
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.

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!

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!

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!

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!

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,!

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.

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.

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.

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).

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.

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.

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
Other great vacation rentals in Richmond

Catskills Cabin on 100 Wooded Acres, Private Lake

"Hemlock Shadow" near Tanglewood on Six Acres

Marie’s Place unit 3

Berkshires! Walk to LAKE, kayaks, dog friendly.

Secluded Mountain and Lake View in Canaan, NY

1800s Carriage house in Berkshires / Hudson Valley

The Kellogg House in the Heart of The Berkshires

The Greylock Cabin
When is the best time to visit Richmond?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €280 | €257 | €221 | €172 | €181 | €228 | €291 | €289 | €250 | €258 | €257 | €270 |
| Avg. temp | -4°C | -3°C | 2°C | 9°C | 15°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | -1°C |
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!
Destinations to explore
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- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Jiminy Peak Mountain Resort
- Windham Mountain
- Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Taconic State Park
- Hunter Mountain Resort
- Mohawk Mountain Ski Area
- Kent Falls State Park
- Bousquet Mountain Ski Area
- June Farms
- Ski Sundown
- Millbrook Vineyards & Winery
- Naumkeag
- Poets' Walk Park
- Hudson Chatham Winery
- Norman Rockwell Museum
- Opus 40





