Apartment holiday rentals in Annapolis

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Top-rated apartment rentals in Annapolis

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Guest favourite

Apartment

4.99 out of 5 average rating, 136 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

Guest favourite

Apartment

4.85 out of 5 average rating, 131 reviews

Lovely, convenient apartment in great location

Historic elevator condo in perfect location. Friendly, 24-hr concierge for easy check-in/out & secure pckgs. Walk to symphony, opera, museum, seasonal festivals, restaurants, drug/food stores. Updated, fully equipped kitchen. 7th floor unit, away from street noise, w natural light from 4 windows & spectacular views from rooftop terrace. Across st from free bus to Inner Harbor & other buses. Laundry room and convenience/beer & spirits store in bldg. Parking available in attached garage for a fee.

Guest favourite

Apartment

4.94 out of 5 average rating, 375 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.

Superhost

Apartment

4.86 out of 5 average rating, 222 reviews

Newly Renovated & Modern 1BR Condo - Unit 2

Completely renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City and National Airport. Spacious unit with free cable TV, secure Internet/Wi-Fi, FREE RESERVED PARKING space in private lot, in-unit Washer/Dryer, Full Kitchen. Steps away from public transit buses that route to multiple Orange/Blue/Silver line Metro train. Comfortably accommodates the traveling professional, those on vacation and is kid friendly.

Guest favourite

Apartment

4.99 out of 5 average rating, 109 reviews

Centrally located Capitol Hill one-bedroom unit

This apartment is a true find and good value! Less than a block from Eastern Market Metro on Capitol Hill, putting key tourist sites within easy reach. The Capitol is within a mile's walk. Just around the corner from the famous 8th Street SE restaurant row. Essential shops are nearby too. In an incredible location but set back from the road giving peace and quiet! This is a light, dry, clean, spacious, and fresh basement unit with private entrance and well equipped with every need provided for.

Guest favourite

Apartment

4.88 out of 5 average rating, 428 reviews

Bright, large zen studio on historic Logan Circle

Bright, open plan nearly 1,000 square foot private studio apartment with space for an entire family in historic Logan Circle neighborhood on a quiet street. This English basement has great ceiling height, good natural light, clean white paint, & a peaceful, zen design. Everything you need for a short or long stay. Short walk to White House, Mall & museums. Logan Circle is DC's hottest & hippest area with a 96 walk score. Stay in a historically preserved brownstone right in the center of it all!

Guest favourite

Apartment

4.97 out of 5 average rating, 107 reviews

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC

Location, location, location. Bright one bedroom condo in prime downtown Bethesda location with designer furnishings. One of the best 1 bedrooms in the building with the best balcony location right off Bethesda Row. Easy walking distance to Metro and includes one of the best underground parking spaces by elevator. Lobby was recently renovated and gym has all new gym equipment. NOTE - key is provided through a lockbox (rather than in person) and will need to be returned back to lockbox.

Guest favourite

Apartment

4.84 out of 5 average rating, 298 reviews

Spacious Bloomingdale 1BR; garage parking included

Enjoy urban, neighborhood living in this beautiful, modern 1-bedroom on a quiet street in the heart of bustling Bloomingdale in NW DC. Perfect for a weekend getaway to enjoy the culture and nightlife the city has to offer, or for the business traveler looking to avoid the downtown hotel scene. Just steps from popular neighborhood restaurants, including Red Hen, DCity Smokehouse, and Big Bear Cafe. NOTE: Refurnished & painted (as shown in photos) in March 2021. New HVAC system in May 2021.

Guest favourite

Apartment

4.89 out of 5 average rating, 113 reviews

Renovated&bright 1-bedroom in heart of DC

Nestled on a quaint tree-lined Bloomingdale street, this bright and newly renovated 1-bedroom unit is minutes away from downtown and all the sights. The area is quiet, and yet provides access to fantastic restaurants like the award-winning Red Hen, Big Bear cafe, or the Gastropub Boundary Stone. Crispus Attucks park, Howard University and the U street corridor are nearby. The owners lovingly appointed the unit mainly for friends and family, but decided to share it with visitors to DC.

Guest favourite

Apartment

4.92 out of 5 average rating, 143 reviews

Sun House in Hampden Private Apartment no stairs

Artists and creatives are welcomed! Stay at our 1920 rowhouse with its mix of 70's era textiles and contemporary style. Only two steps to a welcoming porch and keyless entry to our foyer/Shared hall. Straight ahead is Sun Apartment, private studio with stocked kitchen, comfiest 5 star bed, private bath, laundry and back yard access. Yoga room/ office located in shared hall. No need for a car in the heart of Hampden's Avenue just a block away. LGBTQ+ friendly

Guest favourite

Apartment

4.96 out of 5 average rating, 255 reviews

Annapolis Waterfront Condo - Unit #: A-203

BOOK NOW FOR SUMMER 2025! SPRING and FALL BOAT SHOW AVAILABILITY! Free reserved parking! Walk to show in minutes! Great views - 2nd flr. condo (12 stairs, no elevator.) Pool hours are fixed: Mon: 4pm-8 Tues: Closed Wed: 4-8 Thurs: 4-8 Fri: 3-8 Sat/Sun/Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another location. 15 min. walk to downtown Annapolis/USNA. MULTIPLE Free parking options.

Guest favourite

Apartment

4.84 out of 5 average rating, 412 reviews

Cozy Private Condo in Mt. Vernon w/ Rooftop

This cozy private condo is located in the hip/historic Mt. Vernon neighborhood, and within walking distance to numerous bars, breweries, and museums. Conveniently located right near the highway (I-83) and Penn Station, it's also a quick walk down to the Inner Harbor (only 1 mile away), and a short Uber ride to Fells Point & Fed Hill. Condo includes a 12th floor rooftop overlooking the city with amazing views. UPDATED - high speed WiFi currently available.