Holiday rentals in Dutchess County

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Top-rated holiday rentals in Dutchess County

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Guest favourite

Tiny home in Marlboro

4.96 out of 5 average rating, 319 reviews

Orchard Views from a Light-Filled Tiny Home with a Fire Pit

Wake up in a lofted bedroom wrapped in windows and descend a knotty wood staircase into the open layout of this radiant tiny home. Take a long hot shower and relax. Make coffee in a cozy kitchen, then gather around a slate fire pit in the evening and wait for the stars to emerge. Featured in Travel+Leisure, Time OUT NY + Airbnb Campaigns. #Tinyescapeny for more pics! We are located on the Shawangunk wine trail and nestled in between 15 wineries and orchards. Hike, cook, grill, roast marshmallows and feel the stress just melt away. Wifi, King Casper Mattress, LUX toiletries (Glossier, Keihls, Drunk Elephant etc) . Heating+A/C, Smart TV Moonshadow Valley Tiny home provides an amazing escape! You'll have everything you need so you'll be able to truly relax. Just 90min from New York City! - Short drives will take you to amazing hikes, skiing, local swimming holes, and organic farmstands, bars, and restaurants. Take a short drive to Beacon, Hudson, Woodstock, or Phoenicia! Whatever your desires, you'll find them fulfilled at this beautiful Hudson Valley Tiny House #tinyescapeny for more pics The tiny home features - 276 sq/ft. farmhouse including the second floor and a reading nook! - Panoramic windows, exceptional light - 30 acres of rolling hills, orchard and vineyard + orchard views Sleeping - King sized Eightsleep memory foam mattress and amazing pillows - Twin Memory foam daybed WIFI: - for keeping in touch with the real world and streaming shows on your personal devices. Kitchen - A modern kitchen with a mini-fridge, induction cooktop for cooking, microwave, and electric kettle. Despite the small but well stocked with basics like oil, salt, pepper etc. - Dining table that expands to fit your needs - Outdoor slate fire pit with chairs table, umbrella, and charcoal grill. - we don’t provide wood or charcoal Couch/Daybed - Memory foam twin mattress - Storage ottomans with blankets - Throw pillows + standard pillows Bathroom 36" shower, designer sink, Toto toilet, LED lighting, towel bars, low sohn vent fan, storage shelves. Keeping you toasty: High efficiency split system A/C with heat pump, LP furnace with thermostat. Baseboard heat included We can accommodate up to four people- Camping and tented options available (you provide the tent) FREQUENTLY ASKED QUESTIONS: Q: Can I get to the house without a car? A: The house is about 20-minutes driving from the Beacon train station. If you choose not to drive the whole way there are Zipcar pickups at the train station (reserve in advance!) and Uber/LYFT launched in the area ($20-$30 for the ride from the train). A car is highly recommended (especially if you want to explore the area), but this definitely makes things possible for the car-free—just be sure to show up with everything you need for the stay as the farm is in a semi-rural area that is not particularly walkable. Q: Do I need to bring towels or linens? What about a hairdryer? A: Nope! I provide all these things. Including Keihls + Glossier body products Q: How will I receive the key? A: The house features lockbox that has a one time code Q: Is the place professionally cleaned between guests? A: Yes, and I take pride in providing a clean home for guests. Q: What's up with the cleaning fee? A: I get a lot of questions about this, so I'll just break it down so you understand why it is what it is: All of that (100% ) goes directly to my cleaner. She is a professional who does an exceptional job and who I insist on compensating fairly for her work. The dry-flush toilet cartridges cost me about $20 apiece. (Of course, if you happen to use more than one cartridge, I cover that cost alone). Q: What's my total booking price? A: I honestly have no idea. With fees included, Airbnb only shows the guest, and not the host, the total cost. This figure should be present after you enter your dates. Note that, pricing varies on a daily basis, and Airbnb actually uses some crazy algorithm to adjust it automatically, so I don't actually control this. Q: I am looking for a last-minute stay. Can I make a same-day booking? A: If you're looking for a same-day booking and the place is free, please inquire and I'll try! It depends on whether my cleaning crew can spring into action at the last-minute, which isn't a sure thing. Check-in may also have to be later than the listed time in order to make sure the place is ready. Still, can't hurt to ask. Q: I know it says "No Animals". Can I bring my small/well-behaved dog? A: I love dogs, but there is a farm dog who gets very nervous when other dogs are around, and so we can not allow animals. This is also for your dog's safety, as there are coyotes in the area. Basically: Please don't try to sneak one in--this really doesn't end well as we charge a 500$ fee for unauthorized pets of any kind Q: I'm a blogger/YouTuber/influencer. Can I stay for free? A: No. One last thing: I really, really appreciate that you followed directions and read the whole thing. Please put the phrase "I see Moonshadows!" at the top of your message so I know you did so as such bookings tend to go so much smoother! And thanks for hanging in there! The house features a gorgeous panoramic view and absolute relaxation. Use the firepit and outdoor furniture. Make yourself at home! I am always available to help! Please text or call me with any question you might have. The tiny house is set on a 30-acre farm offering views of rolling vineyards and apple orchards. Restaurants and nightlife spots are close by. Drive 20 minutes to reach the charming town of Beacon, home to great eateries, shops, and art galleries. The house is about 20-minutes driving from the Beacon train station. If you choose not to drive the whole way there are Zipcar pickups at the train station (reserve in advance!) and Uber/LYFT launched in the area ($20-$30 for the ride from the train). A car is highly recommended (especially if you want to explore the area), but this definitely makes things possible for the car-free—just be sure to show up with everything you need for the stay as the farm is in a semi-rural area that is not particularly walkable.. -There's a chicken coop nearby so you're welcome to buy some of our farm-fresh eggs (make breakfast on the cooktop!). Just tell me your order in advance and they'll be waiting for you. -The home features an eco-friendly, odorless, waterless toilet Laveo Flush toilet. This provides the same comfort as a regular flush toilet. This is the same toilet Matt Damon used in The Martian. When you "flush", it basically deposits your business into a sanitary and completely odor-free vessel without using water. It's actually cleaner and smells less (as in: not at all) than a composting or even regular toilet. This system features cartridges that are changed out between guests, and offer around 20 flushes per stay. This is typically adequate for two guests for two nights, but guests are advised to conserve flushes. In addition, I will be sending info on how to "swap" the cartridge if you run out (I cannot overstate how simple this is to do, promise, it’s done in 30 seconds) Guests will also need to dispose of this on their way out (again: I promise it's easy and NOT MESSY!) - We have a regular staircase that takes you to the memory foam king bed. The reading nook requires climbing and the ladder to the loft solid wood and very secure. If you have any restrictions to your movement, we recommend sleeping on the memory foam twin on the first floor Please read: The house is very much immersed in nature. Nature has bugs and animals. You may see both. There may even be an ant, fly, or non smelly stinkbug, or similar such bug in the house. I promise it won't hurt you. This time of year it’s not uncommon to have a fly or lady bug makes its way into the home when the front door is opened. Little tiny bugs can sometimes make it through the mesh on window. -While the house is very isolated and very quiet, you may hear farm equipment on occasion from the neighboring orchards (on our farm, the most you'll see is a tractor/mower). -Theres another tiny home on the property, you may bump into folks going there in the shared parking area, the house itself is still very much private and the other tiny home is completely out of view - We recently reseeded the lawn! There's a bit of hay keeping the seeds warm. Please make a note of this before you book.

Guest favourite

Rental unit in Verbank

4.95 out of 5 average rating, 132 reviews

Large, private apartment in scenic Hudson Valley

We are located right in the middle of the Dutchess County so access to all points is convenient. Many attractions are: historical Hyde Park, Walkway Over The Hudson, Culinary Institute, Vassar & Marist colleges, wineries, breweries, the quaint towns of Millbrook & Rhinebeck, Dutchess County Fairgrounds, and The Links At Unionvale golf course and banquet hall. Great for couples, adventurers and business travelers who love activity but appreciate a comfortable quiet place at the end of the day.

Superhost

Guest house in Dover Plains

4.9 out of 5 average rating, 106 reviews

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Guest favourite

Rental unit in Pine Plains

4.98 out of 5 average rating, 149 reviews

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Guest favourite

Cottage in West Park

4.84 out of 5 average rating, 210 reviews

Rustic, Sunny, Little Red Cottage in the Woods

Just outside of New Paltz, the cottage is 400 square feet, plus loft area, in addition to a 120-square-foot (winterized) screened-in porch with bistro table and additional relaxation spots. The main room hosts a double-size, comfortable futon couch, a dining table for four or more, a fully equipped kitchen providing all the basic amenities. The loft (up a ladder) hosts a super-comfy queen-sized bed. There is a small stone patio with an outdoor dining table with umbrella and a barbeque grill.

Guest favourite

Guest suite in Rhinebeck

4.91 out of 5 average rating, 431 reviews

Contemporary Rhinebeck Private Village Retreat

Quarters covid sanitized.Huge bedroom,CalKing bed.(twin bed avail.upon request,$30/day xtra for 2 people,$55 for 3 people w/extra bed)bathroom,(NO Kitchen)has coffeemaker, fridge,TV,Wifi,A/C, private patio & garden. No pets.PLEASE NOTE:Pic shows front of house so guests can find it,quarters on lower level to private entrance,*See Pics.Close to hiking, shops,26 restaurants,Omega, Bard College, Dutchess Fairgrounds *babies ok. No toddlers or kids under 7. June/July,Aug/Oct-wknds 2 day minimum

Guest favourite

Home in Hyde Park

4.85 out of 5 average rating, 209 reviews

Village Cape Getaway

Village Cape on Albany Post Rd in the historic town of Hyde Park. Surrounded by gardens, stone walls, private parking/entry. This 2 story house offers a 1 bdrm apartment that sleeps 3 on the 2nd floor. Close to markets, shops, restaurants. 1 mi to Vanderbilt Mansion, FDR house and library. 2mi to the Culinary Institute of America. 4mi to Marist College. Hiking trails walking distance. Historic drive-in movie in town. Metro north Poughkeepsie sta 6mi south offering taxi and bus service.

Guest favourite

Bungalow in Saugerties

4.88 out of 5 average rating, 234 reviews

Saugerties Cottage with Creek Access

Enjoy everything the Hudson Valley has to offer in this cozy home nestled between the Esopus Creek and the Village of Saugerties. Our cottage with original hardwood floors and vintage details has deeded access to the Esopus Creek for swimming and kayaking and is just a mile from the heart of the village. Relax with a book and glass of wine in the sunroom or spend the evening roasting marshmallows and watching the stars. A short drive from beautiful waterfalls, hiking trails, & skiing.

Guest favourite

Home in Wappingers Falls

4.92 out of 5 average rating, 182 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

Guest favourite

Farm stay in Ancram

4.96 out of 5 average rating, 297 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

Guest favourite

Rental unit in Salt Point

4.84 out of 5 average rating, 163 reviews

Arcady - Modern, 1br cottage

Renovated 600 sq ft 1br/1ba cottage! Welcome to Arcady - an ideal rustic paradise. Our recently renovated barn cottage situated on 6 acres of land with private creek and within easy drive of Rhinebeck, Millbrook, Omega Institute, Poughkeepsie and thousands of Hudson Valley Attractions. 10 min drive from Omega, 1 min drive from a town beach - enjoy everything area has to offer including hikes, mansions, farm visits, wineries and much more.

Guest favourite

Cottage in Pawling

4.98 out of 5 average rating, 106 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.