Vacation rentals in Richmond

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Top-rated vacation rentals in Richmond

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
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
4.95 out of 5 average rating, 264 reviews

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!

Guest favorite
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
4.93 out of 5 average rating, 198 reviews

Berkshires/Ski/Pet FriendlyTanglewood/PrivateRanch

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!

Top guest favorite
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
5 out of 5 average rating, 199 reviews

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!

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 374 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Guest favorite
A view from a framed window reveals a cozy living space featuring a vintage wood-burning stove. A green sectional sofa provides seating, complemented by a light wood coffee table. Natural light fills the room, highlighting the open layout connecting to the kitchen area.
Cottage in Becket
4.91 out of 5 average rating, 132 reviews

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Top guest favorite
Home in Lee
4.99 out of 5 average rating, 306 reviews

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 relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Top guest favorite
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
4.99 out of 5 average rating, 303 reviews

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.

Guest favorite
Tiny home in New Marlborough
4.94 out of 5 average rating, 168 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Top guest favorite
A living area features a stone fireplace with a roaring fire, surrounded by large windows that invite natural light. A circular coffee table rests on a textured rug, while comfortable seating options include an upholstered chair and wooden accent chairs, complemented by soft lighting.
Cottage in Bennington
4.98 out of 5 average rating, 114 reviews

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

Superhost
Cabin in Stephentown
4.85 out of 5 average rating, 308 reviews

Rustic Cabin | Barrel Sauna | Private Pond

The Hemlock Hideaway is a freshly renovated, charming cabin tucked into 14 acres of quiet woodland in the Berkshire foothills, built for the kind of rest that's hard to find anywhere else. This is a genuine rustic escape: complete with antique furnishings, a wood-burning stove, mid-century stove, no television, and the sound of nature just outside your door.

Guest favorite
A circular stone entryway frames a winding path leading to a quaint cabin nestled among tall trees. Sunlight filters through the forest canopy, casting a gentle glow on the surrounding greenery.
Guesthouse in Lenox
4.94 out of 5 average rating, 117 reviews

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.

Top guest favorite
A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.
Home in Saugerties
4.98 out of 5 average rating, 188 reviews

The Stone House

The Stone House is a historic house built in 1811 beside the Kaaterskill Creek and surrounded by farmers fields and a beautiful Dutch barn. It's 2 hours from the city at the foot of the Catskill Mountains and a perfect base for exploring the Catskills and the Hudson Valley or for spending quiet weekend in the country.

Popular amenities for Richmond vacation rentals

When is the best time to visit Richmond?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Richmond?

    Richmond has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Richmond?

    Experience the best of Richmond with our house rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Richmond?

    Four-legged friends are welcome in Richmond. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Richmond?

    Yes! Work meets play with ease at over 20 vacation rentals in Richmond featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Richmond have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Richmond. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Richmond have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Richmond. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Richmond have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Richmond. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Richmond have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Richmond. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Richmond

  • Total vacation rentals

    Explore 30 vacation rentals in Richmond

  • Nightly prices starting at

    Richmond vacation rentals start at €52 per night before taxes and fees

  • Verified guest reviews

    Over 1,800 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Richmond vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Richmond rentals

  • 4.9 Average rating

    Richmond stays are highly rated by guests—averaging 4.9 out of 5!