Best Vacation Homes in The Berkshires
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
The Berkshires Luxury Rentals
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pet Friendly
- Security/Safety
The Berkshires Pet Friendly Vacation Rentals
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Pool
The Berkshires Large Vacation Homes
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- View
Why Choose Rent By Owner for your The Berkshires Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for The Berkshires Vacation Rentals
Where are the best neighborhoods to stay in The Berkshires?
When exploring The Berkshires in Massachusetts, choosing the right neighborhood to stay in can greatly enhance your vacation experience. Whether you prefer the charming villages known for their cultural attractions or the peaceful countryside offering scenic privacy, each area provides a unique atmosphere to suit your preferences. By selecting a well-suited location within The Berkshires, you'll enjoy easy access to local events, outdoor activities, and the area's renowned arts scene. Discover the perfect spot to unwind and immerse yourself in the natural beauty and rich heritage of this celebrated New England destination.
Sherwood Forest
Nestled in the scenic region, this area offers a peaceful retreat where you can enjoy privacy and tranquility. It’s an ideal choice for those seeking a serene escape within easy reach of outdoor activities and natural beauty.
View 54+ Rentals in Sherwood ForestBest Times to Visit The Berkshires
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination ensures you can enjoy its natural beauty and vibrant cultural scene while securing the best rates and availability for your vacation rentals here.
Peak Season Highlights
Summer (June to August)
During the warm and lively summer months, this destination attracts visitors seeking outdoor activities and cultural festivals. Booking your vacation rentals early ensures you secure the best accommodations in the area.
Fall (September to November)
Experience the region's stunning fall foliage during this popular season. This is an ideal time to enjoy scenic views and local events, making early reservations essential for availability and best rates.
Off-Season Highlights
Winter (December to February)
The quieter winter months offer a peaceful retreat with opportunities for cozy stays. Visiting now allows you to find more affordable vacation rentals and less crowded attractions.
Spring (March to May)
As nature begins to bloom, this shoulder season provides a tranquil escape before the busy summer period. Booking your rental early can help you take advantage of lower rates and better selections.
Weekly Weather Forecast for The Berkshires
How to Book Your The Berkshires Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in The Berkshires
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor space with a private patio or deck perfect for relaxing and hosting.
- Make the most of scenic views from large windows or outdoor seating areas.
- Take advantage of a barbecue grill for outdoor cooking during your stay.
- Benefit from access to lush gardens or landscaped yards ideal for outdoor activities.
- Relax in a hot tub or outdoor shower available at select properties in the region.
- Utilize designated fire pits for cozy evenings and storytelling under the stars.
- Explore nearby trails, gardens, or natural beauty right from your rental’s doorstep.
Top Attractions Around The Berkshires
What attractions are nearby?
During your stay here, you can explore a variety of outdoor activities such as hiking, biking, and nature walks in the scenic surroundings of the region, ensuring a vibrant and engaging experience just moments from your vacation rentals.
Family Activities
- Norman Rockwell Museum: Discover the works of the iconic American artist, inspiring creativity and family discussions in a welcoming environment.
- Family Fun at Jiminy Peak Mountain Resort: Enjoy outdoor activities like skiing, snowboarding, or mountain coaster rides suitable for all ages during your stay here.
- MASS MoCA: Engage with contemporary art installations and interactive exhibits that captivate children and adults alike in this vibrant arts center.
- The Berkshire Botanical Garden: Explore beautiful gardens and participate in family-friendly programs that foster a love of nature amidst scenic surroundings.
Adult Activities
- Visit Tanglewood Music Center: Immerse yourself in world-class performances and explore the scenic outdoor venues that define this renowned music festival in the region.
- Explore the Berkshire Botanical Garden: Enjoy a leisurely stroll through beautifully curated gardens and discover native plants that showcase the area's natural beauty.
- Hike Mount Greylock: Take in breathtaking panoramic views from the highest peak in Massachusetts while hiking along well-maintained trails here.
- Experience the Norman Rockwell Museum: Dive into American art history with exhibits featuring the iconic works of Norman Rockwell, all set within this culturally rich destination.
Other Places to Stay in The Berkshires, MA
The Berkshires Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Arts and Culture: Immerse yourself in the area's renowned art galleries, theaters, and cultural festivals to experience the vibrant community spirit that makes this destination unique.
- Plan Seasonal Outdoor Activities: Take advantage of the region’s natural beauty by hiking, biking, or enjoying outdoor concerts and events during your stay in the area.
- Discover Culinary Gems: Savor local flavors at charming eateries and farmers' markets to get a true taste of the region’s culinary scene.
- Choose the Right Accommodation: Select from a variety of well-maintained vacation rentals that offer comfort and convenience, ensuring a memorable and relaxing visit to the region.
Transportation Options
- Car Rentals: Renting a car gives you the flexibility to explore scenic spots and charming towns at your own pace within this region.
- Public Transportation: The area's bus services connect key towns and attractions, making it a convenient option for getting around without a vehicle.
- Taxis and Rideshare Services: Taxis and popular rideshare apps like Uber and Lyft provide on-demand transportation, ideal for quick trips or when parking is limited.
- Private Shuttle Services: Specialized shuttle services operate between major points of interest and accommodations, offering comfortable and direct travel in this part of Massachusetts.
Local Customs Options
- Respect for the Arts: You’ll find that supporting local artists and performers is a cherished custom here, reflecting the region’s rich cultural heritage.
- Celebration of Seasons: Embracing the changing seasons with festivals and outdoor activities is a major part of life in this scenic area.
- Farmers’ Market Traditions: Visiting community farmers’ markets to enjoy fresh, locally-sourced produce is a common local custom that visitors often partake in.
- Preservation of Nature: Respecting the natural environment by engaging in eco-friendly practices aligns with the region’s commitment to conservation and outdoor exploration.
Frequently Asked Questions About The Berkshires?
1. What are the top vacation rentals in The Berkshires?
There are a lot of options in The Berkshires. If you plan on staying in the The Berkshires area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in The Berkshires:
- Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
- “Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
- 4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
- Unique Condo, Quiet Neighborhood, Walk to Town.
- Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
- Location! Location! Berkshire Glamour (and comfort) Meets Town And Country
- Devonfield Inn B&B
- A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
- An Elegant Time Capsule in Downtown Lenox
- Spectacular 88-acre Berkshires Retreat w/Tennis Court - Family Friendly
2. How many vacation rentals have private pools in The Berkshires?
There are 119 vacation rentals with private pools near The Berkshires. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in The Berkshires are best for families?
If you are looking for a family-friendly vacation home in The Berkshires, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in The Berkshires:
4. How many Rentbyowner vacation rentals are available in The Berkshires?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 1582 in the The Berkshires area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in The Berkshires.
5. What is the cancellation policy for vacation rentals in The Berkshires?
6. How do I contact the property owner or manager before booking in the region?
7. Are there any additional fees I should be aware of when booking a vacation rental here?
8. What amenities are usually included in vacation rentals in this area?
9. Is there a minimum stay requirement for booking vacation rentals in the region?
The Berkshires Top Rated Vacation Rentals
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pool
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
