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Family-friendly vacation rentals in Richmond

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Richmond

  • Total vacation rentals

    Explore 30 vacation rentals in Richmond

  • Nightly prices starting at

    Richmond vacation rentals start at G$20,920 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,250 verified reviews to help you choose

  • 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!

Top-rated family-friendly rentals in Richmond

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
Cabin in Chatham

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

FamilyIndoor spacesSkiing

4.92 out of 5 average rating, 145 reviews
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

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!

Indoor spacesFamilyAccess

4.95 out of 5 average rating, 275 reviews
Top guest favorite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

KitchenFamilyAccuracy

4.97 out of 5 average rating, 107 reviews
Top guest favorite
The charming exterior of a renovated farmhouse features a spacious front porch with a red bench and hanging flower baskets. Large windows allow natural light to fill the entryway, while lush green grass and trees frame the property.
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!

FamilyKitchenHospitality

4.99 out of 5 average rating, 119 reviews
Guest favorite
Cabin in Stockbridge

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood walls & fantastic interior design. Unwind in the reading nook, relax in the en suite bedroom with skylight, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9 minute walk or 2 minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood minutes away.

KitchenFamilyDecor

4.89 out of 5 average rating, 254 reviews
Top 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

Berkshires/Pet Friendly/Tanglewood/Private Ranch

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 Rides /Horse activities available by appt!

FamilyKitchenCheckout

4.94 out of 5 average rating, 207 reviews
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

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.

KitchenIndoor spacesSleep quality

4.91 out of 5 average rating, 187 reviews
Guest favorite
A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.
Guesthouse in Great Barrington

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

FamilyIndoor spacesParking

4.95 out of 5 average rating, 174 reviews
Top guest favorite
Home in Lee

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.

Indoor spacesKitchenLocation

4.99 out of 5 average rating, 318 reviews
Top guest favorite
A serene view features a private in-ground pool surrounded by lounge chairs, each shaded by black umbrellas. Lush green trees border the backyard, and a red house is visible in the background, completing the outdoor vacation atmosphere.
Home in Canaan

Berkshire Lake House, gunite pool, Chef's Kitchen

This newly updated Berkshire lake house with private in-ground pool, is the perfect place for a year-round vacation. Nestled within a small lakefront community where being on the lake is a pass-time in winter, spring, summer or fall. 5 light-filled bedrooms can accommodate a family retreat or 3 families. Enjoy the pool table, chefs kitchen, two living room areas, and wood burning fireplace inside and fire pit outside. All bedrooms and common areas have air conditioning.

KitchenFamilySkiing

4.99 out of 5 average rating, 101 reviews
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

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.

Indoor spacesFamilySleep quality

4.99 out of 5 average rating, 332 reviews
Guest favorite
An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.
Barn in East Chatham

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. A private outdoor sauna will be ready for all stays beginning October 1, 2026. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

KitchenIndoor spacesValue

4.96 out of 5 average rating, 112 reviews

Popular amenities for Richmond family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.
Home in Pittsfield

Hidden Oasis in the Mountains by Evergreen Home

FamilyIndoor spacesGrill

4.97 out of 5 average rating, 156 reviews
Top guest favorite
The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.
Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

KitchenIndoor spacesCleanliness

4.98 out of 5 average rating, 134 reviews
Top 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 Monterey

Jaw dropping mountain & lake views

FamilyIndoor spacesAccess

4.96 out of 5 average rating, 309 reviews
Top guest favorite
A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.
Tiny home in Chatham

Boutique TINY home+private HOT TUB-walk to Main St

FamilyIndoor spacesCheck-in

4.99 out of 5 average rating, 377 reviews
Top guest favorite
A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.
Cottage in Great Barrington

Artist Cottage

Indoor spacesKitchenBiking

4.93 out of 5 average rating, 352 reviews
Top guest favorite
Home in Athens

Lake House close to Skiing & Indoor Hot Tub

KitchenIndoor spacesCleanliness

4.96 out of 5 average rating, 112 reviews
Superhost
Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

Indoor spacesKitchenComfort

4.91 out of 5 average rating, 149 reviews
Guest favorite
Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

FamilyKitchenGrill

4.94 out of 5 average rating, 134 reviews

Family- and pet-friendly home rentals

Top guest favorite
Home in Lenox

Restored 1881 Farm House

Indoor spacesKitchenGetting around

4.96 out of 5 average rating, 113 reviews
Guest favorite
A two-story lodge is nestled among tall trees, with a babbling brook flowing in the foreground. The exterior is a rich brown wood, complemented by green foliage and rocks near the water. A small balcony is visible on the second floor, enhancing the picturesque setting.
Cottage in Austerlitz

Harvey Mountain Lodge by State Forest

FamilyIndoor spacesRiver

4.93 out of 5 average rating, 128 reviews
Top guest favorite
The rustic cabin is framed by lush greenery, with a welcoming front porch featuring wooden steps leading up to the entrance. Tall trees and landscaped shrubs create a serene setting. A stone chimney adds a touch of charm to the inviting exterior.
Cabin in Canaan

Newly Renovated Cabin in the Country

Indoor spacesKitchenLong stay

4.96 out of 5 average rating, 194 reviews
Top guest favorite
A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.
Home in Lee

Stylish Mid-century Modern Berkshires Cape

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 141 reviews
Guest favorite
The bedroom features a spacious bed with a light grey coverlet, accentuated by decorative pillows. Natural light filters through two windows adorned with bamboo shades. A light-colored dresser and a cozy armchair add functionality, complemented by a soft area rug on the hardwood floor.
Apartment in Lenox

Lovely Downtown Lenox apt, walk to everything!

FamilyIndoor spacesCheckout

4.95 out of 5 average rating, 152 reviews
Top guest favorite
A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.
Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

KitchenFamilyHeating

4.95 out of 5 average rating, 320 reviews
Guest favorite
An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.
Home in Stockbridge

Bright Stockbridge country home, near everything!

Indoor spacesFamilySkiing

4.95 out of 5 average rating, 188 reviews
Guest favorite
The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.
Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

KitchenFamilyAccuracy

4.93 out of 5 average rating, 108 reviews

Family-friendly home rentals with a pool

Top guest favorite
A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.
Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

Indoor spacesFamilyAmenities

4.95 out of 5 average rating, 170 reviews
Top guest favorite
A spacious white cottage is set against a vibrant green lawn, framed by blooming white flowers. Expansive trees surround the property, overlooking rolling hills that stretch towards a tranquil river in the distance under a clear blue sky.
Home in Coxsackie

Hudson River estate guest cottage

FamilyKitchenNearby

4.98 out of 5 average rating, 108 reviews
Guest favorite
A comfortable living room features a large sectional sofa and a wooden coffee table. A reclining chair is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through glass doors, which open to the outdoor area. Soft colors and warm tones create a cozy ambiance.
Home in Lee

Berkshire Vacation Home in Lee

KitchenIndoor spacesGrill

4.93 out of 5 average rating, 105 reviews
Guest favorite
A snow-covered entrance showcases a wooden sign featuring 'SMITH UNITS 1061 - 1064.' The residential building, adorned with white siding, includes a window unit air conditioner protruding from the wall. Surrounding shrubs are blanketed with fresh snow.
Townhouse in Hancock

Beautiful Jiminy Peak Townhome Family Friendly

FamilyIndoor spacesHospitality

4.83 out of 5 average rating, 109 reviews
Superhost
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

Hudson getaway w/ hot tub+ plunge pool on 20 acres

Indoor spacesFamilyPool

4.94 out of 5 average rating, 196 reviews
Top guest favorite
The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.
Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

FamilyKitchenParks

4.98 out of 5 average rating, 176 reviews
Guest favorite
Home in Hudson

Hudson River Sunset Getaway

FamilyKitchenTV

4.92 out of 5 average rating, 111 reviews
Superhost
Home in Becket

Berkshires Lodge | Pool, Hot Tub & Fire Pit

FamilyIndoor spacesLocation

4.87 out of 5 average rating, 116 reviews

When is the best time to visit Richmond?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$69,456 GYDG$62,343 GYDG$53,765 GYDG$64,226 GYDG$61,715 GYDG$78,033 GYDG$95,188 GYDG$79,288 GYDG$71,548 GYDG$69,456 GYDG$63,180 GYDG$73,431 GYD
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C

Destinations to explore