House in Maryland
10 guests · 5 bedrooms · 6 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
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.
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.
Amenities at Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
Non-smoking
Pets allowed
Family friendly
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Jun 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
10 / 10Outstanding·Sep 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!!
10 / 10Outstanding·Aug 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!
10 / 10Outstanding·Jul 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."
$$$$
Top rated by guests
10Outstanding
(21 Ratings)
"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"
Evan C.Don't miss out! Price and availability may change
