Vacation rentals with a patio in Lanesborough

5 out of 5 average rating, 20 reviews

A serene lakefront property is viewed from the water, featuring a well-maintained lawn and inviting home. The structure is flanked by mature trees, while a small private dock extends into the lake, providing easy access to the water.

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

Stunning lakefront property on 1-acre on Pontsoosuc Lake in western MA, in the heart of the Berkshires. This beautiful home features 3 bdrms & 2.5 baths. A large primary suite (king bed) sits on one side of the home, w/ two guest bdrms (king bed, queen bed) on the other end of the house. Kitchen, dining, and living room areas are spacious and open, with high ceilings & skylights. Cozy closed-in lakeside backporch opens to a small back deck. Large front side porch is set back from main road.

4.94 out of 5 average rating, 113 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, 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

<b>Hinterland Hall</b> was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay. <b>Follow us @hinterlandhall</b> Please inquire about weddings & events.

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!

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.

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

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!

4.96 out of 5 average rating, 46 reviews

Home in Pittsfield

Beautiful Lake-view Getaway!

Enjoy a weekend away in the heart of The Berkshires! Take in the stunning lake views and beautiful sunsets year-round. Whether you are looking for a lake getaway or Berkshires retreat in the summer, or a place to cozy up after a long day of skiing in the winter, my home will offer all the comforts you need to enjoy your time in The Berkshires. Enjoy the lake views from the hot tub (additional fee), sit around the fire pit and watch the sun set, or enjoy a home cooked meal on the patio!

5 out of 5 average rating, 20 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

Contemporary Berkshires Home-5 Mins to Jiminy Peak

Welcome to our peaceful sanctuary with beautiful views of distant rolling hills and mountain views. Come to relax or come to explore all of the Berkshires activities. Get active w/ the many hiking trails, charming towns, arts and performances and a year-round ski resort for outdoor fun. Mt Greylock, Ramblewild Adventures, Mass MoCA, Tanglewood, Jiminy Peak for a great Berkshires experience. This house is the ultimate retreat for relaxation after exploring all of Berkshires best!

4.89 out of 5 average rating, 83 reviews

Apartment in Pittsfield

Cozy 2-Bedroom Apartment - Close to Downtown !

HUGE DISCOUNTS FOR WEEKLY AND MONTHLY STAYS !!! Clean and sunny two bedroom apartment close to the center of town. Enjoy two queen sized beds and a futon for extra guests or kids. Family and pet friendly. Less than a mile from downtown amenities. Within close driving distance to Barrington Stage, Tanglewood, Bousquet Ski Area, Berkshire Theater Festival, Norman Rockwell Museum, Jiminy Peak, MASS MoCA, The Clark and all of the endless delights of the beautiful Berkshires.

Townhouse in Clifton Park

The spacious bedroom features a king bed adorned with a dark blue throw and neatly arranged towels. Soft lighting is provided by bedside lamps on each side of the bed, while a plant adds a touch of greenery. Two landscape artwork pieces hang above the bed.

5 out of 5 average rating, 221 reviews

Near Saratoga – King Bed, Tub, Fire Pit & Movies

Escape to this family-friendly Clifton Park retreat—just 20 mins to Saratoga Springs and 25 to Albany. Perfect for fall getaways with a fire pit, outdoor movie screen, private playground, basketball court, and garden. Features a king bedroom, home office, full kitchen, fast Wi-Fi, soaking tub, and 20' x 55' parking for RVs or boats. Relax in the crisp autumn air, enjoy backyard movie nights, and stay productive or cozy in a quiet, peaceful neighborhood.

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!

4.99 out of 5 average rating, 317 reviews

A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.

Tiny home in Chatham

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

Blush & Bubbles for December stays. Romantic, boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful oasis just 2 mins from Chatham’s Main Street lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis at @artparkhomes.

Popular amenities for Lanesborough 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

4.97 out of 5 average rating, 211 reviews

Apartment in Hudson

Studio Oasis nr Warren St w porch & yard

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

4.93 out of 5 average rating, 151 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, 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

4.99 out of 5 average rating, 139 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

4.85 out of 5 average rating, 110 reviews

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

Spacious apartment close to skiing and rafting

4.96 out of 5 average rating, 120 reviews

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Apartment in Otis

Enjoy every season the Berkshires have to offer.

House rentals with a patio

4.82 out of 5 average rating, 253 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!

4.96 out of 5 average rating, 71 reviews

A hot tub is positioned outdoors on a wooden deck, surrounded by tall trees. Fresh towels are neatly arranged on a small table nearby. The serene lake, framed by lush greenery, is visible in the background, indicating a peaceful outdoor retreat.

Home in Canaan

Cozy Ski Cabin! Hot Tub • Movie Room • Game Room

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!

4.96 out of 5 average rating, 172 reviews

A spacious cedar hot tub sits peacefully outdoors, surrounded by a natural setting of trees and open space. Bubbles rise from the water, creating a relaxing atmosphere. Clear blue skies are visible above, enhancing the tranquil environment.

Home in Hudson

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4.99 out of 5 average rating, 70 reviews

The exterior of a historic red house is surrounded by lush green grass and trees. A stone path leads to the front entrance, while flowering plants add a touch of color to the landscape. The sky is clear with some clouds, creating a serene outdoor setting.

Home in Old Chatham

The Red House

4.93 out of 5 average rating, 72 reviews

Home in Adams

Mount Greylock View Retreat,3 bedroom,2 1/2 bath.

4.95 out of 5 average rating, 44 reviews

The historic Hancock Village Inn is blanketed in fresh snow, with tall evergreen trees surrounding the property. The white exterior of the building contrasts with the winter landscape, showcasing a peaceful scene with an expansive yard and snow-covered fence.

Home in Hancock

Spacious 6BR by Jiminy | Ski • Hot Tub • Game Room

5 out of 5 average rating, 20 reviews

The exterior of the home is showcased, revealing a charming blend of rustic wooden shingles and modern design. Large windows and a stylish doorway invite natural light, while a stone foundation adds character. Lush grassy areas surround the house, enhancing its serene setting.

Home in East Chatham

Stylish Rural Sanctuary! (+ Summer Pool)

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

4.91 out of 5 average rating, 46 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

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

4.71 out of 5 average rating, 55 reviews

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

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

A modern kitchen is showcased with white cabinets and a dark granite countertop. Stainless steel appliances, including a refrigerator and stove, are visible. A dining table with wooden chairs is situated nearby, while a cozy living area can be seen through the open layout.