Vacation rentals in Shenandoah

4.83 out of 5 average rating, 162 reviews

Cottage in Carmel Hamlet

Lake Cabin Escape–Fenced Yard+Firepit.Dogs welcome

⸻ A cozy, art-filled cabin just over an hour from NYC, steps from a swimmable lake. Decorated with unique treasures collected from around the world, it’s a soulful space made for rest & reconnection. Enjoy a stone fireplace, fenced yard for pups, starry nights by the fire pit & peaceful mornings on the deck. Hike nearby trails & slow down. This isn’t just a cabin — it’s a story-filled retreat designed to help you rest, relax and rediscover what matters. Come for the lake. Stay for the magic!

4.95 out of 5 average rating, 235 reviews

Guesthouse in Mahopac

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

4.83 out of 5 average rating, 681 reviews

Apartment in Beacon

Top Floor 2BR - Just Renovated!

This 2BR apartment is the entire top floor of an 1870 brick house. Extensively renovated in 2021 - all new kitchen, major updates to the bathroom, furniture and decor throughout. Directly behind the house is Fishkill Creek and abandoned railway tracks (you can walk to Main St on them in 10 minutes). The property has a separate patio & treetop hot tub with view of the creek and Mt Beacon for private additional rental (pending availability). Inquire for details. [Permit: 2024-0027-STR]

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, 377 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.

4.86 out of 5 average rating, 189 reviews

Apartment in Newburgh

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

4.87 out of 5 average rating, 661 reviews

Tiny home in Newburgh

Cabin in the heart of the Hudson Valley, Cabin 2

Our little cabin is perfect for one or two guests for short stays while visiting local family, touring the areas wineries or nature trails, or for a clean, quiet over night stop while traveling long distances. Explore the Shawangunk Wine Trail, hike Minnewaska, sip cider at Angry Orchard, visit The Walkway Over the Hudson, or sample and shop the areas diverse farm stands and breweries. There is so much to see and do in the Hudson Valley and our cabin is close to it all!

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.

4.93 out of 5 average rating, 222 reviews

Home in Wappingers Falls

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.

4.89 out of 5 average rating, 101 reviews

Guesthouse in Fishkill

Hudson Valley Studio in the Village of Fishkill NY

This spacious studio is in a quiet cul-de-sac and under a half mile walk from the Village of historic Fishkill, NY. Also, only a 10 minute drive to Beacon, NY! It is a private dwelling that includes a full kitchen, 1 new Queen bed, 1 new pull out bed, and a separate room for laundry. Plenty of drawers and closet place caters to up to 4 guests for whichever Hudson Valley activity you're in town for. Come enjoy the atmosphere of this Hudson Valley studio!

4.99 out of 5 average rating, 314 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!

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Other great vacation rentals in Shenandoah

4.92 out of 5 average rating, 190 reviews

Home in Carmel Hamlet

Lux Bungalow on the Lake

PattiRating, 5 stars1 week ago

This was a few nights getaway with my two adult daughters. The house is adorable, neat and cozy. The beds were very comfortable. Felt right at home. We did a little kayaking on the lake, which was beautiful. The weather wasn’t perfect, but we made the best of it and enjoyed each other’s company. The neighborhood was very quaint. We took a walk around the lake. Nicole was very responsive whenever I messaged her. We felt very comfortable being there. I would highly recommend this home.

4.91 out of 5 average rating, 11 reviews

Home in Holmes

Enchanted Escape | POOL, LAKE, Concierge Services

AnxhelaRating, 5 stars2 weeks ago

We had such a great experience staying at this Airbnb. The house was beautiful, super clean, and the view was just perfect honestly even better than the photos. What really made our stay stand out though was the host, Sunny. He was amazing so helpful, kind, and incredibly thoughtful. As a Muslim family, we really appreciated how respectful and considerate he was. He made sure we had our privacy and went out of his way to make everything as easy and comfortable as possible for us. It honestly felt like staying at a friend’s place. We’d definitely come back and highly recommend this spot to anyone looking for a peaceful, welcoming place to stay.

5 out of 5 average rating, 38 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

BingRating, 5 stars5 days ago

We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!

4.84 out of 5 average rating, 68 reviews

Farm stay in Brewster

Crooked Cottage at Lobster Hill Farm

KileyRating, 5 stars1 month ago

Cute cottage with a rustic camp feel. The front porch is a relaxing hangout spot overlooking a variety of small farm animal enclosures. State lands next door offer a decent place to walk around, and the place is a short drive from town where you can find a variety of restaurants.

5 out of 5 average rating, 37 reviews

Home in Fishkill

Chez Moi-4 beds-3 bedroom-two bath-sleeps 7-

JamesRating, 5 stars1 week ago

We were very content, with all comforts and conveniences met. The neighborhood was quiet and felt safe. Michelle is a very accommodating and attentive hostess. Terrific location for our plans. Overall awesome experience. Thank you,

4.95 out of 5 average rating, 203 reviews

Cottage in New Milford

The Cottage on Babbling Brook

LaurieRating, 5 stars3 weeks ago

We had a short but sweet stay. The surroundings were beautiful and the host’s recommendations were spot on. We highly recommend visiting!

Apartment in Wappingers Falls

5 out of 5 average rating, 29 reviews

Sunset Suite

ArielRating, 5 stars1 month ago

Lovely and clean place. Served our purposes great. Comfortable and cozy. The pullout couch was very serviceable. Only small thing missing was a bedside lamp of any kind to read by at night. Very enjoyable stay overall.