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, 671 reviewsUrban Cottage,MD minutes from DC/National Harbor
Mar 24 – 31
Guesthouse in Washington
4.9 out of 5 average rating, 411 reviewsIngraham Alley Inn - A Quiet & Cozy Micro House
Nov 2 – 9
Guesthouse in Washington
4.87 out of 5 average rating, 749 reviewsCozy Cabin in the City on Cap Hill
Jan 18 – 25
Guesthouse in Washington
4.86 out of 5 average rating, 300 reviewsHistoric Carriage House + Parking!
Feb 20 – 27
Guesthouse in Colonial Beach
4.96 out of 5 average rating, 48 reviewsBeach Carriage House with Pool and Cabana
Aug 19 – 26
Guesthouse in Manassas
4.94 out of 5 average rating, 83 reviewsPrivate Luxury Retreat Close to everything!
Oct 8 – 15
Guesthouse in Fredericksburg
4.7 out of 5 average rating, 188 reviewsHolly Corner Cottage
Jan 23 – 30
Guesthouse in Oxford
4.83 out of 5 average rating, 115 reviewsBonfield Bungalow
Nov 30 – Dec 7
Guest house rentals with a patio
Guesthouse in Alexandria
4.84 out of 5 average rating, 276 reviewsAdorable 1-Bedroom guesthouse with free parking
Mar 16 – 23
Guesthouse in Washington
5.0 out of 5 average rating, 131 reviewsGorgeous Two-Story Guesthouse w/ Free Parking
Jul 31 – Aug 7
Guesthouse in Washington
4.87 out of 5 average rating, 181 reviewsAdorable English Basement on 15th St
Sep 19 – 26
Guesthouse in Washington
4.95 out of 5 average rating, 104 reviewsGardenLevel 4BR/2.5BA+Parking+By Convention Center
Sep 18 – 25
Guesthouse in Brandywine
5.0 out of 5 average rating, 14 reviewsQuiet cottage in the woods. King-bed suite.
Jul 3 – 10
Guesthouse in Colonial Beach
5.0 out of 5 average rating, 12 reviewsLayton's Lookout is a Rappahannock Treasure
Jun 29 – Jul 6
Guesthouse in Ridge
4.96 out of 5 average rating, 25 reviewsThe way
Jun 23 – 30
Guesthouse in Wye Mills
4.94 out of 5 average rating, 17 reviewsAdorable Lake Front 1BR Cottage-fully furnished!
Dec 19 – 26
Guest house rentals with a washer and dryer
Guesthouse in Washington
4.96 out of 5 average rating, 157 reviewsGarden Suite
Feb 19 – 26
Guesthouse in Alexandria
5.0 out of 5 average rating, 172 reviewsSunny, Stylish Carriage House with a View
Nov 17 – 24
Guesthouse in Arlington
5.0 out of 5 average rating, 187 reviewsPrivate Sunny Cottage with King Bed + Yard / Patio
Dec 2 – 9
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
4.94 out of 5 average rating, 257 reviewsVibrant + Artsy - mins to NavyYard, CapHill, Dtown
Aug 15 – 22
Guesthouse in Washington
4.97 out of 5 average rating, 189 reviewsSpacious, Private, Capitol Hill Carriage House
Jun 30 – Jul 7
Guesthouse in Washington
5.0 out of 5 average rating, 116 reviewsTwo-story Historic Carriage House in Vibrant Area
Jul 20 – 27
Guesthouse in Washington
4.89 out of 5 average rating, 121 reviewsHistoric Carriage House on Capitol Hill w/Parking
Jul 15 – 22
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
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- House rentals United States
- Guesthouse rentals United States
- House rentals Washington
- Guesthouse rentals Washington
- Guesthouse rentals Baltimore
- House rentals Baltimore
- House rentals Maryland
- Guesthouse rentals Maryland
- House rentals Maryland
- Guesthouse rentals Maryland
- Rentals with pools Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Rentals with an accessible height toilet Southern Maryland
- Rentals with breakfast Southern Maryland
- Cottage rentals Southern Maryland
- Kid-friendly rentals Southern Maryland
- Rentals with a fire pit Southern Maryland
- Bed and breakfasts Southern Maryland
- Rentals with lake access Southern Maryland
- Family-friendly rentals Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Rentals with a fireplace Southern Maryland
- Rentals with a patio Southern Maryland
- Townhouse rentals Southern Maryland
- Monthly Rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Rentals with a washer and dryer Southern Maryland
- Rentals with a hot tub Southern Maryland
- Rentals with a kayak Southern Maryland
- Waterfront rentals Southern Maryland
- Condo rentals Southern Maryland
- House rentals Southern Maryland
- Beachfront rentals Southern Maryland
- Apartment rentals Southern Maryland
- Rentals with an EV charger Southern Maryland
- Pet-friendly rentals Southern Maryland
- Rentals with outdoor seating Southern Maryland
- Rentals with a home theater Southern Maryland
- Private suite rentals Southern Maryland
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes