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
Jun 6 – 13
Guesthouse in Frederick
4.97 out of 5 average rating, 316 reviewsThe Shady Bear Cabin
Feb 12 – 19
Guesthouse in Aspers (Mail)
4.92 out of 5 average rating, 350 reviewsCottage on our horse farm
Mar 14 – 21
Guesthouse in Keedysville
4.98 out of 5 average rating, 190 reviewsCity Dog Farm
May 7 – 14
Guesthouse in Boston
4.98 out of 5 average rating, 148 reviewsThe Bunkhouse- simple & serene w/mountain views
Sep 21 – 28
Guesthouse in Round Hill
4.78 out of 5 average rating, 428 reviewsPrivate detached garage suite
Apr 17 – 24
Guesthouse in Harpers Ferry
4.84 out of 5 average rating, 143 reviewsRiverkeeper Inn
Aug 16 – 23
Guesthouse in Sperryville
4.96 out of 5 average rating, 357 reviewsRiver Side Tourist Room and Bath Loft-5 min to SNP
Jan 19 – 26
Guest house rentals with a patio
Guesthouse in Bluemont
4.97 out of 5 average rating, 102 reviewsBlueridge Mountain Guest Cabin- Amongst the Trees
Aug 14 – 21
Guesthouse in Fort Valley
4.9 out of 5 average rating, 144 reviewsRomantic Mountain Getaway⛰ hot tub*king bed*sauna
Jul 17 – 24
Guesthouse in Front Royal
4.9 out of 5 average rating, 78 reviewsCozy Shenandoah River Cabin (10min to Nat’l Park!)
Apr 19 – 26
Guesthouse in Stephens City
5.0 out of 5 average rating, 6 reviewsVentura Cottage: 360-views/HotTub/4 acres/Gym
Jan 1 – 8
Guesthouse in Woodstock
4.95 out of 5 average rating, 87 reviewsCozy cottage nestled on 8 acres with mountain view
Aug 17 – 24
Guesthouse in Flint Hill
4.97 out of 5 average rating, 93 reviewsSummer kitchen guesthouse at Caledonia Farm 1812
Jul 10 – 17
Guesthouse in Middletown
5.0 out of 5 average rating, 92 reviewsCottage, Pool, & Breakfast on 100ac Horse Estate
Jul 15 – 20
Guesthouse in The Plains
4.98 out of 5 average rating, 40 reviewsA lovely cottage in The Plains, Virginia
Aug 3 – 10
Guest house rentals with a washer and dryer
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Oct 11 – 18
Guesthouse in Purcellville
4.99 out of 5 average rating, 209 reviewsThe Cottage at Dunthorpe Farm
Jan 14 – 21
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
Jul 17 – 24
Guesthouse in Frederick
5.0 out of 5 average rating, 234 reviewsThe Carriage House at Hessian Overlook, Downtown
Oct 12 – 19
Guesthouse in Fairhope
5.0 out of 5 average rating, 23 reviewsMountain View Acres Getaway
Jan 12 – 19
Guesthouse in Mercersburg
4.89 out of 5 average rating, 28 reviewsThe Haven
Sep 3 – 10
Guesthouse in Connellsville
5.0 out of 5 average rating, 20 reviewsPeggy's Guest Hideaway
Dec 25 – Jan 1
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