Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Oxford, Maryland
$1005 avg/night
Minimum Stay 3 Nights
Bed 5

Bed

Bath 4

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 3 nights

Min Stay

Summary:

Step into history without sacrificing modern comforts. Combsberry is a 1730 waterfront estate nestled on 30 private acres at the northern headwaters of Island Creek. Featuring five beautifully appointed bedrooms, a gourmet kitchen, a heated pool, and serene walking grounds, it’s the ultimate retreat for family gatherings, romantic escapes, or peaceful solo getaways—especially during Maryland’s spectacular fall season.



Talbot County Licensure: STRN-25-43



The Space:

Discover Combsberry, a historic Maryland waterfront estate perfect for your fall getaway. Nestled on 30 acres along Island Creek near St. Michaels, this 1730 property offers five bedrooms, a heated pool, a gourmet kitchen, and stunning autumn foliage. Ideal for family vacations, couples’ retreats, or pet-friendly escapes, Combsberry blends timeless elegance with modern comfort.



What you'll love:

- Unmatched Privacy: 30 acres of tranquil waterfront with no neighbors in sight.

- Historic Beauty: Original architectural details paired with high-end updates.

- Luxury Amenities:waterfront pool, coffee bar, and gourmet kitchen.

- Pet-Friendly: Bring your furry friend along ($200 pet fee).

- Fall Magic: Crisp air, colorful foliage, and cozy evenings by the fireplace.



Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.



Guest Access:

This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.



The Neighborhood:

Private, serene waterfront location — yet close to St. Michaels, Easton and Oxford and seasonal events.



Other Things to Note:

Professional caretakers maintain the estate year-round, ensuring your stay is private, seamless, and unforgettable. Pets welcome with a $200 non-refundable fee. Starter paper goods provided; please bring any additional supplies you may need.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly Service Animals Exempt From Fees
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • KITCHEN

    Blender Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Dock Garden
  • POOL/SPA

    Private Pool Shared/communal Pool
  • BATHROOMS

    4 Bathrooms Hair Dryer Shower Towels Provided
  • WORKSPACES

    Office
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Cycling Nearby Fishing Nearby Golf Privileges Kayak On Site
  • ENTERTAINMENT

    Games TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Rural Location On The River On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Alexandra W.

    Submitted Jun 15, 2026

    Stayed Jun 12, 2026

    We had an excellent experience with this property and will definitely be looking to come back!

  • Evan C.

    Submitted Jun 25, 2025

    Stayed Jun 18, 2025

    Wonderful location for a family reunion. Very close to Oxford but felt nicely secluded. House itself was beautiful and charming, and pool was amazing in this hot weather. Would highly recommend

  • Henry K.

    Submitted Sep 4, 2024

    Stayed Aug 29, 2024

    What a dreamy place to enjoy a long holiday weekend with children and young grandchild! Old colonial house with modern wings accommodated three couples and a toddler effortlessly, and could easily have held more. The location is not to be believed, big lawn with a lovely pool looking out over Island Creek (which flows into the Choptank). Extremely quiet and private. Huge, well apppointed kitchen with a table that sat 10 was our main indoor congregating area. There was also a lot of privacy as the three main sleeping areas were quite far apart, on either end of the more modern wings and on the third floor. We couldn't believe what a great venue this was!!

  • Karen H.

    Submitted Aug 20, 2024

    Stayed Aug 4, 2024

    We absolutely loved our stay at Combsberry! It was the perfect mix of classic comfort and fulfilling adventure. We enjoyed the living areas which brought three generations together every morning and evening, relaxed by the pool and walked the grounds, and explored the beautiful bay. The property is beautiful and welcoming, and the host was very helpful and responsive. Unique find for creating special memories!

  • JP L.

    Submitted Jul 22, 2024

    Stayed Jun 30, 2024

    My wife and I, our two sons, and our grandchildren loved every moment of our week at Combsberry. The downstairs rooms were great. The kitchen was spacious, practical and it had just about everything that anyone would ever need. The dining room, the sitting room, and the library were all very comfy and spacious plus they all had great views of the dock and the water. Upstairs the bedrooms and bathrooms were all different but each was practical and comfortable. The grounds are beautiful and accented with majestic black walnut and magnolia trees, and the lawn was beautifully maintained. We kept the swimming pool in constant use, loving every minute. The house has every convenience, lots of room, great comfort and style. The grounds were sublime. As we were leaving every one of us announced, Let's come back here again.

  • Mark & Kristi S.

    Submitted Jun 25, 2024

    Stayed Jun 20, 2024

    It was beautiful!

  • K H.

    Submitted Jun 19, 2024

    Stayed Jun 6, 2024

    Very nice property. Our host Jennifer responded promptly to any concerns. Great out door space for children …pool, kayaks, plenty of lawn area…. Very quiet and peaceful. Enjoyed our stay.

  • MIKE H.

    Submitted Oct 17, 2023

    Stayed Oct 12, 2023

    Ideal location for enjoying the Eastern Shore. With 3 homes on the property, the Combsberry accommodated all our family.

  • Alden F.

    Submitted Oct 3, 2023

    Stayed Sep 28, 2023

    Wonderful house, super location. Great for large family get-togethers. Highly recommend.

  • Megan G.

    Submitted Aug 9, 2023

    Stayed Jul 22, 2023

    We had a wonderful time in this beautiful home located in a picturesque setting. Every question we had was promptly addressed by Jennifer. It was a care free stay and we would definitely return!

Your dates are Available!

Total

Includes taxes and fees
$977+
View details