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Compare Vacation Homes in Housatonic with updated reviews, rates, and availability.

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is SAR 597
SAR 1,255 total
includes taxes & fees
30 Jun - 1 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Private Lake House in the Berkshires
Lake Side
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, (16)
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Cozy Retreat on Copake Lake in our Charming Home
Front of the house
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, (32)
"Great stay. A short walk to everything the lake has to offer."
Cozy Retreat on Copake Lake in our Charming Home
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Spectacular views and close to Great Barrington.
Private kitchen
Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
Tranquil 3-BR Waterfront Retreat
HRDSC00175.jpg
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (69)
"Top notch!! Will definitely be back. Thanks!!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
Waterview Home in the Berkshires: Near Hiking
Sheffield Vacation Rental | 3BR | 2BA | 2,262 Sq Ft | 2 Steps to Enter
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
Comfortable New Decor in Living Room Equipped w Smart TV and Deck
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
9.8 out of 10, Exceptional, (60)
"This was the 2nd time we have rented this property and again it did not disappoint. The location on the mountain is beautiful. The check in/check out process was easy. The host (Howie) responds to any questions very quickly and enthusiastically. Perfect place for a family with spacious bedrooms, nice kitchen, back deck with grill. Looking forward to going back"
The price is SAR 1,309
SAR 2,415 total
includes taxes & fees
30 Jun - 1 Jul
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
Hot tub, canoe, dog-friendly/family friendly cottage in the Berkshires!!
Property grounds
Hot tub, canoe, dog-friendly/family friendly cottage in the Berkshires!!
10.0 out of 10, Exceptional, (1)
"Absolutely loved it. Perfect getaway when the city is too noisy. Awesome location in the woods surrounded by nothing but forest. If you plan on staying outside in the hot tub, maybe get one of those bug repellent tiki torches however i got no other complaints. Maybe a tv in the adult bedroom? Anyway good kitchen good bathroom good living room good bedroom for adults good room for children. If youre looking to get away, there isnt anything wrong in picking this place if you desire a forest get...
Hot tub, canoe, dog-friendly/family friendly cottage in the Berkshires!!
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Peace and quiet on the lake
Exterior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (187)
"Cute & clean house, awesome location right on the water, great for swimming/fishing/kayaking plus super close to the store for any supplies. Thanks again!"
Peace and quiet on the lake
Berkshire Lake access
Boat on the Lake
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
We're ready for Spring & Summer in Upstate NY!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, (4)
"Arrived at property late in the afternoon. Noticed the house was really close to a busy road. Was a little concerned since we had our dog with us. From the outside, the house looked small, but once we got inside, we were pleasantly surprised. It was very roomy & decorated very nicely. Was able to speak to the owner one day while we were eating dinner outside. He was very nice."
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Private Access To Laurel Lake, Enjoy Lake Life
Private Access To Laurel Lake, Enjoy Lake Life
10.0 out of 10, Exceptional, (6)
"My brother and I came to honor our late father, our family used to own property on Laurel lake so it was especially meaningful to us to have access to it for kayaking. The house has central ac which is harder to find, it's got plenty of bedrooms, two of which are on the first floor."
Private Access To Laurel Lake, Enjoy Lake Life
Private Cabin On Over 12 Acres Of Woods!
Private Cabin On Over 12 Acres Of Woods!
9.6 out of 10, Exceptional, (4)
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
The price is SAR 2,202
SAR 4,215 total
includes taxes & fees
6 Jul - 7 Jul
Private Cabin On Over 12 Acres Of Woods!
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Beautiful open concept for Entertaining friends and family
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, (107)
"Our party of four adults found ample space to spread out and relax at this property. There are quite a few stairs to access all three stories, including the main living space on the second story and the four bedrooms on the third story. The kitchen is well equipped and there is a charcoal grill (bring your own charcoal). There is a very nice deck overlooking the lovely and sprawling grounds below the house. A fire pit was situated behind the house. There is a balcony and patio also off the...
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Cottage at Copake Lake
Property grounds
Cottage at Copake Lake
9.8 out of 10, Exceptional, (57)
"We have enjoyed several stays in this wonderful cottage…usually in the winter. We were so delighted sitting on the porch in the evenings listening to the chorus of frogs by the lake. Absolutely enchanting! Ellen is a wonderful hostess. The cottage is immaculate and well stocked. Hopefully we will visit this cozy cottage again!"
Cottage at Copake Lake
Waterfront Escape +dock +kayaks +firepit +fireplace +games
Property grounds
Waterfront Escape +dock +kayaks +firepit +fireplace +games
10.0 out of 10, Exceptional, (4)
"Great place with lake access & sunset views. Swimming/diving dock wasn't there due to low lake levels, but beach club right next door had a nice place to swim. Kitchen could've used a baking sheet and some olive oil, but other than had everything we needed!"
Waterfront Escape +dock +kayaks +firepit +fireplace +games
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Exterior
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
10.0 out of 10, Exceptional, (25)
"Beautiful property- well maintained and excellent location."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Don't see what you're looking for?
See all available properties in Housatonic
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Housatonic

Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (861)
"Good location"
The price is SAR 634
SAR 696 total
includes taxes & fees
10 Jul - 11 Jul
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Terrace/patio
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (75)
"Only stayed one night, but would have loved to stay for one week! Beautiful grounds and our host, Steven, was super welcoming and greeted us once we arrived to check us in. Local cat also greeted us once we arrived (if you’re driving, check under your car before backing out!)"
The price is SAR 470
SAR 508 total
includes taxes & fees
7 Jul - 8 Jul
Micosta Leisure Inn
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Recent reviews of Housatonic hotels
Expedia verified reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

5/5 Excellent
Comfortable affordable Pittsfield Motel
"Hot breakfast was very well prepared and even though they didn’t have any non-pork meat products they did have a nice flavorful egg patty, which was OK. It was conveniently located to where I need to be and the staff was very friendly"
A verified traveler stayed at Best Western Plus Berkshire Hills Inn & Suites
Posted 4 days ago
Best Western Plus Berkshire Hills Inn & Suites