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Compare 564 Vacation Homes in Craryville with updated reviews, rates, and availability.

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is ¥34,284
¥73,037 total
includes taxes & fees
Oct 7 - Oct 8
Cheerful 3-bedroom cottage with woodstove
Hudson River Way by Woodstock Way Hotel
5.0 star property
The price is ¥198,987
¥222,867 total
includes taxes & fees
Sep 28 - Sep 29
Hudson River Way by Woodstock Way Hotel
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (87)
"Very nice property. Very nice owner. No problems noted."
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
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.
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (20)
"Lovely home, dog friendly ! Amazing stay, great location. "
Stockbridge Home, Come Experience The Berkshires!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (13)
"Me and my husband and my sister and her husband came to the Hudson Valley to place a bench in his hometown in his memory. We thoroughly enjoyed our time at this property. It was just exactly what we needed-quiet and relaxing!"
The price is ¥22,748
¥47,863 total
includes taxes & fees
Oct 8 - Oct 9
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Historic Saugerties Home w/ Deck: River Views!
10.0 out of 10, Exceptional, (13)
"Very peaceful location in our favorite Hudson Valley town, sweet Saugerties! The property manager was extremely responsive, the neighbors were very nice — one even recommended a local swimming hole — and the house was very cute and unique. We loved waking up to the sound of birds and the sunrise over the Hudson. We also loved being able to walk into the village center for dinner and ice cream. The house was clean, comfortable, and we very much enjoyed our stay. "
Historic Saugerties Home w/ Deck: River Views!
Cleo’s Cabin: Private Retreat with Fenced Dog Run
8.8 out of 10, Excellent, (8)
"We were in town for HITS and this was a great place to spend a few nights! The cabin had everything we needed and was exactly as pictured online. Beds were super comfortable too. Highly recommend! "
Cleo’s Cabin: Private Retreat with Fenced Dog Run
Private + Peaceful 2 BR w/ River Views
10.0 out of 10, Exceptional, (7)
"I took my husband on a mystery weekend to upstate NY and arranged to have our friends from Ithaca meet us in Clementon. We loved the house. Found it welcoming and easy to manage - beautiful and clean. We went to OPUS 40 and did some other exploring in the area and enjoyed relaxing in the house and reconnecting with our friends. "
Private + Peaceful 2 BR w/ River Views
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
10.0 out of 10, Exceptional, (2)
"This property is perfectly located between Saugerties and Kingston with easy access to both. We wanted a place that was easy to explore the area from and we scored with this house. Everything was clean and we were provided with everything we could need, pots & pans, soap & shampoo, washer & dryer--all of it. We also had plenty of room to do the work we brought with us. The house stayed cool the whole time (day & night) and we really enjoyed it. "
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
9.2 out of 10, Wonderful, (9)
"We had a great stay at this house. The pool was a good size with a deep end. It was really nice to have a pond behind the house. There were several comfortable beds but the trundle was very uncomfortable. The multiple decks were nice. The shampoo and conditioner provided were very nice. Kitchen was lovely and spacious. The house had a little more wear and tear than was evident from the pictures. There was no hammock but there is a picture of one in the listing. The immediate area wasn’t very...
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
Kingston Crawfish Cottage Near Catskills!
9.8 out of 10, Exceptional, (7)
"AAAAAAAAAAAAA++++++++++!!!!!!!!!!"
Kingston Crawfish Cottage Near Catskills!
4-bedrooms with gym+spa access steps from Garlic Festival
9.2 out of 10, Wonderful, (13)
"Perfect for our stay, close to HITS and had everything we needed. Clean and well maintained."
4-bedrooms with gym+spa access steps from Garlic Festival
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (10)
"Enjoy easy access to Laurel Lake, Lenox and High Lawn Farm from this lovely space! A quick walk to the dock across the street affords time by the water to read, swim or kayak. The kitchen is nicely appointed, the house heats and cools very efficiently and the owners are wonderfully communicative. Had a great stay and would return!"
Private Access To Laurel Lake, Enjoy Lake Life
Hudson River views with pool and hot tub
9.8 out of 10, Exceptional, (19)
"Beautiful location overlooking the Hudson River. Near many cute small towns, nice restaurants and sightseeing opportunities. Weather was dreadfully hot during our stay, so a/c had a hard time keeping the upstairs cool - pool was very welcome respite. Not as clean as we hoped which we communicated to the host after our stay and she waived our cleaning fee."
Hudson River views with pool and hot tub
Saugerties home with gym+spa steps from Garlic Festival
9.2 out of 10, Wonderful, (12)
"Great location, easy access to HITS. Host was great!"
Saugerties home with gym+spa steps from Garlic Festival
Catskill Vacation Rental: Private Deck & Fire Pit
9.6 out of 10, Exceptional, (5)
"Only issue was fire alarm went off in the middle of night 2 times"
Catskill Vacation Rental: Private Deck & Fire Pit
Storybook House in Prime Catskills Location 5 Min to Town/10 Min to Hudson River
9.4 out of 10, Exceptional, (6)
"Cute house on a quiet street close to town. Andrea suggested some good restaurants."
Storybook House in Prime Catskills Location 5 Min to Town/10 Min to Hudson River
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (17)
"At the end of a dead-end street but only two blocks from the center of Stockbridge, this century-old charmer may be the best-kept and best-supplied rental in the Berkshires. We stayed a month(!) and loved it. The location is unbeatable, an easy walk from the Red Lion and within 15 minutes of Tanglewood, The Mount, the Rockwell museum and other attractions. Four local trails begin 100 feet away, including the Ice Glen. A beautiful, productive garden awaits, and the screened front porch may be...
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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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.
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Other property types in Craryville

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (13)
"Me and my husband and my sister and her husband came to the Hudson Valley to place a bench in his hometown in his memory. We thoroughly enjoyed our time at this property. It was just exactly what we needed-quiet and relaxing!"
The price is ¥22,748
¥47,863 total
includes taxes & fees
Oct 8 - Oct 9
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (132)
"Quiet and secluded, but close to everything you may need and plenty of wildlife to observe."
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Sanctuary of the Sacred Dream-Entire Property. Copake Lake Access.
Sanctuary of the Sacred Dream-Entire Property. Copake Lake Access.
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.