Berkshires,Massachusetts. A vibrant destination that is known for having a selection of beautiful vacation villas available. Villas in Berkshires offer a wide variety of amenities at a price that won't break the bank.

Looking for an upscale vacation? Villas are luxuriously decorated, creating an atmosphere of high-end comfort. Whether you're a family looking for a home away from home or a group seeking the perfect getaway, our diverse selection of villas ensures that your stay in Berkshires is not only memorable but tailored to your every need.

Choose your ideal Berkshires villa from our selection and start planning your perfect getaway. Our selection of villas in Berkshires are priced between $39 and $17,561 per night, meaning you can find your ideal home away from home without breaking the bank.

Top Amenities: Internet / Wifi, Kitchen or Kitchenette, Air conditioner, Parking and TV

Points of Interest: Bridge of Flowers, Stanley Park, Springfield Museums, Northwest Park and New England Air Museum

Ready to explore the wonders of Berkshires? Book your villa today and dive into the unique experiences that Massachusetts has to offer.

Top villas in Berkshires

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Colesbrook Cottage
Villa
 in Washington
Garden · Pool · Kitchen or Kitchenette

This Villa in Berkshires, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Stylish Rural Sanctuary Perfect for Every Season!
Villa
 in East Chatham
Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Berkshires, at $84 per night for your next great vacation.

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Stunning All-Season Renovated Barn Escape!
Villa
 in East Chatham
Garden · Pets allowed · Kitchen or Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Berkshires at Stunning All-Season Renovated Barn Escape! for $84 for your next trip.

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Sunny Ridge - PoshPadsCT Best Town Washington
Villa
 in Washington
Pool · Pets allowed · Kitchen or Kitchenette

This Villa for $91 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Beachfront
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Entertainer's Luxury Retreat
Villa
 in Thomaston
Garden · Kitchen or Kitchenette · Air conditioner

Indulge in a peaceful retreat at Entertainer's Luxury Retreat, our elegant Villa in Berkshires. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Built for a US Secretary of State 13K SF in Lenox
Villa
 in Lenox
Garden · Pets allowed · Kitchen or Kitchenette

This Villa for $243 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Villa | 6 bedrooms
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Argyll House by Boutique
Villa
 in Harwinton
Kitchen or Kitchenette · Internet / Wifi

Experience the best of Berkshires with this Villa available for $1,162. This property is equipped with amenities including Internet / Wifi and Kitchen or Kitchenette, and more.

$$$$
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Dining
5.0 / 5.0
Outstanding(106 Ratings)
Captivating Artisan Built Home With Spectacular Water Views
Villa
 in Falls Village
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen or Kitchenette · Air conditioner

The best choice in Berkshires for Villa, for $262 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Villa | 6 bedrooms
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Argyll House by Boutique
Villa
 in Harwinton
2 guests
Kitchen or Kitchenette · Internet / Wifi

Enjoy the best of Berkshires in our Villa, Argyll House by Boutique. A stunning property with amenities including Internet / Wifi and Kitchen or Kitchenette, and more.

$$$$
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Property grounds
4.7 / 5.0
Outstanding(118 Ratings)
Villa with Access to Amazing Amenities!
Villa
 in South Lee
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

This Villa in Berkshires, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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5.0 / 5.0
Outstanding(1 Rating)
The Freeman- 14K SF Estate 40acrs Tennis Vineyard
Villa
 in Sheffield
Garden · Pets allowed · Kitchen or Kitchenette

Looking for a Villa in Berkshires, this Villa for $73 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Interior
5.0 / 5.0
Outstanding(31 Ratings)
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Villa
 in Egremont
30 guests · 7 bedrooms · 6 baths
Garden · Pets allowed · Kitchen or Kitchenette
Top rated

Are you ready to indulge in a relaxing getaway? Our Villa in Berkshires has everything you need for a rejuvenating stay. Treat yourself to The Freeman - Newly Renovated 14K SF Estate on 40 Acres's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$
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Villas with internet & wifi in Berkshires

Property grounds
4.9 / 5.0
Outstanding(17 Ratings)
Spacious Villa with Access to Various Amenities!
Villa
 in South Lee
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking for a Villa in Berkshires, this Villa for $211 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Exterior detail
4.9 / 5.0
Outstanding(16 Ratings)
The Kemble- Built by a US Secretary of State in Lenox
Villa
 in Lenox
35 guests · 13 bedrooms · 14 baths
Garden · Pets allowed · Kitchen or Kitchenette

This inviting Villa in Berkshires can fit your needs for many types of vacations, at $2,715 per night.

$$$$
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Property grounds
4.5 / 5.0
Excellent(16 Ratings)
Villa with Access to Various Amenities
Villa
 in South Lee
4 guests · 1 bedroom · 1 bath
Pool · Kitchen or Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Berkshires at Villa with Access to Various Amenities for $154 for your next trip.

$$$$
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Interior
5.0 / 5.0
Outstanding(11 Ratings)
LUXURY BERKSHIRES RETREAT - Family Compound! - 2 separate but attached homes!
Villa
 in Richmond
12 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner

This inviting Villa in Berkshires can fit your needs for many types of vacations, at $494 per night.

$$$$
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Indoor pool, a heated pool
4.7 / 5.0
Outstanding(10 Ratings)
Beautiful 2BD Villa in Berkshires Resort
Villa
 in Lee
6 guests · 3 bedrooms · 2 baths
Garden · Pool · Pets allowed

Villa in Berkshires, for $295 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Exterior
5.0 / 5.0
Outstanding(4 Ratings)
20 minutes to Jiminy Peak and Bousquet Mountain
Villa
 in New Lebanon
10 guests · 5 bedrooms · 6 baths
Garden · Kitchen or Kitchenette · Air conditioner

This inviting Villa in Berkshires can fit your needs for many types of vacations, at $1,676 per night.

$$$$
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Exterior
5.0 / 5.0
Outstanding(4 Ratings)
The Winthrop Estate - 12K SF 32 Acres
Villa
 in Lenox
24 guests · 11 bedrooms · 11 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Soak up the beauty of Berkshires in our Villa, The Winthrop Estate - 12K SF 32 Acres. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.

$$$$
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Property grounds
5.0 / 5.0
Outstanding(3 Ratings)
Equipped Villa with Access to Amazing Amenities!
Villa
 in South Lee
8 guests · 3 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Berkshires? Look no further than our Villa, Equipped Villa with Access to Amazing Amenities!. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Hot tub or spa, and more.

$$$$
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Interior
5.0 / 5.0
Outstanding(3 Ratings)
Historic Stone Church in The Berkshires
Castle / Palace
 in Lanesborough
2 guests · 1 bedroom · 2 baths
Garden · Pool · Kitchen or Kitchenette

Experience vacation in Berkshires with our Castle / Palace, Historic Stone Church in The Berkshires. Enjoy amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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TV, fireplace, table tennis
5.0 / 5.0
Outstanding(2 Ratings)
Retreat in Style: Luxury for Family & Friends
Villa
 in Thomaston
12 guests · 5 bedrooms · 5 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Nestled in Berkshires, this Villa is perfect for your next vacation. Enjoy Retreat in Style: Luxury for Family & Friends's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Pool
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Argyll House in Litchfield County by Boutique
Villa
 in Harwinton
11 guests · 6 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Experience the best of Berkshires with this Villa available for $1,117. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Indoor pool, outdoor pool
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7 nights in our 1 br, full kitchen villa. Only 110 per night
Villa
 in Lee
4 guests · 1 bedroom · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our Villa in Berkshires has everything you need for a rejuvenating stay. Treat yourself to 7 nights in our 1 br, full kitchen villa. Only 110 per night's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$
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