Shenandoah Valley Vacation Rentals

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Our top choices for Shenandoah Valley vacation rentals

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.0 star property
Stanardsville
9.4 out of 10, Exceptional, (108 reviews)
"Great place"
United States
Ouali
The price is CA $222
CA $316 total
includes taxes & fees
Jul 7 - Jul 8
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (41 reviews)
"Very clean close to every and anything local food was amazing and host had a book that showed a lot about the area which came in handy and grounds was so nice games was fun and pit was amazing bed was so comfortable shower pressure was great water was nice an hot too will come back "
United States
Varnell
The price is CA $146
CA $164 total
includes taxes & fees
Jun 24 - Jun 25
Roadhaven1830

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.2 out of 10, Wonderful, (62 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is CA $111
CA $123 total
includes taxes & fees
Jun 21 - Jun 22
Affordable Suites of America Waynesboro

The West End Flats

The West End Flats
4.5 star property
West End
9.2 out of 10, Wonderful, (125 reviews)
"It's a beautiful space. The host was super helpful. Check in and check out was easy. The location is great. We visited several local restaurants and the transportation museum because of the informational packet within the unit. We would definitely stay again and recommend this place to our friends and family."
United States
Crystal
The price is CA $136
CA $154 total
includes taxes & fees
Jun 30 - Jul 1
The West End Flats

SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (1 review)
"Our stay was perfect. Hotels.com really messed up the booking and I almost didn’t have a place to stay. The host at this property held the room for me and we handled everything directly. He was great, the room was spectacular!"
United States
Crystal
The price is CA $160
CA $183 total
includes taxes & fees
Jun 21 - Jun 22
SONSAK - MONTICELLO

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville
9.8 out of 10, Exceptional, (326 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
The price is CA $218
CA $387 total
includes taxes & fees
Jun 18 - Jun 19
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Chalet High by Coolvacay

Chalet High by Coolvacay
3.0 star property
Basye
8.8 out of 10, Excellent, (391 reviews)
"Everything was good except pool was closed too early I don’t aspect it."
United States
Nur
The price is CA $256
CA $282 total
includes taxes & fees
Jul 6 - Jul 7
Chalet High by Coolvacay

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (155 reviews)
"Lisa we are happy for staying at your places it awesome and we had great time, thank you let us use your home"
United States
Issac S.
The price is CA $154
CA $350 total
includes taxes & fees
Jun 17 - Jun 18
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (116 reviews)
"We loved staying at this apartment!"
United States
Sebastian A.
The price is CA $176
CA $388 total
includes taxes & fees
Jun 17 - Jun 18
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (244 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is CA $144
CA $160 total
includes taxes & fees
Jun 22 - Jun 23
Valley Extended Suites

Postcard Cabins Shenandoah North, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah North, Outdoor Collection by Marriott Bonvoy
2.0 star property
Basye
9.8 out of 10, Exceptional, (70 reviews)
"A nice package for a woodland getaway."
United States
JOHN
The price is CA $209
CA $292 total
includes taxes & fees
Jun 23 - Jun 24
Postcard Cabins Shenandoah North, Outdoor Collection by Marriott Bonvoy

Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is CA $252
CA $479 total
includes taxes & fees
Jun 17 - Jun 18
Firefly on The Ridge

Mountainside Villas at Massanutten by Tripforth

Mountainside Villas at Massanutten by Tripforth
3.5 star property
McGaheysville
9.0 out of 10, Wonderful, (382 reviews)
"Excellent place Gina was amazing the reception"
United States
Dominick
The price is CA $263
CA $352 total
includes taxes & fees
Jun 17 - Jun 18
Mountainside Villas at Massanutten by Tripforth

Historical home, walkable to many restaurants and shops.

Historical home, walkable to many restaurants and shops.
Luray
9.8 out of 10, Exceptional, (91 reviews)
"This is a very charming property and walkable to lots of cute shopping and the River Walk. We had a little hiccup at check in and it was taken care of so promptly!"
United States
Nicky T.
The price is CA $164
CA $361 total
includes taxes & fees
Jun 24 - Jun 25
Historical home, walkable to many restaurants and shops.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (324 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is CA $151
CA $365 total
includes taxes & fees
Jun 22 - Jun 23
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Ivy Rose Cottage nestled b/t Cville & Vineyards

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (80 reviews)
"Lovely cottage. Kitchen had everything for coffee. The beds were super comfortable. Would definitely stay here again when in the area."
United States
Amy N.
The price is CA $271
CA $500 total
includes taxes & fees
Jun 23 - Jun 24
Ivy Rose Cottage nestled b/t Cville & Vineyards

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (53 reviews)
"Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!"
United States
Meredith T.
The price is CA $107
CA $298 total
includes taxes & fees
Jun 30 - Jul 1
Where the Trail Ends

Unit 3 - Luxury King Suite with Private Balcony

Unit 3 - Luxury King Suite with Private Balcony
Charlottesville
10.0 out of 10, Exceptional, (26 reviews)
"Very nice space. Clean, quiet, and comfortable. Host very responsive to any questions or information needs. Would definitely consider staying here again."
United States
Brian T.
The price is CA $251
CA $326 total
includes taxes & fees
Jun 17 - Jun 18
Unit 3 - Luxury King Suite with Private Balcony

Direct Slopeside - 1st Floor Luxury Condo @ Bryce Resort HIKE GOLF BIKE MTB LAKE

Direct Slopeside - 1st Floor Luxury Condo @ Bryce Resort HIKE GOLF BIKE MTB LAKE
Mount Jackson
10.0 out of 10, Exceptional, (107 reviews)
"Great stay. Would stay again."
United States
Jonathan K.
The price is CA $125
CA $323 total
includes taxes & fees
Jun 17 - Jun 18
Direct Slopeside - 1st Floor Luxury Condo @ Bryce Resort HIKE GOLF BIKE MTB LAKE

Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (70 reviews)
"The apartment was beautifully decorated and immaculately clean. It was close to everything we intended to get to and we appreciated how easy it was to check in and check out. It was so comfortable and homey. "
United States
Natalie
The price is CA $210
CA $344 total
includes taxes & fees
Jun 17 - Jun 18
Stay in Crozet Train Suite in Downtown Crozet
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 Valley Hotel Reviews

Find out more about Shenandoah Valley

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Shenandoah Valley. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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