House vacation rentals in Richmond

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Top-rated house rentals in Richmond

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Guest favorite

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Guest favorite

A spacious outdoor area is surrounded by vibrant planters filled with blooming flowers. Comfortable seating is arranged around a fire pit, with a green umbrella providing shade. A pink flamingo float is set nearby, alongside a wooden hot tub and a stock tank plunge pool.

Home in Hudson

4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

Guest favorite

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

4.93 out of 5 average rating, 102 reviews

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?!

Top guest favorite

A two-story house is set amidst greenery, featuring a fenced yard with varied foliage. A spacious deck equipped with a red umbrella is visible. A sunken fire pit is highlighted in the garden area, surrounded by trees and bordered by a quiet road.

Home in Craryville

4.92 out of 5 average rating, 119 reviews

The Gatehouse at Raspberry Ridge

Quiet, private house for a country get-away. Renovated 2 bedroom, 1 bath home can sleep up to 2 couples. Gated and fenced yard offers privacy and security for children or dogs. Enjoy a spacious deck and sunken fire pit for outdoor dining or lounging. Bedrooms and living space upstairs are bright, airy with cozy wood stove for cool evenings. Kitchen is well-stocked; has a dishwasher. Laundry facilities downstairs; entertainment room with large screen TV and pull out couch. WiFi available.

Guest favorite

A single-story wooden lodge with a green metal roof is set amidst a grassy area. The exterior is lined with windows, allowing natural light to fill the interior. Surrounding trees provide a backdrop, and a paved driveway leads to the entrance, enhancing accessibility.

Home in Pittsfield

4.87 out of 5 average rating, 292 reviews

Dancing Horse Lodge

Dancing Horse Lodge is located in the heart of the Berkshire Mountains in Pittsfield, MA, minutes from Tanglewood, Barrington Stage, Jacobs Pillow Ballet, Kripalu Yoga, Shakespeare and Co. and skiing at Bosquet and Jiminy Peak. It is a light and bright residence located on a 20-acre horse farm with nature views out of each window. It is surrounded by miles of woods, great for hiking and cross country skiing. Close to all amenities yet affords beautiful, quiet country living. Come and enjoy!

Top guest favorite

A charming outdoor seating area is situated under a spacious pergola, designed with warm lights. Comfortable seating is set on a stone patio, with a grill nearby, surrounded by a grassy yard. Soft clouds and a gentle twilight sky provide a serene backdrop.

Home in Lee

4.97 out of 5 average rating, 215 reviews

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Superhost

Lush, colorful flowers surround the entrance of the cottage, adding a vibrant touch to the exterior. A combination of greenery and blooms creates a welcoming atmosphere. The cottage features large windows, allowing for ample natural light and offering views of the blooming landscape.

Home in Lenox

4.93 out of 5 average rating, 232 reviews

Heart of Lenox Walk to Town Cozy Cottage!

The cottage is a 2-minute walk to Church St., right in the heart of Lenox. Kennedy Park (1.5 miles) is a short stroll away for great hiking & biking, while multiple 5-star restaurants are all within a few minute walk. Tanglewood (2 miles), Kripalu (3 miles), Shakespeare & Co. (1 mile), Berkshire Theatre Festival & the Norman Rockwell Museum (7 miles), Butternut, Jiminy Peak (15 miles) & Bousquet (5 miles) ski area, Mahaiwe Performing Arts Center & Jacob's Pillow (14 miles) are all close by!

Guest favorite

The living room features a wood stove, providing a focal point for warmth. A large sectional sofa is positioned for comfort, alongside a wooden rocking chair. Natural light filters through sheer curtains, illuminating the space, which is also equipped with air conditioning and a modern floor lamp.

Home in Lee

4.9 out of 5 average rating, 258 reviews

Cozy Berkshires Cottage

Stay in a cozy, newly remodeled Berkshires 1920's cottage! We've added bedrooms and a bathroom with a soaking tub upstairs, expanded the first floor bathroom and added a laundry room. The cottage is set back from the main road, easily accessible yet private. -Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. -Ideal for couples, adventurers, business travelers, and furry friends (pets). -Note: Stairs to the 2nd floor are steep: guests are responsible for child safety.

Top guest favorite

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

4.95 out of 5 average rating, 175 reviews

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!

Guest favorite

A wrap-around porch features a small table with two colorful chairs, overlooking a serene lake framed by lush trees and greenery. The view showcases calm water, complemented by distant hills under a clear blue sky.

Home in Canaan

4.91 out of 5 average rating, 165 reviews

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.

Guest favorite

A charming cottage is framed by large trees and lush greenery. Vibrant bushes with pink blossoms add color in the foreground. The cottage features a welcoming entrance, flanked by decorative lattice. Sunlight filters through the leaves, creating a serene outdoor atmosphere.

Home in Hudson

4.95 out of 5 average rating, 234 reviews

Main Street Cottage

We are located on U.S. Route 9. It is a well traveled, main road but close to everything! It is peaceful but not quiet. For nature lovers, explore the area with hikes on local trails or on a kayak down the river. We are 5miles from the Hudson River Skywalk, Olana and Thomas Cole. We are 3.9miles to Warren Street where you can enjoy a full day of shopping, spa and food. The Catskills has much to offer. The cottage is in the perfect area to enjoy it all year round!

Guest favorite

The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.

Home in Great Barrington

4.97 out of 5 average rating, 263 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.