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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
Dining
TV, fireplace, offices
Exterior
Fridge, microwave, oven, stovetop
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

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  • Kitchen
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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
Information provided by the property may be translated using automated translation tools

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

Map
Oxford, MD

What's nearby

  • Play Ball Dog Park - 6 min drive - 4.6 km
  • Oxford Museum - 6 min drive - 5.3 km
  • The Third Haven Friends Meeting House - 14 min drive - 16.4 km
  • UM Shore Medical Center at Easton - 15 min drive - 17.1 km
  • Avalon Theatre - 15 min drive - 18.5 km

Getting around

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

Restaurants

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

How much is parking at Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways?

On-site parking is available 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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Reviews

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

9.8

Exceptional

9.8

Cleanliness

10

Location
Rating 10 - Excellent. 19 out of 20 reviews
Rating 8 - Good. 0 out of 20 reviews
Rating 6 - Okay. 1 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

Reviews

10/10 Excellent

Evan C.

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

Lovely stay

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
Stayed 4 nights in Jun 2025

10/10 Excellent

Sarah H.

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

Great visit!

The house was beautiful, the setting is lovely and Jennifer, the manager of the property, was incredibly responsive. We had a terrific stay.
Stayed 3 nights in Dec 2021

10/10 Excellent

MIKE H.

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

Beautiful home with amazing property

Ideal location for enjoying the Eastern Shore. With 3 homes on the property, the Combsberry accommodated all our family.
Stayed 4 nights in Oct 2023

10/10 Excellent

Mark & Kristi S.

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

10 year anniversary of girls trip

It was beautiful!
Stayed 4 nights in Jun 2024

10/10 Excellent

K H.

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

Peaceful Retreat

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.
Stayed 3 nights in Jun 2024

10/10 Excellent

Alden F.

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

Fabulous

Wonderful house, super location. Great for large family get-togethers. Highly recommend.
Stayed 4 nights in Sep 2023

10/10 Excellent

Karen H.

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

Ideal retreat!

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!
Stayed 10 nights in Aug 2024

10/10 Excellent

George E., Washington, DC

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

Combsberry

Combsberry is a beautiful property with great amenities. The property manager and caretaker were a pleasure to deal with. I wholeheartedly recommend a visit.
Stayed 4 nights in Aug 2022

10/10 Excellent

Megan G.

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

Oxford, MD

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!
Stayed 14 nights in Jul 2023

10/10 Excellent

Dudley W., Annapolis, MD

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

Great retreat

Our extended family stayed for a long weekend to celebrate our retirement and birthdays. We used the pool, set up games in the large back yard, shared meals in the kitchen overlooking the water, and retired to the library for drinks in the evening. It was a nice getaway, but close to Oxford and St. Michaels. The host, Jennifer, was responsive and helpful.
Stayed 3 nights in Jul 2022

10/10 Excellent

Sherry B.

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

perfect getaway for our group of 9

The house was very spacious, the multiple communal rooms gave us great space for different activities each day. The kitchen is incredibly spacious and you never felt like you were crowding others. The formal dining room was perfect for our private chef dinner. The pool was wonderful and the grounds are immaculate. Jennifer was great at pre and during stay communication. This home is an absolute gem.
Stayed 4 nights in Aug 2022

10/10 Excellent

Henry K.

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

The Old Combsberry Inn was a great find

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!!
Stayed 5 nights in Aug 2024

10/10 Excellent

JP L.

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

80

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."
Stayed 7 nights in Jun 2024

10/10 Excellent

Gerry B.

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

Memorable Memorial Weekend

The Inn is located on a tributary to the Chesapeake, offering tranquil and picturesque views that allow you to disconnect from the hustle and bustle of everyday life. The kitchen had ample space for our family to engage in communal food preparation that also featured a comfortable dining area. One evening we spent enjoying steamed crabs at the outdoor picnic table. A favorite activity was exploring the waterways on the tandem kayak. Kayaking permitted a nice tour of the magnificent houses all along the coast. We ventured into Oxford a couple of times, including having an excellent dining experience at Doc's Sunset Grille in Oxford. The food was delicious, and the ambiance was welcoming and true to the restaurant’s name. We also indulged our sweet tooth at the Scottish Highland Creamery - their ice cream was rich and flavorful, a treat we highly recommend. Shoppers in our group enjoyed exploring the Treasure Chest. The golfers in our group were impressed by River Marsh, which was just a short distance away in Cambridge, MD. The course was beautiful and well-kept, making for a wonderful afternoon of play. Throughout our stay, we appreciated the attentiveness and quick response from Jennifer, who was always ready to assist with any inquiries we had. Our stay at the Combsberry Inn was relaxing and thoroughly enjoyable. We wholeheartedly recommend it to anyone seeking a peaceful getaway filled with beautiful landscapes and comfortable lodging.
Stayed 4 nights in May 2023

10/10 Excellent

Liesel E.

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

Beautiful, historic home on the water

We (myself, husband, our 16-year-old son, our brother and sister-in-law and their 3 and 6-year-old sons, and my husband's parents) stayed in July. Gorgeous, large home with big kitchen, two kayaks (we rented two more from Dockside Boat Rentals in Oxford, who delivered them), and lovely pool. Air conditioning worked great - even on the third floor. 7 minutes from town. Kitchen well-equipped. Plenty of lawn for the kids to run around. We enjoyed fishing on the dock. We would absolutely stay here again. Did I mention that this place is gorgeous??? A couple nit-picks: the grill really should be replaced and located somewhere in the shade. Clear instructions for the pool cover would be a huge plus for both peace of mind with small children and for keeping the heat in at night. Also, the alarm went off unexpectedly and we had no idea how to turn it off. It eventually did so on its own. Stairs to the upper floors may be an issue with older people who struggle with mobility, but it wasn't a problem for us. We really loved Combsberry; it is beautifully furnished and decorated to reflect its history, as it was built in 1730. Very peaceful location, perfect for exploring on kayaks. Jennifer was quick to respond with any questions. Great week and a lovely family vacation!
Stayed 5 nights in Jul 2022

10/10 Excellent

Gail S.

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

Spacious and Private

Writing this review is conflicting because I want to keep this place a secret. Our family of 9 adults enjoyed our stay Immensely! This historic home did not disappoint. The lovely tree-lined drive to the home was reminiscent of southern/plantation-like charm. The large common areas and private bed/baths gave everyone ample space to congregate and peaceful rest when so desired. The house was very clean and well stocked with toilet paper. Other basics included paper towels, dish detergent, trash bags and kitchen seasonings. The beds were comfortable and linens were hotel quality. Modern kitchen amenities made cooking easy, and the large kitchen allowed for multiple chefs. The coffee nook was a treat with options for K cups and fresh brew with filters provided. The pool was refreshing and there was plenty of patio furniture for the group. The river was peaceful for kayaking and fishing . We so enjoyed wildlife like herron, deer (including the young ones prancing around), fox, and the oriole birds who fed off the vine outside the kitchen. The magnolia trees were spectacular! There was plenty of shade and sun. We got crabs from Gay’s and were thankful for the mallets in the kitchen. We ate at Doc’s Sunset Grill. Food was fresh and good. Highly recommend the crab and avocado gazpacho. We played pickle-ball every day at Causeway park a few miles toward town (six portable nets on the courts along with several tennis nets.) We will return! Thank you, Jennifer!
Stayed 4 nights in Jun 2023

10/10 Excellent

Brittany P.

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

Beautiful Old Home

Place was great! Stayed with our whole family and in-laws. Had a beautiful weekend. The place was clean and the caretakers were friendly and helpful.
Stayed 3 nights in Sep 2022

10/10 Excellent

Ann C.

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

A Combsberry Idyll

Combsberry provides a wonderful, romantic trip back to another time. The 300-year-old manor house is grand - elegant but comfortable - with modern conveniences that make it easy to straddle both eras. The property, with its spectacular water view, could not be more beautiful. Our family loved hunting for crabs off the dock, swimming in the pool, kayaking, reading in the library, and gathering around the huge kitchen table at mealtimes. And Jennifer, the property manager is a true gem, responding to our questions almost as soon as we asked them. (I never met anyone who answers texts so quickly.) Combsberry was a lovely experience for all of us.
Stayed 14 nights in Aug 2022

10/10 Excellent

judith l.

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

Classic Country Beauty with Water Views

Beautiful older home with lovely property and water views. Plenty of bedrooms and bathrooms for all, and we especially liked the cozy den and fireplace. Cooking in the oversized kitchen was fun because of the view and close to outdoor grill. A wonderful weekend in the country but less than 10 minutes to all the restaurants in Oxford. The best of both worlds!! Property Manager extremely responsive and helpful.
Stayed 5 nights in Apr 2022

6/10 Okay

Courtland S.

Liked: Check-in, communication, location
Disliked: Listing accuracy
Stayed 4 nights in Apr 2025