Estia Villas - Vacation Rentals in Jacob's Pillow
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
9.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
7 Guests
1517.71 ft²
-
Parking
-
View -
Air Conditioner -
Internet
US $362
/Night
7 Nights - $2,536
US $228
/Night
7 Nights - $1,597
House
10.0
(
5 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
2400 ft²
-
Hot Tub -
Parking
-
Balcony/Terrace
-
Kitchen
US $799
/Night
7 Nights - $5,591
House
9.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
7 Guests
1205.56 ft²
-
Parking
-
Spa -
Internet
-
Child Friendly
US $327
/Night
7 Nights - $2,291
House
10.0
(
5 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
544 ft²
-
Parking
-
Ocean View -
Balcony/Terrace
-
View
US $441
/Night
7 Nights - $3,089
House
8.0
(
1 Review
)
2 Bedrooms
1 Bathroom
7 Guests
818.06 ft²
-
Parking
-
View
-
Internet
-
Child Friendly
US $333
/Night
7 Nights - $2,331
House
10.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $529
/Night
7 Nights - $3,702
Ski Chalet
9.8
(
29 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $534
/Night
7 Nights - $3,740
House
9.8
(
21 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
1512 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $401
/Night
7 Nights - $2,808
House
9.8
(
19 Reviews
)
6 Bedrooms
4 Bathrooms
14 Guests
-
Private Pool -
Hot Tub
-
Parking
-
Pool
US $1,081
/Night
7 Nights - $7,565
House
9.8
(
17 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $725
/Night
7 Nights - $5,075
House
9.8
(
15 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $440
/Night
7 Nights - $3,081
Cabin
9.8
(
12 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $414
/Night
7 Nights - $2,899
House
9.8
(
6 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1530 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $633
/Night
7 Nights - $4,432
House
9.6
(
243 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $259
/Night
7 Nights - $1,810
House
9.6
(
18 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1450 ft²
-
Oceanfront -
Parking
-
Ocean View
-
Balcony/Terrace
US $464
/Night
7 Nights - $3,248
House
9.6
(
11 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
816 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $306
/Night
7 Nights - $2,142
House
9.6
(
8 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1605 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $537
/Night
7 Nights - $3,757
Cabin
9.0
(
11 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $328
/Night
7 Nights - $2,299
House
3 Bedrooms
1 Bathroom
7 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $346
/Night
7 Nights - $2,424
House
10.0
(
103 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
3400 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $438
/Night
7 Nights - $3,065
House
10.0
(
41 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $589
/Night
7 Nights - $4,123
House
10.0
(
2 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
2050 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $976
/Night
7 Nights - $6,830
★ 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 Jacob's Pillow.
Weather in Jacob's Pillow
View the weather forecast for Jacob's Pillow before booking your Jacob's Pillow 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 Jacob's Pillow, MA
Estiavillas offers a large selection of top attractions around Jacob's Pillow. Research things to do on your vacation before you visit Jacob's Pillow.
Tanglewood Music Center
Ski Butternut
Norman Rockwell Museum
National Shrine of the Divine Mercy
Lee Prime Outlets
Cranwell Golf Club
Otis Ridge
October Mountain State Forest
Blandford Ski Area
Beartown State Forest
The Mount
Otis Reservoir
Shakespeare and Company
Kennedy Park
Naumkeag
Chester Town Hall
Lenox Library
Lee Library
Berkshire Botanical Garden
Goose Pond Reservation
Jacob's Pillow Vacation Rental Frequently Asked Questions
How many vacation rentals are available in Jacob's Pillow?
Currently, the total number of properties listed in 2026 is over 62 in the Jacob's Pillow area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Jacob's Pillow.
