Holiday rentals in Shenandoah

5 out of 5 average rating, 210 reviews

Flat in Wappingers Falls

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

PLEASE READ ALL HOUSE RULES PRIOR TO INQUIRIES AND BOOKINGS! 1 night/longer stays can be accommodated upon request and calendar availability. “Home Is Where The Heart Is”. If you love tranquility and coziness combined with sophistication and traditional rural charm, this is the place for your stay (only 4 miles from Beacon). The ground floor apartment with a private entrance (located around the back in a private house) includes a living room, full kitchen, full bathroom and Queen bedroom.

5 out of 5 average rating, 127 reviews

Flat in Beacon

2Blocks to MainSt/Roundhouse-UnderMtBeacon-PvtApt

A cozy, clean, large studio apartment within a two minute walk to Mt. Beacon and Main St. Enjoy your stay with a fully equipped kitchen (coffee, tea, creamer, sugar, etc.), a comfy queen bed with lots of pillows, a full bathroom with shampoo, conditioner, body wash and extras. You will have off-street parking and a beautiful outdoor patio all to yourself. The apartment has WiFi, a Smart T.V. and lots of lighting but also room darkening shades to sleep in. Pickleball courts 2 blocks away.

4.94 out of 5 average rating, 155 reviews

Cabin in Walton

The Mill House: Creekside Catskills Spring Escape

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to a winter retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a meticulous restoration in 2021, marrying its saw mill heritage with contemporary luxuries, including a Nest thermostat, smart speakers, keyless entry, and fast wifi. Original exposed post and beam construction and Scandinavian-inspired design make for a unique and cozy atmosphere.

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.

4.86 out of 5 average rating, 190 reviews

Flat 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!

4.93 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.

4.99 out of 5 average rating, 316 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

4.98 out of 5 average rating, 124 reviews

Cottage in Pawling

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.

4.93 out of 5 average rating, 176 reviews

Flat in Newburgh

Ela - a 1 Bed Escape, Washer/Dryer in Unit

Kick back and relax in this calm, stylish space. Located on the second floor of a historic Newburgh building, this apartment features scenic views from oversized windows, in-unit laundry, LED TV & Fios WiFi, and designer furnishings. Queen bed with Casper mattress. Two flights of stairs required. The neighborhood is quiet, with tree lined streets and historic mansions nearby, just 2 blocks always from the Hudson River waterfront.

Guest house in Stormville

4.97 out of 5 average rating, 174 reviews

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!

5 out of 5 average rating, 209 reviews

Place to stay in Oneonta

Creekside of the Moon A-frame Cabin

Creekside of the moon A-frame glamp. Float, fish and play in the Catskills. Glamp on the Charlotte Creek in a newly built modern tiny a-frame. Sleep under the full moon. A giant moon light hangs over the bed(s) with a stunning reflection in the window at night over the creekview. Perfect for a romantic getaway, fishing trip, or glamping spot in the Catskills. Close to Cooperstown, NY IG @aframe_moon

Tiny home in Hopewell Junction

4.95 out of 5 average rating, 527 reviews

The GlassHouse: Hudson Valley Tiny Home w/Firepit

The GlassHouse is the much talked-about experience that we had crafted within a sprawling forest preserve. Its wrap-around windows allow breathtaking views to bring out the romantic in all of us! We are stone’s throw up against the Appalachian Trail right on the Dutchess/Putnam line and are less than an hour from Manhattan. Minutes from Fahnestock & Hudson Highlands State Parks & the Empire State Trail!

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Popular amenities for Shenandoah holiday rentals

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Free parking on premises

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Other great holiday rentals in Shenandoah

4.91 out of 5 average rating, 100 reviews

Flat in Beacon

Beacon Hills Retreat Apartment

WayneRating, 5 stars3 weeks ago

Dan's home is in a peaceful and private place. Great spot to get away from the "noise" but be within a quick short drive of Beacon or Fishkill, for whatever you need or want to do. The bedroom is a good space that's cozy with windows overlooking nature and a clean comfortable bed. Dan is a kind and considerate person who thinks about details like having a few things in the kitchen for his guests like fresh milk, coffee and even a late night snack if needed. It was a great stay and I would do it again.

5 out of 5 average rating, 27 reviews

Home in Pleasant Valley

The Wildflower House

MatthewRating, 5 stars1 month ago

Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!

4.96 out of 5 average rating, 568 reviews

Loft in Beacon

Luxe Loft 3 on Main St-Steam Shower! Kitchen,W/D!

KateRating, 5 stars3 days ago

The location was perfect to explore the town of Beacon and go on hikes! The apartment was clean and communication with Laurie was easy for checking and checkout. Definitely recommend!

5 out of 5 average rating, 14 reviews

Flat in Holmes

Top Side

AnamariaRating, 5 stars3 months ago

Regan is the hostess with the mostess ! I would definitely visit again 😊

Guest house in Wappingers Falls

4.91 out of 5 average rating, 11 reviews

1723 Guesthouse

JenniferRating, 5 stars3 weeks ago

This guesthouse was a perfect fit for our weekend visit to the Hudson Valley. It had plenty of space and was very clean. The house had a lot of charm and was a good value for the price. The host was friendly and helpful.

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!

4.92 out of 5 average rating, 52 reviews

Home in Narrowsburg

Modern Secluded Retreat

GajaRating, 5 stars3 weeks ago

Beautiful, private, and quiet spot to enjoy a night away. Lovely modern decor, birds chirping, and very comfy bed! We had a great time