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
4.98 out of 5 average rating, 110 reviewsCozy Annapolis Cottage.
26 Jul – 2 Aug
Home in Annapolis
4.97 out of 5 average rating, 114 reviewsGorgeous Historic Downtown Annapolis House
21–28 Jan
Home in Glen Burnie
4.97 out of 5 average rating, 397 reviewsSecluded acre near BWI and Baltimore
16–23 Oct
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
26 Feb – 5 Mar
Home in Edgewater
4.98 out of 5 average rating, 100 reviewsLuxury Modern Home on Water+Hotub- Annapolis 25min
12–19 Aug
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
3–10 Feb
Home in Glen Burnie
4.95 out of 5 average rating, 124 reviewsCozy Home with Relaxing Views - 10 mins. to BWI
19–26 Sept
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
13–20 Dec
Pet-friendly home rentals with a pool
Guest house in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
20–27 Aug
Cottage in Saint Michaels
4.99 out of 5 average rating, 137 reviewsLa Casita on Harris Creek, St. Michaels
25 Jul – 1 Aug
Home in Harwood
4.94 out of 5 average rating, 117 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
15–22 Jun
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
29 Jan – 5 Feb
Flat in Alexandria
4.83 out of 5 average rating, 131 reviewsCozy 1-Bedroom/FREE Parking/Rooftop POOL/ Dog Park
4–11 Aug
Guest suite in Adelphi
4.85 out of 5 average rating, 203 reviewsCozy Suite with Hot Tub and Pool
10–17 Jul
Apartment in Annapolis
5.0 out of 5 average rating, 7 reviewsCharming Annapolis Waterfront Condo
1–8 Jan
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
Cottage in Annapolis
4.94 out of 5 average rating, 172 reviewsSecluded Cozy Cottage in Historic Downtown
21–28 Sept
Townhouse in Annapolis
4.97 out of 5 average rating, 158 reviewsCentrally Located, Charming Historic Townhouse
11–18 Mar
Cottage in Annapolis
4.97 out of 5 average rating, 116 reviewsWaterfront farm retreat for vacation & telework
20–27 Apr
Cabin in Gambrills
4.89 out of 5 average rating, 141 reviewsRelaxing Cabin Get Away Near Annapolis & DC
10–17 Aug
Guest house in Catonsville
4.96 out of 5 average rating, 199 reviewsFox Cottage *Pet Friendly*
4–11 Feb
Guest suite in Silver Spring
4.89 out of 5 average rating, 141 reviewsPrivate guest suite in a newly remodeled home
10–17 Jun
Flat in Glen Burnie
4.85 out of 5 average rating, 324 reviewsQuiet One Bdr Apt at BWI Airport
21–28 Mar
Flat in Silver Spring
4.93 out of 5 average rating, 395 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
7–14 Oct
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
6.5K reviews
Destinations to explore
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