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Compare 385 Vacation Homes in Spencertown with updated reviews, rates, and availability.

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
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
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
10 Jul - 11 Jul
10 Raj. - 11 Raj.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
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Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, (11)
"The property was fabulous and had lots of activities on site(basketball hoops,pickleball court and pool). Excellent location close to Great Barrington downtown which has an amazing selection of restaurants. Overall,fantastic stay!"
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
10.0 out of 10, Exceptional, (7)
"Le Soleil Suite was just as it was pictured. It was very pretty, neat and clean. Sarah provided everything that we needed for our stay and she was very responsive if we had any questions.It was so quiet and peaceful. We truly enjoyed our stay!"
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
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
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
9.8 out of 10, Exceptional, (10)
"The number of bedrooms and bathrooms was great for the 13 of us. The big kitchen, pantry and long dining tables made for fun interaction. The game room with pool table and ping pong table were perfect for after dinner fun. Beautiful property on the river. We plan to go back. Historic homes are tough to maintain and our hope is that it is as nice in the future as it was this week."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
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!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, (3)
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, (2)
"The barn was amazing and just perfect for our weekend away. Ricky was really great to communicate with and very responsive. We can’t wait to go again soon!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
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
Cottage at Copake Lake
9.8 out of 10, Exceptional, (57)
"What an amazing property this was to stay in. Plenty of space but felt cosy. It was cold and snowy when we stayed so couldn’t take advantage of the proximity of the lake, but did get to use the fireplace. Cottage is isolated enough to feel like we were well away from the city but close enough to where we wanted to visit. Close to Bash Bish falls, Rodger’s Book Barn, Coopers Daughter and, of course, the supermarket and Stewart’s. Will definitely book again for our next trip"
Cottage at Copake Lake
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.
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
10.0 out of 10, Exceptional, (12)
"This was a great house! They thought of all the details, had everything you could need. Hot tub was clean and entire house was spotless. Beds were comfortable. Great location, so close to downtown Great Barrington, cute shops and restaurants. And also super close to lots of hikes and ski mountain etc. We had a really fantastic stay and would stay again and recommend!"
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
All the comforts of home
9.0 out of 10, Wonderful, (19)
"Great little place to get away Steven was a great host"
The price is SAR 443
SAR 553 total
includes taxes & fees
21 Jul - 22 Jul
21 Raj. - 22 Raj.
All the comforts of home
Hudson Valley Chalet
9.2 out of 10, Wonderful, (5)
"We had such a nice weekend at this beautiful home! The location was great, there were awesome views, and Marc was a very kind, courteous host! He was very easy to get ahold of if we had any questions. The hot tub was very relaxing and spacious. Also, it had all of the necessities. If you are looking for a family-friendly winter rental this is a great place to book."
Hudson Valley Chalet
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Sleepy Hollow Lake Home w/ Deck, Pool Access!
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay. House is brand new, super clean and bright. We loved the access to bikes, plus tennis, pool, and the lake. Will definitely return!"
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
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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 Spencertown

Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (74)
"Expedia said they have a Sunday buffet, but they didn't."
The price is SAR 470
SAR 528 total
includes taxes & fees
23 Jun - 24 Jun
23 Jum. II - 24 Jum. II
Micosta Leisure Inn
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
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
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 Spencertown hotels
Expedia verified reviews