Top Winter Vacations - Vacation Rentals in Shenandoah

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. From US $255
         

Modern NY Home with Views By Hudson Valley Hiking! From US $377
         

SpringHill Suites by Marriott Fishkill From US $157
         

|
9.6 (1000 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
East Fishkill Escape, Close to Red Wing Park! From US $209
         

Dog-Friendly Fishkill Tiny House in Wine Country From US $242
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Magnificent historic mansion on 12 acres From US $824
         

Rustic Cabin in Fishkill! From US $444
         

10.0 (3 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Shenandoah

Over 91+ Luxury Places to Stay in or Near Shenandoah
The Mansion at Willow Lake From US $1,991
         

Big Log Cabin on a lake in the woods; 4 BR 4 full bathrooms in Putnam Valley From US $957
         

Charming Cold Spring escape on 2.75 acres From US $759
         

Bright and airy retreat with scenic pool! From US $743
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hickory on Willow Lake From US $736
         

9.6 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Shenandoah

Over 34+ Top-Rated Vacation Rentals with a Pool in or Near Shenandoah
Modern Spacious Apartment From US $178
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott Fishkill From US $147
         

|
9.4 (412 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
SpringHill Suites by Marriott Fishkill From US $281
         

|
8.9 (286 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
HYATT house Fishkill/Poughkeepsie From US $124
         

|
8.8 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Best Western Fishkill Inn & Suites From US $122
         

|
8.8 (976 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Fishkill From US $104
         

|
8.6 (1015 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Shenandoah

Over 26+ Pet-Friendly Vacation Rentals in or Near Shenandoah
Enchanting Lake front chalet with backyard and fire pit. Dog friendly. From US $347
         

10.0 (1 Review)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Dog-Friendly Fishkill Tiny House in Wine Country From US $328
         

|
9.7 (3 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Accessibility
Pet-friendly Hopewell Junction Apt w/Grill! From US $229
         

|
4.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet-Friendly Hopewell Junction Home w/Pool From US $216
         

8.4 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy, Historical Cottage on The Appalachian Trail From US $200
         

8.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Pet-Friendly Hopewell Junction Apt w/Grill! From US $195
         

6.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hopewell Junction Apartment w/Community Pool From US $195
         

4.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Shenandoah

Over 13+ Large Vacation Homes & Villas in or Near Shenandoah
Tranquil 4-bedroom house in welcoming Poughquag neighborhood
New
From US $291
         

New
House
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Magnificent historic mansion with amazing barn From US $1,642
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Designer Lakehouse Retreat at Roaring Brook Lake From US $1,453
         

9.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Shenandoah

Over 17+ Wheelchair Accessible Vacation Homes in or Near Shenandoah
Serenity Escape in Hudson Valley. From US $128
         

9.6 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG From US $219
         

Courtyard by Marriott Fishkill From US $119
         

|
8.6 (736 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Hyatt House Fishkill-Poughkeepsie From US $188
         

|
8.4 (274 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG From US $113
         

Best Western Fishkill Inn & Suites From US $174
         

|
8.3 (596 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Spark by Hilton Fishkill From US $103
         

|
7.2 (21 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Residence Inn by Marriott Fishkill From US $211
         

|
8.3 (73 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Shenandoah Varoom and Airbnb Places to Stay Under $200

Over 15+ Shenandoah Varoom and Airbnb Places to Stay Under $200
The Inn at Forge Brook 1818 From US $200
         

New
Apartment
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly
East Fishkill Escape, Close to Red Wing Park! From US $182
         

|
8.0 (4 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Sports/Activities
Le Chambord at Curry Estate From US $180
         

|
9.2 (258 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Lake House with indoor spa, 1 hour from Manhattan From US $150
         

9.8 (9 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Hampton Inn Fishkill From US $176
         

|
8.2 (310 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Extended Stay America Suites Fishkill Westage Center From US $115
         

6.4 (910 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
2-bdrm w/ Deck 1 Hr. from NYC! From US $150
         

New
House
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly
Inn At Arbor Ridge Hotel & Conference Center From US $126
         

6.0 (291 Reviews)
Hotel
  • Parking
  • TV
  • Wheelchair Accessible

Instantly Bookable Vacation Homes in Shenandoah

Over 10+ Instantly Bookable Vacation Homes in or Near Shenandoah
Charming Cabin in Fishkill! From US $422
         

Charming Cabin in Fishkill! From US $420
         

9.6 (4 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
LivingUPstation From US $429
         

10.0 (1 Review)
House
  • Security/Safety
  • Child Friendly

About Shenandoah Vacation Rentals

With more than 100 Shenandoah vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Topwintervacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Shenandoah.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Topwintervacations Shenandoah, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Shenandoah. Places to stay near Shenandoah are 890.05 ft² on average, with prices averaging $422 a night.

Topwintervacations makes it easy and safe to find and compare vacation rentals in Shenandoah with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Shenandoah

Type Count
Vacation Homes 51
Hotels with Suites 25
Holiday Apartments 14
Cabin Rentals 7
Villas 2
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Shenandoah

Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Shenandoah.

Weather in Shenandoah

View the weather forecast for Shenandoah before booking your Shenandoah Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F