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Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Easily escape to the woods on a 14 acre homestead that's only 20 miles from DC. Surrounded by the forest with amazing views, designed by artists, this secluded hideaway is a celebration of Nature and Art. Recharge amongst these ancient trees and all the singing critters that soundtrack the night. Enjoy a fire, frolic in the fields, read on a hammock, strum a guitar, and feel the pressure of modern life melt away. Explore the many bucolic trails nearby. Perfect for retreats and workshops.

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

*PLEASE READ OUR LISTING AND HOUSE RULES IN, PRIOR TO BOOKING OUR HOME. SEASONAL POOL/ HOT TUB DATES* Welcome to your beautiful and spacious home away from home! Featuring 4 beautifully decorated bedrooms and 2.5 bathrooms, each designed with comfort and style in mind. Relax in our spacious living areas, take a plunge in the pool & hot tub or lounge by the fire pit in the huge backyard! Experience luxury and comfort in our beautiful home and make unforgettable memories with your loved ones!

Waterfront Cheerful 5 home

Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 4 Bathroom .one bedroom on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

Gorgeous Two-Story Guesthouse w/ Driveway & W/D

This spacious cottage is the perfect home base for families, couples, or professionals exploring DC. Start the day with breakfast made in a fully stocked chef's kitchen. Take a short walk to the Rhode Island Ave metro (Red Line), Catholic University, trendy Brookland restaurants, breweries, yoga studio, and grocery store. Rent a bike from Capital Bikeshare and hop on the nearby Metropolitan Bike Trail. At night, relax with a glass of wine around a cozy fire pit table on our cobblestone patio.

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a private ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a deadbolt; no shared indoor spaces; separate entrances).

Access to Private Guest House with Patio/Firepit

Centrally located to Washington DC, Annapolis, Baltimore and Northern Virginia, this tiny house is in a rural setting that is close to any amenity thinkable; minutes from the Bowie Town Center boasting restaurants, shopping and entertainment for your enjoyment. Major highways are less than 10 min away and will have you on your way to your commute or seeing any of the major landmarks and places of interest that make the DMV a top area for both tourists and working professionals alike.

Urban Cottage, MD minutes from DC/National Harbor

Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.

Kone Oasis- hot tub, pool, theater/game rm.

Have fun and relax! Near every amenity. Huge Pool w/multiple cabanas, hot tub, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Now offering RV for additional cost to add additonal sleeping space. Basement apt so there is some movement noise. 20 mins to DC & National Harbor

Modern Escape | Near DC, Dining & Entertainment!

Discover the perfect blend of comfort and convenience! This stylish home is perfect for group trips, family getaways, or a relaxing retreat. Just minutes from FedExField, home of the Washington Commanders, and a quick Metro ride to downtown D.C., National Harbor, and Nats Park. Shop and dine at Woodmore Towne Centre, catch a movie at AMC Theatres, explore Watkins Regional Park, or enjoy top equestrian events at Prince George’s Equestrian Center. Unbeatable location—book now!

Garden View, a spacious 1 bedroom with loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.