Vacation rentals in Upperville

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Top-rated vacation rentals in Upperville

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Luray

4.9 out of 5 average rating, 188 reviews

1850's Massanutten Spgs -"Charmed by the Ambiance"

MarandaRating, 5 stars4 days ago

We absolutely loved our stay! The place was easy to find and access. It is conveniently located in Luray close to the town and attractions, but also far enough away to unplug and have privacy. We really enjoyed the hot tub and fire pit while star gazing. Would highly recommend and would book again!

Guest favorite

Cottage in Middletown

4.9 out of 5 average rating, 271 reviews

Charming "Cream of the Crop" Cape ~❤️of Middletown

Mary And TomRating, 5 stars2 weeks ago

The location of Heather's house was an ideal for my sister (from Florida) and I (from Maine) to visit with our family in the area. The home has comfortable beds, great showers, well equipped kitchen and livingroom. A great home base to return to after our days filled with activities. Thank you.

Guest favorite

Cabin in Luray

4.94 out of 5 average rating, 151 reviews

❤️️Wildflower Cabin❤️️ A Luxury Riverfront Retreat

KahariRating, 5 stars4 days ago

Beautiful place inside and out. They warn of connection issues but I really didn’t have a problem at all. Nice fire pit area next to the cottage AND next to the river. I really wish I booked for longer. Fantastic host

Guest favorite

Cottage in Leesburg

4.92 out of 5 average rating, 401 reviews

Romantic Stone Cottage Circa 1869-75 acres to Hike

RebekahRating, 5 stars2 weeks ago

We stayed at Reagan's cottage in the woods for our short babymoon weekend. It was the perfect, quiet retreat we were looking for. We had a lovely dinner out in Leesburg and otherwise enjoyed the peaceful accommodations in the woods. Thanks for a great stay!

Top guest favorite

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 108 reviews

Tequila Sunset, Harpers Ferry. Entire first floor!

MarciaRating, 5 stars2 weeks ago

What an amazing view! Every room is perfectly decorated. Anything you could possibly need was available. We visited during a cold spell so enjoyed the indoor fireplace, complete with plenty of fire starters, seasoned logs, and s’mores fixings! Enjoyed meeting Ozzy the tortoise. Also spotted deer, wild turkeys, squirrels, and a rabbit. We had our binoculars but didn’t get them out as Ally supplied a better pair. Ally responded quickly to questions. We had a terrific anniversary and highly recommend you book here.

Guest favorite

Cabin in Stanley

4.97 out of 5 average rating, 182 reviews

Stunning Mountain Views in Luxurious Log Home!

AndreasRating, 5 stars3 weeks ago

Very nice and tastefully decorated mountain style cabin. Spacious with great look. Clean, quiet and much nature around. Communication with Lisa and Jim was pleasant, to the point and with quick answers. I can highly recommend

Top guest favorite

Home in Edinburg

4.98 out of 5 average rating, 394 reviews

The Burrow ~ Our guest reviews say it all!

DanielleRating, 5 stars1 week ago

The house is beautiful and homey, set on a stunning landscape. A mountain ridge from the blue mountains sets to the east, with woods surrounding all other sides. It is quiet and peaceful. The perfect spot if you’re looking to go hiking in the national park, or to just have some peace and quiet. The host was wonderful and kind.

Guest favorite

Cabin in Harpers Ferry

4.97 out of 5 average rating, 156 reviews

Applemoon: Charming Log Cabin in a Mountain Lake Community

AmyRating, 5 stars2 weeks ago

We had a wonderful stay at this cabin! It has all the necessities and was a very comfortable space. If you come off season, be mindful that you are 20+ minutes from most restaurants and shops. You also are in the mountains so service is limited beyond the WiFi of the cabin!

Guest favorite

Cabin in Rileyville

4.94 out of 5 average rating, 148 reviews

A+ Privacy & Views | HotTub + Firepit + BBQ | Pets

VictoriaRating, 5 stars3 weeks ago

Brian was a proactive and responsive host with a beautiful cabin! The pictures did not do this space justice. If you want a slice of tranquility in the mountain this is your space. I would recommend this area and host to anyone!

Guest favorite

Cabin in Rileyville

4.98 out of 5 average rating, 113 reviews

Luxe Log Cabin, Mountain Views, HotTub, Secluded

BryanRating, 5 stars2 weeks ago

Riverside Rose was a wonderful respite from the busy world. It was a great place to relax and decompress. There is a great view of the Massanutten Mountain and abundant wildlife roaming the property (bunnies, a groundhog, deer, and wild turkeys). The hot tub was an excellent addition. It was a short drive to Luray where we walked their greenway along the Hawsbill Creek. We also walked to the South Fork of the Shenandoah River from RR.

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What guests are saying

Cozy Retreat - Walk to Hunters Head Tavern

4.98 out of 5 average rating, 43 reviews4 months ago

Excellent stay at a super reasonable price for the area over the Thanksgiving holiday. Very cozy, super comfortable and clean, and walkable to shops and restaurants in Upperville. Only a short drive to Middleburg. Highly recommend and would stay again!

Cottage in Upperville

What guests are saying

Ventura Cottage: 360-views/HotTub/4 acres/Gym

5 out of 5 average rating, 17 reviews3 weeks ago

Everything was top notch, pictures don't do the location justice. The ambiance is peaceful quiet fresh air beautiful views, the house is as listed and more, You get what you paid for. Leena is an amazing person very responsive and very hospitable. Don't think twice just book you will not be disappointed.

Guesthouse in Stephens City

What guests are saying

Veda Vista-Closed Patio-EV Charger-Fireplace

4.93 out of 5 average rating, 14 reviews3 months ago

This home was in a beautiful location. we enjoyed the home and felt very comfortable there. Krina did allow us to check in a couple of hours early which made the logistics of our stay much easier for us. we definitely would stay there again on our next visit. Robert Spencer

Home in Harpers Ferry

What guests are saying

The Grand Ranch - luxury stay for large groups

4.79 out of 5 average rating, 52 reviews1 week ago

An amazing retreat with incredible views of the mountains right off the deck & from almost every window. The scenery was breathtaking having 10 private acres to explore we hiked the woods right outside the door, local wildlife was a treat to spot. Spent the evening in a relaxing hot tub & by the firepit it was the perfect spot to watch the stars. We saw both the Sunset & the Sunrise from the Hot Tub, it was spectacular. The house is large with lots of space yet cozy for just 2 of us, it was perfectly appointed, with a log fire, comfy beds, well equipped kitchen. Can't recommend this spot enough for anyone looking to unplug and connect with nature we were looking for a place for a family reunion later this year it is perfect for large parties. Lots of beds & bathrooms all of a high standard. The new Porch was lovely surprise for morning coffee looking at that view. We are still reeling from the experience. 5 stars isn't enough - I'd give it 10 if I could!

Home in Rileyville

What guests are saying

Riverfront Oasis with Mountain Views, Near Town

4.9 out of 5 average rating, 39 reviews6 days ago

Loved our stay! We were here from DC mainly to hike and relax and the space was perfect for both! Location is close to the north entrance of Shenandoah National Park which was wonderful. We cooked most meals in the unit and it was well equipped for basic meals. Beds were comfy, AC/heaters worked great, and the views were spectacular. Host was lovely and quick to respond. Would definitely stay again!

Guesthouse in Middletown

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Vacation rentals for every style

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Hotels

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Homes

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Popular amenities for Upperville vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Upperville's top sights

Hunter's Head Tavern54 locals recommend

The Market at Bluewater Kitchen9 locals recommend

Trinity Episcopal Church4 locals recommend

Other great vacation rentals in Upperville

Guest favorite

Cabin in Augusta ( Capon Bridge)

4.97 out of 5 average rating, 149 reviews

Nirvana, Mountain View

RafaelRating, 5 stars2 months ago

We had an amazing stay, it's a very well equipped cabin, in an amazing, beautiful and very quiet place, exactly the kind of retreat we were looking for. Great mountais view. The nearby town is also very quiet and receptive, where it's easy to buy food and supplies. Su and her husband are amazing people and always willing to help. I can't wait to go back.

Superhost

Apartment in Downtown Frederick

5 out of 5 average rating, 3 reviews

Carroll Creek Charmer/ Sleeps 4 Luxurious King Bed

AndrewRating, 5 stars1 week ago

everything about the house and the host were fantastic! The house is such a neat blend of historic and modern. There was so much space, natural light and beautifully decorated. The house is in the perfect location where everything is within walking distance. The owners were incredibly attentive and responsive. made for a great experience. We absolutely loved everything about our experience.

Guest favorite

Home in Cross Junction

4.87 out of 5 average rating, 124 reviews

The Little Red Schoolhouse

JackelynRating, 5 stars4 days ago

Beautiful views and very peaceful to get away!

Superhost

Cabin in Luray

4.81 out of 5 average rating, 81 reviews

Shenandoah Manor - Pet friendly lodge with a hot t

NicoleRating, 5 stars3 months ago

This was my first Christmas with my husband home as my husband as last year he was deployed. We wanted to do something special and this was just the cabin with the BEST views! The hot tub was amazing the view paired perfectly with coffee! 10 out of 10 would stay here again!

Superhost

Home in Harpers Ferry

4.83 out of 5 average rating, 248 reviews

Larger Families, Hot tub, Campfire Ring, Rural

AdrienRating, 5 stars3 weeks ago

Home was clean and as described. It was large and roomy. Outside had a nice yard to play in. Harper’s Ferry town and the national historic park are amazing places to visit. Lots to do and see even in March. I would visit again and stay at this home again.

Superhost

Apartment in Luray

4.86 out of 5 average rating, 57 reviews

Downtown Luray Getaway ~ Walk to Everything

CoreyRating, 5 stars1 week ago

Responsive and easy to get a hold of. Comfortable and clean, good location in the town, not too far from restaurants and other necessities

Superhost

Home in Germantown

4.8 out of 5 average rating, 54 reviews

Sophia’s victorian

Simrnjit KaurRating, 5 stars4 days ago

Perfect place for our stay in Germantown. Very cozy and the kitchen was fully stocked with cookware. Plenty of rooms for everyone to have their own space and also the family room was big enough for everyone to hang out together.

Guest favorite

Cottage in Front Royal

5 out of 5 average rating, 29 reviews

St. Anne's Cottage with peaceful farm views

PatriciaRating, 5 stars9 months ago

This was a beautiful home with lots of room for our group to spread out. We all had our own private space as well as several common areas to hang out together. The house was clean, spacious, and had great views. Thanks for the great stay!

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Vacation rentals in Upperville

Top-rated vacation rentals in Upperville

Cozy Retreat - Walk to Hunters Head Tavern

Ventura Cottage: 360-views/HotTub/4 acres/Gym

Cozy Mountain Cottage Perfect for Friends & Family

CrescentMoonCabin~SNP~Arcade~Yoga~HotTub~Dogs~ESVE

Veda Vista-Closed Patio-EV Charger-Fireplace

Cedar Breeze Cabin~River~Hiking~Mt Views~Hot Tub

Luxury Home. Hot-tub, Fire Pit, Game Room. IAD/DC

The Grand Ranch - luxury stay for large groups

Riverfront Oasis with Mountain Views, Near Town

Mountain Top Cabin|Near River| High Speed Internet

Dog Friendly Cabin near River on Nearly 5 acres w/

Rustic chic 3 bedroom home with onsite parking.

Vacation rentals for every style

Popular amenities for Upperville vacation rentals

Stay near Upperville's top sights

Other great vacation rentals in Upperville

Destinations to explore