House holiday rentals in Parole

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

Waterfront Chesapeake Bay Sunrises & Fishing Pier!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

"Hilltop Hideaway"- Private basement suite

Location, location! "Hilltop Hideaway" is a private basement apartment just 16 miles from BWI airport, 10 miles from Fort Meade and Annapolis, and less than 30 miles to Baltimore and Washington, DC! Nestled in a wooded setting on 2 acres, it is perfect for 1-2 adults (25yrs old or older). Not suited for children. Offers living space, bathroom, kitchenette w/microwave, toaster oven, coffee maker, crock pot, apartment size fridge and separate dining nook. Private key code entrance and parking.

4 bedrooms, 7 beds, 3 bath completely updated

Not your typical Airbnb. This is our vacation house too and we have it stocked so you can enjoy all of the amenities of home, without having to bring them yourself. Full kitchen with fresh coffee beans, K cups, and tea provided for starters. Breakfast starters provided too. Everything you need if you want to cook. Games for inside (including PS5), and backyard games too. 3 bedrooms on ground floor so no constantly having to go up and down steps. We love our place and know you will too.

Charming Annapolis Retreat with Hidden Wine Room

Discover charm in our 2BR, 1BA Eastport home, just a stroll away from downtown Eastport (under 1 mile), Downtown Annapolis (1.3 miles), the Naval Academy (2.3 miles), and less than 3 miles to Navy Stadium. Relax on our screened porch, by the fire pit, or under the cozy cabana out back. Delight in a secret—a hidden wine cellar awaits below! Plenty of free parking under the carport or on the street. Plus, with the water taxi service at the nearby dock, the best of Annapolis is just a call away.

Annapolis Charm –Bright 3BR in Downtown

Private 3 floor house located at the edge of Annapolis historic district. You can be certain that you will have all the comforts you expect here while within walking distance to the navy football field and the navy academy. You can also enjoy all the wonderful food and exciting shopping in between. The house comes with a furnished basement with bathroom/shower. On the first floor, you will find a stocked kitchen with a dining room and living room. Upstairs has 3 bedrooms with a bathroom/bath.

Spacious 3 Bedrooms House+Patio+Playground

Spacious 3 bedrooms house with functional patio + private playround located in Edgewater, only 15 mins drive to downtown Annapolis. Fully equipped with designer furnitures, with a sense of home! Huge dining room and fully functional kitchen, perfect to enjoy a great evening with your friends and family! Bedrooms are equipped with your own desks if you want to do some works even in your vacation. Easily fit 2 cars in private driveway. Very quiet neighborhood with proximity to everything!

Charming Downtwn Home- Private Parking Patio&Yard!

Welcome home to this Annapolis gem. An adorable 1930 American foursquare with private driveway, located on a quiet cul-de-sac off in downtowns Art's District. This cozy, three bedroom home can hold you and nine guests with plenty of sleeping arrangements for everyone. Enjoy a spacious backyard patio with string lights and deck chairs giving you and your guests plenty outdoor entertaining options. This house is fully furnished. Short walk to everything downtown offers, it just needs you!

Historic & sunny home steps from USNA/downtown

This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the basement) and offers a combination of location and charm that is hard to beat!

Cozy Annapolis Cottage.

Stay in the heart of Annapolis! 1 Gig Internet speeds. 220v outlet for EV charging (bring your own cable).Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly renovated. Professional cleaning team with every turnover of the house. Stay in the comforts of your own home and experience all that Annapolis has to offer. Art throughout home by local artist Amy Holt Cline.