Guesthouse vacation rentals in Western Maryland
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Top-rated guesthouse rentals in Western Maryland
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Western Maryland guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Purcellville
4.8 out of 5 average rating, 256 reviewsBarn Apartment in VA Wine Country
Aug 23 – 30
Guesthouse in Frederick
4.97 out of 5 average rating, 316 reviewsThe Shady Bear Cabin
Feb 16 – 23
Guesthouse in Keedysville
4.98 out of 5 average rating, 191 reviewsCity Dog Farm
Jul 10 – 17
Guesthouse in Boston
4.98 out of 5 average rating, 148 reviewsThe Bunkhouse- simple & serene w/mountain views
Sep 2 – 9
Guesthouse in Aspers (Mail)
4.92 out of 5 average rating, 350 reviewsCottage on our horse farm
Feb 23 – Mar 2
Guesthouse in Harpers Ferry
4.84 out of 5 average rating, 143 reviewsRiverkeeper Inn
May 30 – Jun 6
Guesthouse in Sperryville
4.96 out of 5 average rating, 358 reviewsRiver Side Tourist Room and Bath Loft-5 min to SNP
Dec 12 – 19
Guesthouse in Morgantown
4.95 out of 5 average rating, 442 reviewsTrillium Acres Guest House
Dec 2 – 9
Guest house rentals with a patio
Guesthouse in Bluemont
4.97 out of 5 average rating, 104 reviewsBlueridge Mountain Guest Cabin- Amongst the Trees
Jan 12 – 19
Guesthouse in Fort Valley
4.9 out of 5 average rating, 145 reviewsRomantic Mountain Getaway⛰ hot tub*king bed*sauna
Jul 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
Nov 26 – Dec 3
Guesthouse in Woodstock
4.95 out of 5 average rating, 87 reviewsCozy cottage nestled on 8 acres with mountain view
Jan 11 – 18
Guesthouse in Flint Hill
4.97 out of 5 average rating, 94 reviewsSummer kitchen guesthouse at Caledonia Farm 1812
Jul 30 – Aug 6
Guesthouse in Middletown
5.0 out of 5 average rating, 92 reviewsCottage, Pool, & Breakfast on 100ac Horse Estate
Jul 22 – 27
Guesthouse in Middleburg
5.0 out of 5 average rating, 41 reviews18th Century Middleburg Cottage
Feb 21 – 28
Guest house rentals with a washer and dryer
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Oct 1 – 8
Guesthouse in Purcellville
4.99 out of 5 average rating, 209 reviewsThe Cottage at Dunthorpe Farm
Jan 3 – 10
Guesthouse in Falls Church
4.97 out of 5 average rating, 131 reviewsBeautiful New Apartment Surrounded by Nature
Aug 20 – 27
Guesthouse in New Paris
4.99 out of 5 average rating, 129 reviewsCharming Guest House Bedford County PA
Sep 3 – 10
Guesthouse in Arlington
4.98 out of 5 average rating, 105 reviewsSpacious Guest House 10-15 min to DC
Nov 20 – 27
Guesthouse in Hamilton
4.98 out of 5 average rating, 116 reviewsTrailside Chalet (A storybook chalet with hot tub)
Oct 5 – 12
Guesthouse in Rockville
4.96 out of 5 average rating, 134 reviewsModern Farmhouse Apartment. Close to Metro
Oct 25 – Nov 1
Guesthouse in Waterford
4.92 out of 5 average rating, 121 reviewsCabin On The Creekside
Aug 13 – 20
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