Estia Villas - Vacation Rentals in Berkshire County
Villa
10.0
(
20 Reviews
)
13 Bedrooms
13 Bathrooms
35 Guests
15000 ft²
-
Parking -
Spa -
Balcony/Terrace -
Kitchen
US $2,935
/Night
7 Nights - $20,545
Villa
10.0
(
3 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
-
Hot Tub -
Parking
-
Pool -
Spa
US $258
/Night
7 Nights - $1,809
Villa
9.8
(
22 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $237
/Night
7 Nights - $1,659
Villa
9.4
(
141 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $217
/Night
7 Nights - $1,518
Villa
10.0
(
2 Reviews
)
12 Bedrooms
10 Bathrooms
24 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $5,472
/Night
7 Nights - $38,305
Villa
10.0
(
34 Reviews
)
7 Bedrooms
6 Bathrooms
30 Guests
14000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,518
/Night
7 Nights - $10,623
Villa
10.0
(
4 Reviews
)
11 Bedrooms
11 Bathrooms
24 Guests
11748 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $3,086
/Night
7 Nights - $21,600
Villa
9.0
(
18 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $218
/Night
7 Nights - $1,527
See More Berkshire County Vacation Rentals
Luxury Places to Stay in Berkshire County
Over 1676+
Luxury Places to Stay in or Near Berkshire County
Cabin
10.0
(
5 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Balcony/Terrace
-
Kitchen
-
Internet -
Pet Friendly
Unlock the Best Price
New
House
7 Bedrooms
6 Bathrooms
16 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $5,233
/Night
7 Nights - $36,634
House
10.0
(
8 Reviews
)
10 Bedrooms
9 Bathrooms
16 Guests
11000 ft²
-
Private Pool -
Hot Tub
-
Parking
-
Pool
US $5,142
/Night
7 Nights - $35,991
House
10.0
(
2 Reviews
)
6 Bedrooms
6 Bathrooms
16 Guests
-
Hot Tub
-
Parking
-
Spa
-
Balcony/Terrace
US $4,992
/Night
7 Nights - $34,943
House
5 Bedrooms
3 Bathrooms
10 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $3,134
/Night
7 Nights - $21,940
House
10 Bedrooms
9 Bathrooms
17 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $2,601
/Night
7 Nights - $18,209
Cabin
6.0
(
2 Reviews
)
6 Bedrooms
3 Bathrooms
12 Guests
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Internet
US $2,434
/Night
7 Nights - $17,040
House
9.6
(
50 Reviews
)
3 Bedrooms
2 Bathrooms
14 Guests
1788 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $2,388
/Night
7 Nights - $16,719
Find More Berkshire County Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Berkshire County
Over 485+
Top-Rated Vacation Rentals with a Pool in or Near Berkshire County
Bed & Breakfast
10.0
(
139 Reviews
)
1 Bedroom
1 Bathroom
-
Hot Tub
-
Breakfast -
Parking
-
Pool
US $490
/Night
7 Nights - $3,433
House
10.0
(
76 Reviews
)
3 Bedrooms
3 Bathrooms
7 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,163
/Night
7 Nights - $8,140
Cottage
10.0
(
62 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
450 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $373
/Night
7 Nights - $2,614
House
10.0
(
58 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
4000 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $1,307
/Night
7 Nights - $9,146
Condo
10.0
(
51 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $656
/Night
7 Nights - $4,590
Condo
10.0
(
44 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
US $353
/Night
7 Nights - $2,473
House
10.0
(
40 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
3300 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $558
/Night
7 Nights - $3,904
House
10.0
(
37 Reviews
)
6 Bedrooms
4 Bathrooms
16 Guests
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $997
/Night
7 Nights - $6,979
Pet-Friendly Vacation Rentals in Berkshire County
Over 495+
Pet-Friendly Vacation Rentals in or Near Berkshire County
House
9.6
(
4 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
2500 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $676
/Night
7 Nights - $4,734
House
10.0
(
6 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1097.92 ft²
-
Parking
-
Internet
-
Pet Friendly
-
Child Friendly
US $351
/Night
7 Nights - $2,457
Hotel
9.8
(
28 Reviews
)
1 Bathroom
-
Breakfast
-
Parking
-
Pool
-
Balcony/Terrace
US $265
/Night
7 Nights - $1,853
House
9.2
(
23 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1400 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
US $858
/Night
7 Nights - $6,005
House
10.0
(
49 Reviews
)
7 Bedrooms
4 Bathrooms
16 Guests
4000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $1,254
/Night
7 Nights - $8,781
Cabin
9.6
(
250 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
640 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $266
/Night
7 Nights - $1,861
House
9.6
(
99 Reviews
)
3 Bedrooms
2 Bathrooms
9 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $468
/Night
7 Nights - $3,278
House
9.8
(
72 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2400 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $404
/Night
7 Nights - $2,830
See More Pet-Friendly Vacation Rentals in Berkshire County on PetFriendly.io
Large Vacation Homes & Villas in Berkshire County
Over 308+
Large Vacation Homes & Villas in or Near Berkshire County
House
10.0
(
169 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
2400 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $377
/Night
7 Nights - $2,639
Bed & Breakfast
10.0
(
14 Reviews
)
13 Bedrooms
13 Bathrooms
26 Guests
291.53 ft²
-
Parking
-
Air Conditioner
-
Internet
US $168
/Night
7 Nights - $1,176
House
6 Bedrooms
4 Bathrooms
14 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $826
/Night
7 Nights - $5,782
House
10.0
(
63 Reviews
)
5 Bedrooms
3 Bathrooms
11 Guests
2800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $705
/Night
7 Nights - $4,934
House
10.0
(
83 Reviews
)
5 Bedrooms
2 Bathrooms
9 Guests
2600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $894
/Night
7 Nights - $6,255
House
9.6
(
88 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $503
/Night
7 Nights - $3,524
House
10.0
(
127 Reviews
)
5 Bedrooms
3 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $753
/Night
7 Nights - $5,270
House
10.0
(
65 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
3100 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $859
/Night
7 Nights - $6,013
See More Family Vacation Rentals in Berkshire County on FVR
Wheelchair Accessible Vacation Homes in Berkshire County
Over 153+
Wheelchair Accessible Vacation Homes in or Near Berkshire County
Apartment
10.0
(
21 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $712
/Night
7 Nights - $4,981
House
5 Bedrooms
3 Bathrooms
12 Guests
3799.66 ft²
-
Parking
-
Internet
-
Child Friendly
-
Wheelchair Accessible
US $1,504
/Night
7 Nights - $10,528
House
8.6
(
379 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $124
/Night
7 Nights - $868
Apartment
10.0
(
12 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $272
/Night
7 Nights - $1,902
Apartment
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $254
/Night
7 Nights - $1,780
Apartment
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Pool
-
Kitchen
-
Air Conditioner
-
Internet
US $192
/Night
7 Nights - $1,346
Apartment
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Private Pool
-
Parking
-
Pool
-
Skiing
US $282
/Night
7 Nights - $1,973
Condo
9.8
(
40 Reviews
)
3 Bedrooms
2 Bathrooms
9 Guests
1300 ft²
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
US $300
/Night
7 Nights - $2,100
Berkshire County Vacation Rentals and Airbnb Places to Stay Under $200
Over 279+
Berkshire County Vacation Rentals and Airbnb Places to Stay Under $200
House
10.0
(
9 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
7535 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $193
/Night
7 Nights - $1,348
Apartment
8 Bedrooms
9 Bathrooms
24 Guests
0.97 ft²
-
Private Pool
-
Hot Tub
-
Pool
-
Laundry
US $77
/Night
7 Nights - $539
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $196
/Night
7 Nights - $1,372
Apartment
9.8
(
21 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $192
/Night
7 Nights - $1,346
Apartment
9.8
(
6 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $192
/Night
7 Nights - $1,346
Apartment
9.8
(
6 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $182
/Night
7 Nights - $1,277
Condo
9.2
(
29 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $197
/Night
7 Nights - $1,381
New
Apartment
8.0
(
1 Review
)
1 Bedroom
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $133
/Night
7 Nights - $934
Instantly Bookable Vacation Homes in Berkshire County
Over 747+
Instantly Bookable Vacation Homes in or Near Berkshire County
Apartment
9.8
(
74 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Kitchen
-
Air Conditioner
-
Child Friendly
-
Laundry
US $579
/Night
7 Nights - $4,054
House
10.0
(
1 Review
)
3 Bedrooms
1 Bathroom
5 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $610
/Night
7 Nights - $4,269
Cottage
10.0
(
120 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $266
/Night
7 Nights - $1,865
Ski Chalet
9.8
(
28 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
1800 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $517
/Night
7 Nights - $3,618
New
House
10.0
(
38 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2750 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Child Friendly
US $591
/Night
7 Nights - $4,136
House
9.4
(
33 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1900 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $410
/Night
7 Nights - $2,867
House
9.2
(
21 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $319
/Night
7 Nights - $2,230
House
9.6
(
25 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $362
/Night
7 Nights - $2,537
About Berkshire County Vacation Rentals
With more than 12 Berkshire County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Berkshire County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Berkshire County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Berkshire County. Places to stay near Berkshire County are 3745.67 ft² on average, with prices averaging US $1,252 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Berkshire County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Berkshire County
| Type | Count |
|---|---|
| Villas | 12 |
Use these Quick Filters to Find a Vacation Rental in Berkshire County
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Berkshire County.
Weather in Berkshire County
View the weather forecast for Berkshire County before booking your Berkshire County Vacation Rentals to confirm your best time to go.
December - February
High 42°F Low 16°F
March - May
High 66°F Low 20°F
June - August
High 81°F Low 55°F
September - November
High 77°F Low 28°F
Top Attractions Around Berkshire County, MA
Estiavillas offers a large selection of top attractions around Berkshire County. Research things to do on your vacation before you visit Berkshire County.
Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Ski Butternut
Catamount Ski Area
Norman Rockwell Museum
National Shrine of the Divine Mercy
Lee Prime Outlets
Bousquet Ski Area
Mount Greylock
Williamstown Theatre Festival
Cranwell Golf Club
Jacob's Pillow
Berkshire Museum
Hancock Shaker Village
Otis Ridge
Pittsfield State Forest
October Mountain State Forest
Beartown State Forest
Savoy Mountain State Forest
The Mount
Otis Reservoir
Topia Arts Center
Shakespeare and Company
Kennedy Park
Mount Greylock State Reservation Visitor Center
Sterling and Francine Clark Art Institute
Naumkeag
Colonial Theater
Other Places to Stay Near Berkshire County, MA
The Berkshires
814 Properties
Great Barrington
140 Properties
Lenox
83 Properties
Hancock
83 Properties
Jiminy Peak Mountain Resort
83 Properties
Williamstown
78 Properties
Pittsfield
61 Properties
Lee
49 Properties
Stockbridge
39 Properties
Becket
37 Properties
North Egremont
33 Properties
Egremont
33 Properties
Complexes around Berkshire County, MA
Wyndham Bentley Brook
34 Properties
Jiminy Peak
27 Properties
Ski
26 Properties
Berkshires
3 Properties
Courtyard
3 Properties
Econo Lodge Lee Great Barrington
3 Properties
Fairfield Inn
3 Properties
Fairfield Inn
3 Properties
Hampton Inn Suites
3 Properties
Hilton Garden Inn Pittsfield
3 Properties
Holiday Inn Club Vacations Oak N Spruce Resort
3 Properties
Holiday Inn Express Hotel Great Barrington Ihg
3 Properties
Howard Johnson
3 Properties
The Hill
3 Properties
The Williams Inn
3 Properties
Berkshire County Vacation Rental Frequently Asked Questions
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:
- The Kemble- Built by a US Secretary of State in Lenox
- Equipped Villa with Access to Amazing Amenities!
- Winthrop Estate – An Elegant Home
- Spacious Villa with Access to Various Amenities!
- Villa with Access to Amazing Amenities!
- The Freeman - Newly Renovated 14K SF Estate on 40 Acres
- LUXURY BERKSHIRES RETREAT - Family Compound! - 2 separate but attached homes!
- The Winthrop Estate - 12K SF 32 Acres
- Beautiful 2BD Villa in Berkshires Resort
- Villa with Access to Various Amenities
How many vacation rentals have private pools in Berkshire County?
There are 122 vacation rentals with private pools near Berkshire County. Top-rated homes that have access to a swimming pool include:
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:
How many vacation rentals are available in Berkshire County?
Currently, the total number of properties listed in 2026 is over 12 in the Berkshire County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Berkshire County.
