Entire home

Beach-Front Classic on the Chesapeake Bay

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1930s home, 2600 sq ft on 26000 sq ft property
7 adirondack chairs, umbrella, picnic table, firepit, 2 hammocks, round table
Ground floor, mother-in-law suite, private bathroom walk-in shower, kitchenette
marble vanity, walk-in shower, heated floors ensuite in mother-in-law apartment
ground floor, mother-in-law suite overlooks beach & bay, private full bathroom

Reviews

10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 6241.5 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Barbecue grill
  • Outdoor space
  • Parking available

Explore the area

Map
5516 Beach Dr, St Leonard, MD, 20685
  • Matoaka Beach
    ‪3 min walk‬
  • Jefferson Patterson Park and Museum
    ‪15 min drive‬
  • Calvert Cliffs State Park
    ‪16 min drive‬
  • Leonardtown, MD (LTW-St. Marys County)
    ‪28 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

2 bathrooms, 2 half bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Toilet

Bathroom 3

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Bathroom 4

Soap · Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Separate dining area
Garden
Dining area

About this property

Beach-Front Classic on the Chesapeake Bay

-- Skip lengthy travel and bridge traffic to the ocean. Avoid the crowds!
-- 3 bedrooms with king beds, up to 6 people. **Additional fee for more than 6 guests, $75/pp/nt if you bring air mattresses or Pack&Play (no couch sleeping)
-- Private, mile-long sandy beach (neighborhood-access only)
-- Rooftop patio, sunrise yoga
-- Fire pit, 2 hammocks, seating & tables on grassy, shady12 ft bluff overlooking the beach and bay
-- 2600 sq ft home on a 26,000 sq ft property overlooking the beach and bay
-- Private walk-out where we keep kayaks, rowboat, beach chairs, outdoor hot/cold shower
-- 1h10 m from DCA airport and Annapolis

--If you request a reservation, please let me know the relationship of the adults in your group (so that I may have an idea of the sleeping arrangements), and the ages of any children or infants in your group. Please let me know how you've chosen our area, and from where you come. I appreciate lots of communication so that we're both comfortable with the reservation. If you're unable to be forthcoming in your answers to my questions, I won't be comfortable with your reservation. Apologies in advance.

--3 bedrooms with king beds, sleeps 6 people. If you have more than 6 guests in your group, the fee is an additional $75/person/night for guests beyond 6. Children must be accompanied at all times by an adult inside and outside this home.

This 2,600 sq ft home sits on a 26,000 sq ft yard with a bluff just 12 feet above a mile-long stretch of beach on the Chesapeake Bay. The expansive bay view stretches about seven miles across to Taylors Island on the eastern shore of the Chesapeake Bay. The water remains shallow to 60 ft out with small waves - great for kids. We have spectacular sunrises. Enjoy rooftop yoga, fishing from the shore or jetty, beach fires, and a 5 minute beach walk to the Flag Harbor Yacht Haven -- a great place to explore. You'll see ships traveling between the Baltimore Harbor and the Atlantic Ocean, and you'll spot plenty of wildlife, including herons, eagles, hawks, and egrets. Bring along a kite for windy days!

Descend the steps from our front yard to a mile of sandy beach. On the backside of the property, you will find a private entrance to the beach where we keep the kayaks and rowboat. You'll also find an exterior closet with chairs, sand toys, personal flotation devices, and oars. You'll also find a large "Breezeway Bench" overlooking the ravine and stream where the water flows from the village down to the bay. Where the stream flows onto the beach is a fun spot for making sand castles. We love to lap swim when the conditions are right, so bring along your goggles!

Our ground floor mother-in-law suite with beach and bay views includes a king-size bed; private full bathroom with walk-in shower, heated floors and marble vanity; and kitchenette with sink, mini fridge, microwave and Keurig The ground floor of the main house features a half bathroom; the sun room with mini refrigerator, and French doors to access the yard overlooking the bay; living room with two granite desks that overlook the bay flanking a non-working fireplace, 55" smart (Roku device) with surround sound; the well-stocked kitchen with drip coffee maker, microwave, toaster oven, plenty of spices and utensils; and dining room.

Upstairs, we have two large bedrooms (both with king-size beds) and a shared full bathroom. Both upstairs bedrooms have their own sinks, and the north-facing bedroom also has its own commode (a half bath). Both bedrooms have access to the rooftop patio. Bring along yoga mats for your sunrise practice!

Our main kitchen is fully equipped for preparing meals. We have a gas grill and a double crab cooker in front of our detached garage. You can buy locally-caught crabs from 'Chesapeake's Bounty' farmer's market in our village where they also sell fresh, local produce and other seasonal fish. Have a crab feast on our picnic table overlooking the bay! Enjoy the fire-pit and two hammocks on the bluff, which overlooks the bay.

Our beach is private with neighborhood access only. No lifeguards are on duty. Neighbors may access the beach via the stairs at the distant side of our parking circle. You have a private entrance to the beach on the backside of the house where you'll find the kayaks, rowboat and an outdoor closet holding 6 chairs, life jackets, oars, and plenty of sand toys.

Our rooftop patio is accessible from both bedrooms on the first upper level and overlooks the beach and Bay.

Please, no access to the attic, and to the basement unless you need to turn off the water main in an emergency, or access the circuit breaker.

No unauthorized guests are allowed due to liability concerns. Any guests beyond the number listed on your itinerary will be charged a penalty of $100 per person per night. We reserve the right to terminate your stay without a refund if you exceed your reservation's number of declared guests.

Guests agree to adhere to the rental agreement and general Liability Waiver* provided, below. Please review the rental agreement and liability waiver and send along a note of approval for both in the messaging platform. If there's any reason you can't approve our rules and liability waiver, you will have 48 hours from the time of booking to cancel your reservation penalty-free.

**Liability Waiver: You understand that swimming and the use of kayaks, rowboat are at your own risk. You agree to wear personal flotation devices while using the watercraft to follow US Coast Guard and Maryland law. You accept full responsibility for any bodily injury arising from swimming and use of the watercraft and hold the owner harmless. You understand there are potential dangers that swimming and the use of watercraft may present to children who are not carefully supervised, as well as the danger to any person swimming or using the watercraft if a person has health risks, or if a person swims or uses the watercraft while intoxicated or using any kind of drugs or medication, or while pregnant. You agree to be fully and solely responsible for any accidents you may incur. You understand the risks discussed above and agree that you will assume all responsibility for yourself and for the consequences of those in your party. You agree to waive any claim whatsoever against the owner for accidents or claims arising from swimming or using the attic or watercraft. All guests in my party acknowledge and agree that they have read and understand this waiver and they acknowledge that your confirmation and approval of this liability waiver for water craft use and swimming constitutes a binding and enforceable contract between Vrbo Guests and the Vrbo Host.

Property manager

Jean

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Kids must be accompanied at all times
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
For more than 6 guests in your group, add'l $75/person/night. You must bring your own air mattresses. Children must be accompanied at all times.
No access to the basement unless you need to turn off the water main in an emergency (see orange sign), or access circuit breaker at bottom of steps
Guests agree to Liability Waiver found in rental agreement, and will send approval through the VRBO messaging platform.

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
Cashless transactions are available
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
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

St. Leonard

Located in St. Leonard, this holiday home is on the beach. Cove Point Lighthouse and Drum Point Lighthouse are local landmarks, and the area's natural beauty can be seen at Battle Creek Cypress Swamp Sanctuary and Calvert Cliffs State Park. R&J's PlayPark and Annmarie Sculpture Garden and Arts Center are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
St Leonard, MD

What's nearby

  • Matoaka Beach - 3 min walk - 0.3 km
  • Jefferson Patterson Park and Museum - 15 min drive - 13.7 km
  • Calvert Cliffs State Park - 16 min drive - 15.9 km
  • Breezy Point Beach - 29 min drive - 31.0 km
  • Patuxent River Naval Air Station - 32 min drive - 36.6 km

Getting around

  • Ronald Reagan National Airport (DCA) - 72 min drive

Restaurants

  • ‪Adams Taphouse and Grille - ‬10 min drive
  • ‪Vera's White Sands Beach Club - ‬16 min drive
  • ‪Gateway Restaurant & Lounge - ‬11 min drive
  • ‪The Tavern - ‬4 min drive
  • ‪Frying Pan - ‬13 min drive

Frequently asked questions

Is Beach-Front Classic on the Chesapeake Bay pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Beach-Front Classic on the Chesapeake Bay?

Check-in begins at 3:00 PM.

What time is check-out at Beach-Front Classic on the Chesapeake Bay?

Checkout is at 11:00 AM.

Where is Beach-Front Classic on the Chesapeake Bay located?

Nestled on the beach, this St. Leonard holiday home is within a 15-minute walk of Matoaka Beach and Long Beach. Flag Harbor Marina and Flag Ponds Nature Park are also within 1 mile (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 5 out of 5 reviews
Rating 8 - Good. 0 out of 5 reviews
Rating 6 - Okay. 0 out of 5 reviews
Rating 4 - Poor. 0 out of 5 reviews
Rating 2 - Terrible. 0 out of 5 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Lee Ann S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home on the beach

Absolutely beautiful home and so very clean! We were in town for our daughter’s wedding (6 adults) and the house was perfect for us. It’s has everything you could want/need. Although the weather was not good so we didn’t get to enjoy the beach, the view was beautiful. The home has lots of space to span out and each of us had our own space. It is furnished with the most comfortable big lazy chairs and couches. We rent VBRO always when we travel and this is one of the very BEST we’ve stayed in!!! The host is so easy to teach and the home is STUNNING we will be back!!!
Stayed 5 nights in Apr 2025

10/10 Excellent

Cheryl B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday Beach Trip

The view from the house is beautiful, and the house is very comfortable and clean! Hosts are very friendly and they make sure your stay is going well. Location is unbeatable. Everything you need is here, including beach chairs. The beach was not busy while we were there, and great to walk on. We hope to be back.
Stayed 5 nights in Sep 2024

10/10 Excellent

Amie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful location, well-stocked and spacious home, sandy beachfront on the west-side of the Bay

Jean and Tom did an impressive renovation of this home, and have gone the extra mile in furnishing it and providing all the amenities one needs to relax and enjoy time on a sandy beach on the west-side of the Bay. Well-stocked kitchen, comfortable and spacious bedrooms, lots of seating inside and out including comfortable hammocks overlooking the Bay. Our multigenerational family also made use of the attic - gave us the flexibility when 2 additional family members were able to join us for the weekend. Beautiful sunrise paddles on the placid bay - 80+ year old grandmother has now found her new hobby in kayaking! And kids had endless fun frolicking in the shallow water and playing in the sand. Thank you, Jean & Tom!
Stayed 3 nights in May 2024

10/10 Excellent

Richard U.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beachfront Chesapeake Homr

We loved staying at this beautiful home. It is equipped with everything you need to have a great stay. We had a fire in the fire pit, napped in the hammocks, kayaked, fished, and found a few sharks teeth. Highly recommend!
Stayed 3 nights in Aug 2023

10/10 Excellent

colleen a.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!

Best VRBO experience that we have yet to have. Jean is so nice and accommodating. Beautiful home. Ideal location. The beach and Bay are the backyard. Peaceful and quiet. Perfect respite from the city. Couldn't have been better.
Stayed 4 nights in Jun 2023

About the host

Hosted by Jean

Host profile image
We have spent 20 years overseas -- in the Pacific, Europe and the middle East -- and we thoroughly enjoy meeting new people and hearing their stories. Please know, though, that we will absolutely respect your privacy, quiet and space during your stay if that's your preference!

This 1930s charmer, originally built by the 'League for the Larger Life', was a commune of sorts with nude sunbathing back in the day. The commune included a shuffleboard, outside shower rooms, a boardwalk from the back yard to the beach, a breezeway sitting area, and a rooftop patio overlooking the bay.

Why they chose this property

--As always, children must be accompanied at all times, including in the attic if you have reserved that space. Please use the attic safety gate provided for the stairs. You agree to use the attic space at your own risk.

--Please send a note in the messaging platform that says you have read and approve of our requests in our listing details and the liability waiver for swimming, and kayak and attic safety.**

-- In the yard, we have a double kayak, 3 single kayaks, and a rowboat. Please read and approve the following liability waiver for watercraft use and swimming:

**Liability Waiver: You understand that swimming and the use of watercraft, and attic are at your own risk. You agree to wear personal flotation devices while using the watercraft to follow US Coast Guard and Maryland law. You accept full responsibility for any bodily injury arising from swimming and use of the watercraft and hold owner harmless. You understand there are potential dangers that swimming and the use of watercraft may present to children who are not carefully supervised, as well as the danger to any person swimming or using the watercraft if a person has health risks, or if a person swims or uses the watercraft while intoxicated or using any kind of drugs or medication, or while pregnant. You agree to be fully and solely responsible for any accidents you may incur. You understand the risks discussed above and agree that you will assume all responsibility for yourself and for the consequences of those in your party. You agree to waive any claim whatsoever against owner for accidents or claims arising from swimming or using the attic or watercraft. All guests in my party acknowledge and agree that they have read and understand this waiver and they acknowledge that your confirmation and approval of this liability waiver for attic and water craft use, and swimming constitutes a binding and enforceable contract between Vrbo Guests and the Vrbo Host.

What makes this property unique

--If you request a reservation, please let me know the specific relationship of each of the adults in your group (siblings, parents, in-laws, cousins, friends, neighbors, etc.) so that I may have an idea of the sleeping arrangements. Secondly, let me know the ages of any children or infants in your group. I appreciate lots of communication so that we're both comfortable with the reservation. If you are not forthcoming with answers to my questions, I will not be comfortable with your making a reservation. My apologies in advance.
--We have a strict 'No Sleeping on the Couches' policy. If your group includes more than 6 people you may bring air mattress/pack n play for an additional $75/person/night for more than 6 guests, or you may reserve the attic space for $75/person/night for more than 6 guests.
--No undeclared guests both inside and outside the property without host approval.
--It is your responsibility to child-proof the interior of the house to keep your kiddos safe and also to protect screens, furniture, fabric and mattresses from accidents. Please pay special attention so children don't poke their fingers through the screens in sunroom. Additional repair fees will apply.
--Please communicate any breakage or damages prior to your reservation departure so it can be rectified before the next guests arrive.
--Please be prepared to show me a picture ID to verify your identity.
--3 car maximum in our driveway.
--Our base price includes 3 bedrooms with king beds, sleeps 6 people. If you have more than 6 guests in your group or you need to add our attic space (the 4th bedroom), the fee is an additional $75/person/night for guests beyond 6. If you have 6 or fewer guests in your group and need the attic, there will be an additional $75 cleaning fee. All children under 10 must be accompanied at all times by an adult in attic space.


Languages:

English