Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Barns
Cabins
Cottages
Estates
Farmhouses
Homes
Lodges
Boats
Bungalows
Castles
Chalets
Condos
Hotels
Studios
Townhomes
Villas
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Berkshires Vacation Rentals with Parking Included(85)

85 Results
  • 8 BR,
  • 5 BA,
  • Sleeps 14
(7)
$449 - $949
per night
2 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 15
2 - 3 night minimum stay
(19)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 night minimum stay
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(6)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
1 Review
$125 - $150
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(3)
  • 4 BR,
  • 4 BA,
  • Sleeps 12
30 night minimum stay
2 Reviews
$995
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
2 Reviews
$500
per night
6 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
6 night minimum stay
2 Reviews
$350 - $429
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
(8)
$175 - $300
per night
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(33)
$1,300 - $1,321
per night
2 - 7 night minimum stay
  • 9 BR,
  • 6 BA,
  • Sleeps 20
2 - 7 night minimum stay
1 Review
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
$175
per night
5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
5 night minimum stay
(6)
  • 5 BR,
  • 3 BA,
  • Sleeps 12
(15)
$50 - $325
per night
2 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
(16)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 30 night minimum stay
(11)
  • 3 BR,
  • 2 BA,
  • Sleeps 11
3 night minimum stay
(3)
$1,900 - $1,993
per night
2 - 7 night minimum stay
  • 14 BR,
  • 9 BA,
  • 2 HF BA,
  • Sleeps 30
2 - 7 night minimum stay
1 Review
  • 2 BR,
  • Sleeps 4
(20)
$1,500 - $2,350
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(3)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night minimum stay
1 Review
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 14
2 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 9
1 Review
$100 - $193
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
(16)
$150 - $200
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 11
2 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 6 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
1 Review
 

Recent Berkshires Reviews

This is the one!

5 of 5
I'm sorry for not responding sooner. Your home was the best vacation rental in which I have stayed today and I rent frequently in the Berkshires. I am going to want to stay there again for a week. The home was exactly what my wife and I needed for our family. Your instructions on what to do in the area really helped us out, and John was really wonderful as well. The grounds were beautiful. What can I say, I have finally found the right place.
  • Submitted: Dec 16, 2014
  • Stayed: Nov 2014

Amazing stay! We will be back!

5 of 5
A group of five of us wanted to get away for a fun Autumn weekend, and this was absolutely the perfect spot! The cabin is amazingly cozy. Ilana is very considerate and incredibly accommodating for my friends and me. The area is quiet and right on the lake. It's so peaceful and a great getaway from NYC. We cooked dinner and spent the entire night by the fire pit. The cabin had everything we needed! The only complaint is we weren't able to stay longer! It was honestly the perfect weekend! This place would be perfect any season. We will definitely be coming back for a longer trip!
  • Submitted: Dec 4, 2014
  • Stayed: Oct 2014

Perfect Getaway for Cousins Club Weekend!

5 of 5
We were in search of a large house that could accommodate many families for our cousins club weekend and the Berkshire Country Estate was the perfect find! Plenty of room for families to have their own space but also convene together for dining and game playing. We were all very comfortable in this beautiful, charming home and the owners were a pleasure to deal with and very welcoming. The house is well equipped with cooking utensils and a grill so it was easy to eat in as a family. Also, the game room was a big plus for the kids (they loved the air hockey and pin ball machine) and the outside swing set and basketball hoop were a plus and we all enjoyed ping pong in the barn. We even had a family kick ball game on the large yard. I know there are plenty of sightseeing opportunities close to this property but the house was so great, we never left for the weekend! Thank you for a memorable weekend and we look forward to returning:)
  • Submitted: Nov 13, 2014
  • Stayed: May 2014