Holiday houses in Shenandoah

4.81 out of 5 average rating, 150 reviews

Apartment in Newburgh

Historic Stunner w/WasherDryer, Balcony, 2 bedroom

Our cozy historical 2 bedroom apartment with river views, two porches, and modern upgrades is just what you need for a delightful getaway or focused work-cation. We've preserved historical charms (hardwood floors, historical trim, retro fixtures) while adding in modern amenities (washer/dryer, dishwasher, stylish bathroom, new kitchen, electric car charger, etc!). Less than a mile from the Newburgh-Beacon Ferry launch, which connects you to Metro North Train. Note: Located on the second floor!

4.93 out of 5 average rating, 137 reviews

Apartment in Beacon

Cozy, Small Studio with Backyard & great A/C

Cozy, small studio on quiet block. Near Main Street, Roundhouse, hiking, restaurants. Fully private space & entrance, shared backyard, new A/C, wifi. Walk everywhere. Queen-sized bed. BEFORE YOU BOOK - 200 year old house - hosts live upstairs and there is another guest apartment. You WILL NOTICE sounds from others. QUIET HOURS from 10 PM to 8 AM. As a courtesy to others, please keep conversations quiet after 10 PM. We only book guests with favorable Airbnb reviews. NO SMOKING please.

Guest suite in Marlboro Township

4.97 out of 5 average rating, 472 reviews

Spacious & Private Hudson Valley Getaway

Welcome to Marlboro! This private space in our home features a private entrance, private bathroom with a nice standing shower, eating area (not a kitchen) with tea kettle and coffee machine, toaster, microwave and refrigerator with freezer. There is a table and chairs, love seat couch that transforms into a small cot, queen bed, walk in closet and 55 inch smart TV with a full motion TV stand. We are permitted to operate in the town of Marlboro and a yearly fire inspection is conducted.

Apartment in Marlboro Township

4.98 out of 5 average rating, 376 reviews

Cliff Top at Turtle Rock

Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

4.9 out of 5 average rating, 136 reviews

Guest suite in New Paltz

Newly built apartment steps from Mohonk preserve.

Nestled amongst the trees below Bonticou Crag this is a great base camp for climbing, hiking and biking. Five minutes from New Paltz; I do recommend having a car to access the area. Shared yard and fire pit right outside. My family and I live in the main part of the house. The outside area and house are still under construction, I’m working on it but its not put together yet. The apartment and inside area are clean and newly built with their own mini split and air circulation.

4.89 out of 5 average rating, 113 reviews

Home in Wappingers Falls

LivingUPstation

Sustainable living Upstate NY. The space is the outcome of 10 years of reclaiming materials from various construction projects in NYC. A true example of mid century modern architecture is converted to a sanctuary with a 3 way open wood burning fireplace and Finnish indoor sauna looking at nature less than 90 mins by train from Grand Central. The space introduces guests to unique woodworking and art a few minutes away from great nature escapes, fine dining and Dia Beacon.

4.92 out of 5 average rating, 206 reviews

Guest suite in Newburgh

Hudson River Views-idyllic getaway 75 min. to NYC

Cozy suite with fireplace and private deck views of the majestic Hudson River nestled in a quiet safe residential well-maintained neighborhood away from the city of Newburgh close to the Newburgh-Beacon bridge and the prestigious Powelton Country Club. This suite has a full kitchenette and a separate living space with couch, smart TV, queen bed and table. It has its own deck accessible by a sliding glass door where you can enjoy sunrises and soak in the peaceful views.

4.89 out of 5 average rating, 323 reviews

Guest suite in Beacon

Cozy retreat, centrally located in Beacon NY

Private studio apartment for single person or couple (3rd guest can sleep on sectional sofa). It is walking distance to Metro-North and Main St. Beacon. Private entrance on the right-side of the house. Queen bed with mini-fridge and microwave (no kitchen, no cleaning fee!). A quiet homebase to explore all the Hudson Valley has to offer. **Winter Advisory ** I will refund 100% if you chose to cancel your reservation due to a forecasted snow event within 24hrs of arrival

4.99 out of 5 average rating, 313 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

4.97 out of 5 average rating, 174 reviews

Guesthouse in Stormville

Hudson Valley Cottage with Pond Access

Light and airy cottage situated on the private eighteen acre property surrounded by beautiful mature trees, large lawn area and quick two minute walk to a beautiful large 3 acre pond. Perfect spot for a relaxing weekend in the Hudson Valley; only 60 miles from Manhattan. The cottage has it's own private back yard, with a patio and a fire pit. Perfect place to disconnect and relax. Enjoy your Hudson Valley getaway!

Guest suite in Marlboro Township

4.95 out of 5 average rating, 177 reviews

Viridian House

This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.

Apartment in Carmel-by-the-Sea

4.87 out of 5 average rating, 298 reviews

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.

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Other great holiday rentals in Shenandoah

4.87 out of 5 average rating, 15 reviews

Home in East Fishkill

Hudson Valley Retreat | Hot Tub, Pool & Gym

LindsayRating, 5 stars1 week ago

We enjoyed a wonderful stay in Alissa’s warm and spacious home! Not only is the view splendid but the beds are so comfy. The hot tub overlooking the valley was the perfect way to spend a rainy morning. The kitchen is a roomy gathering place for our group, as was the great room featuring lovely beams and a cozy couch. Alissa was extremely responsive and welcoming; all of our questions were promptly answered. Thank you for the memories! Definitely recommend!

4.85 out of 5 average rating, 13 reviews

Tent in Poughquag

Maybrook Farm "The Ridge"

HeatherRating, 5 stars7 months ago

We have stayed here multiple times. It’s a quick weekend getaway for us and the dogs. The views are stunning every season

Guest suite in Cold Spring

4.88 out of 5 average rating, 81 reviews

Red Door Inn - One Bedroom Suite in Cold Spring.

BrianRating, 5 stars1 week ago

Jeff’s place was outstanding. It’s really a beautiful place! And Jeff was amazing! He really helped out and made our stay fantastic. We would absolutely recommend this place to everyone!

4.77 out of 5 average rating, 79 reviews

Apartment in Newburgh

Charming, Tranquil & Comfy ~ 5★ Location ~ Parking

VirginiaRating, 5 stars1 day ago

We loved staying in Newburgh with Marin! Especially liked the unlock by phone feature, the clean and bright space, and its proximity to local eats/drinks. We also made good use of the projector. Looking forward to a second stay in the future.

4.97 out of 5 average rating, 60 reviews

Cabin in Carmel Hamlet

Cozy Log Cabin Getaway

Meg & DanRating, 5 stars1 week ago

We had a great long weekend in the cabin! Everything was exactly as pictured and it was even stocked with everything we could ever need in the kitchen, allowing us to cook and grill and just relax! We traveled with our 2 year old who also enjoyed the place and appreciated finding some books and coloring books to use as well. Would love to return!

4.99 out of 5 average rating, 582 reviews

Condo in Beacon

Rustic Spa Retreat

MelissaRating, 5 stars1 week ago

Dan’s place is cozy, comfortable and just minutes away from Mt. Beacon in one direction and ten minutes away from Main Street in the other direction. The kitchen is stocked with cooking essentials, though there are so many delicious restaurants nearby- the best of both worlds! The bed was extremely comfortable and the jetted bathtub was a huge bonus. I genuinely relaxed there, which is a rarity for me. Thanks so much, Dan!

Holiday home in Carmel Hamlet

4.86 out of 5 average rating, 58 reviews

Serene 4-bdrm lake house

RegienRating, 5 stars1 month ago

Marilyn’s house in Carmel, NY is amazing. From the terrace you have a beautiful view on the lake and mountains. The house is big and there’s a lot of space to relax and eat on a big table (inside and outside). The facilities are also great. Three bathrooms and a laundry room and lots of toys for little kids to play with. Our boys loved the bunk beds. We really enjoyed our stay. There are lots of beautiful hikes and playgrounds nearby. If you want to go to the city, it’s easy to take the train from Cold Spring. Also Marilyn is really accessible and easy to communicate to. She responds very quickly. Would definitely go back and recommend this house!