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

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Fridge, microwave, dishwasher, coffee/tea maker - Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces (Annapolis)
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TV, fireplace - Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces (Annapolis)
TV, fireplace - Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces (Annapolis)
Interior - Upscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces (Annapolis)
Upscale Family Retreat Near Downtown Annapolis | 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

Entire home

4 bedrooms3 bathrooms204 sq m

Popular amenities

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

Add dates for prices

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

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • 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

Similar properties

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

Pets not allowed (service animals are welcome, and are exempt from fees)

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

We should mention

This property does not have any lifts

Property is also known as

16263

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

  • U.S. Naval Academy
    U.S. Naval Academy
    3 min drive - 2.8 km
  • Navy-Marine Corps Memorial Stadium
    17 min walk - 1.5 km
  • Helen Avalynne Tawes Garden
    17 min walk - 1.5 km
  • St. John's College
    3 min drive - 2.8 km
  • First Baptist Church
    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
  • Taco Bell
    6 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 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).

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

Cleanliness

10

Location

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
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