Compare Cottages, Resorts, & Rentals in The Berkshires, Massachusetts, USA
About The Berkshires Vacation Rentals
There are over 1569 amazing vacation rentals available in The Berkshires. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in The Berkshires.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in The Berkshires, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in The Berkshires. The average size of places to stay near The Berkshires is approximately 1047.15 ft², with prices averaging US $446 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in The Berkshires. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods The Berkshires, MA
Frequently Asked Questions About The Berkshires?
What are the top cottages, summer homes, and lake houses 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
- An Elegant Time Capsule in Downtown Lenox
- A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
- Spectacular 88-acre Berkshires Retreat w/Tennis Court - Family Friendly
How many rentals, hotels, or resorts are available in The Berkshires?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 1569 properties listed by Vacation Cottage in the The Berkshires area for the year 2025, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in The Berkshires.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Sherwood Forest Rental Cottages and Private Getaways in Massachusetts | 54 |
