Owner Direct Vacation
Rentals in Berkshire
The Best Owner Direct Vacation Rentals in Berkshire. Explore thousands of vacation home rentals, large cabins, and villas near Berkshire
GUESTS
Explore the Best Berkshire Vacation Homes
Looking for the perfect place to stay in Berkshire? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Berkshire character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Berkshire Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Berkshire
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Friday Jan 23
Berkshire, Massachusetts
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Berkshire vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Berkshire
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How to Reserve Your Berkshire Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Berkshire Vacation Rental FAQs
1. What are the top vacation rentals in Berkshire?
There are a lot of options in Berkshire. If you plan on staying in the Berkshire area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Berkshire:
- The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
- Unique Condo, Quiet Neighborhood, Walk to Town.
- Devonfield Inn B&B
- An Elegant Time Capsule in Downtown Lenox
- Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
- Elegant 19th Century New England 2BR vacation rental at Garfield House
- Spectacular setting on your own private lake close to it all!
- 5 STAR CASUAL ELEGANCE for 5 STAR GUESTS
- Heart of Lenox Walk to Town Cozy Cottage!
- Enjoy comfortable elegance in this secluded grand home located in town
2. How many vacation rentals have private pools in Berkshire?
There are 12 vacation rentals with private pools near Berkshire. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Berkshire are best for families?
If you are looking for a family-friendly vacation home in Berkshire, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Berkshire:
4. How many vacation rentals are available in Berkshire?
Currently, the total number of properties listed in 2026 is over 301 in the Berkshire area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Berkshire.