Vacation rentals with a patio in Charlemont

5 out of 5 average rating, 109 reviews

The exterior of the country home is showcased, depicting a two-story structure with a welcoming porch. Lush green grass surrounds the house, and vibrant flowers bloom along a stone pathway, enhancing the natural beauty of the tranquil setting.

Home in Shelburne Falls

Charming Brookside Artisan Home

Relax, work & play in this peaceful country home built by a renowned furnituremaker and filled with handmade furniture and art. Explore the countryside, listen to the babbling brook & visit the many local family farms. There is a large firepit and plenty of outdoor activities at your doorstep, including biking, hiking, and x-country skiing. Come get away from it all while being only 10 minutes to Greenfield and the quaint village of Shelburne Falls. Easy 30 minute drive to the five college area.

4.85 out of 5 average rating, 159 reviews

The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.

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.

4.93 out of 5 average rating, 117 reviews

A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.

Chalet in Stamford

Peaceful VT Chalet w/ Mountain View’s

My peaceful 3-bedroom chalet has everything you need for your VT trip. The house comes with a washer, dryer, Roku TV’s, pullout queen couch. 2.5 bathrooms, indoor elec. fireplace, outdoor fire pit and fully equipped kitchen.Short driving distance to several popular golf courses, shops, restaurants, breweries, fishing, white water rafting, hiking, kayaking, ATV/snowmobile trails, & mountain slopes. An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

5 out of 5 average rating, 150 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!

4.99 out of 5 average rating, 172 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

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 !

Place to stay in North Adams

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.

4.94 out of 5 average rating, 170 reviews

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.

Superhost

An open-concept living and dining area is featured, with a wooden dining table surrounded by white chairs. A decorative area rug lies underneath. The adjacent living room is visible, showcasing a brown sofa, two armchairs, and various decorative wall art, all in a soothing color palette.

Apartment in Charlemont

4.85 out of 5 average rating, 110 reviews

Spacious apartment close to skiing and rafting

Located in the village of Charlemont, just one mile away from one of the region's favorite ski/mountain biking resorts, Berkshire East, is this charming apartment. Located on the second floor of the Wells Country Store, which was built in 1845 is a spacious, completely renovated, two-bedroom apartment. Come here for your country getaway and use this space as your launching pad for outdoor adventures. Hiking, fishing, white water rafting, skiing and so much more are right outside your door.

4.99 out of 5 average rating, 160 reviews

The treehouse stands elevated among tall trees, featuring a warm wooden exterior and large windows that allow natural light to fill the interior. A deck extends from the structure, leading to a fire pit area surrounded by gravel.

Treehouse in Putney

Treehouse Haven in Putney-All Seasons

Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.

4.99 out of 5 average rating, 114 reviews

A warm living area features high wooden ceilings and exposed beams. A cozy seating arrangement is set near a stone fireplace, adorned with holiday decorations. A television is mounted above the fireplace. Natural light filters through large windows, creating a welcoming atmosphere.

Cabin in Whitingham

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!

Tucked away in the bends of Burrington Hill Road, you’ll find our family’s Whitingham Wonderland, where our Irish touch is sure to make you feel at home and our NYC energy will keep you entertained. Our home is stocked with games for all ages as well as multiple Smart TVs, a fire pit and grill. To enjoy all Vermont has to offer we are only 30 minutes from Mt Snow and 45 from Stratton with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!

4.99 out of 5 average rating, 156 reviews

A welcoming porch features a decorative swing with two cushions and a small table, creating a serene space. Natural light filters through large windows, and colorful banners hang above, while a wooden structure nestles comfortably in the surrounding greenery.

Cabin in Guilford

Rustically Romantic Cabin Near Sweet Pond

COUPLES RETREAT, SOLO ESCAPES & WRITER'S DREAM in Southern Vermont - No Cleaning Fee Perfect for ENGAGEMENTS, HONEYMOONS & ANNIVERSARIES Authentic log cabin tucked into a private wooded cove outside of Brattleboro. A short tranquil walk to Sweet Pond State Park. Biking galore and Kayaking nearby. A variety of hikes to choose from. ROMANCE SPECIAL Stay 4-nights or more & receive hard cider, cheese & chocolate. Ask Me About ELOPEMENT & VOW RENEWAL CEREMONIES

4.88 out of 5 average rating, 159 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, 125 reviews

A bright living area is highlighted by large windows offering expansive mountain views. A colorful abstract artwork hangs against a brick wall, framed by a green houseplant. A wooden coffee table sits atop a patterned rug, complemented by a cozy sofa and a wall-mounted TV.

Cottage in Williamstown

Artistic Nature Cottage

Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home in this quiet, private and peaceful location. The cottage is overlooking a beautiful forested mountain range, with easy access to hiking, biking, and cross-country ski trails right out the door. Kalarama is bright and sunny with stunning views. Come to unwind, enjoy nature, read, meditate or just work remotely from our 23 acre property!

Popular amenities for Charlemont patio rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.96 out of 5 average rating, 105 reviews

Apartment in Bennington

Suite Sunset 311 Rice Lane Bennington VT

4.99 out of 5 average rating, 138 reviews

A well-equipped kitchen features a stove, microwave, and coffee maker, with light-colored cabinets providing storage. A double sink is positioned beside a window, offering a view of greenery outside. Counter space accommodates small appliances, creating a functional cooking area.

Apartment in Amherst

Amherst Get-a-way retreat

4.96 out of 5 average rating, 130 reviews

A cozy bedroom features a black metal bed frame with a green quilted coverlet. Soft lighting is provided by two bedside lamps on wooden nightstands. A decorative wall clock and framed artwork enhance the space, with a woven chair adding texture to the room.

Apartment in Northampton

Downtown 2BR 1.5 Bath Townhouse Charm

4.99 out of 5 average rating, 125 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

4.99 out of 5 average rating, 166 reviews

Two white lounge chairs are positioned around a small black fire pit in a grassy area. Lush greenery and trees define the backdrop, while an open space creates a sense of privacy and tranquility.

Apartment in Brattleboro

River View apartment

4.95 out of 5 average rating, 116 reviews

A spacious living area features a comfortable, light-colored sofa with multiple cushions. A low, dark wooden coffee table is centered on a textured rug. Green plants are positioned throughout, and ample natural light enters through large windows adorned with simple treatments.

Apartment in Putney

Minimal organic hideaway inspired by nature

4.9 out of 5 average rating, 134 reviews

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.

Apartment in North Adams

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

Superhost

A well-lit bedroom features a spacious bed adorned with a floral-patterned quilt. A daybed is situated next to a window, which offers a view of greenery outside. An armchair sits in the corner, complementing the light color scheme of the room.

Apartment in Northampton

4.81 out of 5 average rating, 142 reviews

Florence ctr 1br apt near town, trails, river!

House rentals with a patio

4.94 out of 5 average rating, 114 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

5 out of 5 average rating, 93 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+Ski Bromley+Holiday Escape!

5 out of 5 average rating, 76 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

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

4.97 out of 5 average rating, 70 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

Ski at Historic Stone Church in The Berkshires

4.95 out of 5 average rating, 202 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

4.9 out of 5 average rating, 135 reviews

A vibrant living room features a plush pink sofa, accented by colorful throw pillows. Two comfortable armchairs provide additional seating. A wooden coffee table is centered on a patterned area rug, surrounded by natural wood flooring. Wall-mounted lights enhance the bright and inviting atmosphere.

Home in North Adams

Central Haus (Cozy Group Getaway)

4.8 out of 5 average rating, 5 reviews

Home in Winchester

Forest Lake Cottage: A Sweetwater Stay

4.92 out of 5 average rating, 24 reviews

The exterior of the cabin showcases a welcoming wooden facade with a metal roof. A stone pathway leads to a front porch with seating and flower planters. Surrounding greenery includes grass and trees, complementing the tranquil rural setting.

Home in Hawley

Berkshire Basecamp: Hike, Bike, Raft & Relax!

Condo rentals with a patio

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.

Condo in Hancock

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

A cozy living area is highlighted by a stone fireplace, featuring firewood neatly stacked beside it. A flat-screen TV is mounted above the mantel, with built-in cabinets on either side. A sectional sofa and wooden coffee table provide comfortable seating for relaxation.

5 out of 5 average rating, 24 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

A cozy living area features a large sectional sofa and a wooden coffee table, set on a spacious area rug. Natural light filters through a large window, with a stone fireplace and a mounted television providing warmth and entertainment.

4.96 out of 5 average rating, 50 reviews

Ski On/Off 2BR w/Pool, Fireplace & Arcade

4.92 out of 5 average rating, 38 reviews

The exterior of the lodge features a blend of stone and wood elements, with multiple balconies and large windows reflecting the surrounding landscape. The entrance is framed by a welcoming staircase, leading to the main doorway marked with a sign that reads 'Hardwood Lodge'.

Condo in Stratton

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

Superhost

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

4.71 out of 5 average rating, 55 reviews

Downtown Adams Vintage Getaway

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

Seasons Condo on mtn-sports center-pool-Ski in-out

A cozy living room showcases two plush couches and a small wooden coffee table. A gas stove is nestled in a brick corner, while sliding doors offer views of the outdoors. Colorful lights frame the window, adding a touch of charm to the space.

4.91 out of 5 average rating, 57 reviews

Ski Condo 5 Min from Mt Snow