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Compare 383 Vacation Homes in Spencertown with updated reviews, rates, and availability.

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing
view of the back decks and steps down to our private dock

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

10.0 out of 10, Exceptional, (127)
"This lovely lake house felt more updated and larger than the pictures suggest for our Fall trip! There was plenty of space for our 8-person, multi-generational family gathering, and the layout was very conducive to both together-time and breaks. We enjoyed the large dining room table for a big family dinner cooked in the high-end kitchen, after which we retired to the great room, which was more spacious than expected, with a perfect lake view. The ground floor bedroom was great for some...
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing
Spectacular views and close to Great Barrington.
Private kitchen

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Main Level LR sliding doors to Front Deck lake view, open to the dining room.

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

10.0 out of 10, Exceptional, (3)
"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Beautiful Berkshire Farm House on 160+ Acres
Exterior

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (35)
"Our family recently stayed at this incredible vacation rental to celebrate a grandparent’s birthday, and it was truly the perfect setting for a special gathering. With 6 adults and 6 children under the age of 7, finding a place that could comfortably accommodate all of us was no small task—but this property exceeded every expectation. The location was ideal, with easy accessibility for family members traveling from different parts of the country and a manageable drive from Hartford airport....
Beautiful Berkshire Farm House on 160+ Acres
Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Private Estate, Heated Yearround Outdoor Pool
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!

Amore Estate - beautiful room with many places to explore and relax in.

9.6 out of 10, Exceptional, (18)
"There was plenty of room for four families. Beds were comfy. If you plan on cooking you might want to bring your own knives and pans. Teflon pans were scraped . Only metal utensil available to flip pancakes. "
Amore Estate - beautiful room with many places to explore and relax in.
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Lenox Vacation Rental | 3BR | 2BA | 2,457 Sq Ft | Step-Free Access

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (37)
"The home was convenient to hiking, shopping and dining. It is on a busy street and can be a bit tricky getting in and out of driveway. Inside the home was warm and welcoming. The kitchen had all cooking pans and tools we needed to make meals. There is a great grocery store right down the road. The beds were comfortable and the bathrooms were clean. The hostess was very helpful and attentive when we had a question about the heat. Be aware the staircase to upstairs bedrooms and 2nd bathroom are...
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
A Grand property in Historic Stockbridge
The Taggart House

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (93)
"Property was beautiful and walkable to town. House is old but very nice. Large enough to accommodate 9 women! Loved sitting outside enjoying perfect weather! All in all had a wonderful experience!"
A Grand property in Historic Stockbridge
Hudson Valley and The Berkshires getaway
Kitchen and dining room

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (4)
"This property is close to many Berkshires and Hudson Valley attractions. In addition to its great location, it is clean, has new appliances, and is on such a peaceful street! There is a lot of space, but it's still incredibly cozy. The beds were extra comfy, as well! I will stay here again if the opportunity presents itself. Thanks for a great stay and the easy check-in/check-out process! "
Hudson Valley and The Berkshires getaway
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Start Your Day Right - Enjoy Complimentary Fresh Bagels From Around the Corner!

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Welcome to River House!

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (12)
"We had a wonderful time in Catskill! The house was lots of fun and had tons of space for everyone. We reached out with some questions before our stay and never received a response, many of the outlets didn’t work and the house could have used an extra cleaning before we arrived but overall we had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

9.0 out of 10, Wonderful, (9)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is AED 584
AED 1,221 total
includes taxes & fees
3 Jan - 4 January 2025
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Elegant 19th Century New England 2BR vacation rental at Garfield House
Exterior

Elegant 19th Century New England 2BR vacation rental at Garfield House

10.0 out of 10, Exceptional, (88)
"Pretty darn perfect but not quite as clean as last year. Maybe different crew?"
Elegant 19th Century New England 2BR vacation rental at Garfield House
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
the most gorgeous location on earth!

PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music

9.8 out of 10, Exceptional, (35)
"We had an incredible time at this beautiful property . Completed secluded , we were in our own private oasis . We had our small intimate wedding on the property , overlooking the water , and it was perfect . The house is clean and cozy . The layout of the house is really nice , and even with many people staying there you aren’t on top of each other . So many things to do outdoors here , we spent the majority of our time enjoying the outdoors , and you really feel like you’re on your own private...
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
Large Barn styled vacation home that fits groups with space to spare.
Property grounds

Large Barn styled vacation home that fits groups with space to spare.

9.8 out of 10, Exceptional, (57)
"Everything was ideal for our Thanksgiving get together. Setting and views were perfect, made even more so with a timely blanket of fresh snow. An amazing amount of cooking provisions allowed us to cook as if we were in our own kitchen. Lots of options for keeping a large group entertained, and sleeping accomodations that pleased everyone. Host was very helpful with check-in communications and gracious with check in and out times without other bookings adjacent to ours. All in all a very special...
Large Barn styled vacation home that fits groups with space to spare.
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Exterior

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (113)
"We had a lovely holiday in this truly beautiful dream home. Everything promised in the VRBO advertisement was a reality - from the fireplace, the 4 bedrooms, the ping pong table, the kitchen and the glorious view. We even had a dusting of snow making the trees glisten. Absolutely lovely. Our host was most attentive as well—checking in with us to be sure we understood the heating units and the fireplace. We really had an ideal stay! "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Pool

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (20)
"This property was excellent for our family of 13 plus two dogs. We loved having a great t.v. room where kids could play and a second living area for the adults. Well equipped with games and puzzles. Great location for bucolic road walks. Summer would be great."
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Dancing Horse Lodge
Dancing Horse Lodge - Entrance View

Dancing Horse Lodge

9.4 out of 10, Exceptional, (38)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
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.
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Other property types in Spencertown

Micosta Leisure Inn
Terrace/patio

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is AED 477
AED 515 total
includes taxes & fees
9 Jan - 10 January 2025
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, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
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.