Guesthouse vacation rentals in Southern Maryland
Find and book unique guesthouse rentals on Airbnb
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 Fort Washington
4.92 out of 5 average rating, 675 reviewsUrban Cottage,MD minutes from DC/National Harbor
Guesthouse in Washington
4.9 out of 5 average rating, 412 reviewsIngraham Alley Inn - A Quiet & Cozy Micro House
Guesthouse in Galesville
4.95 out of 5 average rating, 164 reviewsGorgeous water view studio!
Guesthouse in Washington
4.88 out of 5 average rating, 751 reviewsCozy Cabin in the City on Cap Hill
Guesthouse in Annapolis
4.9 out of 5 average rating, 176 reviewsAnnapolis Guesthouse - Completely Separate Space
Guesthouse in Washington
4.86 out of 5 average rating, 301 reviewsHistoric Carriage House + Parking!
Guesthouse in Herndon
4.77 out of 5 average rating, 203 reviewsHistoric Herndon In-law house, kitchen. By IAD.
Guesthouse in Colonial Beach
4.96 out of 5 average rating, 49 reviewsBeach Carriage House with Pool and Cabana
Guest house rentals with a patio
Guesthouse in Washington
4.99 out of 5 average rating, 134 reviewsGorgeous Two-Story Guesthouse w/ Free Parking
Guesthouse in Alexandria
4.84 out of 5 average rating, 277 reviewsAdorable 1-Bedroom guesthouse with free parking
Guesthouse in Washington
4.87 out of 5 average rating, 183 reviewsAdorable English Basement on 15th St
Guesthouse in Washington
4.95 out of 5 average rating, 108 reviewsGardenLevel 4BR/2.5BA+Parking+By Convention Center
Guesthouse in Brandywine
5.0 out of 5 average rating, 15 reviewsQuiet cottage in the woods. King-bed suite.
Guesthouse in Colonial Beach
5.0 out of 5 average rating, 12 reviewsLayton's Lookout is a Rappahannock Treasure
Guesthouse in Ridge
4.96 out of 5 average rating, 25 reviewsEl Camino
Guesthouse in Lorton
4.95 out of 5 average rating, 39 reviewsVilla Miza Wellness Retreat
Guest house rentals with a washer and dryer
Guesthouse in Arlington
4.98 out of 5 average rating, 107 reviewsSpacious Guest House 10-15 min to DC
Guesthouse in Alexandria
5.0 out of 5 average rating, 174 reviewsSunny, Stylish Carriage House with a View
Guesthouse in Washington
4.96 out of 5 average rating, 159 reviewsGarden Suite
Guesthouse in Washington
4.99 out of 5 average rating, 102 reviewsLuxurious 1Bed Carriage House, 1.5 Blocks to Metro
Guesthouse in Washington
4.94 out of 5 average rating, 265 reviewsVibrant + Artsy - mins to NavyYard, CapHill, Dtown
Guesthouse in Arlington
5.0 out of 5 average rating, 187 reviewsPrivate Sunny Cottage with King Bed + Yard / Patio
Guesthouse in Washington
5.0 out of 5 average rating, 118 reviewsTwo-story Historic Carriage House in Vibrant Area
Guesthouse in Washington
4.98 out of 5 average rating, 128 reviewsCarriage House Studio in the Heart of DC
Destinations to explore
- Baltimore Vacation rentals
- Ocean City Vacation rentals
- Richmond Vacation rentals
- Rehoboth Beach Vacation rentals
- Arlington Vacation rentals
- Charlottesville Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Guesthouse rentals United States
- House rentals United States
- House rentals Washington
- Guesthouse rentals Washington
- House rentals Baltimore
- Guesthouse rentals Baltimore
- Guesthouse rentals Maryland
- House rentals Maryland
- Guesthouse rentals Maryland
- House rentals Maryland
- House rentals Southern Maryland
- Condo rentals Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a fire pit Southern Maryland
- Rentals with a hot tub Southern Maryland
- Bed and breakfasts Southern Maryland
- Family-friendly rentals Southern Maryland
- Rentals with lake access Southern Maryland
- Kid-friendly rentals Southern Maryland
- Monthly Rentals Southern Maryland
- Rentals with outdoor seating Southern Maryland
- Pet-friendly rentals Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Rentals with a kayak Southern Maryland
- Rentals with an accessible height toilet Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Rentals with a washer and dryer Southern Maryland
- Rentals with breakfast Southern Maryland
- Cottage rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Waterfront rentals Southern Maryland
- Beachfront rentals Southern Maryland
- Private suite rentals Southern Maryland
- Rentals with a home theater Southern Maryland
- Apartment rentals Southern Maryland
- Rentals with pools Southern Maryland
- Rentals with beach access Southern Maryland
- Rentals with a patio Southern Maryland
- Rentals with a fireplace Southern Maryland
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom