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Compare 583 Vacation Homes in Hillsdale with updated reviews, rates, and availability.

Historic Hudson Valley 1850 Brick Home
9.0 out of 10, Wonderful, (4)
"Easy to find and great little house. We were very comfortable for the weekend we stayed. When we had a minor issue the host was very responsive."
Historic Hudson Valley 1850 Brick Home
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (65)
"Very relaxing and enjoyable with excellent views and tranquility!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
9.6 out of 10, Exceptional, (43)
"This house had so much going for it! Great location, huge space, every bell and whistle imaginable. Very well furnished and equipped. We had a lovely time, and I can't imagine a place we'd have enjoyed more."
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
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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
Botanical Hideaway: Gorgeous Home w/ Hot Tub & Private Pond
10.0 out of 10, Exceptional, (3)
"This house is even more beautiful in person. From the high-quality dishes to the beautiful design, sauna, outdoor space and fenced-in backyard, it was a great vacation for all of us, including the dog. They were working on the barn during our stay but management was very responsive and the workers were so nice. We can't wait to see what they turn the barn into! Location was convenient to the ski area (to visit friends about 30 minutes away) and my in-laws who were also about 25 minutes away. We...
Botanical Hideaway: Gorgeous Home w/ Hot Tub & Private Pond
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, (31)
"My family and I came in for a wedding weekend. The property was clean and spacious. We all really enjoyed"
Cozy Retreat on Copake Lake in our Charming Home
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!"
The price is SAR 2,250
SAR 4,064 total
includes taxes & fees
6 Jum. II - 7 Jum. II
Peaceful Retreat Compound 10 Minutes to Great Barrington!
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
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (128)
"Our stay at The Barn in New York was unforgettable. This luxury home, converted from a barn and situated at the end of a back road, is surrounded by 50 acres of picturesque fields and has every amenity. With many restaurants a short drive away and only 20 minutes to Great Barrington, MA, and Hudson, NY, we were never short on dining options and The Prairie Whale was our favorite and also dog friendly. The area offered endless adventures with hiking trails, antique stores, galleries, and outdoor...
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
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 596
SAR 1,251 total
includes taxes & fees
30 Jum. II - 1 Raj.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
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!
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
Golf Car ride to HITS! Saugerties home with gym+spa access.
9.2 out of 10, Wonderful, (11)
"Just a work stay for us"
Golf Car ride to HITS! Saugerties home with gym+spa access.
Private Cabin On Over 12 Acres Of Woods!
10.0 out of 10, Exceptional, (3)
"The cabin is cozy and absolutely beautiful. We had everything we needed for a a relaxing stay in The Berkshires. Thanks for the comfort and welcoming hospitality."
The price is SAR 3,653
SAR 6,015 total
includes taxes & fees
6 Raj. - 7 Raj.
Private Cabin On Over 12 Acres Of Woods!
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, (105)
"We attended our daughters wedding in Philmont. House was perfect. Views were amazing! Enjoyed morning walks and sitting outside on the deck. Very tranquil!"
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Historic New Lebanon Hideaway on 33 Private Acres!
10.0 out of 10, Exceptional, (1)
Historic New Lebanon Hideaway on 33 Private Acres!
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
10.0 out of 10, Exceptional, (3)
"Our family had the pleasure of staying at this home during our child’s graduation from the nearby Berkshire school. It was the perfect situation for us in an idyllic setting very close to the campus. The home is over 250 years old and has been lovingly updated. The kitchen has seemingly all new appliances and gorgeous wood plank countertops with an adjacent windowed sitting area with a large hearth. The old and new are beautifully combined. Our family members spent a lot of time looking at the...
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
Special Second Day November discounts @ the River. Text host for discount
9.8 out of 10, Exceptional, (12)
"Beautiful views of the river and was close to all. Place was a bit dusty and the larger bedroom had a very hard bed. Owner was kind and communicative."
Special Second Day November discounts @ the River. Text host for discount
Berkshire Manor for Lasting Memories
10.0 out of 10, Exceptional, (2)
"Leah was a wonderful host to us. She provided easy-to-follow instructions for getting into the house, offered good suggestions on things to do and where to eat. Although the house was a bit larger than we needed, we chose it because of the location, the generous sized and comfortable looking (from photos) casual spaces, the kitchen and the number of bathrooms so we each had our own. This house did not disappoint! It has lots of New England charm, the beds were comfortable, as were the several...
Berkshire Manor for Lasting Memories
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!
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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 Hillsdale

Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (73)
"Expedia said they have a Sunday buffet, but they didn't."
The price is SAR 470
SAR 528 total
includes taxes & fees
6 Jum. II - 7 Jum. II
Micosta Leisure Inn
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very Good, (37)
"Our trip was amazing. We do it again again and again"
The price is SAR 469
SAR 544 total
includes taxes & fees
9 Jum. II - 10 Jum. II
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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 Hillsdale hotels
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