Estia Villas - Vacation Rentals in Chesterwood
House
10.0
(
97 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1600 ft²
-
Parking -
Balcony/Terrace -
Kitchen -
Air Conditioner
US $405
/Night
7 Nights - $2,833
House
10.0
(
2 Reviews
)
8 Bedrooms
3 Bathrooms
8 Guests
3003.13 ft²
-
View -
Air Conditioner
-
Internet -
Child Friendly
US $600
/Night
7 Nights - $4,198
Bed & Breakfast
9.2
(
113 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast -
Parking
-
Pool -
Balcony/Terrace
US $444
/Night
7 Nights - $3,106
House
10.0
(
15 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $466
/Night
7 Nights - $3,261
House
10.0
(
1 Review
)
4 Bedrooms
4 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
View
-
Air Conditioner
US $360
/Night
7 Nights - $2,520
US $264
/Night
7 Nights - $1,846
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
9.5
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1603.82 ft²
-
Parking
-
Spa -
Internet
-
Pet Friendly
US $379
/Night
7 Nights - $2,651
House
10.0
(
70 Reviews
)
4 Bedrooms
2 Bathrooms
7 Guests
1635 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $365
/Night
7 Nights - $2,555
House
10.0
(
39 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1850 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,096
/Night
7 Nights - $7,670
House
10.0
(
18 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2764 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $583
/Night
7 Nights - $4,078
House
10.0
(
12 Reviews
)
5 Bedrooms
2 Bathrooms
12 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,142
/Night
7 Nights - $7,995
House
10.0
(
10 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
-
Hot Tub -
Parking
-
Ocean View -
Balcony/Terrace
US $722
/Night
7 Nights - $5,057
House
10.0
(
8 Reviews
)
3 Bedrooms
4 Bathrooms
7 Guests
2700 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $839
/Night
7 Nights - $5,872
House
10.0
(
6 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $856
/Night
7 Nights - $5,993
Cabin
10.0
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1270 ft²
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $404
/Night
7 Nights - $2,825
Cottage
10.0
(
4 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $382
/Night
7 Nights - $2,676
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $600
/Night
7 Nights - $4,199
House
10.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $380
/Night
7 Nights - $2,661
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $226
/Night
7 Nights - $1,582
House
9.8
(
107 Reviews
)
6 Bedrooms
7 Bathrooms
12 Guests
9000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,575
/Night
7 Nights - $11,022
House
9.8
(
63 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $539
/Night
7 Nights - $3,773
House
9.8
(
14 Reviews
)
5 Bedrooms
5 Bathrooms
10 Guests
4500 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,349
/Night
7 Nights - $9,440
New
House
9.8
(
7 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1700 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $347
/Night
7 Nights - $2,432
★ 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 Chesterwood.
Weather in Chesterwood
View the weather forecast for Chesterwood before booking your Chesterwood 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 Chesterwood, MA
Estiavillas offers a large selection of top attractions around Chesterwood. Research things to do on your vacation before you visit Chesterwood.
Tanglewood Music Center
Ski Butternut
Catamount Ski Area
Norman Rockwell Museum
National Shrine of the Divine Mercy
Lee Prime Outlets
Bousquet Ski Area
Cranwell Golf Club
Jacob's Pillow
Berkshire Museum
Hancock Shaker Village
Pittsfield State Forest
October Mountain State Forest
Beartown State Forest
The Mount
Shakespeare and Company
Taconic State Park
Kennedy Park
Naumkeag
Colonial Theater
Chesterwood Vacation Rental Frequently Asked Questions
How many vacation rentals are available in Chesterwood?
Currently, the total number of properties listed in 2026 is over 129 in the Chesterwood area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesterwood.
