Skyland Holiday Rentals

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Check prices for these dates

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Skyland holiday rentals

Exterior
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.0 star property
Stanardsville
9.6 out of 10, Exceptional, (56)
"Everything is wonderful and comfortable!"
United States
Yasmine
The price is HK$769
HK$1,224 total
includes taxes & fees
7 Jan - 8 Jan 2026
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Garden
Roadhaven1830

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (38)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
United States
Carri
The price is HK$1,007
HK$1,131 total
includes taxes & fees
29 Dec - 30 Dec
Roadhaven1830
Smart TV, stereo
Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (55)
"It was a beautiful getaway from all of the busy mess from our normal lives"
United States
Tailor N.
The price is HK$720
HK$2,106 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Retreat - Hot tub + Mountain Views + Pets
Outdoor dining
Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Outdoor Theatre | Hot Tub | Fire Pit | Dogs
Luray
9.8 out of 10, Exceptional, (59)
"Great place to stay for a quiet getaway in the mountains! Beautiful property"
United States
Lee S.
The price is HK$800
HK$2,377 total
includes taxes & fees
20 Jan - 21 Jan 2026
Outdoor Theatre | Hot Tub | Fire Pit | Dogs
Exterior
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Etlan
9.8 out of 10, Exceptional, (6)
"Loved it, clean and as described, great farm."
United States
Trent R.
The price is HK$629
HK$866 total
includes taxes & fees
3 Jan - 4 Jan 2026
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Outdoor pool
Lakefront, Swim, Fish, Kayak, fire pit, star gazing, pet friendly. All on site!

Lakefront, Swim, Fish, Kayak, fire pit, star gazing, pet friendly. All on site!

Lakefront, Swim, Fish, Kayak, fire pit, star gazing, pet friendly. All on site!
New Market
10.0 out of 10, Exceptional, (34)
"Thank you for the wonderful stay. We enjoyed the getaway. Nice relaxing and quiet. "
United States
amy y.
Lakefront, Swim, Fish, Kayak, fire pit, star gazing, pet friendly. All on site!
Exterior
NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE

NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE

NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
Stanley
9.8 out of 10, Exceptional, (14)
"We enjoyed our stay at the Colorful Cottage. So beautifully decorated and it had everything we needed. The hot tub was perfect for easing our aching muscles after long days of hiking. "
United States
Liesl E.
The price is HK$762
HK$3,030 total
includes taxes & fees
11 Jan - 12 Jan 2026
NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
Property grounds
Elegant Retreat w/Vintage Charm & Modern Comforts

Elegant Retreat w/Vintage Charm & Modern Comforts

Elegant Retreat w/Vintage Charm & Modern Comforts
Luray
9.8 out of 10, Exceptional, (6)
"Quaint house in a small town with a wonderdul trail right behind the residence."
United States
Amber K.
The price is HK$609
HK$1,033 total
includes taxes & fees
4 Jan - 5 Jan 2026
Elegant Retreat w/Vintage Charm & Modern Comforts
Smart TV, fireplace, video games, DVD player
Skyline View: New build! A+ views! Spacious!

Skyline View: New build! A+ views! Spacious!

Skyline View: New build! A+ views! Spacious!
Stanley
10.0 out of 10, Exceptional, (67)
"We had a wonderful stay — the property was beautiful, spacious, and had amazing views. Everything was clean and comfortable, and we truly enjoyed our time here.Overall, it was a great experience and I’d be happy to stay again."
United States
Hana K.
The price is HK$1,229
HK$2,274 total
includes taxes & fees
18 Jan - 19 Jan 2026
Skyline View: New build! A+ views! Spacious!
Smart TV, Hulu, streaming services
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
Luray
10.0 out of 10, Exceptional, (65)
"Charming and clean, beautiful area, and very quiet."
United States
Justin S.
The price is HK$622
HK$1,686 total
includes taxes & fees
14 Jan - 15 Jan 2026
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
Outdoor dining
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Luray
9.6 out of 10, Exceptional, (71)
"Very relaxing and quiet. Nice getaway."
United States
Anonymous traveller
The price is HK$1,020
HK$2,339 total
includes taxes & fees
4 Jan - 5 Jan 2026
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Exterior
Private Cabin in the woods w/ firepit right next to Shenandoah River

Private Cabin in the woods w/ firepit right next to Shenandoah River

Private Cabin in the woods w/ firepit right next to Shenandoah River
Bentonville
10.0 out of 10, Exceptional, (32)
"We really enjoyed everything about this property!"
United States
Sharon W.
The price is HK$1,337
HK$2,786 total
includes taxes & fees
4 Jan - 5 Jan 2026
Private Cabin in the woods w/ firepit right next to Shenandoah River
Terrace/patio
River Access Cabin w Hot Tub, Deck, Grill, & Wifi

River Access Cabin w Hot Tub, Deck, Grill, & Wifi

River Access Cabin w Hot Tub, Deck, Grill, & Wifi
Luray
8.6 out of 10, Excellent, (24)
"As it is described. Clean and peaceful. "
United States
Anna A.
The price is HK$1,145
HK$2,017 total
includes taxes & fees
8 Jan - 9 Jan 2026
River Access Cabin w Hot Tub, Deck, Grill, & Wifi
Fridge, microwave, oven, stovetop
Fully Furnished 1 Bedroom Flat in Historic Downtown New Market

Fully Furnished 1 Bedroom Flat in Historic Downtown New Market

Fully Furnished 1 Bedroom Flat in Historic Downtown New Market
New Market
10.0 out of 10, Exceptional, (6)
"The place was clean, tidy, and spacious. Everything was well-maintained, making it a comfortable and pleasant stay."
United States
Magali B.
The price is HK$629
HK$881 total
includes taxes & fees
5 Jan - 6 Jan 2026
Fully Furnished 1 Bedroom Flat in Historic Downtown New Market
4 bedrooms, iron/ironing board, travel cot, free WiFi
Peaceful Mountain Hideout | Luray Charm

Peaceful Mountain Hideout | Luray Charm

Peaceful Mountain Hideout | Luray Charm
2.0 star property
Luray
10.0 out of 10, Exceptional, (5)
"The stay was beautiful. Beautiful scenery and great for families with pets. Awesome rental property!"
United States
Amy R.
The price is HK$1,243
HK$2,748 total
includes taxes & fees
31 Dec - 1 Jan 2026
Peaceful Mountain Hideout | Luray Charm
TV, fireplace
New/MountainViews/Rustic/HotTub

New/MountainViews/Rustic/HotTub

New/MountainViews/Rustic/HotTub
Stanley
10.0 out of 10, Exceptional, (4)
"Lovely cabin in the foothills which was perfect for my sons and I. The hot tub was a hit. "
United States
PaulAbby L.
The price is HK$855
HK$2,346 total
includes taxes & fees
14 Jan - 15 Jan 2026
New/MountainViews/Rustic/HotTub
Fridge, microwave, oven, stovetop
The Depot Loft at Shenandoah

The Depot Loft at Shenandoah

The Depot Loft at Shenandoah
Shenandoah
10.0 out of 10, Exceptional, (22)
"We only stayed for one night but the rental was great"
United States
Mike B.
The price is HK$664
HK$1,788 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Depot Loft at Shenandoah
Outdoor dining
Balk Retreat/MountainViews/HotTub/Firepit

Balk Retreat/MountainViews/HotTub/Firepit

Balk Retreat/MountainViews/HotTub/Firepit
Stanley
10.0 out of 10, Exceptional, (3)
"The property was very pet friendly. We enjoyed how spacious the cabin is and the kids were well entertained with games down stairs. The view is nice and the location is great for exploring the area."
United States
Mark W.
The price is HK$1,026
HK$2,543 total
includes taxes & fees
13 Jan - 14 Jan 2026
Balk Retreat/MountainViews/HotTub/Firepit
Exterior
Hot tub • Pet Friendly • EV charger • Firepit • Secluded

Hot tub • Pet Friendly • EV charger • Firepit • Secluded

Hot tub • Pet Friendly • EV charger • Firepit • Secluded
2.0 star property
New Market
10.0 out of 10, Exceptional, (1)
"We had the absolute best time during our stay. Everything was perfect and the house and host were wonderful! "
United States
Courtney T.
The price is HK$1,066
HK$2,393 total
includes taxes & fees
20 Jan - 21 Jan 2026
Hot tub • Pet Friendly • EV charger • Firepit • Secluded
Living area
Conductor's Suite at the Depot in charming Shenandoah

Conductor's Suite at the Depot in charming Shenandoah

Conductor's Suite at the Depot in charming Shenandoah
Shenandoah
9.0 out of 10, Wonderful, (8)
"Super cute place in an amazing location. Everyone in town was very friendly and the scenery was incredible. I wish we had more time to explore the area."
United States
Jamison D.
The price is HK$466
HK$1,254 total
includes taxes & fees
4 Jan - 5 Jan 2026
Conductor's Suite at the Depot in charming Shenandoah
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 Skyland Hotel Reviews

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"Beautiful historic hotel, suite was cosy and spacious, staff was very friendly, and southern Sunday brunch was great!"
Boris 1-night trip
Posted 5 days ago
Mimslyn Inn Historic Hotels Of America

Find out more about Skyland

Search for holiday rentals in Skyland on Expedia! You can easily find your home rentals, villas, holiday apartments in Skyland using one of the methods below:

  • View our selection of featured holiday rentals in Skyland
  • Use the map to find apartments and other holiday homes in the Skyland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Skyland while they last

Look no further and take a look at our great range of rental properties in Skyland!

Frequently asked questions

Are there holiday rentals in Skyland?

Yes, there are holiday rentals close to the most popular sights in Skyland, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the majestic mountain landscape in Skyland. Make sure you have time to check out the museums while you're in the area.

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

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4: This holiday home rental outside of Skyland is located in the mountains, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Skyland?

With 264 Expedia holiday rentals, you're guaranteed to find just the right place for your Skyland stay.

What’s there to see and do in Skyland?

Explore the area and family-friendly sights such as Yogi Bear's Jellystone Park, or get out into nature at a spot like Old Rag Mountain. Dark Hollow Falls and Thorton Gap Entrance Shenandoah are a couple of places you'll find in the wider area.

What’s a holiday rental in Skyland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Skyland. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family getaway.