Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways Reviews, Deals & Photos 2026

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

Yes, pets are allowed at this property.

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

On-site parking is available at the property.

Q: 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).

10/10 Excellent

MIKE H.

17 Oct 2023

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.

25 Jun 2024

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

Alden F.

3 Oct 2023

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

K H.

19 Jun 2024

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

Karen H.

20 Aug 2024

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

Megan G.

9 Aug 2023

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

Henry K.

4 Sept 2024

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.

22 Jul 2024

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

Evan C.

25 Jun 2025

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.

4 Jan 2022

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

George E., Washington, DC

26 Aug 2022

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

Dudley W., Annapolis, MD

12 Jul 2022

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.

8 Aug 2022

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

Gerry B.

1 Jun 2023

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.

17 Jul 2022

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.

24 Jun 2023

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.

24 Sept 2022

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.

29 Aug 2022

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.

22 Apr 2022

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.

17 May 2025

Liked: Check-in, communication, location

Disliked: Listing accuracy

Stayed 4 nights in Apr 2025

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

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