Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces
Experience the Difference: Professionally Managed by iTrip Annapolis
Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces
This luxury family retreat offers exceptional flexibility and can be rented as one spacious home or two separate private residences, with distinct main-level and lower-level accommodations. Newly decorated and thoughtfully furnished, the home is tucked away on a quiet cul-de-sac just minutes from Downtown Annapolis, offering a peaceful yet convenient setting.
The open main level features a spacious family room and cozy den—each with a flat-screen TV—alongside a beautifully equipped kitchen perfect for shared meals with three dining spaces in the dining room, at the breakfast bar and a sunny four-stop table in the family room. The main level also includes a serene King Suite with a private en suite bath and direct deck access, a comfortable Queen Guest Room with a full hall bath.
The lower level is perfect for extended families, offering two additional bedrooms, a full bath, a second family room, kitchenette, and laundry for added comfort and privacy.
Outside, enjoy expansive entertaining spaces with two fire pits, a gas grill, and ample seating. With generous parking and easy access to the Naval Academy, boat shows, and Downtown Annapolis, this home is an ideal choice for family gatherings and special occasions.
Sleeping Arrangements | 4 BR / 3 BA | Sleeps 10
Main Level King Suite
King Bed
Private en suite bathroom with separate shower
Direct access to back deck
Main Level Queen Guest Room
Queen Bed
Full hall bath with stand-up shower
Main Level Den
Full sleeper sofa, linens included
Lower Level Queen Bedroom
Queen Bed
Lower Level Twin Bedroom
Two Twin Beds
Lower level bedrooms share a full hall bath with stand-up shower.
Highlights & Amenities
Open-concept main level with Family Room, Den, Dining Area & Kitchen
Dining table seats 8, Breakfast bar seats 6, Four-top Table in Family Room
Fireplace
Spacious outdoor living areas with gas grill (propane provided)
Two fire pits (front patio & side deck)
High-speed WiFi & Smart TVs
Luxury linens, starter toiletries & boutique-level service
Full-size washer & dryer on main level, Full-size combo washer/dryer on lower level
Parking for 3–4 cars
Keyless entry for easy self check-in
Distances
Navy Marine Corp Memorial Stadium: 1.3 miles
U.S. Naval Academy: 1.5 miles
Baltimore: 30 miles
Washington, DC: 32 miles
Additional Details
A starter supply of essentials is provided, including coffee, sweeteners, paper products, soaps, and toiletries. All beds are freshly made with clean linens and towels prior to arrival.
House Rules
Minimum age requirement: At least one guest must be 25 years or older
No parties, events, smoking, or pets
Quiet hours: 9:00 PM – 8:00 AM
Respect the home, neighbors, and neighborhood
Check-in: 4:00 PM
Check-out: 11:00 AM
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Annapolis
Located in Annapolis, this holiday home is near a water park. ARTFX Gallery of Fine Crafts and Arts and Hammond-Harwood House are cultural highlights, and some of the area's landmarks include Stanton School & Community Center and Thurgood Marshall Memorial. Helen Avalynne Tawes Garden and French Soldiers Monument are also worth visiting.
Navy-Marine Corps Memorial Stadium - 17 min walk - 1.5 km
Helen Avalynne Tawes Garden - 17 min walk - 1.5 km
Peters Cove - 2 min drive - 1.8 km
U.S. Naval Academy - 3 min drive - 2.8 km
St. John's College - 3 min drive - 2.8 km
Getting around
Bowie State Station - 25 min drive
Fort Meade, MD (FME-Tipton) - 32 min drive
Restaurants
McDonald's - 7 min drive
RaR Brewing - Chessie's Wharf - 17 min walk
Wawa - 4 min drive
Graul's Market - 3 min drive
Burger King - 7 min drive
Frequently asked questions
Is Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces pet-friendly?
No, only service animals are welcome at the property.
How much does it cost to stay at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?
As of 4 Apr 2026, prices found for a 1-night stay for 2 adults at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces on 20 Jun 2026 start from £426, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?
On-site parking is available at the property.
What time is check-in at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?
Check-in begins at 4:00 PM.
What time is check-out at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?
Checkout is at 11:00 AM.
Where is Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces located?
Situated in Annapolis, this holiday home is within 2 miles (3 km) of Navy-Marine Corps Memorial Stadium, Helen Avalynne Tawes Garden and Peters Cove. U.S. Naval Academy and St. John's College are also within 3 miles (5 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The rooms were extremely clean—the house practically looked brand new. Communication with the host was seemless and the check-in process was smooth. Less than 5 minute drive from the Naval Academy. Plenty of outdoor seating and entertainment space. Beds were excellent—comfortable and clean. Plenty of cooking supplies for meals and feeding 10 people.
Tyler S.
Stayed 9 nights in Mar 2026
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests