Apartment vacation rentals in Annapolis

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Top-rated apartment rentals in Annapolis

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Guest favorite

Apartment in Sykesville

4.96 out of 5 average rating, 131 reviews

Hickory Haven •1B King •Bsmt Apt •Clean •LG

Walk into a generously spacious, open-concept apt. The comfortable furnishings in this home blend authentic styles with modern design. Start your mornings w/ a meticulously clean bathroom. Enjoy movie night in the large living room, or lay on the comfortable king-sized bed. Read through the night by a warm stove fire. Stay in the backyard and enjoy the serenity of Sykesville! Enjoy the high-speed internet and the large space for your work-at-home needs. Stay-a-while and make the place your home.

Aug 17 – 24

ﺩ.ﺇ343 per night

Guest favorite

Apartment in Stevensville

4.98 out of 5 average rating, 240 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Dec 15 – 22

ﺩ.ﺇ699 per night

Guest favorite

Apartment in Annapolis

4.88 out of 5 average rating, 256 reviews

Gybeset Eastport Inn

Enjoy exclusive use of this boutique hotel-styled upstairs apartment in a beautifully restored 1930s craftsman-style building in the heart of Eastport. Private off-street parking. Short walk to downtown Annapolis. Just a few doors away from one of the hottest restaurants in Annapolis, Vin 909. A seasonal farmers' market is located across the street along with restaurants and other amenities. Hotel-like services available for longer stays. Fully licensed by City of Annapolis for AirBnb operation.

Jul 30 – Aug 6

ﺩ.ﺇ787 per night

Guest favorite

Apartment in Annapolis

4.93 out of 5 average rating, 108 reviews

Walk to Water, State House, USNA

Private, 1st FL space in Eastport (architectural) Conservation District. Sleeps 3. Guests' day visitors are welcome; home not appropriate for parties. BR w/king bed, living/dining area w/pullout sofa. FiOS WIFI, 2 Roku TVs. BA w/shower, fully equipped galley - fridge & freezer, DW, disposal, microwave, toaster oven, induction cooktop (portable). WD available. Walk to water; tie up your dinghy gratis at street-end parks. Short walk to downtown, USNA, boating. Stays > 9mos out - pls message!

Jan 25 – Feb 1

ﺩ.ﺇ764 per night

Guest favorite

Apartment in North Beach

4.97 out of 5 average rating, 102 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

Oct 21 – 28

ﺩ.ﺇ489 per night

Guest favorite

Apartment in Occoquan

4.89 out of 5 average rating, 417 reviews

Anne’s River View, couples, Historic Occoquan,hike

Newly designed bathroom!!! If you like a calming relaxing getaway this is the place for you. This place cannot hold parties, or get togethers of any kind. (If you like your music loud and late nights, then this place WILL NOT be a good fit for that.) Your unit is in a building with other commercial space and other tenants. A waterfront deck view with your stay. Welcome to Anne’s Place. Not suitable or safe for children 0-12 years also it’s an older building there are no child friendly spaces.

Aug 27 – Sep 3

ﺩ.ﺇ367 per night

Guest favorite

Apartment in Annapolis

4.91 out of 5 average rating, 122 reviews

Chesapeake Bird Nest

This nest is tucked high in the trees above Eastport. A quiet serene spot to relax and unwind, yet close enough to all the action in beautiful downtown Annapolis. Quiet, separate, apartment space. Walk 1 block to restaurants and bars in Eastport, hop on the water taxi and you are in the heart of Downtown Annapolis, USNA, and historic areas of Annapolis in minutes. This is an Ideal location for the sailing community or anyone visiting our beautiful city. Free street parking available.

Aug 18 – 25

ﺩ.ﺇ523 per night

Guest favorite

Apartment in Church Creek

4.97 out of 5 average rating, 372 reviews

Church Creek Natures' Rest

Nature's Rest is ideally located, just minutes to Blackwater Wildlife Refuge The Harriet Tubman Museum, as well as boat ramps for easy access to the Chesapeake Bay and it's tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

Jan 9 – 16

ﺩ.ﺇ482 per night

Guest favorite

Apartment in Crownsville

4.98 out of 5 average rating, 165 reviews

“River Sweet" Private Apartment

River Sweet has everything you need for a fun and relaxing getaway. Cozy and clean, River Sweet provides all the comforts of home, including your own driveway and entrance. You'll delight in privacy while enjoying a safe, waterfront neighborhood. A local mini mart and restaurant are close by. And, you are centrally located between Annapolis, Baltimore and Washington for fun excursions! Please let us know if you need a long-term stay. We would be happy to accommodate you.

Jun 28 – Jul 5

ﺩ.ﺇ459 per night

Guest favorite

Apartment in Chester

4.97 out of 5 average rating, 234 reviews

Cozy Waterfront Apartment Chester, MD

*We live on the property* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. Plus an easy to assemble blow up air mattress to sleep an additional two. WiFi included. Private porch to sit & enjoy beautiful water views!

Apr 4 – 11

ﺩ.ﺇ468 per night

Guest favorite

Apartment in Sykesville

4.98 out of 5 average rating, 280 reviews

In the Heart of Sykesville! 2 Bedroom Suite

Located in the heart of Sykesville, Linden, a two bedroom basement suite, welcomes you to relax and rewind! We have designed our space to feel like your home away from home.The kitchenette includes a full refrigerator, microwave, slow cooker, Instapot, and a hot plate for meal prep. An easy stroll to Main Street will give your car a rest as you enjoy dining and shopping, live music from May/Oct and a wonderful Splash Park from May/Sept. Discover our hidden gems!

Dec 13 – 20

ﺩ.ﺇ338 per night

Guest favorite

Apartment in Sykesville

4.82 out of 5 average rating, 342 reviews

Quiet Studio Basement Apartment

Welcome to my private studio apartment with a separate entrance and private bath. There is a mini fridge, microwave, toaster oven, coffee pot, tea, sugar, half and half. Bottled filtered water. Recently renovated bathroom, fresh towels, wash cloths and soap, shampoo and conditioner, sheets and bedspread. Iron and ironing board.

Dec 22 – 29

ﺩ.ﺇ241 per night