Entire home

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

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Fridge, microwave, oven, stovetop
Outdoor dining
TV, fireplace
Dining
Shower, hair dryer, shampoo

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms2200 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Annapolis, MD
  • Place, Navy-Marine Corps Memorial Stadium
    ‪2 min drive‬
  • Place, Helen Avalynne Tawes Garden
    ‪2 min drive‬
  • Place, St. John's College
    ‪3 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪33 min drive‬

Room options

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About the neighborhood

Annapolis

This vacation home places you within 2 miles (3 km) of U.S. Naval Academy and Navy-Marine Corps Memorial Stadium. The vacation home includes a kitchen, a fireplace, and a patio.

What's nearby

  • Navy-Marine Corps Memorial Stadium - 2 min drive - 0.9 miles
  • Helen Avalynne Tawes Garden - 2 min drive - 0.9 miles
  • Peters Cove - 2 min drive - 1.1 miles
  • St. John's College - 3 min drive - 1.6 miles
  • U.S. Naval Academy - 3 min drive - 1.6 miles

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
  • ‪Wendy's - ‬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
The vacation home is air-conditioned and features a kitchen, 3 bathrooms, and a patio, and there's space to spread out with 4 bedrooms. Guests can enjoy a TV and stay connected with free WiFi. Other standard amenities include a washing machine, a fireplace, and a coffee maker.

Similar properties

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

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 elevator
  • Stair-free path to entrance
  • Smoking not allowed

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 available

Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Contactless check-out available

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

  • This property doesn't allow pets (service animals welcome)

Children and extra beds

Children allowed: ages 0-17

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • 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, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Additional information about polices, regulations, and more:

  • There are no elevators.

Property is also known as

16263

Frequently asked questions

What's there to do within easy reach of this vacation home?

This vacation home is located in Annapolis, close to Navy-Marine Corps Memorial Stadium, Maryland State House, and Westfield Annapolis Mall. You'll also find Annapolis City Dock and Annapolis Mall Shopping Center within a short drive.

Is parking available on site at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?

No, there isn't parking available at the vacation home.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Is Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces a good place to stay for couples?

Couples staying at this vacation home will appreciate amenities like a fireplace and a kitchen as well as a firepit.

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

No, there isn't a spa tub at this vacation home.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home though service animals are welcome.

Does Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces have connecting rooms available?

No, this vacation home doesn't feature connecting guestrooms.

How far is the airport from this vacation home?

The closest major airport to this vacation home is Fort Meade, MD (FME-Tipton), which is 20.4 mi away (32 minutes by car). Another top airport is Baltimore Washington Intl. Airport (BWI), which is located 28.6 mi away (41-minute drive).

Are there rooms with balconies that I can book at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces?

Yes, every house at Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces comes with a patio.

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

Reviews

10

Exceptional

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

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Sherene L.

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
Verified

10/10 Excellent

Tyler S.

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