Guesthouse vacation rentals in Delmarva Peninsula
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Top-rated guesthouses in Delmarva Peninsula
Guests agree: these guesthouses 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 Delmarva Peninsula guesthouses
Family-friendly guesthouses
Guesthouse in Chestertown
4.88 out of 5 average rating, 157 reviewsCozy Carriage House
Jun. 27 – Jul. 4
Guesthouse in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
Oct. 18 – 25
Guesthouse in Lewes
4.96 out of 5 average rating, 169 reviewsCozy, very private, Country Cottage
Nov. 23 – 30
Guesthouse in Annapolis
4.9 out of 5 average rating, 175 reviewsAnnapolis Guesthouse - Completely Separate Space
Jul. 14 – 21
Guesthouse in Ashland
4.96 out of 5 average rating, 462 reviews2 Bdrms★Pet Friendly★4K Theater★Fire Pit★Fast Wifi
Apr. 4 – 11
Guesthouse in Washington
4.9 out of 5 average rating, 411 reviewsIngraham Alley Inn - A Quiet & Cozy Micro House
Sep. 5 – 12
Guesthouse in Bethesda
4.97 out of 5 average rating, 145 reviewsHidden Gem in Downtown Bethesda
Aug. 20 – 27
Guesthouse in Fort Washington
4.92 out of 5 average rating, 670 reviewsUrban Cottage,MD minutes from DC/National Harbor
Sep. 30 – Oct. 7
Guesthouses with a patio
Guesthouse in Glen Burnie
4.94 out of 5 average rating, 263 reviewsThe Crab House - a Private, Waterfront Guest House
Oct. 16 – 23
Guesthouse in Cape May
5.0 out of 5 average rating, 151 reviewsNew Complete-Living 2-Bedroom Cottage
Dec. 5 – 12
Guesthouse in Petersburg
4.94 out of 5 average rating, 143 reviews"Lofty Cottage" Adorable 1-Bedroom Guest House
Dec. 12 – 19
Guesthouse in Richmond
4.94 out of 5 average rating, 174 reviewsFunky & colorful private guesthouse with parking!
Jan. 20 – 27
Guesthouse in Catonsville
4.96 out of 5 average rating, 199 reviewsFox Cottage *Pet Friendly*
Dec. 30 – Jan. 6
Guesthouse in Towson
4.99 out of 5 average rating, 176 reviewsCute cottage studio with full kitchen and laundry
Dec. 2 – 9
Guesthouse in Towson
4.98 out of 5 average rating, 120 reviewsSunny Guesthouse steps from Towson!
Sep. 21 – 28
Guesthouse in Washington
5.0 out of 5 average rating, 130 reviewsGorgeous Two-Story Guesthouse w/ Free Parking
Jul. 27 – Aug. 3
Guesthouse rentals with a washer and dryer
Guesthouse in Annapolis
4.9 out of 5 average rating, 209 reviewsCalico Cottage Guest House, king bed, free parking
Dec. 25 – Jan. 1
Guesthouse in Cambridge
4.99 out of 5 average rating, 109 reviewsRosses Chance Guest House
Jul. 14 – 21
Guesthouse in Lewes
4.92 out of 5 average rating, 290 reviewsPied a Mer- Downtown Lewes Cottage!
Nov. 27 – Dec. 4
Guesthouse in Riva
4.99 out of 5 average rating, 273 reviewsThe Riva House
Dec. 6 – 13
Guesthouse in Williamsburg
4.98 out of 5 average rating, 304 reviewsFreedom Cottage /King Bed-Jamestown/ Busch Gardens
Aug. 21 – 28
Guesthouse in Falls Church
4.97 out of 5 average rating, 130 reviewsBeautiful New Apartment Surrounded by Nature
Aug. 20 – 27
Guesthouse in Richmond
4.97 out of 5 average rating, 376 reviewsA Place of Peace
Jan. 18 – 25
Guesthouse in Rehoboth Beach
4.83 out of 5 average rating, 266 reviewsThe Winkler
Nov. 2 – 9
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