Entire home

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

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

Welcome to the Fitzgerald Retreat - a resort-like family experience in Annapolis.
The home has many gathering spaces inside and out, like this Den located off the kitchen and dining rooms.
Head outside to the multi-space patio with a cozy lounging space, dining table and two fire pits.
Multiple dining spaces make the home ideal for getting the whole extended family together or a special holiday.
The King Suite on the Main Level is one of 4 bedrooms in the home.

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 102200 sq ft

Popular amenities

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

Rooms & beds

4 bedrooms (sleeps 10)

Lower Level Queen

1 Queen Bed

Lower Level Twins

2 Single Beds

Main Floor Den

1 Double Sofa Bed

Main Floor Queen

1 Queen Bed

Main Floor Suite

1 King Bed

3 bathrooms

Lower Level

Toilet · Shower only

Main Floor EnSuite

Toilet · Shower only

Main Floor Hall Bath

Toilet · Shower only

Spaces

Deck or patio
Kitchen

About this property

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

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed, service animals permitted
default

Smoking

Smoking is not permitted

Important information

You need to know

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.
Map
Annapolis, MD

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

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.
Learn moreOpens in a new window
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

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback