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Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces

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Fridge, microwave, dishwasher, coffee/tea maker
TV, fireplace
TV, fireplace
TV, fireplace
Interior

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms204 sq m

Popular amenities

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

Explore the area

View map
Annapolis, MD
  • Place, Navy-Marine Corps Memorial Stadium
    ‪17 min walk‬
  • Place, U.S. Naval Academy
    ‪3 min drive‬
  • Place, St. John's College
    ‪3 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪27 min drive‬

Room options

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About the area

Annapolis

At this holiday home you'll be 2.1 km (1.3 mi) from Navy-Marine Corps Memorial Stadium and 2.1 km (1.3 mi) from Helen Avalynne Tawes Garden. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .Home features 3 bathrooms, a fireplace and a patio. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a dishwasher. A living room, a TV and a coffee/tea maker are also available. .Near this Annapolis holiday home, you'll find U.S. Naval Academy.

What's nearby

  • 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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Similar properties

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Dishwasher
  • Ice maker
  • Microwave
  • Refrigerator

Dining

  • Dining table

Bedrooms

  • 4 bedrooms

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shampoo
  • Shower

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Service animals only (pets not allowed)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift
  • Stair-free path to entrance
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Things to do

  • Bicycle parking
  • Bicycle storage

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • At least 80% lighting from LEDs
  • Bicycle parking
  • Bicycle storage
  • Energy-saving switches in guestrooms
  • Recycling
  • Unit size: 2,200 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed, but service animals are welcome

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. 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. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in all accommodation.

Property is also known as

16263

Frequently asked questions

Are there any beaches close to Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?

The closest beach to Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces is Sandy Point Beach (10.5 km).

Does Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces have a pool?

No, this holiday home doesn't have a pool.

Is there a free airport shuttle available at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?

No, Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces does not offer an airport shuttle service.

What time are check-in & check-out at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?

Check-in begins at 4:00 PM. Check-out time is 11:00 AM.

Are pets allowed at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?

No, only service animals are allowed.

Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Tyler S.

Liked: Cleanliness
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