Vacation rentals in Richmond

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Top-rated vacation rentals in Richmond

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Guest favorite

Home in Canaan

5.0 out of 5 average rating, 133 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

Mar 25 – Apr 1

€ 147 per night

Guest favorite

Home in Lee

4.9 out of 5 average rating, 202 reviews

1817 Berkshire Farmhouse- Close to Everything.

*Close to ski resorts & tubing! We are nestled at the foot of October Mountain State Forest, yet close to the centers of Lee, Lenox, & Pittsfield. Our charming house was built in 1817- original wood beams, wood floors, and quite a history. Whether you enjoy skiing, exploring local restaurants & downtowns, venturing outdoors or experiencing the local art scene, the Berkshires has something for everyone. Our little farmhouse serves as the perfect "home base" for all of your Berkshire adventures.

Apr 24 – May 1

€ 184 per night

Guest favorite

Guest suite in Richmond

4.92 out of 5 average rating, 170 reviews

Ski/Private Ranch/Kid friendly/Pet Friendly/Horses

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!

Apr 24 – May 1

€ 220 per night

Guest favorite

Farm stay in New Lebanon

4.95 out of 5 average rating, 184 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!

May 28 – Jun 4

€ 215 per night

Superhost

Home in Dalton

4.88 out of 5 average rating, 113 reviews

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

Dec 1 – 8

€ 135 per night

Guest favorite

Guest suite in Hancock

4.83 out of 5 average rating, 154 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Dec 3 – 10

€ 92 per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 276 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Sep 5 – 12

€ 158 per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 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 take a walk on our hiking trail.

Jul 19 – 26

€ 164 per night

Guest favorite

Guesthouse in Stockbridge

4.96 out of 5 average rating, 175 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a brand new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Apr 23 – 30

€ 174 per night

Superhost

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Get a small rustic-modern cabin feel in this cozy and self-sufficient space. 10 minutes from Chatham, 15-20 minutes from Great Barrington, Lee, Lenox, Kripalu Center for Yoga & Health, Catamount Ski Resort, TangleWood Institute and seconds away from a beautiful hike up Harvey Mountain in Austerlitz, NY. The wood-stove will keep you warm in the winter months and the large field and creek in the backyard will relax you in the summer.

Dec 23 – 30

€ 85 per night

Guest favorite

Apartment in Lenox

4.88 out of 5 average rating, 169 reviews

Station House 1E Private Room & Bath

Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.

Jun 17 – 24

€ 82 per night

Guest favorite

Cottage in West Stockbridge

4.98 out of 5 average rating, 106 reviews

Historic 1810 Farmhouse - Fully Renovated

Charm and history meet modern convenience in this stunning renovated farmhouse. Built in 1810, this beautiful home was once the residence of Mr. Prince, who presided over the Tobey Quarry Farm. Just steps into town, the cottage is the ideal retreat for a low-key, cozy getaway. Or as a launch pad to the area's many outdoor/cultural offerings. We warmly welcome you!

Jun 3 – 10

€ 234 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Richmond vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Richmond's top sights

Mass Audubon's Pleasant Valley Wildlife Sanctuary41 locals recommend

Olivia's Overlook51 locals recommend

Bartlett's Orchard27 locals recommend

Parsons Marsh Reserve8 locals recommend

Boston University Tanglewood Institute5 locals recommend

Hollow Fields4 locals recommend

Other great vacation rentals in Richmond

Guest favorite

Home in Canaan

4.9 out of 5 average rating, 150 reviews

Berkshire Lakefront House with Amazing Views

Dec 16 – 23

€ 299 per night

Superhost

Apartment in Lee

4.78 out of 5 average rating, 106 reviews

Cozy Berkshire Cottage Style Apartment

Jun 6 – 13

€ 120 per night

Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 83 reviews

Mountain View Getaway

Aug 27 – Sep 3

€ 111 per night

Guest favorite

Apartment in Pittsfield

4.92 out of 5 average rating, 25 reviews

Comfortable Pittsfield Loft

Nov 7 – 14

€ 87 per night

Superhost

Home in Richmond

4.91 out of 5 average rating, 11 reviews

Berkshire Beauty-Full Home

Jan 4 – 11

€ 361 per night

Guest favorite

Home in Richmond

5.0 out of 5 average rating, 49 reviews

MAGIC FARMHOUSE Berkshire Retreat VIEWS! 3bd/2.5ba

Mar 10 – 17

€ 306 per night

Guest favorite

Home in Richmond

4.96 out of 5 average rating, 23 reviews

Escape to The Berkshires w/Pool by Evergreen Home

May 13 – 20

€ 714 per night

Guest favorite

Guesthouse in Pittsfield

4.98 out of 5 average rating, 47 reviews

The Nest at Birdland

Oct 11 – 18

€ 179 per night

Show all

Quick stats about vacation rentals in Richmond

Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
€ 66 before taxes and fees

Frequently Asked Questions

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.
How much does it cost to stay in house rentals in Richmond?
Experience the best of Richmond with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Richmond?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.
Are there family-friendly vacation rentals in Richmond?
Richmond has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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.

Vacation rentals in Richmond

Top-rated vacation rentals in Richmond

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Richmond vacation rentals

Stay near Richmond's top sights

Other great vacation rentals in Richmond

Home in Canaan

Apartment in Lee

Apartment in Canaan

Apartment in Pittsfield

Home in Richmond

Home in Richmond

Home in Richmond

Guesthouse in Pittsfield

Quick stats about vacation rentals in Richmond

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Richmond have free parking?

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

What are the most popular amenities for House Rentals in Richmond?

Do house rentals in Richmond have wifi?

Are there family-friendly vacation rentals in Richmond?

Are there vacation rentals with a dedicated workspace in Richmond?

Do house rentals in Richmond have air conditioning?

Do house rentals in Richmond have a kitchen?

Destinations to explore