Guesthouse vacation rentals in Southern Maryland
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Top-rated guesthouse rentals in Southern 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 Southern Maryland guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Glen Allen
4.84 out of 5 average rating, 470 reviewsPrivate and Quiet Pool House Convenient Location
Oct 2 – 9
Guesthouse in Fort Washington
4.92 out of 5 average rating, 670 reviewsUrban Cottage,MD minutes from DC/National Harbor
Apr 2 – 9
Guesthouse in Washington
4.9 out of 5 average rating, 411 reviewsIngraham Alley Inn - A Quiet & Cozy Micro House
Sep 12 – 19
Guesthouse in Galesville
4.95 out of 5 average rating, 163 reviewsGorgeous water view studio!
Oct 15 – 22
Guesthouse in Washington
4.87 out of 5 average rating, 749 reviewsCozy Cabin in the City on Cap Hill
Jul 30 – Aug 6
Guesthouse in Bethesda
4.97 out of 5 average rating, 144 reviewsHidden Gem in Downtown Bethesda
Sep 15 – 22
Guesthouse in Annapolis
4.9 out of 5 average rating, 175 reviewsAnnapolis Guesthouse - Completely Separate Space
Oct 1 – 8
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 Glen Burnie
4.94 out of 5 average rating, 263 reviewsThe Crab House - a Private, Waterfront Guest House
Jan 17 – 24
Guesthouse in Alexandria
4.84 out of 5 average rating, 274 reviewsAdorable 1-Bedroom guesthouse with free parking
Feb 8 – 15
Guesthouse in Washington
5.0 out of 5 average rating, 130 reviewsGorgeous Two-Story Guesthouse w/ Free Parking
Jul 23 – 30
Guesthouse in Washington
4.87 out of 5 average rating, 181 reviewsAdorable English Basement on 15th St
Jun 19 – 26
Guesthouse in Washington
4.95 out of 5 average rating, 102 reviewsNew, Modern Garden-Level 4BR/2.5BA-Metro + Parking
Jul 18 – 25
Guesthouse in Brandywine
5.0 out of 5 average rating, 13 reviewsQuiet cottage in the woods. King-bed suite.
Jun 27 – Jul 4
Guesthouse in Ridge
4.96 out of 5 average rating, 24 reviewsThe way
Jan 23 – 30
Guesthouse in Colonial Beach
5.0 out of 5 average rating, 12 reviewsLayton's Lookout is a Rappahannock Treasure
Jun 21 – 28
Guest house rentals with a washer and dryer
Guesthouse in Arlington
4.98 out of 5 average rating, 102 reviewsSpacious Guest House 10-15 min to DC
Dec 26 – Jan 2
Guesthouse in Alexandria
5.0 out of 5 average rating, 171 reviewsSunny, Stylish Carriage House with a View
Dec 31 – Jan 7
Guesthouse in Washington
4.94 out of 5 average rating, 254 reviewsVibrant + Artsy - mins to NavyYard, CapHill, Dtown
Sep 20 – 27
Guesthouse in Washington
4.96 out of 5 average rating, 157 reviewsGarden Suite
Nov 1 – 8
Guesthouse in Washington
4.99 out of 5 average rating, 102 reviewsLuxurious 1Bed Carriage House, 1.5 Blocks to Metro
Jul 2 – 9
Guesthouse in Washington
4.97 out of 5 average rating, 188 reviewsSpacious, Private, Capitol Hill Carriage House
Jul 2 – 9
Guesthouse in Washington
5.0 out of 5 average rating, 116 reviewsTwo-story Historic Carriage House in Vibrant Area
Jul 18 – 25
Guesthouse in Arlington
5.0 out of 5 average rating, 187 reviewsPrivate Sunny Cottage with King Bed + Yard / Patio
Aug 12 – 19
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