Vacation Rentals By Owner In Richmond, MA

Evergreen Home Vacation Rentals invites you to this stylish 4-bedroom home, filled with cheeky pop art and comfortable spaces. Nearly every room offers stunning mountain views, and the private, heated saltwater pool (available May–Sept) is the perfect spot for groups.brbrExplore hiking trails right from your door or take a 5-minute drive to Richmond Pond. Just 7 minutes to Bousquet Mountain and 10 minutes to Tanglewood, this home blends artful design with a prime location. brbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrbrSituated on a private property with beautiful mountain views and close to many attractions in the Berkshires.brbrGuests will have private access to the entire home, and property.brbrThis stylish and remodeled ranch home is flooded with natural light and looks out onto mountain views from all positions in and outside the house. The modern kitchen is well equipped with brand new appliances and everything you could need for a meal at home. The kitchen opens up to the dining area that can seat 5 guests and additional bar seating is provided in the form of stools at the island. brbrThe comfortable living room and wood burning fire place provides plenty of space to kickback and relax. Sit by the fire with a book or enjoy a night in watching a movie on the large frame TV. The living room has a slider door that exits onto the back deck. brbrThe primary bedroom features a king sized bed, ensuite bathroom with zero entry shower, and access to the deck. Also on the first level is the second bedroom with a queen sized bed and the guest bathroom with a tub/shower combo. The third bedroom also serves as an office space with a twin trundle bed. The laundry closet is also in the third bedroom. The 3 bedrooms on the first floor have SleepEZ Latex Matresses.brbrDownstairs is a family room with plenty of comfortable seating and a second frame TV. A full kitchen is also on the lower level with access to the backyard. The bedroom on this level contains a queen bed and an ensuite 3/4 bathroom. brbrThe large and private property is really the main draw of this beautiful home. Experience the gorgeous mountain views while using the outdoor BBQ or enjoying dinner on the deck using the outdoor dining set. Or gather around the firepit for roasted marshmallows, conversation and good times after a long day exploring the Berkshires. The private, heated saltwater pool is available May- Sept. brbrVenture out your front door to explore the hiking trails nearby. There is a hike starting at the Richmond Fire Tower. Walk or drive and park at end of Osceola Rd and hike the unmaintained extension of road. Turn left ascending to fire tower at the top of Lenox Mountain. Great views of Richmond, Mt. Greylock. Further trails along the ridge to Yokun Ridge, Mahanna Cobble & Bousquet summit. Or hop in your car for a 5 minute drive to Richmond Pond;10 minutes to Tanglewood!brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbrbr⭐️ LOCATION: Situated on a private property with beautiful mountain views, and close to many popular Berkshires attractions.brbr⭐️ PETS: Small dogs allowed with prior owner approval. No dogs under 2 years old, no multiples. A $100 pet fee applies if approved.brbr⭐️ PARKING: Free on-site parking available.brbr⭐️ POOL: Open seasonally May through October, with exact dates determined by weather.br• June 1–Labor Day: Heated to 82°F at no additional cost. Guests may request a higher temperature for an extra fee—please contact us in advance.br• May & after Labor Day: Pool heating may be available for $150/day, but not guaranteed. Advance notice required.br• Pool heating above 82°F during June 1–Labor Day is available for an additional fee—please confirm prior to arrival.brbr⭐️ ANIMALS: Four horses reside on the property. Please do not feed or touch them.brbr⭐️ SECURITY: Exterior security cameras are installed at the front entrance.brbr⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, allowing you to relax and enjoy your stay with peace of mind. If any damage occurs, please notify us so we can arrange timely replacements for the next guest.

Escape to The Berkshires w/Pool by Evergreen Home

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$440.31

Evergreen Home Vacation Rentals invites you to this charming 3-bedroom, 2-bath ranch, perfect for comfortable one-level living. Relax in the sun-filled porch or unwind in the private hot tub. The spacious basement offers a large living area ideal for group gatherings.brbrLocated in a quiet neighborhood, you can walk to Bartlett’s and reach Richmond Pond or Tanglewood in minutes. Just 6 minutes to Bousquet and 13 minutes to Lenox, this decorated retreat blends comfort with convenience. brbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrThis home is ideally located just a short stroll from Bartlett's Orchard, nestled off the main road in a peaceful, private neighborhood. brbrGuests will be given a lockbox code to enter through the front door.brbrUpon entering, you'll be greeted by an open, fully stocked kitchen, perfect for all your culinary needs. The spacious kitchen island, complete with a wine fridge, invites you to relax and entertain. brThe kitchen flows into the cozy living room, featuring a smart TV and a mini-split AC for comfort. Step out onto the sun-drenched porch, a perfect spot to unwind with a book or simply enjoy the tranquility. brAll three bedrooms are conveniently located on the main level, with a full bath. Two bedrooms offer queen-sized beds, while the third features two twin beds, each with its own mini-split AC for personalized comfort.brbrThe basement level is an entertainer's dream, featuring a cozy sectional ideal for TV and game nights, and a stylish bar for your favorite drinks. It also includes a full bathroom and a dedicated workspace if you need to work on your trip. Step through the back door to access the private hot tub, offering a serene escape for ultimate relaxation and privacy.brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbr⭐️ LOCATION: This home is just a short stroll from Bartlett's Orchard, tucked away off the main road in a peaceful, private neighborhood. Richmond Town Beach is only 6 minutes away, Downtown Lenox just 13 minutes, and Great Barrington’s cultural attractions are only 25 minutes from your door.brbr⭐️ PETS: No pets permitted.brbr⭐️ PARKING: Private driveway with space for 3 cars.brbr⭐️ SURVEILLANCE: Security camera above the garage monitors the driveway.brbr⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, so you can relax and enjoy your stay. If any damage occurs, please let us know so we can arrange timely replacements for the next guest.

Richmond Ranch w/ Hot Tub by Evergreen Home

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(8)

$1492.7

Morning Face is a meticulously restored Italian villa with privacy and mature gardens. Set on 20 acres, the beautifully landscaped grounds feature sweeping lawns, woodland gardens, wisteria clad pergola, covered porch, heated pool (in season) and a formal terrace with fountain. The comfortable grand rooms are tastefully decorated. brbrMorning Face includes 4 bedroom suites in addition to the library, living room, fireplaced den, additional den with twin daybed, dining room, breakfast room, custom kitchen and upstairs office with twin daybed.brbrWe are unable to accommodate events.

Morning Face - Berkshire estate with heated pool, views and privacy.

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(12)

$409.54

Dublinshire Farm is a giant shaker barn that has three private apartments. This newest listing, #3, is a charming 2 story, with soaring ceilings, great kitchen, vast romantic primary king bedroom, Loft den with large flat screen and queen sofa bed, loft bonus bedroom with double bed. Large kitchen and wonderful outside space with deck, BBQ, hammock, fire pit, the works! All charming and comfy. Very private and convenient to all Berkshire attractions. NOTE: Bonus bedroom with double bed is accessed by climbing under a beam, so this is not for someone with mobility issues! Also, there are quite a few stairs, so again, not best for anyone who can't get around easily. No wheelchair access to the upstairs. Den is also a loft room with a giant flat screen and queen sofa bed. All beds have new high quality mattresses. There is a twin bed in an alcove of the giant primary bedroom, in case you have a child you want to keep close by. Shared laundry. This is a truly special place, a great romantic country getaway. brPet friendly! A $25 per pet per day fee will be charged. br10 min to West Stockbridge, 12 min to Tanglewood, 10 min to Bousquet ski area, 3 min from Balderdash vineyard, 5 min to Richmond Pond for swimming! Access to many hiking trails nearby. brAlso available to rent the entire barn for larger groups: Apt 1 and 2 are 1 bed/1 ba each. See listings 3260523 and 3161143 to view the other apartments.

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$580.36

Escape to this 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 sun porch, curl up by the wood burning stove, or enjoy a soak in the jacuzzi tub.brbrCentrally located in the Berkshires:brbr- 10 minutes to Tanglewood/Lenoxbr- 7 minutes from West Stockbridge/ I-90br- 20 minutes to Great Barrington, Stockbridge & PittsfieldbrbrWhether grilling on the back deck, sitting down around the large dining table for a family meal, or hosting game night - there is something for everyone at Hideaway Hollow!brbrThe kitchen is well-appointed and you should have everything you need to create a delicious meal including olive oil and spices.brbrMattresses are all new and offer luxury Brooklinen sheets and a variety of pillow options.brbrNo need to log into your streaming accounts, we provide Netflix, Max and Hulu.brbr600 Mbps internet speeds and office space.brbrThe house has central heating and air conditioning, and offers a delicious cross-breeze on cool summer nights.brbrWood burning stove keeps you cozy in winter, or head outside and roast marshmallows around the fire pit. Wood provided.brbrThrow a playlist on the central audio system and enjoy!brbrMaster: 1 King Bedbr2nd Bed: 1 Queen Bedbr3rd Bed: 1 Queen Bedbr4th Bed: 1 Twin XLbrMaster Bath: Large shower, double vanity, and jacuzzi tubbr2nd Bath: Shower, storage space for toiletriesbrGuest accessbrbrWasher and Dryer are located in the basement and available for guest use.brbrPET INFORMATIONbrbr- We allow up to 3 dogs. Sorry, no cats.brbr- We have dog beds, bowls, and crates available for usebrbr- Dog run is fully fenced and ~1 acrebrbrPlease pick up after your pet and monitor your pet at all times!

Pet Friendly Oasis on 5 Private Acres, 10 min to Tanglewood

Richmond, Massachusetts, United States

Bed

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Sleeps

Exceptional(18)

$303.17

This ranch home is in the heart of The Berkshires of Western Massachusetts, in the small town of Richmond. (West Stockbridge, Pittsfield and Lenox are the surrounding towns). The large private deck in the back of the house allows for outdoor dining, sunbathing or just enjoying the wildlife in the yard.brbrThe house itself is calming and well furnished with a large well-equipped kitchen. There is a spacious yard surrounding the house. Two bedrooms (one queen bed and one twin bed) and two full bathrooms allow for up to 3 people to stay here comfortably. brbrAir conditioner window units are available in summer/fall months and ceiling fans are in most of the rooms. There are two different indoor porches on either side of the house to dine or relax in. There is an outdoor area for a fire and plenty of firewood. Richmond Pond is just a few miles away.brbrThere is an apple orchard just across the street, and local attractions a 10 minute drive away like Tanglewood, Kripalu, Shakespeare & Company and the Norman Rockwell Museum. brbrThere are two TV’s in the home (one in the living room with cable access and one in the bedroom that has a queen bed) and there is Unlimited WiFi. brbrAt least 3 cars can fit in the private driveway. Pets are not allowed (exceptions can be made on a case by case basis.) This home has one small non-shedding dog living in it at times, so if you have allergies, please be aware of that. brbrThere is access to laundry in the house in the basement. Check in time and check out time is 12pm noon, however an earlier check-in is available if needed as well as a late check-out.brbrIf you want to visit a city for the day during your stay Albany, NY is just a 1-hour drive away from this house. If you are flying: the nearest airports are Bradley Airport (BDL) in CT, Albany Airport (ALB) in New York and Boston Logan Airport (BOS) in Boston, MA.brbrPlease contact me if you have any special requests to make your stay more comfortable. This is a smoke free home, but if you want to smoke anything- you may smoke outside on the deck.

Lovely ranch home getaway in The Berkshires- just 6 miles to Tanglewood

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(23)

$237.69

Berkshire living at its best! This lovely shaker barn on 2 open acres has three apartments. All are private. Rent one or more for your group! This apartment (#2) is a one bedroom/one en suite bath with full equipped kitchen, dining area, comfortable living room with sofa bed, bedroom with new queen bed and desk. Large walk in closet and dresser. Quiet with lots of light. Shared entry hall and laundry, but unit is completely private, charming and comfortable. Private outdoor area with seating, fire pit and barbecue (summer only). Around the corner from Hancock Shaker Village where this barn was moved from 100 years ago. Minutes from Balderdash Cellars winery, and Hilltop Orchards. Use of Richmond Pond, a clear lake with a lovely beach only 8 minutes away for swimming, boating or skating. Ski at Bousquet (9 minutes) or Jiminey Peak (21 minutes) or take a picnic to Tanglewood in Lenox (13 min). Close to all Berkshire attractions-- theaters, dance, museums, restaurants, shopping, farmers markets and the great outdoors! 10 minutes to the charming village of West Stockbridge. Lots of nearby trails for hiking, snow shoeing, X-country sking. A stunning part of the Berkshires, Richmond is home to celebrities and farmers. It is a magical place. 3 night minimum stay, longer term rates available. Check out our second one bedroom apartment in the barn at VRBO, unit 3260523.

Private apartment in beautiful country barn

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$423.06

Welcome to Cheeverhollowfarm in picturesque Richmond/Lenox. Please Contact me for specific details or requests. We are just 2 miles from the Main gate at Tanglewood and 2 more to the center of Historic Lenox. Central to all the Berkshires attractions natural and cultural. Cheever Hollow Farm is Set on 24 open and forested acres with expansive, gardened , wooded areas for peace fun, entertaining and walking trails. The home offers large open spaces and tranquil places that invite you in. Whether in the cathedral cielinged living room , the heavenly cuppula or in one of the many outdoor areas, you will find your space to relax, explore, play and more. A wonderful cooks kitchen and BBQ area let you indulge your favorite foods. Central to many attractions, music, restaurants, cultural and outdoor activities yet wonderfully peaceful, you will love it. I can manage most special requests ...here at Cheeverhollowfarm. come ask me . enjoy ... the hollow. Thank you for looking.

Cheever Hollow Farm an essential retreat central to Lenox and the Berkshires

Richmond, Massachusetts, United States

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Bath

Sleeps

$471.52

Consider this house your home away from home while you visit the Berkshires. Excellent location! minutes from Tanglewood, Kripalu, West Stocckbridge and downtown Lenox. Private trail access from the property. This lovely property boasts 4 bedrooms, including 1 king bed, 3 queen beds, and 1 twin bed. With 3 bathrooms featuring a bathtub and hair dryer, guests will feel right at home. Enjoy the excellent heating and AC during your stay. We think our place will help you experience the best the Berkshires has to offer.

Classic New England 4-bedroom house with Yukon Ridge trail access

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(15)

$836.46

Located near Lenox, Stockbridge, and Lee, this private and peaceful country house with modern amenities offers a relaxing haven in a prime location to enjoy the Berkshires! You are minutes away from music at Tanglewood, plays at Shakespeare & Co., art at Norman Rockwell Museum, and much more. When staying on the property, enjoy the many spaces to socialize or relax inside or outside the house while gazing at 3.8 acres of country landscape.brbr**The Space**brThe house offers 5 bedrooms, 2 full bathrooms, 1 half bath, 3 living spaces, a kitchen and a dining room. The open plan kitchen is fully stocked and organized to whip up an amazing meal while keeping the conversation going. The dining room has a large 10-person dining table. The bedrooms are located on either side of the common areas offering tranquil spaces to relax, work, or sleep. The entertainment room offers a 65” flatscreen TV to stream your favorite media. The house offers heating and air conditioning with the ability to control the temperature independently across 4 separate zones.brbrOn the grounds of the property, you’ll find a covered outdoor living room, an outdoor dining area, a grill, a fire pit, a deck with deck chairs, and a massive lawn with a picnic table and a seasonal stream.brbr**Guest access**brYou will have access to the entire house and the grounds. Upon arrival, you can self-check-in using a keypad.

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$433.85

Built in the 1770s | Writer’s Workspace | Wooded Setting | 8 Mi to Stockbridge BowlbrbrBreathe in the fresh air and let creativity flow at this 4-bedroom, 2.5-bathroom Richmond vacation rental home — an inviting haven for solo wellness retreats, romantic escapes, or group getaways. Stroll nature trails that begin at your doorstep, then unwind on the patio for al fresco evenings paired with a glass of local wine. Here, history and tranquility meet, offering a balance of adventure and rest.brbr-- THE PROPERTY --brbrC0548092490brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Bedroom 4: 1 full bedbr- Additional Sleeping: 1 portable cribbrbrOUTDOOR LIVINGbr- Large yard w/ fencingbr- Screened porch w/ furnishings & bistro lightsbr- Deck w/ gas grillbr- Patio w/ dining set & large Connect 4 gamebrbrINDOOR LIVINGbr- Smart TV, board gamesbr- 2 dining tablesbr- Library w/ booksbr- Record player/stereo w/ vinyl collectionbr- Acoustic guitarbr- Workspace w/ desk & monitor, Playstationbr- Fireplaces & wood-burning stove (decorative only)brbrKITCHEN br- Stove/oven, refrigerator, dishwasherbr- Microwave, toaster, blender, slow cookerbr- Nespresso coffee maker (coffee pods provided)br- French press (bring your own coffee)br- Ice maker, cooking basics, spicesbr- Dishware/flatwarebr- Trash bags & paper towelsbr- High chairbrbrGENERAL br- Free WiFibr- Washer & dryer (detergent provided)br- Central A/C & heatingbr- Linens/towels, complimentary toiletriesbr- Iron/board, hair dryerbrbrFAQ br- Pet fee (paid pre-trip)br- Quiet hours (after 8:00 PM)brbrACCESSIBILITYbr- 2-story home, 3 steps to enterbr- All bedrooms & full bathrooms on 2nd floorbrbrPARKINGbr- Driveway (3 vehicles)brbr-- THE LOCATION --brbr- Classic Berkshires retreat near hiking, lakes & legendary art venuesbr- 3 miles to Hancock Shaker Villagebr- 5 miles to Richmond Pondbr- 7 miles to Tanglewoodbr- 8 miles to Norman Rockwell Museum & Lenoxbr- 8-9 miles to Stockbridge's downtown area: shops & diningbr- 29 miles to Hudson Amtrakbr- 44 miles to Albany Int'l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking of any kindbr- Pet friendly w/ $50 fee (+ fees & taxes, 1 max)br- No events, parties, or large gatheringsbr- Must be at least 18 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- Please observe quiet hours after 8:00 PMbrbrADDITIONAL INFORMATIONbr- This 2-story home requires 3 steps to enter; all bedrooms and full bathrooms are located on the 2nd floorbr- The fireplaces and wood-burning stove are decorative only and not for guest use

1 Mi to Vineyard: Serene Berkshires Country Escape

Richmond, Massachusetts, United States

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Bath

Sleeps

Most popular vacation rentals in Richmond

$237.69

Private apartment in beautiful country barn

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$395.35

Cottage

Designer Berkshire Cottage

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$409.54

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$433.85

1 Mi to Vineyard: Serene Berkshires Country Escape

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$440.31

Richmond Ranch w/ Hot Tub by Evergreen Home

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$803.78

Escape to The Berkshires w/Pool by Evergreen Home

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$836.46

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$1492.70

Morning Face - Berkshire estate with heated pool, views and privacy.

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$303.17

Lovely ranch home getaway in The Berkshires- just 6 miles to Tanglewood

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$580.36