Cottage holiday rentals in Maryland
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Maryland
Guests agree: these cottages 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 cottage rentals in Maryland
Cottage rentals with a hot tub
Cottage in Swanton
4.92 out of 5 average rating, 203 reviews*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
Cottage in Oakland
4.95 out of 5 average rating, 188 reviewsPet-Friendly Cozy Home w/Hot Tub & Fire Pit
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Cottage in Charlestown
4.98 out of 5 average rating, 63 reviewsLong Beach Cottage, (romantic couple’s getaway)
Cottage in Saint Leonard
4.98 out of 5 average rating, 98 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Cottage in Easton
5.0 out of 5 average rating, 84 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Cottage in Annapolis
4.85 out of 5 average rating, 54 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Cottage in North East
5.0 out of 5 average rating, 47 reviewsCozy Cottage on the Chesapeake with Hot Tub
Pet-friendly cottage rentals
Cottage in Westover
4.92 out of 5 average rating, 146 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Cottage in Middletown
4.91 out of 5 average rating, 227 reviewsCharming "Cream of the Crop" Cape ~❤️of Middletown
Cottage in Oakland
4.97 out of 5 average rating, 105 reviewsPet friendly-Cottage in the Woods
Cottage in Saint Michaels
4.98 out of 5 average rating, 183 reviewsThe Little Anchor Cottage, St. Michaels, MD
Cottage in Neavitt
4.9 out of 5 average rating, 124 reviewsThe Middle Point Cottage at Saint Michaels
Cottage in Sharpsburg
4.86 out of 5 average rating, 104 reviewsPeaceful River House on Potomac- King Size Bed
Cottage in Pasadena
4.97 out of 5 average rating, 159 reviewsFt. Smallwood Overlook. Waterfront with Kayaks!
Cottage in Annapolis
4.97 out of 5 average rating, 119 reviewsWaterfront farm retreat for vacation & telework
Private cottage rentals
Cottage in Cambridge
4.98 out of 5 average rating, 112 reviewsChurch Creek - waterfront cottage & pool - private
Cottage in Leonardtown
4.93 out of 5 average rating, 128 reviewsBreton Breeze
Cottage in Sharpsburg
4.96 out of 5 average rating, 158 reviewsLock Keepers Cottage on C&O Canal/Potomac River
Cottage in Rock Hall
4.96 out of 5 average rating, 137 reviewsThe Blissful Retreat @theblissfulretreat
Cottage in Aberdeen
4.95 out of 5 average rating, 153 reviewsTranquil Carriage House*MCM *Country *Wildlife
Cottage in Smith Island
4.97 out of 5 average rating, 191 reviewsLevering Creek Cottage with Private Docking
Cottage in Leonardtown
4.93 out of 5 average rating, 196 reviewsPotomac River Freedom Cottage
Cottage in Tracys Landing
4.9 out of 5 average rating, 340 reviewsCharming Waterfront on Chesapeake Bay
Destinations to explore
- Private suite rentals Maryland
- Rentals with an EV charger Maryland
- Ski-in/ski-out rentals Maryland
- Boutique hotel rentals Maryland
- Rentals with a cinema Maryland
- Guest house rentals Maryland
- Tiny house rentals Maryland
- Rentals with outdoor seating Maryland
- Cabin rentals Maryland
- Rentals with lake access Maryland
- Smoking-friendly rentals Maryland
- Mansion rentals Maryland
- Family-friendly rentals Maryland
- Lakehouse rentals Maryland
- Bungalow rentals Maryland
- Campsite rentals Maryland
- Farm stay rentals Maryland
- Monthly Rentals Maryland
- Beach house rentals Maryland
- Rentals with an accessible-height toilet Maryland
- Rentals with a firepit Maryland
- Wheelchair-accessible rentals Maryland
- Rentals with a kayak Maryland
- Rentals with pools Maryland
- Bed and breakfasts Maryland
- Rentals with a fireplace Maryland
- Flat rentals Maryland
- Villa rentals Maryland
- Aparthotel rentals Maryland
- Pet-friendly rentals Maryland
- Beachfront rentals Maryland
- Family-friendly rentals Maryland
- Rentals with a sauna Maryland
- Apartment rentals Maryland
- Rentals with a hot tub Maryland
- Rentals with an accessible-height bed Maryland
- Townhouse rentals Maryland
- Rentals with a washing machine and dryer Maryland
- Fitness-friendly rentals Maryland
- Hotel rentals Maryland
- Rentals with a patio Maryland
- Chalet rentals Maryland
- House rentals Maryland
- Waterfront rentals Maryland
- Rentals with beach access Maryland
- Rentals with breakfast 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