Entire home

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

Vacation home near U.S. Naval Academy in Annapolis

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A modern kitchen with a central island, stainless steel appliances, and wooden bar stools.
A spacious living room with a sofa set, a coffee table, and a TV.
A spacious living area with a blue sofa, two striped armchairs, a round coffee table, and a wooden cabinet.
A modern kitchen with a central island, bar stools, and a dining area with a long table and blue chairs.
A room with a wooden floor, a grey cabinet, and a painting above it.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms204 sq m

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 area

Annapolis

In Annapolis .Within 2 miles (3 km) of this Annapolis vacation home, you'll find U.S. Naval Academy and Navy-Marine Corps Memorial Stadium. Helen Avalynne Tawes Garden and Peters Cove are also within 2 miles (3 km).

What's nearby

  • 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
  • U.S. Naval Academy - 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
  • ‪RaR Brewing - Chessie's Wharf - ‬17 min walk
  • ‪Wawa - ‬4 min drive
  • ‪Graul's Market - ‬3 min drive
  • ‪Taco Bell - ‬6 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 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

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

  • Bicycle parking
  • Bicycle storage
  • Recycling
  • Some LED lighting used
  • 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

  • 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
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
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, 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.

Property is also known as

16263

Frequently asked questions

How close is Upscale Family Retreat Near Downtown Annapolis w Resort-Style Outdoor Spaces to the airport?

This vacation home is 20.4 mi (32-min drive) away from the Fort Meade, MD (FME-Tipton) airport, the closest popular airport to the property.

Does Upscale Family Retreat Near Downtown Annapolis w Resort-Style Outdoor Spaces have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Upscale Family Retreat Near Downtown Annapolis w Resort-Style Outdoor Spaces to the beach?

This vacation home is 5.9 mi (20-min drive) from Sparrows Beach and 5.9 mi (13-min drive) from Carrs Beach. Don't forget your sunscreen!

Does Upscale Family Retreat Near Downtown Annapolis w Resort-Style Outdoor Spaces offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Upscale Family Retreat Near Downtown Annapolis w Resort-Style Outdoor Spaces?

No, there is no casino at this vacation home.

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

Check-in begins at 4:00 PM.

Is there free parking at Upscale Family Retreat Near Downtown Annapolis w Resort-Style Outdoor Spaces?

Free parking is not available at this vacation home.

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

This vacation home does not have a pool.

Does Upscale Family Retreat Near Downtown Annapolis w Resort-Style Outdoor Spaces have a spa?

There are no spa services available at this vacation home.

How close is Upscale Family Retreat Near Downtown Annapolis w Resort-Style Outdoor Spaces to downtown Annapolis?

This vacation home is 1.7 mi away from Parole.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

Reviews

Verified review

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 review

10/10 Excellent

LouAnn & Andrew S.

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

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