House holiday rentals in Annapolis

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Top-rated house rentals in Annapolis

Guests agree: these houses are highly rated for location, cleanliness and more.

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Guest favourite

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favourite

Home in Saint Michaels

4.85 out of 5 average rating, 121 reviews

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Top guest favourite

Home in Rock Hall

5 out of 5 average rating, 85 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

Guest favourite

Home in Oxford

4.96 out of 5 average rating, 207 reviews

The Oxford House

Enjoy water views from the backyard or visit with friends on the screened in porch. The light and airy, 3bd, 2bath house is a short walk to Oxford’s best restaurants and favorite ice-cream shop. You can find the best beach in oxford only 75 yards from our front door or take the Ferry to the neighboring town of Saint Michaels, Maryland. You will love the scenic views and historical charm of this little town, the Oxford house has a central location allowing you to walk or bike to everything.

Superhost

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

Accepting 2025 bookings as of May 1st.... "Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take our kayaks to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acres in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home.

Top guest favourite

Home in Hampden

4.97 out of 5 average rating, 154 reviews

Full house in “coolest neighborhood in America”

Small but cozy single family in Northern Baltimore, located in the very sought after Hampden neighborhood. 5 minute walk to “the Avenue” and 34th Street lights at Xmas. Directly across the street is a Walgreen’s, MOM’s Organic Market, gym, restaurants, UPS Store, etc. A private driveway, manicured back yard w/ hardscape, fire pit and tons of indoor amenities offer a convenient and relaxing stay in this quaint Baltimore hood. Cleaned by COVID-trained professionals after each reservation.

Superhost

Home in Edgewater

4.81 out of 5 average rating, 21 reviews

South River Beach Front House

New 2024 Renovated Stunning WATERFRONT South River Beach home!! BEST WATERFRONT LOCATION!!! with heated POOL on the river side & deck 10' from waters edge. Beach, 125' private pier for crabbing & fishing. Comm w/ beach, pier, tennis & basketball courts. (1) Main LVL: entry foyer, sunroom, stunning kitchen, dinning area, & living room w/FP. Main level owners suite w/full bath, & 1/2 bath. (2) Upper level: 2 bedrooms w/ full bath & upper LVL sitting area & sun deck w/expansive river views

Guest favourite

Home in Deale

4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath house with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views, & wildlife. Hidden but close to services. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

Guest favourite

Home in Annapolis

4.92 out of 5 average rating, 127 reviews

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 )and home to some very famous neighbors it's one one of the most desirable locations in town. A short stroll across a quaint drawbridge and your downtown for shopping USNA . Very spacious home with 4 bedrooms 4 baths , parking for 4 cars and a pool table. Truly a million plus dollar property !

Superhost

Home in Falls Church

4.93 out of 5 average rating, 15 reviews

Trailing Houses for FS! Designer Home/Location!

This beautiful split-level home is centrally located. You can be in DC or Arlington in just minutes or head to Old Town, Alexandria in no time! Everyone comments on how comfortable and clean this house is! With a great big backyard, fantastic light and beautiful furniture, you are sure to find everything you need to feel at home! Quiet neighborhood close to retail shops, grocery stores, restaurants. Free Costco membership during your stay!!

Guest favourite

Home in Annapolis

4.92 out of 5 average rating, 112 reviews

Historic Downtown House with Off Street Parking

Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park your car off street (up to 3 cars) and you won't need it again! Gourmet kitchen fully stocked and ready for entertaining, enjoy the outdoor space. The whole group will enjoy easy access to everything from this centrally located place.

Superhost

Home in Annapolis

4.73 out of 5 average rating, 122 reviews

West Annapolis SuperHost!

Welcome! We are eager to continue providing our quests with an upgraded experience. This is a one story house! Best of AirBnb! Perfect location close to art and culture, the city center, and parks. Great house for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). One block from Navy Marine Corps Stadium!