Holiday homes in Annapolis

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Top-rated holiday homes in Annapolis

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Guest favourite

Condo in Annapolis

4.99 out of 5 average rating, 126 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

21 – 28 Nov

$2,969 AUD total

Guest favourite

Condo in Annapolis

4.94 out of 5 average rating, 347 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.

20 – 27 Feb

$2,385 AUD total

Guest favourite

Condo in Washington

4.93 out of 5 average rating, 107 reviews

Monumental Getaway

Located in historic Bloomingdale, this charming 2nd-floor 1-bedroom apartment in an 1895 row house offers a comfortable living space with modern conveniences and vintage appeal. Features a queen Murphy bed, inviting eat-in kitchen, full bath with tub, ceiling fan, window A/C, ample natural light, private entrance with digital access, and optional off-street parking. Experience the rich history and community spirit while enjoying a unique living experience in this well-maintained vintage setting.

11 – 18 Dec

$1,682 AUD total

Guest favourite

Condo in Washington

4.9 out of 5 average rating, 448 reviews

Gorgeous, large, modern 1 BR on Hist. Logan Circle

Gorgeous, bright, open plan nearly 1,000 square foot 1 bedroom condo with space for an entire family in historic Logan Circle neighborhood on a quiet street. Short walk to White House, Mall & museums. Built in 1900, this brownstone was thoughtfully renovated to blend modern (in-ceiling lighting, stainless steel appliances, bamboo flooring) with historic features (original exposed brick & trim). Warm, spacious & comfortable for your stay. Logan is DC's hottest & hippest area with a 96 walk score.

6 – 13 Sept

$2,193 AUD total

Guest favourite

Condo in Baltimore

4.91 out of 5 average rating, 113 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. Straight ahead is Sun House door, private studio with stocked kitchen, comfiest 5 star bed, private bath, laundry and back yard access. All on one floor. Find our yoga/office space in same hallway shared/usually empty. No need for a car in the heart of Hampden's Avenue just a block away. LGBTQ+ friendly

7 – 14 Jan

$1,538 AUD total

Superhost

Condo in Baltimore

4.86 out of 5 average rating, 113 reviews

Lovely, perfect location, amazing safety, friendly

Lovely, historic elevator condo in perfect location. Friendly, 24-hr staffed front desk for easy check-in/out. Walk to symphony, museum, 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 the street from free bus to Inner Harbor and other buses. Laundry room and convenience/beer & spirits store in bldg. Parking available in attached garage for a fee.

$96 AUD per night

Guest favourite

Condo in Arlington

4.93 out of 5 average rating, 212 reviews

Newly Renovated & Modern 1BR Condo - Unit 3

Newly 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. Sorry, NO parties.

8 – 15 Feb

$1,960 AUD total

Superhost

Condo in Washington

4.88 out of 5 average rating, 676 reviews

Stylish DC Apt - Convenient, Clean and Private

Modern furnished large one bedroom apartment in downtown NW DC, with optional gated parking. Perfect for anyone visiting DC for business, fun, family vacations -- or even if you're a local and need more accommodations for visitors. The listing is for the entire private apartment, completely separate with its own entrances. We have gated parking spaces that can be made available upon request. Great for guests traveling through or those who don't want to think about street parking rules.

12 – 19 Apr

$1,956 AUD total

Guest favourite

Condo in Occoquan

4.92 out of 5 average rating, 677 reviews

The Bird's Nest in Historic Occoquan (Mins to DC)

Spacious condo in the heart of walkable historic Town of Occoquan. Full kitchen, bath, a comfortable queen bed, work station & free parking. The Town of Occoquan offers unique experiences (kayaking, fishing, birdwatching and shopping) all within walking distance. Excellent dining choices from award winning restaurants to casual eateries. Mins to I-95, 123, VRE. D.C. (35min); Fort Belvoir (20min); The Pentagon (25min); Quantico (25min); Potomac Mills (10min). Tysons (25min).

24 – 31 Jan

$1,514 AUD total

Guest favourite

Condo in Baltimore

4.84 out of 5 average rating, 390 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.

19 – 26 July

$883 AUD total

Guest favourite

Condo in Fort Washington

4.84 out of 5 average rating, 188 reviews

The Get-Away at National Harbor

This is the perfect place if you want to be near the National Harbor and MGM. You will be a short 5 minute drive away from shopping, restaurant, family fun activities and night life. Old town Alexandria as well as Washington DC is just a 15 minute drive away. Once you are finished enjoying the busy attractions, come home to your well groomed quiet neighborhood. Where you can relax in your charming newly renovated 2 bed 2 bath sanctuary.

31 May – 7 June

$2,189 AUD total

Guest favourite

Condo in Oxford

4.98 out of 5 average rating, 112 reviews

Cozy Oxford Getaway

Welcome to our cozy Oxford getaway. Located in the center of town, next to the Oxford Market, and across from the park. The apartment is centrally located and walking distance to all the restaurants, shops, and marinas. Oxford is a quaint little town that was founded in 1683. It was home to Robert Morris, the financier of the American Revolution.

22 – 29 Dec

$2,330 AUD total