over the entry, and a lantern hangs above. A gravel pathway leads to the door, surrounded by greenery and natural landscaping.

4.91 out of 5 average rating, 99 reviews

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom, full bathroom. The spacious room features a queen bed and a small table for dining and working, a small frig, microwave, toaster oven, and pour-over coffee in a nook outside the bedroom. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. Fire Pit. NEED MORE SPACE FOR CHRISTMAS WEEK? Check out Christmas in the Berkshires to rent the whole house.

4.99 out of 5 average rating, 301 reviews

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

4.99 out of 5 average rating, 276 reviews

A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.

Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

4.91 out of 5 average rating, 292 reviews

A cozy living room is furnished with two comfortable sofas and a coffee table set on a patterned rug. Natural light enters through a window, illuminating wall art and decorative elements. A door leads to a balcony area, enhancing the space's inviting feel.

Flat in Pittsfield

Marie's Place

This newly renovated bright sunny apartment is minutes from Bosquet ski area & also close to downtown. It has a large kitchen and pantry. Beautiful oak dining room table. Comfy living room set, with a 43 inch Roku TV. Electric fireplace. Queen size beds in both bedrooms. Large walk-in closet in. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters.

Popular amenities for outdoor seating rentals in Pittsfield

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.99 out of 5 average rating, 170 reviews

A vintage-style freestanding bathtub is filled with water, complemented by a wooden tray featuring a book and a glass of white wine. A soft glow is provided by a candle placed nearby, enhancing the serene atmosphere of the bathroom.

Home in Dalton

Cleveland House - renovated Berkshires' gem.

4.92 out of 5 average rating, 189 reviews

A bright dining area features a large table surrounded by four chairs. Natural light filters through multiple windows, highlighting the warm wood floor. Potted plants are positioned near the windows, and wall art adds a touch of color to the neutral space.

Home in North Adams

A paradise in the woods, minutes from MASS MoCA

4.95 out of 5 average rating, 264 reviews

An open kitchen and dining area feature rustic wooden beams and warm wooden floors. A round dining table with black chairs is positioned near double glass doors leading to a deck. An island with stools offers additional seating, with kitchen amenities visible in the background.

Home in Ghent

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

4.93 out of 5 average rating, 198 reviews

An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.

Home in Dalton

Brooksong, the perfect Berkshires getaway

4.99 out of 5 average rating, 139 reviews

Home in Great Barrington

Granite Ledge, Modern home in a unique setting

5 out of 5 average rating, 237 reviews

The exterior of the house showcases a modern rustic design, featuring a stone and wood façade. Large picture windows reflect the surrounding nature, while an outdoor fire pit is surrounded by several Adirondack chairs on a grassy area. A dining table and chairs are positioned nearby.

Home in Rhinebeck

Eagle Rock House

4.98 out of 5 average rating, 134 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

4.92 out of 5 average rating, 256 reviews

Home in Adams

1890 House

Apartment rentals with outdoor seating

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.

4.99 out of 5 average rating, 125 reviews

Historic Victorian - Entire 3rd floor

The exterior of the condominium building is highlighted, featuring a two-story design with a light blue facade. Lush greenery surrounds the property, enhancing the natural setting. A gravel pathway leads to the entrance, and outdoor seating areas are visible in the landscaped garden.

4.99 out of 5 average rating, 208 reviews

Overlooking the city in a quiet 7 unit building.

4.9 out of 5 average rating, 135 reviews

An airy interior showcases exposed wooden beams and a blend of modern and rustic decor. A kitchen counter with stools is positioned towards the left, complemented by a dining table with chairs in the center. A cozy bedroom is visible through the doorway on the right.

Flat in Philmont

Beautiful space in the heart of Philmont

4.95 out of 5 average rating, 287 reviews

A wide expanse of green grass is framed by a line of trees under a blue sky dotted with fluffy white clouds. The landscape conveys a sense of open space and tranquility, characteristic of the surrounding rural setting.

Flat in Plainfield

Sunny carriage house apartment

4.95 out of 5 average rating, 176 reviews

A cozy living area features a light grey sofa paired with a wooden coffee table. An accent chair with a textured throw sits beside a basket. A large cow print hangs on the wall, with two framed pieces nearby. A patterned rug covers the floor.

Flat in Bennington

Cooper's Place

A welcoming bedroom features a spacious bed with a light duvet and decorative pillows. A wooden dresser stands beside the bed, and natural light filters through a window adorned with light curtains. Soft wooden flooring enhances the room's warm ambiance.

4.92 out of 5 average rating, 131 reviews

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT

4.99 out of 5 average rating, 136 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.

Flat in Coxsackie

Hudson River Beach House

4.91 out of 5 average rating, 215 reviews

A living area features a comfortable green sofa and beige chairs, complemented by a decorative coffee table. A dining table with chairs is positioned adjacent to the kitchen. A brick accent wall hosts an electric fireplace, with natural light streaming through nearby windows.

Flat in Troy

Sunny Troy Private Deck Parking Wi-Fi Top Floor

Apartment rentals with outdoor seating

Apartment in Litchfield County

A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.

4.93 out of 5 average rating, 30 reviews

Meadow View

4.95 out of 5 average rating, 62 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

4.83 out of 5 average rating, 107 reviews

A snowy landscape showcases the mountain in the background with ski trails visible. The foreground features a winter scene with snow-covered ground and trees. A building is partially visible on the left, adding to the serene atmosphere.

Apartment in Dover

Mount Snow Ski Chalet

4.93 out of 5 average rating, 45 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.

Apartment in Lenox

Spacious 3 bedroom apt in Lenox historic downtown

4.99 out of 5 average rating, 124 reviews

A modern living room features a traditional wood-burning fireplace framed by a brick facade. A large TV is mounted above the mantle, while a plush recliner, a small seating area, and a neatly stacked firewood display complete the cozy setting.

Apartment in Dover

Winter Dream! The Handle Lodge at Snowtree Condos

Apartment in Saratoga Springs

A spacious living area features large windows offering panoramic views of the lake. A dining table is positioned near the window, while comfortable seating is arranged around the space. Ceiling fans contribute to ventilation, and sunlight brightens the room, enhancing the open atmosphere.

4.86 out of 5 average rating, 51 reviews

Gorgeous Waterfront - Close to track & Saratoga