Guesthouse vacation rentals in Maryland
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Top-rated guesthouse rentals in Maryland
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 Maryland guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Annapolis
4.9 out of 5 average rating, 175 reviewsAnnapolis Guesthouse - Completely Separate Space
Jul 10 – 17
Guesthouse in Frederick
4.97 out of 5 average rating, 316 reviewsThe Shady Bear Cabin
Feb 15 – 22
Guesthouse in Middletown
4.95 out of 5 average rating, 246 reviewsIndulge, Fresh Flowers, Frederick County Haven
Sep 21 – 28
Guesthouse in Fort Washington
4.92 out of 5 average rating, 671 reviewsUrban Cottage,MD minutes from DC/National Harbor
Mar 24 – 31
Guesthouse in Chestertown
4.88 out of 5 average rating, 157 reviewsCozy Carriage House
Mar 5 – 12
Guesthouse in Bethesda
4.97 out of 5 average rating, 146 reviewsHidden Gem in Downtown Bethesda
Aug 25 – Sep 1
Guesthouse in Glen Burnie
4.81 out of 5 average rating, 156 reviewsPrivate 1 bedroom house
Oct 21 – 28
Guesthouse in Galesville
4.95 out of 5 average rating, 163 reviewsGorgeous water view studio!
Aug 1 – 8
Guest house rentals with a patio
Guesthouse in Catonsville
4.96 out of 5 average rating, 199 reviewsFox Cottage *Pet Friendly*
Mar 20 – 27
Guesthouse in Towson
4.99 out of 5 average rating, 176 reviewsCute cottage studio with full kitchen and laundry
Dec 10 – 17
Guesthouse in Towson
4.98 out of 5 average rating, 121 reviewsSunny Guesthouse steps from Towson!
Sep 20 – 27
Guesthouse in Wye Mills
4.94 out of 5 average rating, 17 reviewsAdorable Lake Front 1BR Cottage-fully furnished!
Sep 29 – Oct 6
Guesthouse in Clarksville
4.93 out of 5 average rating, 14 reviewsUnique guest house spa retreat
Sep 13 – 20
Guesthouse in Silver Spring
5.0 out of 5 average rating, 8 reviewsThe Little Wooded Casita
Jun 5 – 12
Guesthouse in Mount Airy
4.99 out of 5 average rating, 77 reviewsTreasured Hideaway on the Hill
Sep 24 – Oct 1
Guesthouse in Queenstown
4.9 out of 5 average rating, 21 reviewsWaterfront Getaway
Dec 4 – 11
Guest house rentals with a washer and dryer
Guesthouse in Rockville
4.97 out of 5 average rating, 133 reviewsModern Farmhouse Apartment. Close to Metro
Jun 19 – 26
Guesthouse in Cambridge
4.99 out of 5 average rating, 109 reviewsRosses Chance Guest House
Oct 2 – 9
Guesthouse in Baltimore
4.88 out of 5 average rating, 182 reviewsWoodberry Studio Retreat
Jul 25 – Aug 1
Guesthouse in Annapolis
5.0 out of 5 average rating, 106 reviewsGarden View, a spacious 1 bedroom with loft.
Dec 27 – Jan 3
Guesthouse in Annapolis
5.0 out of 5 average rating, 139 reviewsPrivate Art-Filled Guesthouse near Naval Academy
Mar 23 – 30
Guesthouse in Baltimore
4.83 out of 5 average rating, 165 reviewsCottage in beautiful Mount Washington
Jul 30 – Aug 6
Guesthouse in Frederick
5.0 out of 5 average rating, 234 reviewsThe Carriage House at Hessian Overlook, Downtown
Oct 6 – 13
Guesthouse in Frederick
5.0 out of 5 average rating, 77 reviewsA Quiet Haven
Oct 10 – 17
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