Estia Villas - Vacation Rentals in The Berkshires
Villa
10.0
(
20 Reviews
)
13 Bedrooms
13 Bathrooms
35 Guests
15000 ft²
-
Parking -
Spa -
Balcony/Terrace -
Kitchen
US $4,804
/Night
7 Nights - $33,625
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
(
143 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $201
/Night
7 Nights - $1,406
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 The Berkshires Vacation Rentals
Luxury Places to Stay in The Berkshires
Over 1671+
Luxury Places to Stay in or Near The Berkshires
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
5 Bathrooms
16 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $5,227
/Night
7 Nights - $36,590
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 $2,576
/Night
7 Nights - $18,032
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
10.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
10 Guests
-
Hot Tub
-
Air Conditioner
-
Internet
-
Child Friendly
US $2,414
/Night
7 Nights - $16,899
Cabin
10.0
(
51 Reviews
)
6 Bedrooms
7 Bathrooms
14 Guests
7500 ft²
-
Parking
-
Spa
-
Balcony/Terrace
-
Kitchen
US $2,041
/Night
7 Nights - $14,289
Find More The Berkshires Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in The Berkshires
Over 481+
Top-Rated Vacation Rentals with a Pool in or Near The Berkshires
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 $1,159
/Night
7 Nights - $8,112
Cottage
10.0
(
63 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
450 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $376
/Night
7 Nights - $2,632
House
10.0
(
59 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
(
45 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
US $335
/Night
7 Nights - $2,347
House
10.0
(
40 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
3300 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $560
/Night
7 Nights - $3,917
House
10.0
(
37 Reviews
)
6 Bedrooms
4 Bathrooms
16 Guests
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $1,001
/Night
7 Nights - $7,010
Pet-Friendly Vacation Rentals in The Berkshires
Over 502+
Pet-Friendly Vacation Rentals in or Near The Berkshires
House
9.6
(
4 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
2500 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $630
/Night
7 Nights - $4,410
House
10.0
(
6 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1097.92 ft²
-
Parking
-
Internet
-
Pet Friendly
-
Child Friendly
US $381
/Night
7 Nights - $2,667
Hotel
9.8
(
32 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Balcony/Terrace
US $260
/Night
7 Nights - $1,822
House
9.2
(
23 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1400 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
US $890
/Night
7 Nights - $6,228
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
(
253 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
640 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $238
/Night
7 Nights - $1,669
House
9.6
(
99 Reviews
)
3 Bedrooms
2 Bathrooms
9 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $513
/Night
7 Nights - $3,592
House
9.8
(
72 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2400 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $419
/Night
7 Nights - $2,932
See More Pet-Friendly Vacation Rentals in The Berkshires on PetFriendly.io
Large Vacation Homes & Villas in The Berkshires
Over 307+
Large Vacation Homes & Villas in or Near The Berkshires
House
10.0
(
169 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
2400 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $365
/Night
7 Nights - $2,557
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 $715
/Night
7 Nights - $5,004
House
10.0
(
84 Reviews
)
5 Bedrooms
2 Bathrooms
9 Guests
2600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $701
/Night
7 Nights - $4,910
House
9.6
(
89 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $461
/Night
7 Nights - $3,227
House
10.0
(
127 Reviews
)
5 Bedrooms
3 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $832
/Night
7 Nights - $5,827
House
10.0
(
65 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
3100 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $845
/Night
7 Nights - $5,915
See More Family Vacation Rentals in The Berkshires on FVR
Wheelchair Accessible Vacation Homes in The Berkshires
Over 154+
Wheelchair Accessible Vacation Homes in or Near The Berkshires
Apartment
10.0
(
22 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
(
13 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $262
/Night
7 Nights - $1,837
Apartment
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $176
/Night
7 Nights - $1,233
Apartment
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Pool
-
Kitchen
-
Air Conditioner
-
Internet
US $251
/Night
7 Nights - $1,758
Apartment
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Private Pool
-
Parking
-
Pool
-
Skiing
US $176
/Night
7 Nights - $1,233
Apartment
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $176
/Night
7 Nights - $1,233
The Berkshires Vacation Rentals and Airbnb Places to Stay Under $200
Over 296+
The Berkshires Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
8 Bedrooms
9 Bathrooms
24 Guests
0.97 ft²
-
Private Pool
-
Hot Tub
-
Pool
-
Laundry
US $77
/Night
7 Nights - $539
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
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $196
/Night
7 Nights - $1,372
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $198
/Night
7 Nights - $1,388
Apartment
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
850 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $172
/Night
7 Nights - $1,207
Apartment
9.8
(
21 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $176
/Night
7 Nights - $1,233
Apartment
9.8
(
9 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $176
/Night
7 Nights - $1,233
Apartment
9.8
(
6 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $185
/Night
7 Nights - $1,294
See More The Berkshires Vacation Rental Deals
Instantly Bookable Vacation Homes in The Berkshires
Over 757+
Instantly Bookable Vacation Homes in or Near The Berkshires
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 $265
/Night
7 Nights - $1,853
Ski Chalet
9.8
(
28 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
1800 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $518
/Night
7 Nights - $3,626
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 - $4,140
House
9.4
(
35 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1900 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $526
/Night
7 Nights - $3,680
House
9.2
(
22 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $342
/Night
7 Nights - $2,393
House
10.0
(
14 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $299
/Night
7 Nights - $2,096
About The Berkshires Vacation Rentals
With more than 12 The Berkshires 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 The Berkshires.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas The Berkshires, 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 The Berkshires. Places to stay near The Berkshires are 3745.67 ft² on average, with prices averaging US $1,407 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in The Berkshires 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 The Berkshires
| Type | Count |
|---|---|
| Villas | 12 |
Use these Quick Filters to Find a Vacation Rental in The Berkshires
★ 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 The Berkshires.
Weather in The Berkshires
View the weather forecast for The Berkshires before booking your The Berkshires Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around The Berkshires, MA
Estiavillas offers a large selection of top attractions around The Berkshires. Research things to do on your vacation before you visit The Berkshires.
Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Ski Butternut
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
Other Places to Stay Near The Berkshires, MA
Berkshire County
849 Properties
Great Barrington
142 Properties
Hancock
93 Properties
Jiminy Peak Mountain Resort
93 Properties
Lenox
83 Properties
Williamstown
80 Properties
Pittsfield
63 Properties
Lee
51 Properties
Stockbridge
40 Properties
Becket
37 Properties
South Lee
34 Properties
North Egremont
34 Properties
Complexes around The Berkshires, 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
The Berkshires Vacation Rental Frequently Asked Questions
What are the top vacation rentals in The Berkshires?
There are a lot of options in The Berkshires. If you plan on staying in the The Berkshires area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in The Berkshires:
- 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 The Berkshires?
There are 121 vacation rentals with private pools near The Berkshires. Top-rated homes that have access to a swimming pool include:
Which vacation homes in The Berkshires are best for families?
If you are looking for a family-friendly vacation home in The Berkshires, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in The Berkshires:
How many vacation rentals are available in The Berkshires?
Currently, the total number of properties listed in 2026 is over 12 in the The Berkshires area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in The Berkshires.
