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Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces

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A modern kitchen with a central island, stainless steel appliances, and wooden bar stools. - Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces (Annapolis)
A modern kitchen with a central island, bar stools, and a dining area with a long table and blue chairs. - Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces (Annapolis)
A spacious living area with a blue sofa, two striped armchairs, a round coffee table, and a wooden cabinet. - Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces (Annapolis)
A room with a wooden floor, a grey cabinet, and a painting above it. - Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces (Annapolis)
A spacious living room with a sofa set, a coffee table, and a TV. - Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces (Annapolis)
Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces provides amenities, such as a firepit and laundry facilities. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

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About this property

Upscale Family Retreat Near West Annapolis w 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

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About the area

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. Visit our Annapolis travel guide
View more Holiday homes in Annapolis
Map
Annapolis, MD

What's nearby

  • A large building with ornate architecture, a cannon, and a sign reading "Bancroft Hall".
    U.S. Naval Academy
    3 min drive - 2.5 km
  • Navy-Marine Corps Memorial Stadium
    2 min drive - 1.4 km
  • Helen Avalynne Tawes Garden
    2 min drive - 1.4 km
  • Peters Cove
    2 min drive - 1.8 km
  • St. John's College
    3 min drive - 2.5 km

Getting around

  • Bowie State Station
    25 min drive
  • Fort Meade, MD (FME-Tipton)
    32 min drive

Restaurants

  • McDonald's
    7 min drive
  • Wawa
    4 min drive
  • Graul's Market
    3 min drive
  • Taco Bell
    6 min drive
  • Burger King
    7 min drive

Frequently asked questions

Is Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces pet-friendly?

No, only service animals are welcome at the property.

How much is parking at Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces?

On-site parking is available at the property.

What time is check-in at Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces?

Check-in begins at 4:00 PM.

What time is check-out at Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces?

Checkout is at 11:00 AM.

Where is Upscale Family Retreat Near West Annapolis w 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).

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Reviews

Upscale Family Retreat Near West Annapolis w Resort-Style Outdoor Spaces Reviews

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 10 out of 10 reviews
Rating 8 - Good. 0 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 9 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an excellent stay at this lovely house. It totally met our needs and allowed everyone their own space. The suite was excellent for our 3 nieces who were with us. The kitchen was well equipped and was used for our 2 dinners. The fire pit proved fun and useful to make our s'mores. The location was excellent to get to the Marina as well as downtown. We even saw a deer going thru the yard. Thank you for giving a wonderful time to celebrate and enjoy our company.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great proximity to USNA Gate 8. IYKYK. Beautiful house with great amenities. Decor and furnishings make you feel like you are at a resort.
Stayed 3 nights in Apr 2026