Title: Shenandoah Vacation Home Rentals from CA $363: Search Top Private Vacation Homes for Rent | Expedia.ca

 

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# Shenandoah Vacation Rentals

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## Check prices for these dates

Next weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975866239&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635975866239&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975866239&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975866239&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Shenandoah Vacation Homes

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/9015258a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/8dd5c447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/dd7ed082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/6db641f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Escape -Strong Wi-Fi -Prime Location

Poughkeepsie

7.0/10

Good

(4)

"Apartment was clean but certain areas seemed to have litter box smell. This apartment is located up some narrow stairs. I didn't feel like the listing accurately explained that. We had one in our group that uses a cane & has a lot of difficulty with stairs so we intentionally search for ADA friendly - no stairs required and so when we had the stairs felt as it wasn't an accurate listing. Also listing shows parking onsite. It is actually street parking - luckily on our second time around the...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laurie H.

CA $122

CA $441 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Poughkeepsie-Hotels-Cozy-Escape-Strong-Wi-Fi-Prime-Location.h110643700.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6b825ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/8fad8a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/26c9de37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/a9738f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls

9.4/10

Exceptional

(3)

"Home was very peaceful and serene, My Boys really enjoyed the relaxing and laid back vibe this stay had to offer. My kids did mention it would be a summer vacation stay, because of the creek in the back. Overall is was clean and accommodating. Host did their best for all my accommodation. I would give them a 5- Star White Glove on this. Thanks, Hope to revisit! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Akail S.

CA $173

CA $633 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/33b86b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/fd769a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/d8805194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/bdac6c18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Country outside the city " 3 bedrooms 2 full bathrooms

Holmes

9.6/10

Exceptional

(4)

"Great house! We had a fantastic weekend!! Thank you so much "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

pamela w.

CA $345

CA $901 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/280bea60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/8c15249f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/cbf53a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/0dcdc2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

9.0/10

Wonderful

(10)

"We had a wonderful time staying at this charming and unique getaway! The accommodations were very comfortable. The property was beautiful and felt secluded without being isolated. The chapel itself is beautiful. The bathroom was overall nicer than we anticipated; just be mindful to put the camping shower out in the sun so the water warms up! Overall, highly recommend this experience. The hosts were also very responsive and kind."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Avery D.

CA $214

CA $363 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Hopewell-Junction-Hotels-Cozy-1845-Chapel-Escape-Near-Appalachian-Trail-And-Fahnestock-Park.h88181115.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/a7dbb900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/8bc06f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining tables](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/eda946f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/393a7982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Carmel Hamlet

9.8/10

Exceptional

(12)

"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hannah P.

CA $234

CA $499 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/cde347d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/e34b64d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/8e1f1f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/3089dd8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

New Fairfield

10/10

Exceptional

(13)

"Was a great find. Updated, spacious and clean."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul B.

CA $321

CA $771 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/New-Fairfield-Hotels-Peaceful-All-Season-Lake-Community-Home.h100167349.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/f4c5b854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/719e347a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/e5c54a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/599dbda5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls

10/10

Exceptional

(7)

"Celebrated my son’s HS graduation with my father-in-law along for the adventure, Joe’s townhouse is super convenient to Thayer Gate and eating establishments along Main St. Grill worked well and the beds made for sound slumber. For mixed company an extra half bath might be desired, but 3 guys who know each other well managed just fine. The basement washer & dryer are top of line."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James W.

CA $263

CA $498 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/75b18da9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/f3de8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/9c93ce23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/62a1e2aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie

10/10

Exceptional

(1)

"Great host"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lindsey F.

CA $235

CA $832 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Poughkeepsie-Hotels-Stunning-5-Bedroom-House-With-AC-Heat-In-Charming-Poughkeepsie-NY.h120384809.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/1ffbe7a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/8cbcd139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/26b38c44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/116022ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fabulous 3bdrm Home w/parking!

Highland Falls

8.0/10

Very good

(2)

"Great place. Close to West Point activity. Clean and new."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joanne V.

CA $246

CA $463 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/d9fd7f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/c7d67b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/3745699f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/eed0e9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Contemporary Cozy Cottage

Lake Peekskill

10/10

Exceptional

(30)

"Very clean comfortable quiet place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mauro C.

CA $316

CA $590 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/cf889632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/04bc58ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/8b35ed40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/2bdd6486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Highland Falls

10/10

Exceptional

(2)

"Looked like this property was recently renovated. Very clean and nice. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ellie M.

CA $236

CA $680 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/d7ec344a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/f114158e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/1719048e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/009311c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fun, Friends, and Family Lakefront Home w/Dock and Beach

Mahopac

10/10

Exceptional

(12)

"Super convenient location :)"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sean M.

CA $474

CA $1,023 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Mahopac-Hotels-Fun.h83925171.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/9f0ce022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/22655253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/c553f5f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/852b7fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large,Cozy,Bright Apartment, Business Themed.

Newburgh

9.0/10

Wonderful

(15)

"Very cozy stay with responsive host"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Adhith P.

CA $607

CA $971 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Newburgh-Hotels-Large.h63527962.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83420000/83412500/83412482/w1170h755x0y0-416eda80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83420000/83412500/83412482/665b3941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83420000/83412500/83412482/cc85addb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/84000000/83420000/83412500/83412482/1e4c322d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family friendly Spacious 4 bedroom 3 bathroom getaway

Poughkeepsie

10/10

Exceptional

(4)

"Very easy checkin, great communication from owner. Bring your own travel soap shampoo etc. Store was right down the road for these things so not a big deal. Would rent again in a heartbeat."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ann H.

[](https://www.expedia.ca/Poughkeepsie-Hotels-Family-Friendly-Spacious-4-Bedroom-3-Bathroom-Getaway.h83412482.Hotel-Information)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/e65bd3e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/e36fc455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/bd51dca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121910000/121901300/121901234/9a7fa637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Point Villa - Jacuzzi Pool BBQ Games Pets

Cornwall

CA $824

CA $1,005 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Cornwall-Hotels-West-Point-Villa-Jacuzzi-Pool-BBQ-Games-Pets.h121901234.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120670000/120662200/120662144/18bc41ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120670000/120662200/120662144/9ccdb1d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120670000/120662200/120662144/98cb5754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120670000/120662200/120662144/fd92cdbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunkissed Escape Bright Sunroom + Hammock Fun

Poughkeepsie

CA $330

CA $526 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Poughkeepsie-Hotels-Sunkissed-Escape-Bright-Sunroom-Hammock-Fun.h120662144.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/2af1ac8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/86da8ea2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/1bd3c0a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/fbb02298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Fishkill

9.6/10

Exceptional

(45)

"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa B.

CA $365

CA $471 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information)

![Dining tables](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/7d1ae479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/0da715d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/ee5fa657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/f326c1ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chestnut on Willow Lake

Fishkill

9.4/10

Exceptional

(3)

"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lara S.

CA $633

CA $893 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Fishkill-Hotels-Charming-3-Bedroom-Cottage-In-Wonderful-Fishkill.h112584776.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/w1436h1440x0y0-175a22f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/16dfe03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/46f74edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/105000000/104380000/104373800/104373791/239d3285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Awesome Lake Home with tons of fun!

New Fairfield

9.6/10

Exceptional

(4)

"Great spot "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mike P.

CA $633

CA $1,074 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/New-Fairfield-Hotels-Awesome-Lake-Home-With-Tons-Of-Fun.h104373791.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/104000000/103200000/103194000/103193912/6efe15bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103200000/103194000/103193912/304f93b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103200000/103194000/103193912/06cb6686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103200000/103194000/103193912/22e8d7f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### complete privacy vacation home \[private pool\]

Newburgh

9.8/10

Exceptional

(9)

"Wonderful property! The pool was so fun!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Audrey H.

CA $905

CA $1,588 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Newburgh-Hotels-Complete-Privacy-Vacation-Home-Private-Pool.h103193912.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20&regionId=553248635975866239&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FShenandoah-Private-Vacation-Homes.d553248635975866239-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShenandoah-Private-Vacation-Homes.d553248635975866239-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Shenandoah Hotel Reviews

![Hampton Inn & Suites Poughkeepsie](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg)

### Hampton Inn & Suites Poughkeepsie

10/10 Excellent

"Service and staff was A+++++"

[](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information)

![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](//images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg)

### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent

"Friendly staff, easy checkin and clean room! I’ve stayed here twice this year (2025) and wasn’t disappointed. "

[](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information)

![Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG](//images.trvl-media.com/lodging/1000000/700000/690800/690766/f70c64c6_y.jpg)

### Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

10/10 Excellent

"Excellent comfortable rooms and staff"

[](https://expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information)

![SureStay Plus Hotel by Best Western Highland Poughkeepsie](//images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg)

### SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent

"Property Clean, parking area well lit, room was clean, staffing pleasant- great place for family, will return. "

[](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information)

![DoubleTree by Hilton Poughkeepsie Convention Center](//images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg)

### DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent

"Spotless room, friendly staff, convenient parking and great location for events at Bardavon, Hudson pedestrian bridge in walking distance. We'd stay here again!"

[](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information)

![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](//images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/w4000h2662x0y0-e2ffacae_y.jpg)

### Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Very nice hotel across the CIA It is a beautiful hotel Great rooms They have a great gym and laundry room Great location "

[](https://expedia.ca/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information)

![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg)

### Overlook Lodge at Bear Mountain

10/10 Excellent

"staff was very helpful and the view was very nice"

[](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information)

![Hyatt Place Poughkeepsie / Hudson Valley](//images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd_y.jpg)

### Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent

"We have good time at the hotel. Nice and clean "

[](https://expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information)

![FairBridge Inn & Suites at West Point](//images.trvl-media.com/lodging/1000000/30000/26800/26729/a83d6afb_y.jpg)

### FairBridge Inn & Suites at West Point

8/10 Good

"Parking is easy if you have a car and an easy check in. Staff is friendly and we’re really helpful during a stressful time traveling. My stay plans had changed and they were very helpful in giving me my refund for half the stay I was there. There is no breakfast and if your someone who likes to DoorDash or uber eats this is not the location for you I would like to make this VERY clear. You will be frustrated so please don’t bother trying they don’t have a lot of dashers within their area but they have a beautiful C town grocery store up the road and a gas station for all your small needs. Overall a great spot if your upstate and need a quick stay as well as a beautiful escape into the the mountains with a very clean and modern high rise ceiling room to keep you warm and cozy at night. Will absolutely come back if I need a quick stay upstate! "

[](https://expedia.ca/Newburgh-Hotels-FairBridge-Inn-Suites-At-West-Point.h26729.Hotel-Information)

## Find out more about Shenandoah

## Shenandoah Vacation Homes information

| Number of reviews | 163 |
| --- | --- |
| Accommodation | 229 Vacation Homes |
| Lowest Price | CA $363 |
| Highest Price | CA $1,588 |

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-   [Flights from Edmonton (YEG) to Poughkeepsie (POU)](https://www.expedia.ca/lp/flights/yeg/pou/edmonton-to-poughkeepsie)
-   [Flights from Halifax (YHZ) to Poughkeepsie (POU)](https://www.expedia.ca/lp/flights/yhz/pou/halifax-to-poughkeepsie)
-   [Flights from Ottawa (YOW) to Poughkeepsie (POU)](https://www.expedia.ca/lp/flights/yow/pou/ottawa-to-poughkeepsie)
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-   [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)
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