Apartment vacation rentals in Annapolis

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Top-rated apartment rentals in Annapolis

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Guest favourite

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. 11 – 18

$149 CAD per night

Guest favourite

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.

Mar. 9 – 16

$289 CAD per night

Guest favourite

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. 15 – 22

$356 CAD per night

Guest favourite

Apartment in Annapolis

4.92 out of 5 average rating, 110 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!

Nov. 8 – 15

$339 CAD per night

Guest favourite

Apartment in North Beach

4.96 out of 5 average rating, 103 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

$207 CAD per night

Guest favourite

Apartment in Annapolis

4.98 out of 5 average rating, 124 reviews

Old Orchard Cottage

Welcome to Old Orchard Cottage, built on land that was originally settled by 80 Puritans in 1659, portions of which eventually became known as Dreams Landing and Lindamoor. We are located 2 miles from the Navy Marine Corps Stadium and 2.7 miles from the Naval Academy and Historic Annapolis. Nearby are markets, shops, restaurants, movie theaters, and the Annapolis Westfield Mall. Our apartment is located in the entire lower level of our home with a private entrance and a key lock box.

Mar. 3 – 10

$397 CAD per night

Guest favourite

Apartment in Bowie

4.98 out of 5 average rating, 117 reviews

Couple's Retreat - Private Entrance Basement Apt

Gem! This open and airy basement apartment is great for a weekend getaway or a longer stay -- all the comforts of home. It contains a fully equipped kitchen, living room with large sectional, TV and electric fireplace, dining area, bedroom with queen bed, a nook with sleep sofa, full bath, and washer/dryer. Private entrance with patio and a zen koi pond garden! Couples, travel nurses, and other medical professionals love this private apartment close to hospitals and health facilities.

Jul. 20 – 27

$193 CAD per night

Guest favourite

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

$233 CAD per night

Guest favourite

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.

Apr. 4 – 11

$191 CAD per night

Guest favourite

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.

Oct. 21 – 28

$153 CAD per night

Guest favourite

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. 3 – 10

$138 CAD per night

Guest favourite

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.

Jul. 31 – Aug. 7

$101 CAD per night