Holiday Rentals in Shenandoah

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Our top choices for Shenandoah holiday rentals

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is €298
includes taxes & fees
2 Mar - 3 Mar
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.0 out of 10, Wonderful, (26 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is €173
includes taxes & fees
26 Feb - 27 Feb
Cabin in the heart of the Hudson Valley, Cabin 4

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (18 reviews)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is €164
includes taxes & fees
23 Mar - 24 Mar
Cozy 1-bedroom retreat minutes from West Point!

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is €242
includes taxes & fees
26 Feb - 27 Feb
Cabin in the Heart of the Hudson Valley, Cabin 1

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is €245
includes taxes & fees
25 Mar - 26 Mar
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.4 out of 10, Exceptional, (60 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is €242
includes taxes & fees
26 Feb - 27 Feb
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is €361
includes taxes & fees
26 Feb - 27 Feb
Contemporary Cozy Cottage

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is €239
includes taxes & fees
26 Feb - 27 Feb
Charming 1-bedroom apartment in Carmel with WiFi, AC

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (35 reviews)
"Stunning property!!"
United States
Samantha
The price is €403
includes taxes & fees
2 Mar - 3 Mar
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is €263
includes taxes & fees
26 Feb - 27 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
10.0 out of 10, Exceptional, (2 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is €417
includes taxes & fees
3 Mar - 4 Mar
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is €504
includes taxes & fees
2 Mar - 3 Mar
"Country outside the city " 3 bedrooms 2 full bathrooms

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (67 reviews)
"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."
United States
Lou F.
The price is €270
includes taxes & fees
26 Feb - 27 Feb
Cozy country efficiency in the Hudson Valley

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.6 out of 10, Exceptional, (4 reviews)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is €167
includes taxes & fees
26 Feb - 27 Feb
Hoppy Hill Farm House

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.6 out of 10, Exceptional, (5 reviews)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is €347
includes taxes & fees
26 Feb - 27 Feb
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Stylish & Pet-Friendly Apartment in Beacon

Stylish & Pet-Friendly Apartment in Beacon
Beacon
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and great place to stay. "
United States
Charlene D.
The price is €223
includes taxes & fees
16 Mar - 17 Mar
Stylish & Pet-Friendly Apartment in Beacon

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (53 reviews)
"We havld a good time. The room was comfortable and perfectly located!"
United States
Brandy C.
The price is €212
includes taxes & fees
1 Mar - 2 Mar
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.0 out of 10, Wonderful, (10 reviews)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is €240
includes taxes & fees
25 Mar - 26 Mar
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is €209
includes taxes & fees
26 Feb - 27 Feb
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shenandoah Hotel Reviews

Find out more about Shenandoah

Everything you need to know about Shenandoah holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shenandoah holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shenandoah holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shenandoah holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shenandoah. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shenandoah holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shenandoah holiday rentals we have selected for you start as low as €173 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shenandoah rentals

At Expedia, we put the best Shenandoah holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shenandoah rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shenandoah holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shenandoah. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Shenandoah?

Yes, there are holiday rentals close to the most popular sights in Shenandoah, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Shenandoah has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Shenandoah offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Shenandoah?

Explore the area and family-friendly sights such as SplashDown Beach, or get out into nature at a spot like Lake Mahopac. Chuang Yen Monastery and Stormville Airport Antique Show & Flea Market are a couple of places you'll find in the wider area.

What are holiday rentals like in Shenandoah?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shenandoah. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for families.