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
Get the amount of space that is right for you
Popular amenities for Maryland guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Fort Washington
4.92 out of 5 average rating, 670 reviewsUrban Cottage,MD minutes from DC/National Harbor
Jan 4 – 11
Guesthouse in Annapolis
4.9 out of 5 average rating, 175 reviewsAnnapolis Guesthouse - Completely Separate Space
Jul 6 – 13
Guesthouse in Middletown
4.95 out of 5 average rating, 246 reviewsIndulge, Fresh Flowers, Frederick County Haven
Sep 13 – 20
Guesthouse in Frederick
4.97 out of 5 average rating, 316 reviewsThe Shady Bear Cabin
Sep 25 – Oct 2
Guesthouse in Chestertown
4.88 out of 5 average rating, 156 reviewsCozy Carriage House
Feb 19 – 26
Guesthouse in Bethesda
4.97 out of 5 average rating, 144 reviewsHidden Gem in Downtown Bethesda
Jul 19 – 26
Guesthouse in Galesville
4.95 out of 5 average rating, 163 reviewsGorgeous water view studio!
Aug 11 – 18
Guesthouse in Glen Burnie
4.81 out of 5 average rating, 155 reviewsPrivate 1 bedroom house
Dec 24 – 31
Guest house rentals with a patio
Guesthouse in Catonsville
4.96 out of 5 average rating, 198 reviewsFox Cottage *Pet Friendly*
Oct 30 – Nov 6
Guesthouse in Grantsville
4.92 out of 5 average rating, 117 reviews“The Loft” Guest House w/wifi workspace, gym etc
Nov 1 – 8
Guesthouse in Towson
4.98 out of 5 average rating, 120 reviewsSunny Guesthouse steps from Towson!
Sep 9 – 16
Guesthouse in Wye Mills
4.94 out of 5 average rating, 16 reviewsAdorable Lake Front 1BR Cottage-fully furnished!
Oct 9 – 16
Guesthouse in Rockville
4.82 out of 5 average rating, 17 reviewsMojgan's Home
Sep 9 – 16
Guesthouse in Elk Mills
4.98 out of 5 average rating, 40 reviewsPrivate Country Guesthouse Getaway Minutes from UD
Sep 6 – 13
Guesthouse in Clarksville
4.92 out of 5 average rating, 13 reviewsUnique guest house spa retreat
Jul 5 – 12
Guesthouse in Mount Airy
4.99 out of 5 average rating, 75 reviewsTreasured Hideaway on the Hill
Feb 19 – 26
Guest house rentals with a washer and dryer
Guesthouse in Baltimore
4.88 out of 5 average rating, 181 reviewsWoodberry Studio Retreat
May 31 – Jun 7
Guesthouse in Rockville
4.97 out of 5 average rating, 132 reviewsModern Farmhouse Apartment. Close to Metro
Jun 17 – 24
Guesthouse in Cambridge
4.99 out of 5 average rating, 109 reviewsRosses Chance Guest House
Nov 10 – 17
Guesthouse in Annapolis
5.0 out of 5 average rating, 106 reviewsGarden View, a spacious 1 bedroom with loft.
Jul 29 – Aug 5
Guesthouse in Annapolis
5.0 out of 5 average rating, 139 reviewsPrivate Art-Filled Guesthouse near Naval Academy
Nov 4 – 11
Guesthouse in Frederick
5.0 out of 5 average rating, 234 reviewsThe Carriage House at Hessian Overlook, Downtown
Oct 13 – 20
Guesthouse in Baltimore
4.83 out of 5 average rating, 163 reviewsCottage in beautiful Mount Washington
Aug 2 – 9
Guesthouse in Pomfret
4.99 out of 5 average rating, 75 reviewsAdorable 1 Bedroom Getaway Retreat
Dec 13 – 20
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