Guesthouse holiday rentals in Maryland
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Maryland
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Maryland guesthouses
Family-Friendly guesthouses
Guesthouse in Bethesda
4.97 out of 5 average rating, 160 reviewsHidden Gem in Downtown Bethesda
Guesthouse in Chestertown
4.88 out of 5 average rating, 166 reviewsCozy Carriage House
Guesthouse in Annapolis
4.89 out of 5 average rating, 187 reviewsAnnapolis Guesthouse - Completely Separate Space
Guesthouse in Galesville
4.95 out of 5 average rating, 168 reviewsNautical Charm and relaxing waterview!
Guesthouse in Frederick
4.97 out of 5 average rating, 327 reviewsThe Shady Bear Cabin
Guesthouse in Glen Burnie
4.81 out of 5 average rating, 161 reviewsPrivate 1 bedroom house
Guesthouse in Oxford
4.83 out of 5 average rating, 127 reviewsBonfield Bungalow
Guesthouse in Highland
4.98 out of 5 average rating, 277 reviewsWoodland Retreat
Guesthouses with a patio
Guesthouse in Elk Mills
4.97 out of 5 average rating, 86 reviewsPrivate Country Guesthouse Getaway Minutes from UD
Guesthouse in Grantsville
4.94 out of 5 average rating, 145 reviews“The Loft” Guest House w/wifi workspace, gym etc
Guesthouse in Middletown
5 out of 5 average rating, 109 reviewsCottage, Pool, & Breakfast on 100ac Horse Estate
Guesthouse in Catonsville
4.97 out of 5 average rating, 231 reviewsFox Cottage *Pet Friendly*
Guesthouse in Towson
4.98 out of 5 average rating, 146 reviewsSunny Guesthouse steps from Towson!
Guesthouse in Edgewater
4.99 out of 5 average rating, 83 reviews1 large room efficiency in detached garage.
Guesthouse in Rockville
4.93 out of 5 average rating, 40 reviewsAdorable, secluded 2 Bdrm guesthouse shared pool.
Guesthouse in Brandywine
5 out of 5 average rating, 30 reviewsQuiet cottage in the woods. King-bed suite.
Guest house rentals with a washing machine and dryer
Guesthouse in Annapolis
5 out of 5 average rating, 154 reviewsPrivate Art-Filled Guesthouse near Naval Academy
Guesthouse in Baltimore
4.87 out of 5 average rating, 201 reviewsWoodberry Studio Retreat
Guesthouse in Annapolis
4.84 out of 5 average rating, 215 reviews"Cape Saint Claire Hostel"
Guesthouse in Baltimore
4.83 out of 5 average rating, 184 reviewsCottage in beautiful Mount Washington
Guesthouse in Frederick
4.98 out of 5 average rating, 172 reviewsRomantic Getaway - Heated Spa Open Year Round
Guesthouse in Cambridge
4.99 out of 5 average rating, 118 reviewsRosses Chance Guest House
Guesthouse in Cumberland
4.96 out of 5 average rating, 125 reviewsNo cleaning fees - The Dove’s Nest
Guesthouse in Hanover
5 out of 5 average rating, 13 reviewsNew spacious private guest suite
Destinations to explore
- Guesthouse rentals United States
- House rentals United States
- House rentals Washington
- Guesthouse rentals Washington
- Rentals with a sauna Maryland
- Rentals with an accessible height bed Maryland
- Rentals with an EV charger Maryland
- Beach condo rentals Maryland
- House rentals Maryland
- Rentals with a hot tub Maryland
- Family-friendly rentals Maryland
- Lakehouse rentals Maryland
- Cabin rentals Maryland
- Apartment rentals Maryland
- Cottage rentals Maryland
- Aparthotel rentals Maryland
- Rentals with breakfast Maryland
- Condo rentals Maryland
- Rentals with a fireplace Maryland
- Rentals with beach access Maryland
- Bed and breakfasts Maryland
- Rentals with a kayak Maryland
- Rentals with pools Maryland
- Hotel rentals Maryland
- Tiny house rentals Maryland
- Bungalow rentals Maryland
- Beach house rentals Maryland
- Rentals with a patio Maryland
- Rentals with a washing machine and dryer Maryland
- Boutique hotel rentals Maryland
- Rentals with a home theatre Maryland
- Townhouse rentals Maryland
- Mansion rentals Maryland
- Chalet rentals Maryland
- Rentals with a fire pit Maryland
- Rentals with an accessible height toilet Maryland
- Beachfront rentals Maryland
- Campsite rentals Maryland
- Farmstay rentals Maryland
- Monthly Rentals Maryland
- Rentals with lake access Maryland
- Smoking-friendly rentals Maryland
- Rentals with outdoor seating Maryland
- Fitness-friendly rentals Maryland
- Private suite rentals Maryland
- Pet-friendly rentals Maryland
- Waterfront rentals Maryland
- Villa rentals Maryland
- Ski-in/ski-out rentals Maryland
- Kid-friendly rentals Maryland
- House rentals Baltimore
- Guesthouse rentals Baltimore
- House rentals Ocean City
- 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
- Things to do United States
- Sports activities United States
- Food and drink United States
- Art and culture United States
- Wellness United States
- Sightseeing United States
- Entertainment United States
- Nature and outdoors United States
- Things to do Maryland
- Art and culture Maryland
- Sightseeing Maryland
- Nature and outdoors Maryland
- Food and drink Maryland