Guesthouse holiday 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.
Holiday 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
31 Mar – 7 Apr
Guesthouse in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
6–13 Sep
Guesthouse in Lewes
4.96 out of 5 average rating, 169 reviewsCozy, very private, Country Cottage
29 Jan – 5 Feb
Guesthouse in Glen Allen
4.84 out of 5 average rating, 470 reviewsPrivate and Quiet Pool House Convenient Location
5–12 Oct
Guesthouse in Annapolis
4.9 out of 5 average rating, 175 reviewsAnnapolis Guesthouse - Completely Separate Space
9–16 Jul
Guesthouse in Galesville
4.95 out of 5 average rating, 163 reviewsGorgeous water view studio!
22–29 Oct
Guesthouse in Ashland
4.96 out of 5 average rating, 462 reviews2 Bdrms★Pet Friendly★4K Theater★Fire Pit★Fast Wifi
6–13 Apr
Guesthouse in Washington
4.9 out of 5 average rating, 411 reviewsIngraham Alley Inn - A Quiet & Cozy Micro House
5–12 Sep
Guesthouses with a patio
Guesthouse in Glen Burnie
4.94 out of 5 average rating, 264 reviewsThe Crab House - a Private, Waterfront Guest House
13–20 Apr
Guesthouse in Yorktown
4.97 out of 5 average rating, 203 reviewsCharming Yorktown Battlefield Cottage
26 Sep – 3 Oct
Guesthouse in Petersburg
4.94 out of 5 average rating, 143 reviews"Lofty Cottage" Adorable 1-Bedroom Guest House
21–28 Nov
Guesthouse in Lovettsville
4.94 out of 5 average rating, 122 reviewsThe Patent House
20–27 Aug
Guesthouse in Richmond
4.94 out of 5 average rating, 174 reviewsFunky & colorful private guesthouse with parking!
20–27 Oct
Guesthouse in Cape May
5.0 out of 5 average rating, 151 reviewsNew Complete-Living 2-Bedroom Cottage
19–26 Sep
Guesthouse in Catonsville
4.96 out of 5 average rating, 199 reviewsFox Cottage *Pet Friendly*
30 Dec – 6 Jan
Guesthouse in Towson
4.99 out of 5 average rating, 176 reviewsCute cottage studio with full kitchen and laundry
2–9 Dec
Guest house rentals with a washing machine and dryer
Guesthouse in Cambridge
4.99 out of 5 average rating, 109 reviewsRosses Chance Guest House
17–24 Jul
Guesthouse in Lewes
4.92 out of 5 average rating, 290 reviewsPied a Mer- Downtown Lewes Cottage!
27 Nov – 4 Dec
Guesthouse in Riva
4.99 out of 5 average rating, 273 reviewsThe Riva House
6–13 Dec
Guesthouse in Williamsburg
4.98 out of 5 average rating, 304 reviewsFreedom Cottage /King Bed-Jamestown/ Busch Gardens
16–23 Sep
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
18–25 Jul
Guesthouse in Richmond
4.97 out of 5 average rating, 376 reviewsA Place of Peace
23–30 Jan
Guesthouse in Falls Church
4.97 out of 5 average rating, 130 reviewsBeautiful New Apartment Surrounded by Nature
20–27 Aug
Guesthouse in Rehoboth Beach
4.83 out of 5 average rating, 266 reviewsThe Winkler
4–11 Nov
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