Vacation rentals in Richmond

4.92 out of 5 average rating, 396 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.

Guesthouse 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.

4.82 out of 5 average rating, 28 reviews

The cabin is nestled in a wooded area, surrounded by lush greenery. A large deck extends from the front of the home, with firewood stacked neatly beside it. The architecture features an A-frame design, blending harmoniously with the natural landscape.

Chalet in Lenox

Berkshires Escape | Stylish Chalet + Scenic Views

Elegant, light-filled cabin blending modern comfort with much charm; in Lenox besides Kennedy Park. Enjoy mesmerizing foliage views from the expansive deck, a cozy wood stove and a serene private garden. Main suite upstairs with bath and comfy sitting area; downstairs offers a queen room, twin ensuite, and TV lounge. Perfect luxe Berkshires retreat for intergenerational families. Games, ping pong and top-tier destinations minutes away: Butternut, Bousquet and plenty leaf peeping & hiking options

4.95 out of 5 average rating, 434 reviews

A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

4.93 out of 5 average rating, 193 reviews

A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.

Guest suite in Richmond

Fall Foliage/Private Ranch/Kid&Pet Friendly/Horses

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail ride lessons /Horse activities available by appt!

A blue front door with an oval glass inset stands prominently against a white wooden facade. A small porch is visible, featuring a wooden bench and a gray chair. Fallen leaves are scattered across the gray decking.

4.97 out of 5 average rating, 31 reviews

Sunshine Cottage

Sunshine Cottage a peaceful place to rest and relax while being centrally- located to many of the attractions that make this area a beautiful place to visit. We are about 15 minutes away from Balderdash Winery, Hilltop Orchard/ Winery and Home Range Winery. Tanglewood, Berkshire Botanical Gardens, Jacobs Pillow, Red Lion Inn and Hancock Shaker Village bring culture and magnificent shows. You can ski at Bousquet Mountain, Ski Butternut and Jiminy Peak Mountain Resort. Come visit the Berkshires.

4.95 out of 5 average rating, 198 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.

4.98 out of 5 average rating, 255 reviews

A spacious bedroom features a large queen bed with a white duvet and decorative pillows. Two sets of French doors open to an outdoor view, flanked by soft curtains. A cozy seating area with a light-colored sofa adds comfort, illuminated by natural light from the windows.

Guest suite in Valatie

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

4.95 out of 5 average rating, 42 reviews

A spacious living area features a comfortable gray sofa and a small black table. A green decorative vase and natural branches are placed beside a traditional stove on a brick hearth. A light rug covers the wooden floor, creating an inviting space.

Guest suite in Richmond

Berkshire Mountain Retreat

Studio apartment with private entrance nestled in bucolic Richmond. Located on a quiet mountain road adjacent to miles of hiking and biking trails. Close to 4 ski areas and minutes to Tanglewood, Kripalu, Clark Art Museum, Mass MoCA, Hancock Shaker Village, the Mass Audubon Wildlife Sanctuary and more. A short drive to Lenox, Stockbridge, and Great Barrington where shopping and fine dining await. Your relaxing vacation begins here with an expansive yard, views and in ground pool!

Earthen home in West Sand Lake

The entrance to a Hobbit house is framed by lush greenery and natural stone. A curved, grassy roof merges with the surrounding trees, while a stone pathway leads to the large wooden door. Decorative lanterns are positioned above the entrance, enhancing the rustic charm.

4.97 out of 5 average rating, 208 reviews

The Hobbit House at June Farms

Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Scottish highland cows, Gloucestershire spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

4.99 out of 5 average rating, 289 reviews

A spacious kitchen is complemented by large windows that allow natural light to fill the area. An island with a countertop of mixed materials serves as a central gathering spot. A colorful rug lies on the concrete floor, while various kitchenware is neatly arranged on shelves.

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, 257 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.

Guesthouse in Stockbridge

A modern kitchenette is visible, featuring black cabinetry and open shelving with dishware. A dining area with a table and four chairs is situated nearby, while light streams in through a skylight and window, illuminating the open space.

4.96 out of 5 average rating, 246 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Vacation rentals for every style

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A space thats all yours, with room for everyone

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Richmond vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Richmond

4.95 out of 5 average rating, 241 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

An aerial view showcases a classic New England home and its private in-ground pool set amidst a lush landscape. Surrounding trees provide natural greenery, while a well-maintained yard leads to open fields, creating a serene outdoor environment.

4.89 out of 5 average rating, 9 reviews

Classic New England Home

The home's exterior is framed by vibrant red foliage, creating a striking entryway. A path made of stone leads to the entrance, while steps adorned with leaves provide access. Surrounding greenery enhances the natural setting, offering a serene and inviting atmosphere.

4.94 out of 5 average rating, 18 reviews

"Hemlock Shadow" near Tanglewood on Six Acres

A serene landscape is displayed, featuring a red barn and a single-story blue house surrounded by lush green grass. Leafless trees and gentle hills create a peaceful backdrop under a partly cloudy sky.

4.92 out of 5 average rating, 12 reviews

Bucolic Pet Friendly Oasis | 10 min to Tanglewood

Place to stay in New Lebanon

A kitchen features light blue cabinetry and a central island with a granite countertop. Above the island, open shelving displays decorative bowls and glassware. A dining table with wooden chairs is positioned nearby, while a cozy seating area is visible in the background.

5 out of 5 average rating, 29 reviews

20 minutes to Tanglewood

Guesthouse in Lanesborough

5 out of 5 average rating, 9 reviews

The Carriage House: Spotless, Charming 2 Bedroom

4.99 out of 5 average rating, 68 reviews

A modern kitchen features clean lines and natural light. The space includes a refrigerator, stove, and a dining table with two chairs. Soft white cabinetry is complemented by a wooden tabletop, while a window offers views of the outdoors, enhancing the open and airy feel.

Apartment in Stockbridge

Stockbridge private apartment

A charming farmhouse exterior is framed by a well-maintained garden, featuring a gravel path leading to a welcoming front door. Lush greenery surrounds the house, complemented by seasonal foliage. The expansive lawn stretches toward the gently rolling landscape in the background.