Pet-friendly holiday rentals in Annapolis

Crab Cakes and Football Historic District

Soak up the vintage charm of this restored property. The house features a private master suite balcony, an open-plan living space, chic eclectic furnishings, exposed brick, a wood burning fireplace, a front garden, and an outdoor back BBQ area. STR# 143754 When we decided to convert to a short term rental I looked at other properties in the area and how they described them. I could tell you the house was built in 1901 and is located in one of the most sought after neighborhoods in historic Annapolis. That's all well and good but to be honest there's a book on the coffee table that will tell you all the history (if you really want to know). I might not know a lot about writing a great summary but after almost 3 decades of living in Annapolis I think I know what people want: 1) Great food and drink! 2) Great location for walking to everything and.. 3) An outdoor area to enjoy the mornings and evenings during any down time. Unfortunately the one thing that can really ruin the fun is PARKING! Well guess what, we've got all the things I listed above and not one parking spot, but TWO (right at your back door!). Don't be fooled when other properties offer you a parking pass. That does not mean you'll be parking near your rental! Enjoy full access to our home. We do not live there so it is not cluttered with "stuff". Consider it a hotel with all the amenities of home! We live 5-10 minutes from the property so you'll have your privacy but we are nearby if you need assistance. We are available by text or calling for any questions or help you may need. The home is in the Art District of Annapolis right in the middle of all the fun. Enjoy the hustle and bustle of the city center during the day and evening, but return to a quiet neighborhood to recharge. Free designated parking for 2 cars. Park upon arrival and you my never need your car again until your departure! No parties. Dogs welcome on a case by case basis.

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.

Historic 3 Bedroom Downtown Annapolis Townhome

Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, Downtown Restaurants, Bars, Shopping, and Festivals. Enjoy and relax on your large private, fenced-in patio or in your modern living room. While the restaurant scene is mouth-watering in Annapolis, you can also stay "home" and cook in your gourmet kitchen. Explore all that Annapolis has to offer from the comfort of your home away from home! No on-site parking but lots of off.

Charming City Oasis. Walk to harbor, eateries.USNA

Easily, you will enjoy the year-round charm & convenience of this cozy vintage cottage. Just blocks from shops, restaurants, pubs.. Free parking. Enjoy a secluded patio garden for family gatherings, a chimnea & blankets to wrap up in. Furnishings from Robert Redford's Sundance, modern appliances, ceiling fans, AC/heat, bathrooms with comfort-height toilets & grab bars, original pine floors. Corn Hole boards available. Game on. USNA 2028, 2029 Com Wk available. 6-night min applies to CW.

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay 100ft away. Water views from most rooms plus treehouse vibes. 4 bedrooms + 4 full bath. Custom luxury upgrades, new appliances. Pull out daybed +2 folding queen mattresses, rustic leather sectional sofas can sleep 4 more (14+total), outdoor grills, covered balconies, hot tub, kayaks. Access to community fishing/crabbing piers/beach/picnic area. Close to beautiful Thomas Point & Quiet Waters park. A unique escape for nature lovers!

Carriage House near Navy Stadium, parking, pets

Close to downtown. Free parking. 🐶 Quick walk to Navy Stadium, 1.2 mile walk to downtown Annapolis and Academy, 30 min to Baltimore and 45 min to Washington DC. Immaculate private space. Safely tucked away a charming carriage house apartment in private backyard - 2 br, family room, well equipped kitchen and sparkling clean shower and bath. Pets welcomed but must be approved in advance +$50 pet fee. Note - 7 night min. during USNA Commissioning Week. 2 night minimum preferred on weekends.

Chesapeake Comfort, Annapolis.

Veteran Superhost! Annapolis Bungalow Home. Professionally cleaned and a full time Airbnb. I have been a Superhost with my listings for over 10 years. Walking distance to Navy Stadium and to Park Place where you can jump on the trolley and take a ride through town. Enjoy the spacious backyard deck and yard. Bring your kayaks and store on our rack and walk it down to the launch. Queen Bedroom on ground floor. 2nd Queen Bedroom on lower level w/bathroom. Loft bedroom has 2 full size beds.

Eastport Haven House

Welcome to our custom Craftsman in the exclusive Maritime Eastport section of Annapolis. Surrounded by the city's best restaurants (Ruth's Chris, ChartHouse, Vin 909 and many, many others) as well as home to some very famous neighbors it's one of the most desirable locations in town. A short stroll across a quaint drawbridge and your downtown for shopping and USNA. Very spacious home with 4 bedrooms 4 baths, parking for 4 cars and a pool table. Truly a million plus dollar property!

Cozy 1-Bedroom Retreat Near Annapolis, Sleeps 4

*New hot tub and pergola installed!* 💗 This updated suite is designed for comfort & convenience. Enjoy a king bed and a LoveSac sofa that converts into a queen bed, perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!

Renovated Apt In Historic Dist w/2 Parking Spots

Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid mattresses, 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 12.

Waterfront-View of Bay from your Bed-Steamy Sauna

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.

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit. Twin bed can be set up and made up at guest request.