Guesthouse vacation rentals in Jefferson County
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Top-rated guesthouse rentals in Jefferson County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Jefferson County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Smithsburg
4.97 out of 5 average rating, 645 reviewsJewel Vinsota Artist's Guesthouse
Feb 3 – 10
Guesthouse in Keedysville
4.98 out of 5 average rating, 191 reviewsCity Dog Farm
Jul 10 – 17
Guesthouse in Middletown
4.95 out of 5 average rating, 247 reviewsIndulge, Fresh Flowers, Frederick County Haven
Apr 5 – 12
Guesthouse in Frederick
4.97 out of 5 average rating, 316 reviewsThe Shady Bear Cabin
Feb 16 – 23
Guesthouse in Front Royal
4.88 out of 5 average rating, 253 reviews"Cabbin" at Mountain Home B&B
Dec 20 – 27
Guesthouse in The Plains
4.87 out of 5 average rating, 79 reviewsStylish 1 Bedroom Studio Middleburg
Feb 19 – 26
Guesthouse in Berkeley Springs
4.83 out of 5 average rating, 288 reviewsTerrapin Cabin. A sunny, quiet cabin in the woods.
Jul 22 – 29
Guesthouse in Hagerstown
4.87 out of 5 average rating, 23 reviewsValentia farm guest cottage
Dec 11 – 18
Guest house rentals with a patio
Guesthouse in Myersville
4.93 out of 5 average rating, 192 reviewsSpruce Run Cottage, Farm stay on Catoctin Mountain
Jul 11 – 18
Guesthouse in Lovettsville
4.94 out of 5 average rating, 122 reviewsThe Patent House
Apr 24 – May 1
Guesthouse in Bluemont
4.97 out of 5 average rating, 104 reviewsBlueridge Mountain Guest Cabin- Amongst the Trees
Jan 12 – 19
Guesthouse in Front Royal
4.9 out of 5 average rating, 78 reviewsCozy Shenandoah River Cabin (10min to Nat’l Park!)
Dec 10 – 17
Guesthouse in Stephens City
5.0 out of 5 average rating, 6 reviewsVentura Cottage: 360-views/HotTub/4 acres/Gym
May 21 – 28
Guesthouse in The Plains
4.98 out of 5 average rating, 40 reviewsA lovely cottage in The Plains, Virginia
Jan 14 – 21
Guesthouse in Middleburg
5.0 out of 5 average rating, 41 reviews18th Century Middleburg Cottage
Feb 21 – 28
Guesthouse in Middletown
5.0 out of 5 average rating, 92 reviewsCottage, Pool, & Breakfast on 100ac Horse Estate
Jul 22 – 27
Guest house rentals with a washer and dryer
Guesthouse in Bluemont
4.99 out of 5 average rating, 310 reviewsSkyhorse Retreat Guest House
Aug 9 – 16
Guesthouse in Berkeley Springs
4.97 out of 5 average rating, 288 reviewsPond Hill Guesthouse- 2 Bedroom w/Hot Tub & WiFi!!
Apr 2 – 9
Guesthouse in Hamilton
4.98 out of 5 average rating, 116 reviewsTrailside Chalet (A storybook chalet with hot tub)
Oct 5 – 12
Guesthouse in Waterford
4.92 out of 5 average rating, 121 reviewsCabin On The Creekside
Aug 13 – 20
Guesthouse in Bluemont
5.0 out of 5 average rating, 56 reviewsBluemont Escape:Walk to Bears Den; Bear Chase Brew
Jul 16 – 23
Guesthouse in Purcellville
4.94 out of 5 average rating, 72 reviewsThe Nest on Nixon Road
Nov 24 – Dec 1
Guesthouse in Leesburg
4.99 out of 5 average rating, 83 reviewsPrivate 2 BR, 1 Bath Carriage House Near Wineries!
Jun 22 – 29
Guesthouse in Frederick
4.97 out of 5 average rating, 31 reviewsBoutique space at Marble Ridge
Mar 29 – Apr 5
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