Vacation rentals in Richmond

4.93 out of 5 average rating, 184 reviews

Guest suite in Richmond

Tanglewood/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!

The entrance to a cottage is highlighted, featuring a blue front door with an oval window. White railings frame the steps leading up to the door, which is flanked by potted plants. Gravel and a concrete base surround the area, contributing to a tidy appearance.

4.94 out of 5 average rating, 18 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.

4.88 out of 5 average rating, 185 reviews

A cozy outdoor seating area is highlighted by a stone fire pit, with flames dancing above a bed of volcanic rocks. In the background, a high-definition TV displays a sports event. Barstools and a wooden structure suggest a welcoming spot to relax.

Apartment in Petersburgh

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

5 out of 5 average rating, 66 reviews

Home in Canaan

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

4.94 out of 5 average rating, 36 reviews

A serene outdoor space features a circular pool surrounded by a stone patio. Lounge chairs sit nearby on a grassy area, and a grill is positioned under a wooden pergola. Lush trees provide a natural backdrop, enhancing the tranquil setting.

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!

4.99 out of 5 average rating, 219 reviews

A wooden sign with the text 'BITTERSWEET FARM' is displayed prominently. Below the sign, a flower bed contains vibrant orange and yellow marigolds, adding a touch of color to the entrance. The surrounding grassy area is well-maintained, enhancing the welcoming appearance of the farm.

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.

4.98 out of 5 average rating, 40 reviews

A modern cottage exterior is pictured, featuring a multi-tiered wooden deck leading up to large glass doors. The deck is furnished with comfortable seating, surrounded by lush greenery, and bathed in warm afternoon sunlight, creating a welcoming space for relaxation.

Home in Pittsfield

Cozy Cottage on Peaceful Pond, Close to Winery

This little slice of heaven is located on the serene Richmond Pond. Right down the street from Balderdash Winery and a 15 minutes drive to charming downtown Lenox and Tanglewood, where you can find multiple fantastic restaurants. There is plenty of hiking and biking around this area. This cozy cottage has everything you need for a Berkshire retreat especially in the fall. Cozy up next to the fireplace inside or out, take a break and unwind at this peaceful oasis.

4.93 out of 5 average rating, 376 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

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Guesthouse in Stockbridge

The kitchenette features modern black cabinetry, open wooden shelves, and a sleek countertop. A microwave and a compact oven are included, along with a sink below a skylight. Glassware, jars, and dishware are neatly arranged along the shelves, enhancing functionality and style.

4.95 out of 5 average rating, 234 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.

4.92 out of 5 average rating, 262 reviews

Apartment in Pittsfield

Marie's Place

This newly renovated bright sunny apartment is minutes from Bosquet ski area & also close to downtown. It has a large kitchen and pantry. Beautiful oak dining room table. Comfy living room set, with a 43 inch Roku TV. Electric fireplace. Queen size beds in both bedrooms. Large walk-in closet in. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters.

Cottage in West Stockbridge

A modern kitchen showcases soft gray cabinetry with gold hardware and a spacious countertop. Natural light filters through multiple windows, illuminating the area. A coffee maker and kitchen appliances are neatly arranged, enhancing the functional design and inviting atmosphere.

4.95 out of 5 average rating, 136 reviews

Historic 1810 Farmhouse - Fully Renovated

Charm and history meet modern convenience in this stunning renovated farmhouse. Built in 1810, this beautiful home was once the residence of Mr. Prince, who presided over the Tobey Quarry Farm. Just steps into town, the cottage is the ideal retreat for a low-key, cozy getaway. Or as a launch pad to the area's many outdoor/cultural offerings. We warmly welcome you!

4.93 out of 5 average rating, 105 reviews

A kitchen counter is equipped with a coffee maker, a toaster oven, and a blender. Glass jars and mugs are neatly arranged alongside a cheerful sign that reads 'BE HAPPY.' The countertop is finished in a light grey texture, providing a practical workspace.

Guesthouse in Lenox

The East Street Cabin

This adorable cabin is your perfect escape for rest and relaxation. This is a perfect place for people coming to the Berkshires for Tanglewood or any of the other wonderful things the area has to offer. The cabin is located down a path through the woods about 100 yards from the main house. We are excited to share our cabin with you.

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Popular amenities for Richmond vacation rentals

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Wifi

Pool

Free parking on premises

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Other great vacation rentals in Richmond

4.97 out of 5 average rating, 93 reviews

A spacious great room features high ceilings with wooden beams and large triangular windows. A wooden dining table is situated near the windows, while comfortable seating arrangements with neutral-toned upholstery are arranged around a central fireplace. Natural light fills the space, enhancing the open concept design.

Chalet in Richmond

Updated Berkshires Chalet Mins to Tanglewood/Lenox

GlennRating, 5 stars9 months ago

This was our 2nd stay at this property. If you love the Berkshires and all the activities available, this house and property are perfect. It is very well maintained and the great room is perfect for our large family. Nothing like the hot tub and sitting around a fire after a busy day of hiking and Tanglewood. Wendy is an excellent host, never a problem.

4.95 out of 5 average rating, 225 reviews

The spacious interior features high wooden beams and a stone fireplace at its center. Natural light fills the area through large windows, highlighting the open floor plan. A loft area is visible above, and comfortable seating arrangements support relaxation and gatherings.

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

JenniferRating, 5 stars1 month ago

The space was beautiful, clean, and exactly as pictured! We enjoyed a weekend away and appreciated the local recommendations shared in the guide. We spent time exploring the farm, the surrounding area, and also were able to kick back and relax in the amazing property.

4.75 out of 5 average rating, 20 reviews

Idyllic Berkshires Farmhouse

LaurenRating, 5 stars3 weeks ago

Beautiful space in a wonderfully scenic location. Space is fully equipped with anything you might need & is conveniently located close to several towns in the area. Lots of natural light. We loved our stay!

The exterior of the home is surrounded by vibrant red foliage, with scattered leaves covering a stone path leading to a deck area. Dark wooden siding contrasts with the natural landscape, and the house is nestled among trees, enhancing a sense of seclusion.

4.9 out of 5 average rating, 10 reviews

"Hemlock Shadow" near Tanglewood on Six Acres

VictoriaRating, 5 stars5 months ago

We gathered for New Year's with all our kids and a grandchild. The place is very well setup with bedrooms on 3 levels, so wonderful privacy for all. The living space is cozy with lots of comfortable seating. All the holiday decorations were a nice surprise and put us in a festive mood as soon as we got there. The whole house feels lived in and we immediately felt at home. Kitchen has a huge variety of small appliances and an amazing coffee machine. We'll be back!

Cabin in West Stockbridge

5 out of 5 average rating, 7 reviews

Serene rustic mountain cabin in the Berkshires!

KellyRating, 5 stars3 weeks ago

Would love to come Back!

A sprawling green lawn stretches underneath a large tree, providing ample shade. A hammock is gently draped beside the tree, surrounded by a colorful garden of plants and flowers, creating a serene outdoor space for relaxation.