Pet-friendly holiday rentals in Annapolis
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Top-rated pet-friendly home rentals in Annapolis
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Annapolis pet-friendly home rentals
Pet-friendly house rentals
Home in Annapolis
4.97 out of 5 average rating, 114 reviewsGorgeous Historic Downtown Annapolis House
3–10 Dec
Home in Annapolis
4.98 out of 5 average rating, 109 reviewsCozy Annapolis Cottage.
17–24 Jul
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
3–10 Sep
Home in Edgewater
4.98 out of 5 average rating, 100 reviewsLuxury Modern Home on Water+Hotub- Annapolis 25min
17–24 Jun
Home in Glen Burnie
4.97 out of 5 average rating, 397 reviewsSecluded acre near BWI and Baltimore
22–29 Jul
Home in Glen Burnie
4.95 out of 5 average rating, 124 reviewsCozy Home with Relaxing Views - 10 mins. to BWI
21–28 Sep
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
1–8 Feb
Home in Grasonville
4.94 out of 5 average rating, 226 reviewsRiver Front, Private Single Family Home
17–24 Nov
Pet-friendly home rentals with a pool
Guest house in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
2–9 Oct
Cottage in Saint Michaels
4.99 out of 5 average rating, 137 reviewsLa Casita on Harris Creek, St. Michaels
4–11 Jun
Guest house in Owings Mills
4.96 out of 5 average rating, 120 reviewsShamrock cabin with hot tub, large yard
11–18 Jun
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
27 Jan – 3 Feb
Flat in Alexandria
4.83 out of 5 average rating, 131 reviewsCozy 1-Bedroom/FREE Parking/Rooftop POOL/ Dog Park
30 Aug – 6 Sep
Guest suite in Adelphi
4.85 out of 5 average rating, 203 reviewsCozy Suite with Hot Tub and Pool
8–15 Jul
Apartment in Annapolis
5.0 out of 5 average rating, 7 reviewsCharming Annapolis Waterfront Condo
12–19 Dec
Apartment in Annapolis
4.73 out of 5 average rating, 71 reviewsAmazing Views from Spa Creek 2BD Condo with Pool
5–12 Jan
Private, pet-friendly home rentals
Flat in Chester
4.97 out of 5 average rating, 234 reviewsCozy Waterfront Apartment Chester, MD
15–22 Feb
Townhouse in Annapolis
4.97 out of 5 average rating, 158 reviewsCentrally Located, Charming Historic Townhouse
14–21 Feb
Cottage in Annapolis
4.94 out of 5 average rating, 172 reviewsSecluded Cozy Cottage in Historic Downtown
19–26 Sep
Cottage in Annapolis
4.97 out of 5 average rating, 116 reviewsWaterfront farm retreat for vacation & telework
18–25 Mar
Guest suite in Chestertown
4.99 out of 5 average rating, 191 reviewsBeautiful Waterfront Chestertown Getaway
13–20 Sep
Cabin in Gambrills
4.89 out of 5 average rating, 140 reviewsRelaxing Cabin Get Away Near Annapolis & DC
10–17 Aug
Guest suite in Silver Spring
4.89 out of 5 average rating, 141 reviewsPrivate guest suite in a newly remodeled home
12–19 Aug
Flat in Church Creek
4.97 out of 5 average rating, 372 reviewsChurch Creek Natures' Rest
9–16 Jul
Quick stats about holiday rentals that are pet-friendly in Annapolis
Total rentals
180 properties
Wifi availability
180 properties include access to wifi
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Family-friendly rentals
140 properties are a good fit for families
Total number of reviews
6.5T reviews
Destinations to explore
- Baltimore Holiday rentals
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