Best Vacation Homes in Berkshire County
House
10.0(186 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $307/Night
7 Nights - US $2,150
Bed & Breakfast
10.0(14 Reviews)
13 Bedrooms
13 Baths
26 Guests
291.53 ft²
Parking
Air Conditioner
Internet
US $168/Night
7 Nights - US $1,176
Bed & Breakfast
10.0(137 Reviews)
1 Bedroom
1 Bath
Hot Tub
Pool- Balcony/Terrace
Breakfast
US $300/Night
7 Nights - US $2,103
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
Bed & Breakfast
10.0(12 Reviews)
6 Bedrooms
6 Baths
15 Guests
12.55 ft²
Skiing- Fireplace/Heating
- Balcony/Terrace
- View
US $170/Night
7 Nights - US $1,190
Cabin
10.0(129 Reviews)
3 Bedrooms
1 Bath
5 Guests
1100 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $307/Night
7 Nights - US $2,150
Ski Chalet
10.0(126 Reviews)
2 Bedrooms
1 Bath
6 Guests
1350 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $307/Night
7 Nights - US $2,150
Cottage
10.0(118 Reviews)
2 Bedrooms
1 Bath
5 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $227/Night
7 Nights - US $1,591
Berkshire County Luxury Rentals
Cabin
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
Unlock the Best Price
House
10.0(2 Reviews)
6 Bedrooms
6 Baths
16 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $5,685/Night
7 Nights - US $39,795
Villa
10.0(2 Reviews)
12 Bedrooms
10 Baths
24 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $4,993/Night
7 Nights - US $34,950
House
10.0(8 Reviews)
10 Bedrooms
9 Baths
16 Guests
11000 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $3,774/Night
7 Nights - US $26,417
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
Cabin
6.0(2 Reviews)
6 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $2,286/Night
7 Nights - US $16,001
House
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $2,233/Night
7 Nights - US $15,630
Berkshire County Pet Friendly Vacation Rentals
House
10.0(114 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Skiing
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $316/Night
7 Nights - US $2,215
House
10.0(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
1097.92 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $268/Night
7 Nights - US $1,874
Bed & Breakfast
10.0(28 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $466/Night
7 Nights - US $3,264
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
Bed & Breakfast
10.0(4 Reviews)
7 Bedrooms
7 Baths
17 Guests
325.99 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $400/Night
7 Nights - US $2,800
Cottage
10.0(60 Reviews)
1 Bedroom
1 Bath
3 Guests
450 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $300/Night
7 Nights - US $2,097
House
10.0(58 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $354/Night
7 Nights - US $2,476
House
10.0(34 Reviews)
2 Bedrooms
2 Baths
6 Guests
984 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $445/Night
7 Nights - US $3,116
Berkshire County Large Vacation Homes
Cottage
10.0(4 Reviews)
1 Bedroom
1 Bath
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $268/Night
7 Nights - US $1,874
House
10.0(2 Reviews)
8 Bedrooms
3 Baths
8 Guests
3003.13 ft²
- Fireplace/Heating
- View
- Air Conditioner
- Internet
US $600/Night
7 Nights - US $4,198
House
6 Bedrooms
4 Baths
14 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $826/Night
7 Nights - US $5,782
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
House
10.0(2 Reviews)
5 Bedrooms
4 Baths
10 Guests
2723.27 ft²
- Fireplace/Heating
- View
- Parking
- Internet
US $947/Night
7 Nights - US $6,629
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
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
New
Cottage
5 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $574/Night
7 Nights - US $4,021
Why Choose Rent By Owner for your Berkshire County 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 County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit can enhance your experience here, allowing you to enjoy the region’s natural beauty and local charm at its best.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for exploring the scenic outdoors and cultural events that this destination offers.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall (September to November)
Autumn brings vibrant foliage and cooler temperatures, creating a picturesque setting perfect for outdoor activities and appreciating the region’s natural beauty.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Off-Season Highlights
Winter (December to February)
The winter season offers a quieter atmosphere, allowing you to experience the area’s charm without the crowds, especially if you enjoy winter sports or cozying up indoors.
Average Temperature Daytime: 25-35°F - Nighttime: 10-20°F
Early Spring (March to April)
This period sees fewer visitors as the landscape transitions from winter, providing a peaceful environment and opportunities for early blooms and serene outdoor escapes.
Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F
Weekly Weather Forecast for Berkshire County
How to Book Your Berkshire County 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 County
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 outdoor dining with a private patio or deck perfect for summer meals in the region's lush surroundings.
- Take advantage of spacious yards ideal for outdoor games, picnics, or relaxing in nature.
- Relax in a hot tub or spa area, offering a soothing retreat after exploring the area's scenic landscapes.
- Make the most of your stay with access to a fire pit, perfect for cozy evenings and marshmallow roasting under the stars.
- Experience outdoor activities like kayaking or canoeing if your rental is near local lakes or rivers.
- Utilize a barbecue grill for family cookouts, making it easy to enjoy fresh grilled meals amidst the region's natural beauty.
- Engage in hiking or trail walking directly from the property, immersing yourself in the area's picturesque scenery.
Top Attractions Around Berkshire County
What attractions are nearby?
While staying in this destination, you can explore nearby outdoor activities such as hiking, boating, and scenic drives that showcase the natural beauty of the region, making it an ideal choice for those looking to enjoy the best of Berkshire County’s outdoors.
Family Activities
- Mass MoCA: Explore innovative art installations and engaging family-friendly exhibits at this renowned cultural venue in the area.
- Berkshire Botanical Garden: Discover a variety of beautiful plant collections and scenic walking trails perfect for family outings amidst nature.
- The Clark Art Institute: Enjoy inspiring art collections and outdoor sculpture gardens that offer engaging activities suitable for all ages.
- Norman Rockwell Museum: Experience the world of beloved American illustrator Norman Rockwell through interactive displays and family-oriented programs in this destination’s vibrant arts scene.
Adult Activities
- Exploring the Berkshire Botanical Garden: Wander through this lush garden to enjoy a peaceful retreat and connect with the region’s vibrant plant life.
- Attending performances at Tanglewood: Experience world-class concerts in the area’s renowned outdoor music venue nestled within scenic surroundings.
- Visiting The Mount, Edith Wharton's Home: Discover the historic estate that offers insight into classic American literature and stunning landscape views.
- Hiking in the Appalachian Trail: Embark on scenic hikes along this famous trail, which showcases the natural beauty of the region’s rolling hills and lush forests.
Other Places to Stay in Berkshire County, MA
The Berkshires
Great Barrington
Williamstown
Hancock
Jiminy Peak Mountain Resort
Pittsfield
Stockbridge
North Egremont
Egremont
Becket
Berkshire County Travel Tips
How Can You Make the Most of Your Stay?
- Explore the Local Arts Scene: Take advantage of the area's vibrant arts community by visiting local galleries, theaters, and craft fairs to truly immerse yourself in the region’s cultural offerings.
- Visit Seasonally Unique Attractions: Plan your visit around the region's seasonal events and outdoor activities to experience the destination at its most authentic and lively times of year.
- Discover Scenic Outdoor Activities: Make the most of the beautiful natural surroundings with outdoor pursuits such as hiking, biking, or simply enjoying the tranquil parks nearby your vacation rental.
- Sample Local Cuisine: Relish the flavors of the region by dining at locally renowned eateries or visiting farmers’ markets for fresh, regional produce that complements your stay.
Transportation Options
- Massachusetts Bay Transportation Authority (MBTA): You can access regional rail and bus services that conveniently connect to the area, making it easy to explore without a car.
- Commercial Airlines: Major airports nearby provide flights into the region, offering quick access for travelers coming from across the country or internationally.
- Rental Car Services: Car rental companies operate at local airports and stations, giving you flexibility to explore Berkshire County's scenic landscapes at your own pace.
- Local Taxis and Ride-Sharing: Taxis and ride-sharing options like Uber and Lyft are available here, providing convenient transportation within and around the destination.
Local Customs Options
- Quilt Making Tradition: You can experience the region’s historic quilting practices, which remain a respected craft passed down through generations here in Berkshire County.
- Local Art and Craftsmanship: Engaging with local artisans allows you to appreciate the area's rich tradition of handcrafted art, reflecting its cultural heritage during your stay.
- Seasonal Harvest Festivals: Participating in seasonal harvest festivals offers insight into the community's agricultural roots and celebrates the area's bounty throughout the year.
- Historic Preservation Customs: Respect for historic sites and architectural preservation remains integral to the region’s identity, providing a glimpse into its proud history for visitors like you.
Berkshire County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Berkshire County?
There are a lot of options in Berkshire County. If you plan on staying in the Berkshire County 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 County:
- 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
- St Anne`s Manor | Walk to Downtown! Sleeps 8
- Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!
2. How many vacation rentals have private pools in Berkshire County?
There are 126 vacation rentals with private pools near Berkshire County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Berkshire County are best for families?
If you are looking for a family-friendly vacation home in Berkshire County, 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 County:
4. How many Rentbyowner vacation rentals are available in Berkshire County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1722 in the Berkshire County 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 County.
5. What is the cancellation policy for vacation rentals in Berkshire County, Massachusetts?
Cancellation policies vary depending on the property listing. You should review the specific rental's cancellation terms listed on the booking page or contact the owner directly to understand any potential fees or restrictions.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or security deposits are often listed on the property page. Be sure to read the detailed fee breakdown or reach out to the owner for clarification before completing your reservation.
7. How do I confirm the availability of a vacation rental in this region?
Availability can be checked through the booking platform by selecting your desired dates. If you have specific questions about availability, contacting the property owner directly can provide immediate clarification.
8. What amenities are typically included in Berkshire County vacation rentals?
Amenities vary by property but commonly include essentials like Wi-Fi, parking, and kitchen facilities. For precise details, review the property’s amenities list or contact the owner to ensure it meets your needs.
9. Is there a minimum stay requirement for booking a vacation rental here?
Minimum stay requirements differ among properties and are specified in each listing. Check the individual property details or contact the owner to confirm any stay restrictions before booking.
Berkshire County Top Rated Vacation Rentals
House
10.0(76 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,271/Night
7 Nights - US $8,894
House
10.0(56 Reviews)
4 Bedrooms
4 Baths
12 Guests
4000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $753/Night
7 Nights - US $5,270
Condo
10.0(51 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
US $596/Night
7 Nights - US $4,173
House
10.0(45 Reviews)
4 Bedrooms
3 Baths
12 Guests
2500 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
US $725/Night
7 Nights - US $5,072
Condo
10.0(43 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
US $342/Night
7 Nights - US $2,393
House
10.0(40 Reviews)
4 Bedrooms
2 Baths
8 Guests
3300 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $551/Night
7 Nights - US $3,857
House
10.0(37 Reviews)
6 Bedrooms
4 Baths
16 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,061/Night
7 Nights - US $7,428
Condo
10.0(34 Reviews)
3 Bedrooms
3 Baths
8 Guests
1850 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $427/Night
7 Nights - US $2,992
