Best Vacation Homes in Berkshire
Condo
10.0(150 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Fireplace/Heating
Kitchen
Parking
Air Conditioner
US $346/Night
7 Nights - US $2,424
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1506.95 ft²
- Fireplace/Heating
View
Pet Friendly- Parking
US $451/Night
7 Nights - US $3,157
Bed & Breakfast
10.0(137 Reviews)
1 Bedroom
1 Bath
Hot Tub
Pool
Balcony/Terrace
Breakfast
US $300/Night
7 Nights - US $2,103
House
10.0(99 Reviews)
2 Bedrooms
1 Bath
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $237/Night
7 Nights - US $1,662
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
12916.69 ft²
- Parking
- Air Conditioner
Internet
Child Friendly
US $405/Night
7 Nights - US $2,835
Apartment
10.0(47 Reviews)
2 Bedrooms
1 Bath
5 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $363/Night
7 Nights - US $2,541
Cottage
10.0(47 Reviews)
3 Bedrooms
1 Bath
4 Guests
650 ft²
Ocean View- Balcony/Terrace
- View
- Kitchen
US $241/Night
7 Nights - US $1,688
Apartment
10.0(37 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $260/Night
7 Nights - US $1,820
Berkshire Luxury Rentals
Villa
10.0(19 Reviews)
13 Bedrooms
13 Baths
35 Guests
15000 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $3,490/Night
7 Nights - US $24,433
House
10 Bedrooms
9 Baths
17 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $2,314/Night
7 Nights - US $16,197
House
10.0(8 Reviews)
4 Bedrooms
4 Baths
10 Guests
Private Pool- Fireplace/Heating
- Pool
- Ocean View
US $1,389/Night
7 Nights - US $9,724
House
9.8(115 Reviews)
6 Bedrooms
5 Baths
16 Guests
5500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,385/Night
7 Nights - US $9,696
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
2050 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,272/Night
7 Nights - US $8,907
House
9.8(18 Reviews)
6 Bedrooms
4 Baths
14 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,191/Night
7 Nights - US $8,335
House
9.2(34 Reviews)
6 Bedrooms
4 Baths
12 Guests
4500 ft²
- Private Pool
- Hot Tub
- Pool
- Kitchen
US $1,108/Night
7 Nights - US $7,754
House
10.0(250 Reviews)
6 Bedrooms
5 Baths
20 Guests
7000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,078/Night
7 Nights - US $7,543
Berkshire Pet Friendly Vacation Rentals
House
10.0(25 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $237/Night
7 Nights - US $1,662
House
9.8(5 Reviews)
4 Bedrooms
2 Baths
4 Guests
1291.67 ft²
Skiing- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $399/Night
7 Nights - US $2,793
House
1 Bedroom
1 Bath
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $394/Night
7 Nights - US $2,760
House
10.0(24 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $298/Night
7 Nights - US $2,087
House
9.0(1 Review)
2 Bedrooms
2 Baths
7 Guests
1506.95 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $379/Night
7 Nights - US $2,653
House
10.0(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $237/Night
7 Nights - US $1,662
Apartment
10.0(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $555/Night
7 Nights - US $3,887
House
9.8(57 Reviews)
2 Bedrooms
3 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $420/Night
7 Nights - US $2,943
Berkshire Large Vacation Homes
Villa
9.8(21 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $271/Night
7 Nights - US $1,899
Bed & Breakfast
9.0(52 Reviews)
15 Bedrooms
15 Baths
37 Guests
334.45 ft²
- Skiing
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $518/Night
7 Nights - US $3,626
US $895/Night
7 Nights - US $6,265
Villa
9.4(140 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $244/Night
7 Nights - US $1,705
House
9.0(1 Review)
10 Bedrooms
2 Baths
10 Guests
1905.21 ft²
- Skiing
- Fireplace/Heating
- Pool
- Air Conditioner
US $649/Night
7 Nights - US $4,543
Villa
9.0(17 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $210/Night
7 Nights - US $1,470
House
10.0(127 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $899/Night
7 Nights - US $6,294
House
10.0(98 Reviews)
5 Bedrooms
3 Baths
14 Guests
2800 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $975/Night
7 Nights - US $6,825
Why Choose Rent By Owner for your Berkshire Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Berkshire
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience and ensure you enjoy all that this destination has to offer, whether you're seeking vibrant seasons or quieter getaways within Berkshire’s scenic surroundings.
Peak Season Highlights
Summer (June to August)
During the warm summer months, visitors flock to this destination for outdoor activities and festivals, making it an ideal time to explore local culture and scenery.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall (September to November)
The vibrant fall foliage draws many travelers seeking scenic views and outdoor adventures, providing a colorful backdrop for your stay.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Off-Season Highlights
Winter (December to February)
In the quiet winter months, you can enjoy a peaceful retreat with fewer crowds and cozy accommodations in the region.
Average Temperature Daytime: 30-40°F - Nighttime: 15-25°F
Spring (March to May)
As the area transitions into bloom, spring offers a serene atmosphere and more affordable options for those looking to avoid peak crowds.
Average Temperature Daytime: 50-60°F - Nighttime: 30-40°F
Weekly Weather Forecast for Berkshire
How to Book Your Berkshire Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Berkshire
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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 private outdoor spaces such as patios or decks to relax and unwind in the fresh air.
- Take advantage of well-maintained gardens or landscaped yards that enhance your outdoor experience.
- Make the most of outdoor dining areas perfect for al fresco meals during warm summer days.
- Benefit from access to scenic walking or hiking trails directly from your rental property.
- Soak up the sun on a spacious lawn ideal for outdoor games and family activities.
- Utilize outdoor furniture designed for lounging, entertaining, or enjoying picturesque views.
- Depending on the property, you might find amenities like a fire pit or barbecue grill to enhance your outdoor gatherings.
Top Attractions Around Berkshire
What attractions are nearby?
In this charming destination, you can enjoy a variety of outdoor activities and cultural experiences just moments from your Berkshire vacation rentals, making it an ideal spot for exploring the natural beauty and vibrant arts scene of the region.
Family Activities
- Norman Rockwell Museum: Discover the works of the iconic American artist and inspire creativity through engaging family-friendly exhibits in the region.
- Stockbridge Bowl: Enjoy a relaxing day by the water with swimming, paddleboarding, or picnicking at this scenic lake nestled in the area.
- Berkshire Botanical Garden: Explore beautiful gardens and participate in family programs designed to foster an appreciation for nature in this tranquil setting.
- Tanglewood Music Center: Introduce the family to world-class outdoor concerts and cultural performances set against the picturesque backdrop of the destination.
Adult Activities
- Hiking at Mount Greylock State Reservation: Discover breathtaking views and scenic trails perfect for exploring nature and enjoying the outdoors in this iconic destination.
- Visiting Tanglewood: Experience world-class music performances and cultural events set against the backdrop of lush landscapes in this renowned summer venue.
- Exploring The Berkshire Museum: Engage with fascinating exhibits and artistic displays that showcase the region’s rich history and creative spirit.
- Shopping and Dining in Great Barrington: Enjoy a vibrant selection of boutique shops and farm-to-table restaurants to indulge your senses while immersing yourself in local culture.
Berkshire Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Seasonal Events: Schedule your trip to coincide with local festivals or cultural events to immerse yourself in the area's vibrant community atmosphere.
- Explore Local Attractions and Natural Beauty: Take advantage of the region’s scenic parks, outdoor activities, and historic sites to truly experience what makes this destination unique.
- Select a Prime Location for Your Stay: Choose a well-situated property that offers easy access to key attractions and outdoor adventures within the area.
- Communicate with Your Host: Engage with your host to receive personalized recommendations and insider tips that enhance your experience during your stay here.
Transportation Options
- Amtrak Station: You can conveniently access train travel via Amtrak, providing seamless connections to nearby cities and regions from here.
- Berkshire Regional Transit Authority (BRTA): This regional bus service offers reliable transportation options within the area, making it easy to explore local attractions.
- Rental Car Services: Several rental car agencies operate locally, giving you the flexibility to explore the countryside and surrounding towns at your own pace.
- Private Shuttle Services: Private shuttle providers offer tailored transportation solutions for visitors seeking comfort and convenience during their stay in the region.
Local Customs Options
- Traditional Berkshire Folklore: You might encounter local stories and legends that reflect the area’s rich cultural history during your stay.
- Seasonal Harvest Festivals: Participating in seasonal agricultural festivals is a cherished custom where locals celebrate the region’s farming heritage.
- Historic Preservation Practices: Respect for historic sites and participating in preservation efforts are common customs embraced by the community here.
- Community Art and Craft Displays: Supporting local artisans and viewing traditional crafts at regional markets are customary ways to engage with this destination’s creative spirit.
Berkshire Vacation Rental Frequently Asked Questions
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
- St Anne`s Manor | Walk to Downtown! Sleeps 8
- Elegant 19th Century New England 2BR vacation rental at Garfield House
- Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
- 5 STAR CASUAL ELEGANCE for 5 STAR GUESTS
- Spectacular setting on your own private lake close to it all!
- Enjoy comfortable elegance in this secluded grand home located in town
- 33 Main
2. How many vacation rentals have private pools in Berkshire?
There are 13 vacation rentals with private pools near Berkshire. Top-rated RBO 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 Rentbyowner vacation rentals are available in Berkshire?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 323 in the Berkshire 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 Berkshire.
5. What is the cancellation policy for booking a vacation rental in Berkshire, Massachusetts?
Cancellation policies vary by property, so it’s important to review the specific listing details or contact the owner directly to understand the terms and any potential fees involved.
6. How do I ensure my reservation will be secure when booking a vacation rental in Berkshire?
Our platform uses secure payment methods and verified listings to ensure your reservation is safe. Always read the listing reviews and contact the owner if you have any questions before confirming your stay.
7. Are there any additional fees I should be aware of when booking through this destination?
Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing details. It’s advisable to review these carefully or reach out to the host for clarification before finalizing your booking.
8. What amenities are commonly available at Berkshire vacation rentals, and how can I find one that suits my needs?
Most properties in the area offer amenities like Wi-Fi, kitchens, and outdoor spaces. Use the search filters and review the detailed descriptions on each listing to select a rental that meets your specific preferences.
9. Can I modify my reservation once it has been confirmed in Berkshire?
Modification policies depend on the individual property owner. Contact the host directly through the platform to request changes or check the listing’s terms to see what options are available for adjustments.
Berkshire Top Rated Vacation Rentals
House
10.0(18 Reviews)
11 Bedrooms
6 Baths
23 Guests
6000 ft²
- Private Pool
Oceanfront- Spa
- Fireplace/Heating
US $1,032/Night
7 Nights - US $7,225
Other
10.0(11 Reviews)
5 Bedrooms
3 Baths
9 Guests
3000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $574/Night
7 Nights - US $4,021
Hotel
10.0(7 Reviews)
2 Baths
- Pool
- Kitchen
- Air Conditioner
- Internet
US $258/Night
7 Nights - US $1,806
Hotel
10.0(4 Reviews)
4 Baths
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $423/Night
7 Nights - US $2,964
Condo
10.0(4 Reviews)
4 Bedrooms
4 Baths
14 Guests
2500 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $407/Night
7 Nights - US $2,850
Other
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
2500 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
US $676/Night
7 Nights - US $4,729
House
10.0(3 Reviews)
4 Bedrooms
2 Baths
9 Guests
2497 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $429/Night
7 Nights - US $3,003
Villa
10.0(3 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $279/Night
7 Nights - US $1,955
