Holiday rentals in Richmond

Bucolic Pet Friendly Oasis | 10 min to Tanglewood

Escape to our peaceful retreat on 5 private acres. Large picture windows envelope you in the gorgeous surroundings, and the tree lined property creates a sense of utter tranquility. Bask in the breeze on the three-season sun porch, curl up by the wood burning stove, or enjoy a lounge on the deck. Centrally located in the Berkshires: ⭐️ 10 minutes to Tanglewood/Lenox ⭐️ 7 minutes from West Stockbridge/ I-90 ⭐️ 20 minutes to Great Barrington, Stockbridge & Pittsfield Enjoy our oasis all year!

Classic New England Home with direct trail access

Classic New England Home with DIRECT trail acess – 4BR in Richmond Enjoy the charm of the Berkshires in this spacious 4-bedroom, 2.5-bath home in peaceful Richmond. Perfect for families or remote work, the home features fast Wi-Fi, fully equipped kitchen and 7 acres of natural privacy. Enjoy direct access to spectecular hiking trails, unwind on the patios, restaurants, and historic sites. Minutes from Tanglewood, Kripalu, Lenox and West Stockbridge. Book your stay and make yourself at home!

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Guest favourite

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

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!

Luxury Barn Near Hudson with New Private Sauna

A secluded luxury barn retreat near Hudson and the Berkshires, now featuring a private sauna for year-round relaxation. Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

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Guest favourite

Secluded Chic Mountain Chalet near Tanglewood

Escape to Tranquility Glade, a newly designer-renovated modern chalet on 5.5 private forest acres near Tanglewood & Kripalu. Bathed in natural light with cathedral ceilings, skylights, and a dramatic stone fireplace, this serene retreat blends modern style with woodland calm. Enjoy curated furnishings, a sleek European galley kitchen, outdoor firepit, tranquil forest views, and easy access to lakes, waterfalls, hiking, and skiing—perfect for cozy evenings or peaceful mornings among the trees.

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Guest favourite

Modern, Renovated Lakefront Escape

Evergreen Home Vacation Rentals invites you to the East Beach Lakehouse, a stylish, recently renovated retreat on the shores of Richmond Pond. Situated on over an acre of land, this stunning property features a private dock and guest watercraft for the ultimate lakefront experience. Enjoy the heart of the Berkshires from the screened porch or host a BBQ on the grill. With ample space and modern amenities, it’s the perfect setting for relaxation and water adventures. Book your lake escape!

Berkshires/Pet Friendly/Tanglewood/Private Ranch

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 Rides /Horse activities available by appt!

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

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Guest favourite

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!

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Guest favourite

Berkshires Colonial on 2 Acres by Evergreen Home

Evergreen Home Vacation Rentals invites you to this grand Colonial on 2.7 private acres in picturesque Richmond. This spacious home is the perfect base for quiet country living, located just 1 minute from Balderdash Cellars and 10 minutes from Bousquet Mountain. Enjoy effortless access to Tanglewood, apple picking, and world-class museums. Whether you're heading 30 minutes to Butternut or exploring local trails, this estate offers the ideal blend of tranquility and convenience.

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Guest favourite

Modernized 1860s Getaway w/ Queechy Lake Passes*

Unwind in our quiet, spacious, light-filled, rural home without leaving modern conveniences behind. Located in Historic Lebanon Springs, our newly restored antique home is near both Hudson Valley restaurants and shops and the Berkshire's vast outdoor activities. We took great care to save this home's historic details while creating a fully modernized, comfortable retreat. Every room is thoughtfully curated with local antiques, artwork, and many unique touches you'll enjoy.