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Entire home

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

Waterfront holiday home with private pool and kitchen

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

Pool
Exterior
TV, fireplace, offices
Fridge, microwave, oven, stovetop
Dining
Located in Talbot County, Combsberry is a historic estate that seamlessly blends classic architecture with modern luxury. Soak up the ambiance of soaring ceilings and ornate moldings in the living spaces or unwind by the waterfront pool just minutes from renowned dining experiences.

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms6 bathroomsSleeps 10

Popular amenities

  • Washer
  • Dryer
  • Fireplace
  • Kitchen
  • Barbecue grill
  • Pool

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.

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

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: Heated 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.

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 6 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Toilet paper
  • Towels provided

Living spaces

  • Fireplace

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Dock
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Service animals only (pets not allowed)

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location
  • On the waterfront

Things to do

  • Bicycles
  • Optional golf privileges
  • Cycling nearby

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)
  • Fire extinguisher

General

  • Bicycles
  • Garden

Similar properties

Property grounds

Stunning Chesapeake Waterfront Home

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
10.0 out of 10, Exceptional, 1 review
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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Rules

Guests are required to sign both a lease and a safety addendum. this will be forwarded to guests once payment is made.

Pets

Pets not allowed (service animals are welcome, and are exempt from fees)
Note from host: Free

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property accepts cash
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
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

6202a4c3326dbc003154aca4

About the area

Located in Oxford, this holiday home is in a rural area and on the waterfront. The area's natural beauty can be seen at Bill Burton Fishing Pier State Park and Long Wharf Park, while Oxford Museum and Academy Art Museum are cultural highlights. Easton Cycle and Sport and Ruark Boatworks are also worth visiting. Take the opportunity to explore the area for outdoor excitement like cycling.
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Map
Oxford, MD

What's nearby

  • Oxford Museum - 7 min drive - 5.3 km
  • Choptank River Lighthouse - 29 min drive - 29.9 km
  • Long Wharf Park - 30 min drive - 30.2 km
  • Gerry Boyle Park at Great Marsh - 32 min drive - 31.2 km
  • St. Michaels Winery - 35 min drive - 36.4 km

Getting around

  • Cambridge Station - 28 min drive
  • Easton, MD (ESN-Easton - Newnam) - 20 min drive

Restaurants

  • ‪Doc's Sunset Grille - ‬7 min drive
  • ‪The Coffee Trappe - ‬13 min drive
  • ‪t at The General Store - ‬27 min drive
  • ‪Capsize - ‬7 min drive
  • ‪Momma Maria's - ‬14 min drive

Frequently asked questions

Does Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways have a pool?

Yes, this property has a pool.

Is Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways pet-friendly?

No, only service animals are welcome at the property.

What time is check-in at Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways?

Check-in begins at 4:00 PM.

What time is check-out at Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways?

Checkout is at 10:00 AM.

Where is Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways located?

Situated on the waterfront, this holiday home is within 9 miles (15 km) of Play Ball Dog Park, Oxford Museum and The Third Haven Friends Meeting House. Academy Art Museum and UM Shore Medical Center at Easton are also within 9 miles (15 km).

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