Pet-friendly holiday rentals in Annapolis

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Annapolis

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Condo in Annapolis

4.99 out of 5 average rating, 126 reviews

New Downtown Annapolis Condo With Free Parking

This newly constructed property brings chic, low-maintenance living to the heart of the Arts District in Annapolis. No parties, events, or large gatherings! Week long stay discount is 20%! Month long stay discount is 30%! Pets are only $100 per stay! Additional guests are $15 per person per night :) For stays greater than 90+ days, ask host about leasing to avoid service fees. Monthly rates start at $5,000! We would be happy to accommodate flexible check in and check out times if available

21 – 28 Nov

$2,973 AUD total

Guest favourite

Cottage in Annapolis

4.96 out of 5 average rating, 336 reviews

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

14 – 21 Nov

$2,602 AUD total

Guest favourite

Condo in Annapolis

4.94 out of 5 average rating, 347 reviews

Brand New Reno in Historic Dist w 2 Parking spots

Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District . Everything is high end ,brand new and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split A.C/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid matresess, Keurig coffee bar, toiletries . Walk to town in 10 min or less or take the free trolley to Main st,USNA,Churches,AYC. No children under 10.

26 Nov – 3 Dec

$2,389 AUD total

Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 116 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

11 – 18 Jan

$5,380 AUD total

Guest favourite

Cottage in Annapolis

4.94 out of 5 average rating, 314 reviews

Wright’s Cottage, Pets Welcome!

We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!

6 – 13 Oct

$2,078 AUD total

Guest favourite

Cottage in Glen Burnie

4.92 out of 5 average rating, 141 reviews

Home away from home

This is a small house with private parking close to Baltimore and Annapolis. I have one queen size Murphy bed, one single pull out couch. It has an updated kitchen, updated bathroom, walk-in closet, Internet and heating and cooling. I also have a pellet stove. my kitchen is fully stocked with dishes, knives, forks, pots and pans. The bathroom has towels and rugs. I tried to add all the amenities to make it as comfortable as home. Look at pet rules under the other things to note section.

16 – 23 Sept

$1,097 AUD total

Guest favourite

Guesthouse in Highland

4.98 out of 5 average rating, 263 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool and adjacent walking trails.

30 July – 6 Aug

$1,494 AUD total

Guest favourite

Guesthouse in Stevensville

5.0 out of 5 average rating, 208 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

23 – 30 Dec

$3,157 AUD total

Guest favourite

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 263 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

13 – 20 Dec

$2,901 AUD total

Guest favourite

Guest suite in Arnold

4.97 out of 5 average rating, 128 reviews

Pet Friendly Captains Quarters, Near Annapolis, EV

Yes, the hot tub IS open! 24/7/365 :-) This space has been fully updated with all the conveniences and amenities to make your stay enjoyable! We offer: - a king bed so you get a stellar night's sleep, - a queen bed sleeper sofa for family travels, - high speed internet, - a furnished kitchen, - private en-suite bathroom, and - a coffee bar. We're close to everything - located four miles from my hometown Annapolis!

21 – 28 Aug

$2,462 AUD total

Guest favourite

Home in Annapolis

4.95 out of 5 average rating, 103 reviews

The Navy House-Walk or Shuttle Downtown! 3 bd

Your family will be close to everything when you stay at this centrally-located home. 3 blocks from the Navy stadium and walking distance to amazing restaurants! Here is your Annapolis home away from home. Our 3 bedroom 2.5 bath bungalow retreat is perfect for 6-7 people wanting to relax and see all that beautiful Annapolis has to offer. There’s also a free shuttle that takes you downtown to the water. Come, enjoy!

5 – 12 Aug

$5,265 AUD total

Guest favourite

Guesthouse in Annapolis

5.0 out of 5 average rating, 106 reviews

Garden View, a spacious 1 bedroom with loft.

Take it easy at this unique and tranquil getaway located in a quiet neighborhood. Route 50, I-95, and Downtown Annapolis are all minutes away. Garden View is centrally located for Naval Academy sports, The Renaissance Festival, Boat Shows, and golf at The Preserve. Staying in? No problem, the kitchen is fully equipped, and with free wi-fi working at the desk is a breeze.

29 July – 5 Aug

$2,349 AUD total