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Holiday rentals in Dutchess County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Dutchess County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Fabulous Lemon Cottage in Rhinebeck, NY
Entire cottage · 4 guests · 1 bed · 1 bathroom

Fabulous Lemon Cottage in Rhinebeck, NYThis cozy, clean, and light-filled cottage with its bedroom loft provides a perfect Hudson Valley getaway anytime of the year. When you do venture out, you're in the heart of it all; only a few miles from "downtown" Rhinebeck, but also close to Red Hook, Kingston, Woodstock, Hudson, etc. Make yourself at home at this quiet, private cottage with views of the woods. LGBTQIA+ friendly. All people from all cultures and backgrounds, without exception, are welcome.

Sunset Bungalow-Mt views on 130acre forest & falls
Entire cabin · 4 guests · 2 beds · 1 bathroom

Sunset Bungalow-Mt views on 130acre forest & fallsNewly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, and comfortable bedroom- learn more at

Cozy Cape w/ vaulted ceilings and backyard firepit
Entire residential home · 5 guests · 3 beds · 1 bathroom

Cozy Cape w/ vaulted ceilings and backyard firepitGuests are treated to a carefully manicured landscape upon entering the driveway. The rustic walkway leads to a warm, inviting entry. Once inside the home your eyes will be drawn to the dramatic vaulted ceilings tastefully finished in pine and featuring recessed lighting. The main living space is open, bright and airy. Natural light is provided through huge windows. Minutes from the Taconic State parkway makes this a great home base to visit local hiking spots, wineries, and much more

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Dutchess County holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Dutchess County

  1. Private room
  2. Pleasant Valley
Cedarhurst 2
  1. Entire residential home
  2. Rhinebeck
Lake House Retreat
  1. Entire guest house
  2. Beacon
Modern Cottage in the Woods
  1. Entire cottage
  2. Rhinebeck
Acorn Hill Cottage -A mid century farmhouse gem
  1. Entire rental unit
  2. Ulster Park
The Carriage House
  1. Entire residential home
  2. Beacon
NEW! Stylish Home in the Heart of Beacon
  1. Entire cottage
  2. Rhinebeck
Lakefront Writer's Cottage in Rhinebeck
  1. Entire guest suite
  2. Holmes
Getaway! Full Fl Apt in CarriageHouse w/POOL!
  1. Entire cottage
  2. Rhinebeck
Ridgetop 2 Br Cabin- Views, 130acre forest & falls
  1. Entire townhouse
  2. Kingston
DeMew Townhouse in Historic Kingston
  1. Entire guest house
  2. Hyde Park
Modern cottage with Hudson River view
  1. Barn
  2. Pine Plains
The Nook - An Adorable Secret Get Away

Top-rated things to do in Dutchess County

Unique activities hosted by local experts vetted for quality

  • Sanctuary Tour and Pamper a Pig
    How often do you have the chance to spend time with an adorable pot belly pig? Well, here is your chance! All of the pot belly pigs at Wayward Ranch Animal Sanctuary have been rescued, whether from abuse, neglect, or simply owners who were not properly educated about how to care for them. With so many myths being perpetuated about these so called "mini pigs" we want to educate about what they are really like while we have fun spoiling them with you. Come and enjoy a piggy day when you can come, take a tour of our entire facility, learning about the work we do with horses, goats, dogs, cats, and pigs. Finish the tour by helping us to feed our pigs their dinner and some treats and you will get happy grunts and tail wags in return! Other things to note Whenever you are interacting with animals, it is important to keep in mind that animals can be unpredictable. They may accidentally scratch you or even grab a finger when they mean to grab a treat from your hand. Our pigs are not aggressive generally, but it is always best to be cautious around all animals!
    From Price:£29/person
  • Hugs, Hike, and Hang with Rescue Goats
    Did you know that spending time around animals reduces stress and increases feelings of happiness? You can double that when they are rescued goats! Come spend outdoor time in a small group with ample room for social distancing to meet some of the most affectionate goats there are. Visitors will get to meet and learn about each goat and breed as well as their rescue stories, behaviors and unique characteristics of the species. We are loaded with goat fun facts and corny goat puns to add a little laughter into our day! You'll also become part of the herd when we proceed to hike through marked trails on our 9 acre property with the goats, who enjoy navigating the trails and foraging along the way. Watching the goats in a natural habitat and bonding with them is truly magical. We end with extra quality time with all of the goats, who love lots of attention, allowing for plenty of hugs, scratches, and photo ops. Everyone leaves with a small goat fun fact booklet and sticker of their favorite goat. This experience is fun for all ages - we have an equal amount of adults and children. If a date or time isn't available on our calendar, please ask! We have an open schedule and would love to accommodate you if we can! Other things to note This experience is rain or shine. Bringing water bottles is recommended. *Please note that there is no public restroom on-site.
    From Price:£26/person
  • Secret Ruin Hike Tour, Woodstock
    Come with me and my certified guide and enjoy the very special Secret Ruin Hike! We'll be hiking and under-covering some of the most beautiful secret treasures of Overlook Mountain right in the heart of Woodstock! We will meet at the trailhead entrance and hike a moderate incline up Overlook mountain to the skeletal ruins of the Overlook mountain hotel. The hotel’s remains are close to the summit of Overlook Mountain, which rises 3,140 feet over Woodstock, New York. We will be stepping back in time and walking through the main hall and glancing into side rooms of the former luxury hotel whilst stopping for lunch. From there we will be hiking to the summit and climbing to the highest point of Overlook mountain - the Fire Tower. You will get to enjoy the 360 degree views, on bright clear days you will be able to see as far as Connecticut and Massachusetts. Our trail leads us to Eagles Point. Not only is this an awesome outlook for memorable views of the Catskill Mountains but an excellent place to spot Eagles. We will also be showing you the flat rock at Eagles point where lovers and friends would etch their names in stone in the 1800's. Our hike ends at the Karma Triyana Dharmachakra Tibetan Buddhist Monastery where we will visit the golden shrine room temple. I'll be providing good company and fun conversation! :)
    From Price:£44/person
  • Catskills Hiking and Photo Adventure
    Guests will meet host near the entrance to the Catskills in Palenville, New York. After a brief intro and gear check, well head up into the mountains - with scenic vistas, gushing waterfalls, and pristine summits - there's an adventure waiting - no matter your skill level. Learn about the flora, fauna and geography along the way as you immerse in the best of Upstate New York with a licensed hiking guide. After meeting and a brief safety orientation, we will head to the specified trailhead and begin a guided trail hike, stopping for occasional breaks, snacks and moments of admiration. Throughout the hike, I will shoot candid and instagram-worthy stills during your hike, which I will AirDrop (email for Android users. For full day hike options, send host a message! If you are active duty/veteran, firefighter, teacher, essential worker, healthcare worker, medical first responder, police officer, please inquire about a small discount Other things to note -I am a NYS DEC Licensed hiking guide (Badge #8246 - CPR, AED, & First Aid Certified -Groups larger than 4, please message prior to booking! Single travelers please message prior to booking, as I will try to match up with other solo bookers. Most trips I do require a 2 person minimum but am flexible!
    From Price:£66/person
  • Five Element Walking Meditation
    We will meet at Poets Walk - nearby trail that is inspired by artists and poets of the Hudson Valley and beyond. This trail is a scenic 2-mile loop with various lookouts and places to sit and meditate throughout the grounds. We will begin together at the head of the trail to review the guidance on breathing practices for your walk and a focus for your medicine. With social distance and mask requirements if this area you are expected to also practice compassion :) While together masks are requested and once we begin and we choose to separate at least 6 feet apart from each other - you may remove your mask to fully breathe in the mountain air and relax - please be mindful of others on the trail as well. Once we arrive to our designated meditation spot ( a gazebo overlooking the water and woods ). You will be guided through gentle physical movement to prepare for a guided meditation. Beginners are encouraged and seasoned meditators are encouraged to practice what you know and deepen your awareness. As part of your meditation practice, you will receive a healing gemstone picked just for you and your intentions. You will be given instructions on usage and care for you to take with you on your meditation journeys. Upon returning to the beginning of the trail space is given to talk about your meditation and receive a healing Reiki charge as our goodbye. Namaste! Other thin
    From Price:£22/person