Berkshire Cottage Rentals

Compare Cottages, Resorts, & Rentals in Berkshire, Massachusetts, USA

From US $585 per night
|
10.0 (1 Review)
2 Bedrooms 4 Guests
New Newly Renovated Lakefront Haven In Lenox
New
4 Bedrooms 10 Guests
From US $399 per night
|
9.5 (2 Reviews)
4 Bedrooms 4 Guests
From US $479 per night
|
10.0 (127 Reviews)
1 Bedroom 2 Guests
Bed & Breakfast
From US $514 per night
|
10.0 (70 Reviews)
1 Bedroom 2 Guests
From US $295 per night
|
10.0 (5 Reviews)
1 Bedroom 2 Guests
Bed & Breakfast
From US $367 per night
|
8.9 (52 Reviews)
10 Bedrooms 15 Guests
From US $381 per night
|
9.8 (98 Reviews)
1 Bedroom 2 Guests
Bed & Breakfast
From US $426 per night
8.4 (18 Reviews)
10 Bedrooms 11 Guests
Bed & Breakfast
From US $223 per night
|
9.6 (365 Reviews)
1 Bedroom 2 Guests
From US $244 per night
|
8.3 (82 Reviews)
7 Bedrooms 16 Guests
From US $164 per night
|
9.6 (264 Reviews)
1 Bedroom 2 Guests
|
8.3 (3 Reviews)
1 Bedroom 12 Guests
From US $234 per night
|
9.4 (152 Reviews)
1 Bedroom 2 Guests
|
8.0 (1 Review)
2 Bedrooms 6 Guests
From US $180 per night
|
8.8 (313 Reviews)
1 Bedroom 2 Guests
|
New
10 Bedrooms 10 Guests
From US $267 per night
|
8.6 (121 Reviews)
1 Bedroom 2 Guests
|
9.0 (1004 Reviews)
1 Bedroom 2 Guests
|
New
5 Bedrooms 12 Guests
From US $320 per night
|
9.0 (42 Reviews)
1 Bedroom 2 Guests
|
8.6 (485 Reviews)
1 Bedroom 2 Guests
New
5 Bedrooms 12 Guests
From US $268 per night
8.6 (244 Reviews)
1 Bedroom 2 Guests
From US $450 per night
New
1 Bedroom 18 Guests
From US $113 per night
8.2 (1000 Reviews)
1 Bedroom 2 Guests
From US $219 per night
|
9.5 (20 Reviews)
14 Bedrooms 31 Guests
From US $148 per night
|
7.8 (467 Reviews)
1 Bedroom 2 Guests
From US $175 per night
9.4 (151 Reviews)
14 Bedrooms 14 Guests
From US $367 per night
|
7.8 (188 Reviews)
1 Bedroom 2 Guests
From US $489 per night
9.3 (28 Reviews)
3 Bedrooms 6 Guests
From US $97 per night
7.6 (387 Reviews)
1 Bedroom 2 Guests
From US $506 per night
|
8.9 (10 Reviews)
9 Bedrooms 9 Guests
From US $203 per night
|
7.0 (84 Reviews)
1 Bedroom 2 Guests
|
8.4 (526 Reviews)
52 Bedrooms 26 Guests
|
8.2 (448 Reviews)
15 Bedrooms 6 Guests
From US $99 per night
5.3 (539 Reviews)
28 Bedrooms 14 Guests
6.2 (597 Reviews)
1 Bedroom 2 Guests
From US $159 per night
5.8 (308 Reviews)
1 Bedroom 2 Guests

About Berkshire Vacation Rentals

There are over 58 amazing vacation rentals available in Berkshire. 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 Berkshire.

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 Berkshire, 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 Berkshire. The average size of places to stay near Berkshire is approximately 753.88 ftยฒ, with prices averaging US $316 per night.

Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Berkshire. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.

Frequently Asked Questions About Berkshire?

What are the top cottages, summer homes, and lake houses in Berkshire?

How many rentals, hotels, or resorts are available in Berkshire?

Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 58 properties listed by Vacation Cottage in the Berkshire 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 Berkshire.