Holiday rentals with outdoor seating in Charlemont

4.97 out of 5 average rating, 235 reviews

A charming two-story cabin is set against a backdrop of lush forest. It features a spacious front porch with multiple windows, allowing for abundant natural light. A well-maintained lawn surrounds the cabin, with a gravel pathway leading to a parked vehicle nearby.

Cabin in Savoy

The Camp - hiking trails right outside your door

Enjoy the peaceful silence, private forested expanses, wildlife, and unforgettable starry night skies from this wonderful home. Only 8 minutes to the village of Charlemont and 5 to the Tannery Falls entrance of the Savoy State Forest. During your escape on the mountain rest assured that you’re only a 30 minute drive to Norths Adams, Greenfield. Highlight your visit with journeys to Berkshire East Ski Resort, Thunder Mountain Biking, Zoar Outdoor River Rafting, MASS MoCA, or the Clark Art Museum.

Guest house in Cummington

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.

5 out of 5 average rating, 143 reviews

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!

4.98 out of 5 average rating, 237 reviews

A serene sleeping area is present, featuring a spacious bed adorned with a patterned duvet. Large windows frame the view of the surrounding trees, inviting natural light into the space. A small bookshelf stands in the corner, complementing the wooden floors and walls.

Cabin in Cummington

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

4.99 out of 5 average rating, 324 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

4.99 out of 5 average rating, 128 reviews

A charming lodge is nestled within a wooded landscape, showcasing a vast back deck with seating and a central fire pit surrounded by comfortable chairs. Colorful autumn leaves frame the scene, highlighting the welcoming atmosphere of the outdoor space.

Chalet in Charlemont

The Lodge on Warner Hill

On your journey to our lodge, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding dead-end dirt road. Our home sits in a quiet, peaceful 5-acre setting. It has been completely remodeled with earth-tone charm. Enjoy your time with friends and family relaxing, reading a book, playing pool, barbequing on the back deck, gazing at the stars, or hanging out by the fire pit. Located less than 10 minutes from Berkshire East and the Deerfield River

4.99 out of 5 average rating, 171 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.

Flat in Charlemont

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

4.97 out of 5 average rating, 600 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!

Guest suite in Charlemont

A spacious living area is characterized by a combination of blue and neutral tones. A comfortable bed is positioned against one wall, while a cozy seating area contains a sofa and armchair. Natural light enters through an open door that leads to a kitchen beyond.

4.91 out of 5 average rating, 219 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

4.96 out of 5 average rating, 199 reviews

A spacious, two-story dark wooden building is nestled among trees, showcasing a welcoming entrance with a large front porch. Lush green grass surrounds the structure, enhancing its serene setting. Bright blue skies and scattered clouds further complement the inviting atmosphere.

Flat in Conway

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

4.88 out of 5 average rating, 157 reviews

The exterior of a charming yellow cottage is visible, featuring dark green shutters and a welcoming porch with decorative elements. A well-kept garden with colorful flowers and greenery surrounds the cottage, while a gravel pathway leads to the entrance under a partly cloudy blue sky.

Cottage in Monroe

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

4.98 out of 5 average rating, 722 reviews

An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.

Cottage in Shaftsbury

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

4.88 out of 5 average rating, 162 reviews

The log home is framed by lush greenery, with a rainbow arching over the hillside in the background. Solar panels are visible on the roof, and a small, illuminated outdoor lamp stands in the foreground, providing a welcoming touch to the natural setting.

Flat in Hawley

Green Acres Hawley Upper Studio (Bonus Room)

This space is a Large Studio Apartment in the Bonus Room above the Garage of a large log home overlooking Berkshire East Mountain Resort. Guests have shared access to the hot tub, deck, fire pit barbecue area and limited access to host's laundry facilities. You'll have sole access to the bonus room, deck & grill and full private bath. Space is comfy and charming, accessible from a private staircase or spiral into the main house's entrance hall.

Popular amenities for outdoor seating rentals in Charlemont

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.96 out of 5 average rating, 135 reviews

Home in Guilford

Green River Cottage-A Peaceful Country Retreat

4.98 out of 5 average rating, 322 reviews

A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.

Home in Bennington

Cozy Modern Sugar House with spectacular views.

4.92 out of 5 average rating, 188 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

4.94 out of 5 average rating, 185 reviews

A charming red farmhouse is set against a backdrop of rolling hills and blue skies. The property includes a separate red building nearby, surrounded by lush green grass and a landscaped stone garden featuring colorful flowers and greenery.

Home in Colrain

Secluded Farmhouse Retreat - stunning views

Superhost

The historic farmhouse is presented under a clear blue sky, surrounded by a blanket of snow. The white exterior features large windows, a porch with seating, and a red door on the side. Shadows from nearby trees stretch across the snowy landscape.

Home in Whitingham

4.95 out of 5 average rating, 104 reviews

Foliage Ready! Play Area, Crib, 11 Acre Farmhouse

4.94 out of 5 average rating, 110 reviews

An aerial view captures the expansive landscape featuring a charming property nestled among vibrant autumn foliage. The surrounding hills and valley are visible, with a small town in the distance, showcasing the serene beauty of the country setting.

Home in Shelburne Falls

Buckland House - A World Apart

4.94 out of 5 average rating, 129 reviews

A spacious living room features a vaulted ceiling and an arched window that allows natural light to flood the space. Comfortable seating arrangements include two red sofas and a patterned area rug. Shelving units display decorative items, while a media system is positioned above the fireplace.

Home in Brattleboro

Modern Spacious Home with Mountain Views

4.95 out of 5 average rating, 204 reviews

A spacious kitchen and dining area with a large wooden table and seating for 10 is complemented by stylish bar stools. An air hockey table is visible nearby, and ample natural light fills the room, reflecting off the polished hardwood floors.

Home in Colrain

Fallinlove with the falls AirHockey Firepit

Apartment rentals with outdoor seating

4.98 out of 5 average rating, 104 reviews

A spacious living area features a light-colored sectional sofa and armchair, with a cozy ottoman nearby. Large windows provide natural light, highlighting the wooden beams on the ceiling. A dining table and kitchenette can be seen in the background, complemented by decorative accents and a comfortable window seat.

Flat in Schuylerville

Serene Studio Retreat 20 Minutes to Downtown

4.91 out of 5 average rating, 391 reviews

An enclosed porch is furnished with a white rocking chair and various seating options adorned with colorful cushions. A woven storage box sits beside a patterned area rug that features large floral designs. Natural light filters through multiple windows, creating a bright atmosphere.

Flat in Brattleboro

Quiet St in Town, gardens, terrace

4.99 out of 5 average rating, 123 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.

Flat in North Adams

Historic Victorian - Entire 3rd floor

4.99 out of 5 average rating, 207 reviews

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.

Flat in North Adams

Overlooking the city in a quiet 7 unit building.

4.88 out of 5 average rating, 426 reviews

A serene view from the deck showcases a green meadow leading to a small pond surrounded by grass. Rolling hills can be seen in the distance, framed by trees. A few outdoor chairs are placed near the pond, inviting relaxation in the natural setting.

Flat in Guilford

Apartment with a view

4.89 out of 5 average rating, 205 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

4.92 out of 5 average rating, 144 reviews

A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.

Flat in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

4.95 out of 5 average rating, 175 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

Apartment rentals with outdoor seating

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.

4.83 out of 5 average rating, 107 reviews

Mount Snow Ski Chalet

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.

4.99 out of 5 average rating, 124 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

4.98 out of 5 average rating, 47 reviews

The living area features a spacious sectional sofa arranged around a coffee table, complemented by a cozy wood-burning fireplace. Natural light fills the room through large windows, which overlook the snowy landscape. A dining table for six and a media console housing a Smart TV are also present.

Apartment in Stratton

Ski In/Out, Cozy 3BR Condo steps to Village

A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.

4.94 out of 5 average rating, 77 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

4.94 out of 5 average rating, 105 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

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.

4.94 out of 5 average rating, 95 reviews

Cozy Mt Snow Ski In / Out

A living room features a wood-burning fireplace with an exposed brick surround, accompanied by neatly stacked firewood. A large flat-screen television is mounted above the mantle. Natural light enters through sliding glass doors, which lead to an outdoor seating area.

4.81 out of 5 average rating, 129 reviews

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

The condo building is surrounded by a thick blanket of snow, with multiple units visible. The exterior features a green color and large windows. Snow collects on rooftops and the ground, creating a serene winter scene with trees in the background.