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Book Online or call HomeAway Booking Assistance 888-640-7927

Stunning Waterfront Estate on Chesapeake with Private Guesthouse at end of Pier

Bedrooms 4
Half Baths2
Property type estate
Minimum Stay 2 - 5 nights


About the property

Enjoy this spectacular one-of-a-kind property on the Chesapeake Bay. This secluded home offers the best of outdoor living as you experience large grassy yards, big trees, your own beach, outdoor hot tub, and stunning views. The home features a gourmet kitchen, stone fireplace, beautiful master suite, and an old fashioned covered porch. The property includes a one-of-a-kind guest house which sits at the end of one of the longest private piers on the Chesapeake Bay - fully equipped with kitchen, bathroom and living room with sleeping sofa. Bring your fishing gear or just a glass of wine-- views are magnificent! You can literally sleep on the bay with the wind and the water luring you to sleep. The waterfront estate property is situated amidst 85 acres of woods and horse farm, adjacent to a 245-acre park (Downs Park) with miles of paved bike paths and nature trails (we have for bikes to offer). We are located 25 minutes from Annapolis, Baltimore inner harbor and BWI airport - and just 45 minutes from Washington D.C.

FUN FACT: Historic records show that our property was owned in colonial times by Charles Carroll of Carrollton, who served as a delegate to the Continental Congress and was the longest-lived (and last surviving) signatory of the Declaration of Independence.

More Details

Elaine Little, owner
Member since: 2017
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great traveler experience.

Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
January 18, 2018


Pasadena Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
House Rules:
  • Check-in: 2:00 PM
  • /
  • Check-out: 12:00 PM
  • Max. occupancy: 14
  • Max. adults: 14
  • Min. age of primary renter: 25
  • Parties/events not allowed ...
  • Pets not allowed ...
  • Non smoking only
Location Type:
  • Beachfront
  • Water View
  • Waterfront
  • Adventure
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Fireplace
  • Fitness Room / Equipment ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Free Wifi
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 12 people
  • 3 Bathrooms
  • 2 Half Baths
  • Bathroom 2 - toilet , combination tub/shower
    Bathroom 3 - toilet , combination tub/shower , This bathroom is full of charm with original double sinks
    Bathroom 4 - toilet
    Bathroom 1 Master - toilet , tub , shower , Large custom bath with huge shower and two sinks
    Bathroom 5 - toilet , In the Guesthouse at end of pier
  • 4 Bedrooms, Sleeps 14
  • Bedroom 1- Master Suite - 1 king
    Bedroom 2 - 1 queen
    Bedroom 3 - 1 king , 1 double , 1 twin/ single
    Bedroom 4 - 1 queen
    Bedroom 6 - 1 sleep sofa /futon , Guesthouse at the end of the pier
    Bedroom 5 - 1 twin/ single
  • Books
  • DVD Player
  • Game Room ...
  • Games ...
  • Ping Pong Table
  • Satellite / Cable
  • Television ...
  • Video Games
  • Balcony ...
  • Bicycles
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill ...
  • 1 bicycles
  • Long-term Renters Welcome
  • wheelchair inaccessible
Pool / Spa:
  • Hot Tub ...
  • bay/sound
  • churches
  • cinemas
  • forests
  • library
  • marina
  • museums
  • playground
  • restaurants
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • gambling casinos
  • horseback riding
  • outlet shopping
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • hiking
  • mountain biking
  • pier fishing
  • roller blading
  • sailing
  • snorkeling
  • sound/bay fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing


Exceptional! 5/5 -
(14 traveler reviews)

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Stunning Waterfront Estate on Chesapeake with Private Guesthouse at end of Pier
average rating of 5.0 based on 14 reviews

A gorgeous, comfortable getaway on the Bay!

  • 5 of 5

From the moment we drove down the tree-lined roadway and got our first glimpse of this waterfront estate, it was clear we had made the perfect choice for our getaway. This stately home sits on a glorious piece of land with a large, lush, back lawn that spills right into the Chesapeake. We marveled at the view from the stone patio and immediately began planning which of the comfortable loungers we'd claim to watch the evening sunset.

The grounds were impressive, but then we entered the house. WOW! The main floor was large, open, and so inviting with a baby grand piano, large TV, AND furnishing that were the perfect balance of beautiful and comfortable. I especially loved the huge kitchen. The high-end appliances made cooking a treat, and the farm table made it easy for us to enjoy meals together in absolute comfort. We also enjoyed the attached screened porch on nights when we wanted to enjoy the Bay breeze while sitting around one of the picnic tables.

When it came to selecting bedrooms, there were no arguments or disappointed members of our party. While the first floor master bedroom is the superior room (it offers a full, en suite bath and unobstructed views of the bay through large, lovely windows) the other bedrooms were all generous in size and beautifully appointed, with easy access to full baths.

These accommodations would have been enough to satisfy even the pickiest vacationer -- but this home offered one more special surprise -- a private boat house! Situated at the end of a long, well-maintained peer, the charming boat house is like a private island. On one occasion we packed the essentials and enjoyed a meal there, then sat on the little back deck and watched the sun go down. The casual furniture inside invited you to flop and relax a while before heading back "home" to the main house.

It was tempting to never leave the sanctuary of the estate, but the weather was so nice, we took an easy walk to the nearby waterside park for some fresh air and exercise. And later, we made the short run into town for ice cream and stopped at the local grocery store for essentials.

What a wonderful experience! If you are looking for a beautiful and unique place to escape that offers privacy, peace and quiet, but is also close to "civilization", you can't go wrong with renting this gem! We give this property the highest ratings and will definitely be visiting again.

  • Submitted: Apr 12, 2017
  • Stayed: November 2016
  • Source: HomeAway
Owner's Response: Thank you so much! We are so delighted you enjoyed the property!!
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Networking Retreat

  • 5 of 5

We just returned from a networking retreat for clients and prospects that we held at this property. In the main house, the property was as described and there were lots of places for gathering, large and small spaces. The kitchen had everything we needed and the sleeping rooms were quiet and comfortable. This weekend is an annual event we host in advance of a larger national conference that moves to different cities. The next time this convention takes place in DC, we will rent this property again. We had 11 women total.

  • Submitted: Oct 16, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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Girls weekend away

  • 5 of 5

From the beginning planning stages with Elaine to when we departed this wonderful home it was all so seamless, and let me just say there were 9 woman (dear friends) staying for 4 days and 3 nights...what a house!! it was clean, it was gorgeous, it was had all the creature comforts of home and when 9 woman get together we like things just so---well there is nothing we would have changed from the towels to the bedding to the spices on hand, and all the wonderful cozy throw blankets---the kitchen was enormous we practically lived in the kitchen all of us cooking and laughing and eating, and then there was the magnificent view of the Chesapeake Bay from sunrise to moonrise it was spectacular, soothing, and relaxing. When we were not laughing or reading or playing games together we were napping out on the lawn listening to the water, or out at the one of a kind Boat house sitting on the back deck soaking up the sun and talking. My sister slept out there every night not because there was no room in the house but because it was so wonderful !! We saw a massive bald eagle scoop a fish out of the bay and fly directly in front of the house to the woods next door to eat his fish on a tree limb...we can't wait to come back. Thank you Elaine for sharing your amazing home and all the precious memories we made !!!

  • Submitted: Sep 12, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
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Awesome Surprise Crab Feast for Hubby's 50th Bday

  • 5 of 5

This was the perfect location to host a surprise crab feast and weekend getaway for my husband's 50th birthday. The house and grounds were perfect for the crab feast and we were able to accommodate all of our guests despite an uncooperative mother nature (it rained).

We rented paddleboards and enjoyed the water and the lawn was perfect for games.

The owners were very gracious. Definitely recommend this beautiful home.

  • Submitted: Aug 30, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
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Outstanding space, even better hosts

  • 5 of 5

Our organization needed a space for our annual faculty retreat. We had our pick of several dozen places that fit the requirements. We chose this property for its proximity, space layout, reasonable price point, and unique features like the pier and boathouse.

When I met Rick, I was overwhelmed by his friendliness and demeanor. Both he and Elaine are clearly people who understand what world-class hospitality looks and feels like. The process for both check in and check out was unobtrusive but thorough.

The space itself was perfect for our needs. Every member of the faculty was in a bed (no need for sofas or floor sleeping) and we used six distinct areas for breakout sessions and workshops. Truly, it was the most productive we've been in years, and a big part of that, was the space.

On a personal note, sitting on the deck at the end of the pier, on the bay side of the boathouse, I saw about half a dozen shooting stars in an hour. A great place to contemplate one's life's work.

We'll be back if they'll have us.

  • Submitted: Aug 29, 2017
  • Stayed: August 2017
  • Source: HomeAway
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Wonderful property!

  • 5 of 5

We had an amazing weekend. Check in and check out was easy and well organized. The property itself is hard to describe in a few words. It was stunning and comfortable. The property has so many areas to explore. We are already planning a return visit. Could not ask for more!

Thank you for sharing your home!

  • Submitted: Aug 22, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Nearest Airport
15 Miles
BWI Airport
Nearest Train
15 Miles
BWI Airport Amtrack Station
Nearest Motorway
13 Miles
Interstate 95
Car: necessary

Our property is located right on the Chesapeake Bay equal distance by water between Baltimore's beautiful inner harbor and the smaller quaint Annapolis harbor. Baltimore's many attractions include the National Aquarium, Maryland Science Center, Hard Rock Cafe, the Walters Art Museum, Port Discovery Children's Museum, the Baltimore Orioles and Ravens, and many excellent restaurants and events year round.

Annapolis also has many year-round fun activities ranging from the famous Blue Angels performances, the Naval Academy, antique shops, historic tours, jazz clubs, coffee shops and much more.

And it's about an hour's drive to Washington D.C. -- with so much to see and do -- from the Smithsonian on the National Mall to the National Zoo, and so much more.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $300
Damage Insurance $99

Owner's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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