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Browse Select Rhinebeck Holiday Homes

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
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
10.0 out of 10, Exceptional, (11)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Hudson River Way by Woodstock Way Hotel
5.0 star property
The price is £1,207
includes taxes & fees
21 Sept - 22 Sept
Hudson River Way by Woodstock Way Hotel
The Calf Pen
10.0 out of 10, Exceptional, (21)
"The property was very convenient for an event we had traveled to and it was a welcome relaxing spot at the end of a couple of long days. All we needed for a comfortable stay was supplied from kitchen to bathroom to bedroom. "
The Calf Pen
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
10.0 out of 10, Exceptional, (34)
"My partner and I so enjoyed our 3 night stay in such a spacious and clean place. They even Provided eggs milk butter champagne and welcome cookies. That was a first!! Walking distance to lots of fine restaurants and sights and a private garden backyard as well. We will definitely return again Alex and Brian. Ithaca "
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
4-bedrooms with gym+spa access steps from Garlic Festival
9.0 out of 10, Wonderful, (12)
"We enjoyed our stay and Chris was very responsive to any questions. Would definitely stay again."
4-bedrooms with gym+spa access steps from Garlic Festival
Historic Saugerties Home w/ Deck: River Views!
10.0 out of 10, Exceptional, (12)
"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!
Ukihaus Hudson: Enchanting Hudson Valley A-Frame
9.4 out of 10, Exceptional, (3)
"My wife and I enjoyed staying in this A-frame with our dog for a few days. It had some simple, yet, well-chosen furnishing and decorations. Importantly, it was clean and welcoming. We were concerned about the proximity to route 87, and indeed you can see cars through gaps in the trees and hear the traffic if you are outside. Inside, however, was very quiet and we couldn't even hear a heavy down pour of rain."
Ukihaus Hudson: Enchanting Hudson Valley A-Frame
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
10.0 out of 10, Exceptional, (1)
"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.
The Studio at the Inn at High Falls
8.0 out of 10, Very good, (21)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The price is £198
includes taxes & fees
21 Oct - 22 Oct
The Studio at the Inn at High Falls
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (30)
"We had a wonderful time in this cabin in the woods. We saw fireflies, a bear, a fox and countless deer. The Wifi was great so the adults could work while the kids were at camp. "
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (161)
"We had a wedding nearby. House was great-very spacious and nicely furnished. Very well-located"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Esopus Creek modern Tiny house Retreat!
9.4 out of 10, Exceptional, (11)
"We were in town for a family gathering and this house was in a great location and was exactly as described."
The price is £175
includes taxes & fees
3 Oct - 4 Oct
Esopus Creek modern Tiny house Retreat!
Hudson River views with pool and hot tub
9.8 out of 10, Exceptional, (18)
"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
Spacious New 5-bedroom holiday house in lovely Hudson Valley
9.6 out of 10, Exceptional, (4)
"Clean, spacious, beautiful house and was a great experience!"
The price is £579
includes taxes & fees
26 Sept - 27 Sept
Spacious New 5-bedroom holiday house in lovely Hudson Valley
Catskill Vacation Rental: Private Deck & Fire Pit
10.0 out of 10, Exceptional, (4)
"Great place to stay, spacious inside with full kitchen and family friendly layout, and nice outdoor fire pit area. Roughly 15-30 min to our chosen destinations, close to groceries & gas for those forgotten items."
Catskill Vacation Rental: Private Deck & Fire Pit
The Chapel at Upland, with heated salt water pool and new tennis/bball court
9.8 out of 10, Exceptional, (6)
"My husband and I stayed at the Chapel on Lisa's beautiful property for a quick mid-week getaway. Lisa was a delight and incredibly welcoming. The space and property exceeded expectations! A wonderful visit all around. "
The Chapel at Upland, with heated salt water pool and new tennis/bball court
<br>Escape to our incredibly private home on 30 acres!
10.0 out of 10, Exceptional, (126)
"Lovely property, inside and out. Views of the forest that surround the home could be seen from every window and were especially beautiful at sunrise and sunset. One day we were entertained by two adolescent deer and their mother. The kitchen is well supplied. If we are in the area again, we would love to stay at this property."
<br>Escape to our incredibly private home on 30 acres!
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
10.0 out of 10, Exceptional, (172)
"Really wonderful location; the first thing we ntoiced was how quiet and secluded the house was, yet we were only a 5 minute car drive from the center of Woodstock. Couldn't be better. The house is large, though a bit old, but the owner was very amenable and responsive to all our requests. "
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
The Queen City Cottage
7.4 out of 10, Good, (16)
"My wife and I, along with my two daughters and grandchildren stayed at the Queen City Cottage for 4 nights. We needed to add an extra day at the last minute and Marissa was very responsive and accommodating. The house was clean upon our arrival and entry was a breeze. It's a bedroom, 1.5 bath, with extra bathroom in basement in laundry room. Location wa great! Restaurants and shopping minutes away. Outdoor space was tranquil with table and chairs under covered back porch. Wifi was fine, TV had...
The Queen City Cottage
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Other property types in Rhinebeck

Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (100)
"Booked a last minute 2 night stay and wish it could have been longer. The house and property is exactly as described. Comfortable, spacious, clean and on a nice quiet piece of land. Loved the outdoor spaces, enjoying coffee on the deck in the mornings and a drink by the fire pit during the evenings. Nicely located to easily enjoy Woodstock, Kingston and Rhinebeck. I bet it will be beautiful as the leaves start to change in the next month!"
The price is £288
includes taxes & fees
6 Oct - 7 Oct
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
The Farm at Hyde Park
9.8 out of 10, Exceptional, (60)
"We loved the church, loved the farm. Just what we needed. "
The Farm at Hyde Park
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (37)
"IT WAS IDYLLIC."
The price is £213
includes taxes & fees
20 Oct - 21 Oct
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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.