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
Nov 7 – 14
Guesthouse in Frederick
4.97 out of 5 average rating, 316 reviewsThe Shady Bear Cabin
Feb 6 – 13
Guesthouse in Keedysville
4.98 out of 5 average rating, 190 reviewsCity Dog Farm
May 13 – 20
Guesthouse in Boston
4.98 out of 5 average rating, 148 reviewsThe Bunkhouse- simple & serene w/mountain views
Oct 13 – 20
Guesthouse in Aspers (Mail)
4.92 out of 5 average rating, 349 reviewsCottage on our horse farm
Feb 14 – 21
Guesthouse in Harpers Ferry
4.84 out of 5 average rating, 143 reviewsRiverkeeper Inn
Jul 19 – 26
Guesthouse in Round Hill
4.78 out of 5 average rating, 428 reviewsPrivate detached garage suite
Feb 16 – 23
Guesthouse in Sperryville
4.96 out of 5 average rating, 356 reviewsRiver Side Tourist Room and Bath Loft-5 min to SNP
Aug 20 – 27
Guest house rentals with a patio
Guesthouse in Bluemont
4.97 out of 5 average rating, 102 reviewsBlueridge Mountain Guest Cabin- Amongst the Trees
Dec 29 – Jan 5
Guesthouse in Fort Valley
4.9 out of 5 average rating, 144 reviewsRomantic Mountain Getaway⛰ hot tub*king bed*sauna
Jul 16 – 23
Guesthouse in Front Royal
4.9 out of 5 average rating, 77 reviewsCozy Shenandoah River Cabin (10min to Nat’l Park!)
Dec 5 – 12
Guesthouse in Stephens City
5.0 out of 5 average rating, 6 reviewsVentura Cottage: 360-views/HotTub/4 acres/Gym
Dec 28 – Jan 4
Guesthouse in Woodstock
4.95 out of 5 average rating, 87 reviewsCozy cottage nestled on 8 acres with mountain view
Jan 2 – 9
Guesthouse in Flint Hill
4.97 out of 5 average rating, 93 reviewsSummer kitchen guesthouse at Caledonia Farm 1812
Jul 18 – 25
Guesthouse in Middletown
5.0 out of 5 average rating, 91 reviewsCottage, Pool, & Breakfast on 100ac Horse Estate
May 7 – 12
Guesthouse in Middleburg
5.0 out of 5 average rating, 40 reviews18th Century Middleburg Cottage
Jul 25 – Aug 1
Guest house rentals with a washer and dryer
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Oct 14 – 21
Guesthouse in Purcellville
4.99 out of 5 average rating, 208 reviewsThe Cottage at Dunthorpe Farm
Dec 9 – 16
Guesthouse in New Paris
4.99 out of 5 average rating, 129 reviewsCharming Guest House Bedford County PA
Aug 25 – Sep 1
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
May 30 – Jun 6
Guesthouse in Frederick
5.0 out of 5 average rating, 234 reviewsThe Carriage House at Hessian Overlook, Downtown
Oct 13 – 20
Guesthouse in Fairhope
5.0 out of 5 average rating, 21 reviewsMountain View Acres Getaway
Aug 2 – 9
Guesthouse in Connellsville
5.0 out of 5 average rating, 19 reviewsPeggy's Guest Hideaway
Aug 26 – Sep 2
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