
The Berkshires Vacation Rentals
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Our top choices for The Berkshires vacation rentals

1. Berkshire Mountain Lodge
Berkshire Mountain Lodge
2. Vacation Village in the Berkshires
Vacation Village in the Berkshires
3. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
4. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
5. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
6. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
7. Cozy 1-bedroom studio in serene Great Barrington with AC
Cozy 1-bedroom studio in serene Great Barrington with AC
8. Cozy Camper tucked into the woods
Cozy Camper tucked into the woods
9. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
11. Home in Great Barrington
Home in Great Barrington
12. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
13. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
14. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
15. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the Berkshires
16. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
17. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love it
18. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
19. Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to Shops
20. Sweet Cozy Victorian in Housatonic. Close to everything.
Sweet Cozy Victorian in Housatonic. Close to everything.Find vacation rentals that suit your style
Top The Berkshires Hotel Reviews

Courtyard by Marriott Lenox Berkshires
Find out more about The Berkshires
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with The Berkshires. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
Explore a world of travel with Expedia
- Hotels near Lee Premium Outlets
- Westfield Hotels
- Luxury Hotels in Berkshire County
- Quality Inn Westfield
- Hotels near Tanglewood Music Center
- Pet-Friendly Hotels in Western Massachusetts
- Cheap Hotels in Sandisfield
- The Red Door B&B
- 3 Star Hotels in Pittsfield
- Hotels near National Shrine of the Divine Mercy
- Villas in Beartown State Forest
- Hupi House
- West Stockbridge Hotels
- Becket Hotels
- Great Barrington Hotels
- Family Hotels in The Berkshires
- Holiday Inn Express & Suites Pittsfield
- Pet-Friendly Hotels in Sheffield
- Resorts in The Berkshires
- B&B in Lee
- Pet-Friendly Hotels in Stockbridge
- Hotels near Maple Corner Farm Cross Country Ski Area
- The Whitlock
- Springfield Hotels
- Quality Inn Great Barrington
- Luxury Hotels in The Berkshires
- Chestnut Lodge
- Historic 1804 house in N Becket Village in the Berkshires
- Relais & Chateaux Hotels in The Berkshires
- Sheffield Hotels
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- Resorts in Mount Washington
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- Cheap Hotels in Lenox
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- Hotels near Frelinghuysen Morris House and Studio
- Cottages in Mill River
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Historic Rectory Retreat in Stockbridge – Getaway for 8
- Lee Hotels
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- Condo Rentals in Otis
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- The Egremont Village Inn
- Motels in Egremont
- Private Island
- B&B in Russell
- Southwick Hotels
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- One Bedroom Luxury Cottage at Blantyre
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