House vacation rentals in Middleburg

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Popular amenities for Middleburg house rentals

House rentals with a pool

Guest favorite
Home in Boston
4.96 out of 5 average rating, 143 reviews

Peacefield - Blue Ridge views near Culpeper

ClaudiaRating, 5 stars3 weeks ago
Fabulously beautiful location. Picturesque. Home was lovely, comfortable and delightful to stay in. Many great places to sit, enjoyable amenities. Host was kind to allow us some flexibility to support our family's needs. So appreciated! Highly recommend!
Guest favorite
Home in Harpers Ferry
4.88 out of 5 average rating, 204 reviews

The Historic Booth House at the Harpers Ferry KOA

JimRating, 5 stars1 month ago
The house was great. clean, lots of towels, loved the hot tub. There are two things I would point out. The steps to the upstairs are very hard for people with mobility issues but there are four bedrooms on first floor. There are two single steps on the first floor.
Guest favorite
Home in Harpers Ferry
4.97 out of 5 average rating, 195 reviews

Harpers Ferry Farmhouse, Heated Year Round Pool

WendyRating, 5 stars1 week ago
Everyone enjoyed our stay here ! S’mores by the firepit, family games around the huge kitchen table and mornings rocking on the front porch rockers . We wished we could stay longer !!!
Guest favorite
Home in Adamstown
4.96 out of 5 average rating, 103 reviews

Wizard's Escape | Sleep15+ | Pool | 2 EscapeRooms

EugeniaRating, 5 stars3 days ago
Our group had the MOST MAGICAL time!! Even the people who knew very little about Harry Potter were in total awe of all the details around the home. The scavenger hunt was a group favorite and the Escape Rooms were top notch!! We fully intend to revisit when the add-ons are complete!! Nate was an excellent communicator and host.
Superhost
Home in Strasburg
4.76 out of 5 average rating, 269 reviews

Cedar Creek Wayside Castle

TraceyRating, 5 stars1 week ago
I needed a place that my family, from out of state, could stay while attending a graduation. The house was perfect! I told Bob what I wanted to do and he was encouraging and helpful. He made sure we had propane for grilling and answered all my questions. He was very prompt when I reached out to him. We had an amazing time. I would stay there again.
Top guest favorite
Home in Luray
4.98 out of 5 average rating, 101 reviews

Walnut Lane

LynneRating, 5 stars2 weeks ago
My husband, brother, and two of our friends spent the weekend at Brad’s house and we had a lovely time. It was extremely conducive to relaxing. We cooked our meals there. The kitchen was very clean and we had found everything we needed for our meals. We were able to use lies the front porch. The pool was closed, but it looked very nice. Brad is an amazing host. He will answer your questions quickly. I would highly recommend staying at Brad’s place to anyone.
Guest favorite
Home in Leesburg
4.97 out of 5 average rating, 121 reviews

Potomac Overlook Farms: 6 BR, 10 Acre River Estate

MelissaRating, 5 stars2 weeks ago
We had a wonderful family reunion here with 3 generations. Each family had their own private space but there was tons to do on the property together as well. The hosts were very responsive to our questions and made sure we were comfortable and happy! We appreciated that the kitchen was well stocked, too.
Superhost
Home in Aldie
4.82 out of 5 average rating, 11 reviews

Relaxing Aldie Retreat, with Fireplaces and Pool

LaurenRating, 5 stars2 weeks ago
This was the perfect city get away for a weekend trip! The location is great, in the country but also only 10 minutes from Middelburg shops and restaurants. The home was even better than pictured, especially the outside area. The yard, pool and outside seating areas were absolutely beautiful, just so peaceful. The home was absolutely lovely, very clean, comfortable and with all the amenities you would need, including in the kitchen. Really hope to come back, I would highly recommend this rental. Thank you for sharing it with us!

Weekly house rentals

Superhost
Home in Purcellville
4.92 out of 5 average rating, 24 reviews

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

DeborahRating, 5 stars1 month ago
I would recommend this home greatly. We were on a girls weekend. We enjoyed the home the surroundings and the peacefulness. It’s in a beautiful setting close to many great restaurants and wineries. The beds were comfortable and the homeless clean. Should we ever find ourselves that way again we’ve already decided we would stay here.
Top guest favorite
Home in Delaplane
5 out of 5 average rating, 31 reviews

The Shire at Fox Hollow

ReubenRating, 5 stars1 month ago
This was a peaceful as it could get. We wanted a relaxing getaway and this place delivered. Highly recommend
Guest favorite
Home in Delaplane
4.85 out of 5 average rating, 34 reviews

Wine Country, Hikes & Dogs!

TaylorRating, 5 stars1 week ago
The Airbnb was truly the best! The views were breathtaking, and it was peaceful for the most part! I would recommend it to anyone wanting to visit the area! You’ll be pleased ✨
Guest favorite
Home in Upperville
4.91 out of 5 average rating, 58 reviews

The Upperville Academy

VickiRating, 5 stars1 month ago
Very nice property ...Jennifer was excellent.
Guest favorite
Home in Bentonville
5 out of 5 average rating, 43 reviews

Shenandoah Modern Retreat

WendyRating, 5 starstoday
Another wonderful stay . Beautiful, peaceful, well curated with everything we would need. We will definitely stay there again.
Top guest favorite
Home in The Plains
5 out of 5 average rating, 18 reviews

Guest House on Horse Farm -2 bedrooms/2 bath

RitaRating, 5 stars2 weeks ago
A peaceful, quiet and secluded home right in the middle of beautiful northern VA horse country. I spent a few relaxing days there with my sister and her husband visiting from overseas. So many nearby wineries, parks, restaurants and quaint villages made this the perfect getaway. The house was comfortable and had all the needed amenities for a perfect stay.
Top guest favorite
Home in Harpers Ferry
5 out of 5 average rating, 60 reviews

Mountaintop Home in Harpers Ferry

StephenRating, 5 stars1 week ago
Lindsay’s place was perfect. She’s thought of every detail. There are two bedrooms upstairs (each with a bathroom) and one downstairs (also with a bathroom). Upstairs is the pullout sofa bed and downstairs there’s also another tv area with sofa (no pullout) you could sleep on if needed. Everyone loved the home, amenities, and views. The build quality is very high as such you can tell they also visit and enjoy the home themselves. The home is about 15 minutes from Charles Town, and about 25 from downtown Harpers Ferry, with scenic drives to each one. Lots of hikes, coffee shops, wineries and breweries nearby. She was super responsive and helpful all along. We would 100% come back.
Top guest favorite
Home in Markham
4.99 out of 5 average rating, 79 reviews

Modern 4 bedroom farmhouse on four scenic acres

DannyRating, 5 stars4 days ago
One of our favorite Airbnb stays out of well over 100. The property is beautiful and peaceful. The house is cozy and comfortable. Everything you need is in Marshall or Strasburg. Will look to stay here every time we visit the area. Outstanding value and extremely private location. Great host that makes everything easy.

Private house rentals

Guest favorite
Home in Upperville
5 out of 5 average rating, 11 reviews

Reynard's Retreat in Upperville

PhilipRating, 5 stars5 months ago
Beautiful house with nice amenities. Master bedroom on main floor allows for privacy. Also, great stay if you bring a dog. Safe backyard fenced area and mud room allow space to feed. Hint - walk up to Trinity Episcopal Church about 1/4 mile away and walk in 30+ acre fields behind the church. Accessible and great for walking.
Top guest favorite
Home in Paeonian Springs
4.97 out of 5 average rating, 30 reviews

The Fort At Workhorse

NaamonRating, 5 stars2 months ago
A wonderful place. Family of 4 with a very energetic 3 year old, and he had no problem within the space. Clean, calming, designed very well with great thought. Would for sure come back again.
Top guest favorite
Home in Purcellville
4.95 out of 5 average rating, 19 reviews

The Cabin at Blue Valley Farm

DanielleRating, 5 stars1 month ago
Wonderful stay, family of 4. Clean, beautiful views, plenty to do. Meghan and Scott are wonderful hosts. My kids cannot wait to come back!!!!!
Guest favorite
Home in Leesburg
4.98 out of 5 average rating, 56 reviews

The Cottage at Oakland Green Farm

KimberlyRating, 5 stars2 weeks ago
Our countryside escape was just what we needed. The home was peaceful and full of charm — exactly as described. Waking up to the quiet sounds of nature and sipping coffee with scenic views made each day feel like a retreat. The host was thoughtful and responsive, making check-in and communication seamless. We left feeling refreshed and grateful for such a warm and relaxing stay. Highly recommend to anyone looking for a serene getaway! Thank you Sara!
Guest favorite
Home in Purcellville
4.91 out of 5 average rating, 33 reviews

Recently Renovated Rolling Hills Retreat

MorganRating, 5 stars2 weeks ago
Jill is a wonderful host! Seven of us stayed at her place for a girls’ wine weekend, and it was the best experience. The house is absolutely perfect—full of beautiful natural light, spotless, & very spacious. Our favorite part was the deck, where we were lucky enough to watch cattle grazing in the mornings. The location made it easy to explore many of the local wineries. 10/10—highly recommend and would definitely stay here again!
Guest favorite
Home in Haymarket
4.98 out of 5 average rating, 97 reviews

Luxury Cabin Retreat at Hickory Hollow!

DouglasRating, 5 stars1 month ago
The property was fantastic. It was in a gorgeous setting in the woods that was private, but not too private. The house was quite lovely with everything we needed for a great vacation. The kitchen was very functional with everything we needed for cooking and grilling. The 2 bedrooms on the first floor were very comfortable with a shared bathroom. The entire house was very clean, which was huge for us. The primary bedroom upstairs was terrific. The ensuite bathroom was awesome, and the bed was excellent. We particularly liked the little office area around the corner from the bedroom. A great place to check e-mails. The property was like a little compound with a couple of out-buildings by a great firepit. This was the kind of house to just hand and relax. We would love to return at some point.
Guest favorite
Home in Harpers Ferry
4.98 out of 5 average rating, 56 reviews

Cedar Hill Cabin (A-Frame)

OliviaRating, 5 stars1 week ago
My bridesmaids and I stayed her a few nights leading up to the wedding and my husband and I stayed here the night of our wedding!! It was AWESOME! The day before our wedding, something went wrong with the plumbing and they had to shut off the water for about 24 hours, but Ryan was SO helpful and responsive. He even got us another Airbnb to stay at if we wanted to (we just ended up showering there but it was really nice of him)! He kept us updated as soon as he heard something and was so kind the whole time!
Top guest favorite
Home in Berryville
4.99 out of 5 average rating, 77 reviews

Deer Chase

MistyRating, 5 stars1 week ago
Fast and easy communication. The place was beautiful, clean, well stocked, and easy to access. Had a lovely stay and would def would recommend the place and Jeanne.

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