Holiday houses in Shenandoah

4.92 out of 5 average rating, 105 reviews

Apartment in Amenia

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

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!

Apartment in Wappingers Falls

5 out of 5 average rating, 210 reviews

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

Apartment 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.

4.84 out of 5 average rating, 311 reviews

Apartment in Newburgh

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

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.

4.99 out of 5 average rating, 826 reviews

Tiny home in New Paltz

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

4.89 out of 5 average rating, 577 reviews

Apartment in Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge

First floor apartment in historic colonial house in the middle of Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original pieces of art. It has a fireplace stove and a wood fired sauna in the backyard. Full kitchen is equipped with everything guests need to prepare a great meal. It is perfect for all seasons. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

4.98 out of 5 average rating, 142 reviews

Tent in Livingston Manor

Milkweed Camp - Glamping in a Blueberry Field

Our off-grid canvas tent is situated at the edge of a meadow, surrounded by blueberry bushes. It's just 4.5 miles to Main St in Livingston Manor, and 35 minutes to Bethel Woods. We provide a full-size bed (w/ heated mattress pad), fire pit, firewood, propane heater, and solar power. You have access to a private outhouse with composting toilet & outdoor shower on-site, and a conventional shared bathroom if you preferred. We are an LGBTQ+ inclusive space.

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.

4.97 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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4.91 out of 5 average rating, 100 reviews

Apartment 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, 8 reviews

Bus in Hopewell Junction

BIG RED the Bus at Menlo Pond

NatalyaRating, 5 stars1 month ago

great place to relax and very peaceful. fantastic fire pit.

4.82 out of 5 average rating, 308 reviews

Apartment in Cold Spring

Spacious Studio in Hudson Valley

KathrynRating, 5 stars2 weeks ago

Lorelei’s place was clean, quiet and spacious, a great location for visiting Cold Spring, Beacon and FDR’s home, museum & library. We appreciated the chocolate bar, delicious donuts and good coffee!

4.97 out of 5 average rating, 58 reviews

Cabin in Saugerties

Luxury A-Frame Cabin in the Woods with Sauna

YaaraRating, 5 stars2 weeks ago

The cabin is beautifully designed, with great taste and attention to every detail. It was one of the best experiences I can remember – quiet, thoughtful, and simply perfect. Everything felt carefully considered, and Nicholas was highly responsive communicative, kind, and easy to reach. Thank you so much!

4.94 out of 5 average rating, 123 reviews

Cabin in Mountain Dale

Private lake cabin w/hot tub, views and fruit

RudyRating, 5 stars4 days ago

Alex’s cabin was charming and comfortable. I appreciate that there was no TV- instead, a large picture window over-looking the pond valley (which we appeared to have exclusive access to.) Everything listed in the property description and amenities was there when we arrived. Also, it was a woodland birder’s paradise! We can’t wait to come back!

4.99 out of 5 average rating, 438 reviews

Bungalow in Cairo

Riverfront-swim & float the river-20 min to Hudson

MichelleRating, 5 stars1 week ago

Molly knows how to host. Such a gracious and lovely host that made us feel so welcome and had the best touches - bottle of wine and handwritten note on arrival, Aesop bath products, plenty of games, and helpful instructions and local recommendations. The property is beautiful situated right on the creek. It rained 1/2 the time we were there but we still had a great time as it was so peaceful and the cabin is very cozy. Mollys dog Charlie was so friendly, sweet and careful with our small toy poodle. We wished he visited more we loved him so much! Highly recommend a stay and that you take her up on every recommendation. They did not disappoint. 🤍

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!