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, (91 reviews)
"Second time staying with the family here. We had so much fun! Kids love the experience! Highly recommended! "
United States
Yan
$179 nightly
The price is $203
Apr 27 - Apr 28
Total with taxes and fees
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
United States
Carri
$135 nightly
The price is $152
Apr 26 - Apr 27
Total with taxes and fees
Roadhaven1830

The West End Flats

The West End Flats
4.5 star property
West End
9.4 out of 10, Exceptional, (111 reviews)
"The property is pet friendly, clean, laundry in room and quiet"
United States
Charles
$107 nightly
The price is $121
Apr 26 - Apr 27
Total with taxes and fees
The West End Flats

SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
$127 nightly
The price is $145
Apr 29 - Apr 30
Total with taxes and fees
SONSAK - MONTICELLO

Mountainside Villas at Massanutten by Tripforth

Mountainside Villas at Massanutten by Tripforth
3.5 star property
McGaheysville
9.0 out of 10, Wonderful, (378 reviews)
"Beautiful place and lots of amenities "
United States
Janay
$229 nightly
The price is $253
May 7 - May 8
Total with taxes and fees
Mountainside Villas at Massanutten by Tripforth

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (55 reviews)
"Always a pleasant stay."
United States
MARJORIE
$83 nightly
The price is $92
May 3 - May 4
Total with taxes and fees
Affordable Suites of America Waynesboro

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (222 reviews)
"Nice place"
United States
Orhan
$114 nightly
The price is $127
Apr 26 - Apr 27
Total with taxes and fees
Valley Extended Suites

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
$216 nightly
The price is $235
Apr 26 - Apr 27
Total with taxes and fees
Love Ridge Mountain Lodging

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

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (108 reviews)
"Very nice, updated place with everything we needed. We would definitely stay here again!"
United States
Kimberly M.
$254 nightly
The price is $285
Apr 26 - Apr 27
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

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, (152 reviews)
"Very clean and pet-friendly "
United States
Heston
$215 nightly
The price is $241
Apr 26 - Apr 27
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Postcard Cabins Shenandoah North, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah North, Outdoor Collection by Marriott Bonvoy
2.0 star property
Basye
9.6 out of 10, Exceptional, (65 reviews)
"Very Cute, clean and cozy! We had a great time! Only downfall is you run out of hot water pretty fast, so shower quickly! Calm, peaceful surroundings, and a walking trail if you choose to venture away from your campsite"
United States
Samantha
$169 nightly
The price is $186
Apr 28 - Apr 29
Total with taxes and fees
Postcard Cabins Shenandoah North, Outdoor Collection by Marriott Bonvoy

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
$210 nightly
The price is $236
Apr 24 - Apr 25
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (58 reviews)
"Loved out stay! "
United States
Emilee
$367 nightly
The price is $394
Apr 26 - Apr 27
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg

Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.
Charlottesville
10.0 out of 10, Exceptional, (51 reviews)
"Comfy rooms, great layout, pretty scenery, exceeded expectations "
United States
Molly P.
$257 nightly
The price is $294
Apr 27 - Apr 28
Total with taxes and fees
Unique Cypress cottage, close to Charlottesville with mountain views.

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (107 reviews)
"Very clean and amazing location. Owners are very communicative. We certainly plan on returning in the future. "
United States
Anthony C.
$308 nightly
The price is $331
Apr 27 - Apr 28
Total with taxes and fees
High Street | Walk to Everything Crozet | Pet-Friendly

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, (318 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
$211 nightly
The price is $237
Apr 26 - Apr 27
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (33 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
$236 nightly
The price is $265
Apr 26 - Apr 27
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (126 reviews)
"Everything was as is listed, we were off season so hiking and scenic views is what there was to do, relaxing. Host was accessible on phone, place was clean. "
United States
David L.
$230 nightly
The price is $258
Apr 26 - Apr 27
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!

Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
$190 nightly
The price is $211
Apr 26 - Apr 27
Total with taxes and fees
Fishersville Oasis

Cozy Cabin w Lake, Hot Tub, Huge Deck & Fire Pit

Cozy Cabin w Lake, Hot Tub, Huge Deck & Fire Pit
Mathias
10.0 out of 10, Exceptional, (36 reviews)
"The cabin was perfect for our weekend getaway. The home was incredibly clean and tidy."
United States
Brian E.
$320 nightly
The price is $346
Apr 26 - Apr 27
Total with taxes and fees
Cozy Cabin w Lake, Hot Tub, Huge Deck & Fire Pit
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

Everything you need to know about Shenandoah Valley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shenandoah Valley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Valley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shenandoah Valley vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $92 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shenandoah Valley rentals

At Expedia, we put the best Shenandoah Valley vacation 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 Valley 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 Valley vacation.

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 Valley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.