House holiday rentals in Highland County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Highland County

House rentals with a pool

Top guest favourite
Home in Wintergreen Resort
4.96 out of 5 average rating, 106 reviews

Cliffs Edge- Hike, Play & Splash into Summer!

MaxRating, 5 stars3 days ago
Our stay at Julie’s place was fantastic- it was plenty big enough for our group of 6 and had everything we needed. The deck view is as amazing as it looks on the listing and Julie was very responsive and helpful. Would definitely stay again!
Guest favourite
Home in Swoope
5 out of 5 average rating, 37 reviews

The Pool House: Hot Tub + Pool + 15 mins downtown

ErinRating, 5 stars8 months ago
An absolutely perfect weekend at a beautiful home and property. Exceeded our expectations. We will definitely be back! Thank you!
Top guest favourite
Home in Wintergreen Resort
4.88 out of 5 average rating, 137 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

KarenRating, 5 stars4 days ago
We had 10 in our party….6 adults and 4 kids. We had plenty of space for relaxing and everyone had a bed to sleep in! Leif was more than generous in recommending hikes/walks for us. Excellent check-in and check-out instructions - very detailed. It was a nice visit for our family!
Guest favourite
Home in Wintergreen Resort
4.96 out of 5 average rating, 106 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

NikiRating, 5 stars2 months ago
Our family of four needed a quiet get away, and we enjoyed the beautiful days and evenings, inside and on the deck! Hikes nearby, spa nearby, restaurants, grocery, gas also nearby. Great resort year round! Lots of activities if you want them, and lots of peaceful nature if you want. Great!
Guest favourite
Home in Wintergreen Resort
4.89 out of 5 average rating, 66 reviews

Hot Tub EV Charger Mntn View Fireplace Grill Pool

Adou,MRating, 5 stars1 month ago
I was looking for a quiet place in the middle of the nature for our 10 years of marriage anniversary and I think we found the best one. Charlotte was so kind and helpful, she helped me surprised my wife with such a beautiful decoration. We were so impressed. My kids were so happy 😊😊 to see something different. If you’re looking for something really peaceful, nice, looking at the beautiful nature in the mountains, you are definitely at the right place. Thank you Charlotte for making our stay so special.😊😊😊😊 It was a really good experience and we definitely have to go back….
Top guest favourite
Home in Wintergreen Resort
4.97 out of 5 average rating, 115 reviews

Bear's Mountain Escape

LauraRating, 5 stars2 weeks ago
Great stay! Perfect location and space was great. A tad smaller than what it looked like in the photos, but overall, great! The kitchen did not have any pantry space, but we made do with a shelf above the microwave and bins on top of the fridge. A day prior to check-in, I received an email stating the pool in the complex was closed for repairs. A bit disappointed at first, but it ended up working out really well. We had access to the SPA indoor and outdoor pools and the outdoors ended up being too cold to swim in. The indoor pool was no problem at all and they were very accommodating with lettings us have access throughout our stay. We would stay here again for sure!
Guest favourite
Home in Snowshoe
4.86 out of 5 average rating, 22 reviews

1ST FLOOR! Snowshoe Getaway! Ski IN & OUT

RobertRating, 5 stars3 days ago
The home very nice . exactly what we expected! Christopher was also excellent. I would recommend him and his home anytime . Thank you for letting us stay . beautiful!
Guest favourite
Home in Wintergreen Resort
4.97 out of 5 average rating, 198 reviews

Hottub Ski In/Ski Out Renovated Chalet Lower Tyro

AshleighRating, 5 stars1 month ago
Joes property was absolutely beautiful! The views are amazing from the cozy hot tub on the back porch. Everything was super clean and the beds were super comfortable! This airbnb would be great for a family stay or a friends getaway. It was everything we needed and more! Joe was quickly responsive when i had questions. This air bnb is stocked with EVERYTHING you may need. Beautiful spot, 10/10!

Weekly house rentals

Top guest favourite
Home in Monterey
5 out of 5 average rating, 17 reviews

Blue View Lodge

KaraRating, 5 stars1 week ago
This home was perfect for our stay for a family of 5 in the area for a wedding. The kitchen had everything we could have ever wanted, even gourmet coffee instructions. There was a full length mirror, iron, and ironing board. Johnny left detailed instructions for just about everything that were super helpful. The bedrooms were more spacious than expected and it was amazing to have 2 bathrooms in order to get ready on time for a family of 5. We enjoyed the bookcase of games! I hope we have reason to return to the area for another season! I'd love to see that hillside in fall, it's so very peaceful. Managed to have 2 meals at the Curly Maple. Highly recommend! Thanks, Johnny!
Top guest favourite
Home in Pendleton County
5 out of 5 average rating, 15 reviews

The Cozy Cottage

ElisabethRating, 5 stars1 month ago
We were looking for a peaceful, private getaway with amazing views for our cycling trip, and this location exceeded our expectations. The cottage was beautiful and cozy, with all the amenities we could possibly need. Our host checked in with us shortly after our arrival and was very responsive to any questions we had. We will definitely be back!
Guest favourite
Home in Durbin
4.88 out of 5 average rating, 180 reviews

River House: A Cozy Mountain Getaway

KennethRating, 5 stars2 days ago
A great place for a mountain getaway for a outdoor family. We did a lot of fishing. Spent the evenings on back porch listening to the river or around the fire pit making smores. Will definitely be back.
Home in McDowell
4.63 out of 5 average rating, 8 reviews

McDowell ‘Highland County River Retreat’ w/ Views!

GregRating, 5 stars2 weeks ago
Just finished a two-night stay in this lovely home outside of McDowell, Virginia. The place was spotless and included all the amenities we needed, even an outdoor charcoal grill which came in handy. The downstairs has central air which was fantastic. The upstairs is cooled with an window unit that worked wonderfully. The pictures shown on the listing are very accurate. The deck is a nice place to relax and has nice views of the valley. There is another home about 100-150 meters away but we didn't hear a thing during out stay. I would definitely book this place again.
Top guest favourite
Home in Monterey
4.98 out of 5 average rating, 96 reviews

Lodging on Main

DavidRating, 5 stars1 month ago
This was the best, most comfortable and cleanest rental we have ever been in, the most at home feeling. Even the pictures on the walls were well thought out and chosen. The beds were most comfortable and warm. I can go on and on but the bottom line is that we confidently want to go back and enjoy a wee bit more time.
Top guest favourite
Home in Franklin
4.97 out of 5 average rating, 189 reviews

Pine Ridge Manor-Private Hot Tub, Secluded Hilltop

JessicaRating, 5 stars1 week ago
We feel truly blessed to have been able to stay at Pine Ridge Manor. The home was gorgeous, loved the modern country feel. We truly enjoyed sitting outside and seeing the beautiful views and all the wildlife. Thank you for letting us stay :)
Top guest favourite
Home in Arbovale
5 out of 5 average rating, 20 reviews

The Boyer Camp House

WhitneyRating, 5 stars4 months ago
We had a GREAT weekend - the house was exactly what we needed for the weekend! My kids said it was a super cozy house and they liked it a lot!!! 10 out of 10 Recommended The host are super friendly and helpful!! Thank you Mike and Karen!!!
Top guest favourite
Home in Pendleton County
5 out of 5 average rating, 19 reviews

Secluded and quiet mountain home with a hot tub.

BethRating, 5 stars8 months ago
Our whole group enjoyed our stay at the farmhouse. The house was fully stocked with everything you could need and more. We found the place to be very neat and tidy. The mountain view was very nice and we could check out the fall colors. Make sure you walk the "Loop" trail on the property! The directions to the house were easy to understand and the check in was simple. We would definitely stay here again!

Private house rentals

Top guest favourite
Home in Monterey
5 out of 5 average rating, 17 reviews

Blue View Lodge

KaraRating, 5 stars1 week ago
This home was perfect for our stay for a family of 5 in the area for a wedding. The kitchen had everything we could have ever wanted, even gourmet coffee instructions. There was a full length mirror, iron, and ironing board. Johnny left detailed instructions for just about everything that were super helpful. The bedrooms were more spacious than expected and it was amazing to have 2 bathrooms in order to get ready on time for a family of 5. We enjoyed the bookcase of games! I hope we have reason to return to the area for another season! I'd love to see that hillside in fall, it's so very peaceful. Managed to have 2 meals at the Curly Maple. Highly recommend! Thanks, Johnny!
Top guest favourite
Home in Pendleton County
5 out of 5 average rating, 15 reviews

The Cozy Cottage

ElisabethRating, 5 stars1 month ago
We were looking for a peaceful, private getaway with amazing views for our cycling trip, and this location exceeded our expectations. The cottage was beautiful and cozy, with all the amenities we could possibly need. Our host checked in with us shortly after our arrival and was very responsive to any questions we had. We will definitely be back!
Guest favourite
Home in Durbin
4.88 out of 5 average rating, 180 reviews

River House: A Cozy Mountain Getaway

KennethRating, 5 stars2 days ago
A great place for a mountain getaway for a outdoor family. We did a lot of fishing. Spent the evenings on back porch listening to the river or around the fire pit making smores. Will definitely be back.
Home in McDowell
4.63 out of 5 average rating, 8 reviews

McDowell ‘Highland County River Retreat’ w/ Views!

GregRating, 5 stars2 weeks ago
Just finished a two-night stay in this lovely home outside of McDowell, Virginia. The place was spotless and included all the amenities we needed, even an outdoor charcoal grill which came in handy. The downstairs has central air which was fantastic. The upstairs is cooled with an window unit that worked wonderfully. The pictures shown on the listing are very accurate. The deck is a nice place to relax and has nice views of the valley. There is another home about 100-150 meters away but we didn't hear a thing during out stay. I would definitely book this place again.
Top guest favourite
Home in Monterey
4.98 out of 5 average rating, 96 reviews

Lodging on Main

DavidRating, 5 stars1 month ago
This was the best, most comfortable and cleanest rental we have ever been in, the most at home feeling. Even the pictures on the walls were well thought out and chosen. The beds were most comfortable and warm. I can go on and on but the bottom line is that we confidently want to go back and enjoy a wee bit more time.
Top guest favourite
Home in Franklin
4.97 out of 5 average rating, 189 reviews

Pine Ridge Manor-Private Hot Tub, Secluded Hilltop

JessicaRating, 5 stars1 week ago
We feel truly blessed to have been able to stay at Pine Ridge Manor. The home was gorgeous, loved the modern country feel. We truly enjoyed sitting outside and seeing the beautiful views and all the wildlife. Thank you for letting us stay :)
Top guest favourite
Home in Arbovale
5 out of 5 average rating, 20 reviews

The Boyer Camp House

WhitneyRating, 5 stars4 months ago
We had a GREAT weekend - the house was exactly what we needed for the weekend! My kids said it was a super cozy house and they liked it a lot!!! 10 out of 10 Recommended The host are super friendly and helpful!! Thank you Mike and Karen!!!
Top guest favourite
Home in Pendleton County
5 out of 5 average rating, 19 reviews

Secluded and quiet mountain home with a hot tub.

BethRating, 5 stars8 months ago
Our whole group enjoyed our stay at the farmhouse. The house was fully stocked with everything you could need and more. We found the place to be very neat and tidy. The mountain view was very nice and we could check out the fall colors. Make sure you walk the "Loop" trail on the property! The directions to the house were easy to understand and the check in was simple. We would definitely stay here again!

Destinations to explore