Your Dream Vacation Starts Here
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Your Dream Vacation Starts Here

Evergreen Home Vacation Rentals is a locally owned and operated concierge vacation rental management company.
We represent over 40 curated properties in the beautiful Berkshires of Massachusetts and Columbia County, New York.

Evergreen Home Vacation Rentals is a locally owned and operated concierge vacation rental management company. We represent over 40 curated properties in the beautiful Berkshires of Massachusetts and Columbia County, New York.

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5 Star Reviews
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5 Star Reviews

Choose Your Adventure

Ski Rentals in the Berkshires

SKI

Lake Rentals in the Berkshires

LAKE

Countryside Rentals in the Berkshires

COUNTRY

Choose Your Adventure

Ski Rentals in the Berkshires

SKI

Lake Rentals in the Berkshires

LAKE

Countryside Rentals in the Berkshires

COUNTRY

Rentals with a Pool in the Berkshires

POOL

Rentals with Views in the Berkshires

VIEWS

Rentals with a Hot Tub in the Berkshires

HOT TUB

Rentals for Events in the Berkshires

EVENT FRIENDLY

Rentals with a Fireplace in the Berkshires

FIREPLACE

Family Friendly Rentals in the Berkshires

FAMILY FRIENDLY

Rentals with a Sauna in the Berkshires

SAUNA

Pet Friendly Rentals in the Berkshires

PET FRIENDLY

Long Term Rentals in the Berkshires

LONGTERM FRIENDLY

Curated Interiors,
Thoughtfully Outfitted

Our passion is working with people to create beautiful spaces to be enjoyed for years to come, or a quick getaway.
Every one of our properties has been thoughtfully curated, attentively maintained, and thoughtfully stocked to ensure your ideal experience. We believe that you should “Love Where You Live” whether it’s for a weekend, a month or a lifetime. Welcome to your Evergreen Home!

Curated Interiors, Thoughtfully Outfitted

Our passion is working with people to create beautiful spaces to be enjoyed for years to come, or a quick getaway. Every one of our properties has been thoughtfully curated, attentively maintained, and thoughtfully stocked to ensure your ideal experience. We believe that you should “Love Where You Live” whether it’s for a weekend, a month or a lifetime. Welcome to your Evergreen Home!

Featured Properties

Idyllic Retreat with Hot Tub/Sauna

Hot Tub, Dry Sauna, Full Gym, 7 Minutes to Downtown Great Barrington
3 Bedroom ∙ 4 Beds ∙ 3 Bathrooms ∙ 8 Guests

Mountain Blossom Retreat

Heated Pool, Hot Tub, Full Gym, Mountain Views, 60 Private Acres
3 Bedroom ∙ 4 Beds ∙ 3.5 Bathrooms ∙ 8 Guests

Guest Reviews

Follow Us on Instagram

@evergreenberkshires

JUST SOLD...A magical full-circle moment for Evergreen Home. Our buyer clients had a clear vision for their ideal home, and after a rigorous search, they initially found a place they loved outside the Berkshires. We kept in touch over time, knowing their dream was still in the Berkshires. When the perfect property finally hit the market, we knew it well, having occasionally managed it as a vacation rental. With offers already on the table, the buyers drove two hours that day, viewed the home, and made a winning offer. Their long-searched-for Berkshire dream home was finally theirs...a wonderful ending for everyone.
JUST SOLD...this great house on over 20 acres in Hinsdale found a new family to call it home. Just 4 months from saying they were thinking of moving to the closing date, this all happened fast but they just knew it was right. As always a pleasure to work with @maggiebarrygavin and @homesweetberkshires
New Rental Listing, A Renovated Country Retreat in Old Chatham, NY. 🍁 Discover serenity nestled on 11 private acres, just 10 minutes from the charming village of Old Chatham. With 3 spacious bedrooms and 3.5 baths, there’s plenty of room for family and friends. Additional sleeping options ensure everyone has a comfortable place to rest. Delight in picturesque pond views, host a game night in the cozy basement family room complete with a foosball table, and gather around the fire to roast s’mores under the twinkling stars. Book direct and save: www.evergreenhomevacationrentals.com 🌿
A true testament to patience and trusting that what’s meant to be will happen. My buyers came to me two years ago with a clear vision, and despite viewing numerous properties, their dream never wavered. When we finally saw the one, it was instantly clear, and even more special when they realized their friends shared the same vision. This property and location exceeded their expectations, offering endless possibilities. It couldn’t have been a more perfect fit! A huge thank you to John Burns at @barnbrookrealty for trusting me to represent both your clients and mine to make this dream a reality, and to @suzannward for ensuring a smooth transaction. We couldn’t be happier for this wonderful group of friends who will now live happily ever after!
🍂 There’s something truly magical about fall in the Berkshires. The vibrant foliage, crisp air, and cozy vibes make this season one of our absolute favorites! 🍁 Whether it’s hiking through the brilliant colors, exploring local farms, or simply enjoying the peaceful charm of the countryside, we are constantly reminded of how lucky we are to call this place home. 🧡

Follow Us on Instagram

@evergreenberkshires

JUST SOLD...A magical full-circle moment for Evergreen Home. Our buyer clients had a clear vision for their ideal home, and after a rigorous search, they initially found a place they loved outside the Berkshires. We kept in touch over time, knowing their dream was still in the Berkshires. When the perfect property finally hit the market, we knew it well, having occasionally managed it as a vacation rental. With offers already on the table, the buyers drove two hours that day, viewed the home, and made a winning offer. Their long-searched-for Berkshire dream home was finally theirs...a wonderful ending for everyone.
JUST SOLD...this great house on over 20 acres in Hinsdale found a new family to call it home. Just 4 months from saying they were thinking of moving to the closing date, this all happened fast but they just knew it was right. As always a pleasure to work with @maggiebarrygavin and @homesweetberkshires
New Rental Listing, A Renovated Country Retreat in Old Chatham, NY. 🍁 Discover serenity nestled on 11 private acres, just 10 minutes from the charming village of Old Chatham. With 3 spacious bedrooms and 3.5 baths, there’s plenty of room for family and friends. Additional sleeping options ensure everyone has a comfortable place to rest. Delight in picturesque pond views, host a game night in the cozy basement family room complete with a foosball table, and gather around the fire to roast s’mores under the twinkling stars. Book direct and save: www.evergreenhomevacationrentals.com 🌿

@evergreenberkshires

JUST SOLD...A magical full-circle moment for Evergreen Home. Our buyer clients had a clear vision for their ideal home, and after a rigorous search, they initially found a place they loved outside the Berkshires. We kept in touch over time, knowing their dream was still in the Berkshires. When the perfect property finally hit the market, we knew it well, having occasionally managed it as a vacation rental. With offers already on the table, the buyers drove two hours that day, viewed the home, and made a winning offer. Their long-searched-for Berkshire dream home was finally theirs...a wonderful ending for everyone.
JUST SOLD...this great house on over 20 acres in Hinsdale found a new family to call it home. Just 4 months from saying they were thinking of moving to the closing date, this all happened fast but they just knew it was right. As always a pleasure to work with @maggiebarrygavin and @homesweetberkshires
New Rental Listing, A Renovated Country Retreat in Old Chatham, NY. 🍁 Discover serenity nestled on 11 private acres, just 10 minutes from the charming village of Old Chatham. With 3 spacious bedrooms and 3.5 baths, there’s plenty of room for family and friends. Additional sleeping options ensure everyone has a comfortable place to rest. Delight in picturesque pond views, host a game night in the cozy basement family room complete with a foosball table, and gather around the fire to roast s’mores under the twinkling stars. Book direct and save: www.evergreenhomevacationrentals.com 🌿