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Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

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Property grounds - Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. (Galena)
Fridge, microwave, oven, stovetop - Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. (Galena)
Interior - Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. (Galena)
Property grounds - Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. (Galena)
Fridge, microwave, oven, stovetop - Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. (Galena)
River views and nature surround you in this charming waterfront home. Completely restored from its original 1830 build, enjoy the perfect blend of old-world charm and modern comforts. Take a dip in the creek side, or simply sit back on the screened-in porch with family over lunch or morning coffee.

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms2 bathroomsSleeps 12

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

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About this property

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

  • This home was originally built in 1830 and has been completely restored lovingly by its owners, and sits upon an overlook of the river. You'll feel like you've stepped back in time but still get to enjoy all of the modern conveniences. Nature is all around you in this waterfront home. Birdwatchers especially love watching the Eagles, Osprey, ducks and other waterfowl. We see deer frolicking on the embankments and the sunsets are spectacular!

    The property includes the use of an additional efficiency unit above the garage. (We lovingly call it "Fonzies Apartment" if you grew up in the era of "Happy Days." The kids love it, and adults do too. It's cozy and comfortable and a nice space to get away from the main the house. The property can sleep up to 12 guests overnight. The property includes a screened-in porch facing the waterfront view, a fire pit, kayaks and paddleboards, and fishing from the dock. (Bring your own poles and bait.) You can explore the shoreline or take a nap in the window seat overlooking the water. Some folks even enjoy a swim on the creek side of the house. Our guests tell us that the screened-in porch is their favorite part of their stay. It's serene. Morning coffees, and family time together over lunch or dinner and just sitting there together talking are really special.
    Secluded and out-of-the-way, yet 15 minutes from major shopping. There are multiple nearby marinas and great restaurants like Deep Blue at the Kitty Knight House and The Granary, both are just a 2 minute drive. A mile away, the friendly folks at Twinney's serve up home style favorites. For night life and other fun, go to Chesapeake City (We like The Chesapeake Inn, Schaefers Canal House and Prime.) You can also head to Chestertown for another vibe and great options. Annapolis is only an hour away if you are feeling adventurous! If you like to get your steps in, a walk up the drive to the main road is relaxing. Within 5 minutes, you'll find great produce, baked goods and everything you need at Cross Street Market, there is also a convenience store with liquor, packaged goods and sandwiches. In Middletown, you'll find everything you need including Dutch Country Farmers Market open Thursdays, Fridays and Saturdays. We offer a wide selection of board games for the homebodies who want to bond around the table with some competitive fun and family memories!

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location
  • Near the bay
  • Near the marina
  • On a river
  • On the waterfront

Things to do

  • Kayak
  • Winery tours 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
  • Deadbolt lock

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Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM
Contactless check-out

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

Waterfront and dock areas are "use at your own risk". You must wear life jackets when using the SUPs or kayaks. Guest watercraft are not permitted.
Please close all doors/windows when running the A/C, or the heat.
No parking on the grass at any time.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

Events allowed: family gatherings and birthday parties
Small family gatherings are fine.

Smoking

Smoking is not permitted

Important information

You need to know

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
Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 18
Note from host: Small family gatherings are fine.
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 and a deadlock
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

Frequently asked questions

Is Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. pet-friendly?

No, pets are not allowed at this property.

How much is parking at Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.?

On-site parking is available at the property.

What time is check-in at Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.?

Check-in begins at 3:00 PM.

What time is check-out at Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.?

Checkout is at 11:00 AM.

Where is Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. located?

Situated on the waterfront, this holiday home is within 1 mile (2 km) of Toal Park, Sassafras Harbor Marina and Granary Marina. Duffy Creek Marina and Skipjack Cove Yachting Resort are also within 2 miles (3 km).

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Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 24 out of 25 reviews
Rating 8 - Good. 0 out of 25 reviews
Rating 6 - Okay. 0 out of 25 reviews
Rating 4 - Poor. 1 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

10

Cleanliness

9.8

Location

Reviews

Verified

10/10 Excellent

Julie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is lovely and the host was very responsive when we had to contact them about a plumbing issue in the above garage unit. The amenities were great with linens and towels that went beyond our needs. It was great not to have to worry about packing those items along with paper goods and some toiletries. The kitchen was well stocked with ample items for our large group. The only suggestion we have for the hosts is maybe a bit more instruction on how to use the remotes to get to menu to log into our own streaming services.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Pat K.

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

Peaceful scenic getaway

Perfect setting for our family get together. Plenty of space and beautifully decorated. Spent most of our time on the screened in porch.Beautiful sunset in the evening and lovely view of the river.Several family members used the kayaks and enjoyed the experience.Host was very helpful and went all out to make sure we had everything we needed.
Stayed 4 nights in May 2025
Verified

10/10 Excellent

Lisa M.

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

Family Vacation

The home was perfect for our family of 10. We spent most of our time on the beautiful screened in porch overlooking the river. The location was within a 5 min drive to all our favorite restaurants. The owners are very accommodating and quick to answer any questions.
Stayed 5 nights in Aug 2024
Verified

10/10 Excellent

maggi W.

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

Lovely retreat on the river

My family had a relaxing, fun weekend at the house. My 20-something children all loved the window seat where they curled up and read. We enjoyed time on the river with the kayaks and paddleboards. The beds were comfy, kitchen well stocked and overall the house is cozy. It was the perfect get-away for our family!
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Jennifer W.

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

Relaxing Retreat!

Highly recommend this rental! We were very impressed by this beautiful home and would love to stay here again. It surpassed our expectations. The screened in porch was our most used space. The view was breathtaking and so peaceful. Beware there is a very steep drop from the back lawn down to the water. (Our party was adults only, but I definitely wouldn’t feel comfortable letting young children play back there). The homeowners were very kind & responsive. Highly recommend this rental!
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Dwight B.

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

Secluded with a view!!

From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you
Stayed 4 nights in Aug 2024
Verified

4/10 Poor

Thomas W.

Liked: Location
Disliked: Listing accuracy

Outside pictures need to be updated

If you plan to take advantage of the beautiful Sassafras river, request updated photos of the outside, specifically the steps to the water, dock, water access area and the kayak/paddleboards before booking this property. The pictures provided do not represent the current status. Water access area was not cleared of poison ivy and kayaks / paddleboards had to be cleared of debris and drained. Generally the house is ok and the location is good but the first renters of summer should not be expected to get the outdoor space ’summer ready’.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Ken K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful property, well stocked, and great location. Would definitely stay here again!
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Alexandria D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was very welcoming and accommodating!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Dori L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay with family over Thanksgiving! The beds were cozy, the house was beautiful and we had everything we needed. The view overlooking the water was exceptional!
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Levi M.

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

Awesome house

We had a great stay and the host was responsive and kind!!!
Stayed 6 nights in Jul 2025
Verified

10/10 Excellent

will u.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property overlooking the Sassafras river. Home and property above and beyond pictures. Renter easy to work with and accommodating
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Mary G.

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

Great home!

Beautiful home with great views. Plenty of room for our large family group. Kitchen was great with plenty of dishes, pots and pans. Beds were super comfortable!
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Stephanie R.

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

Great stay!

We had a wonderful time here. My husband and I met old college friends and we spent the weekend catching up. We had 6 people and plenty of space. Thank you!
Stayed 2 nights in May 2024
Verified

10/10 Excellent

JEFF C.

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

Great Stay!!

This was everything the listing said it was and more! Great location on the water…beautiful views. The house was clean as bright. Everything worked. We were all very pleased!
Stayed 6 nights in Jul 2023
Verified

10/10 Excellent

Regina L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a very nice stay, with a group of friends. Pros: Gorgeous setting, ample space to spread out for a group of 9, great kitchen for cooking. We had an issue with the warm water in the garage unit and the owner addressed it in a timely matter, even though it was late in the evening. Cons: This probably can’t be controlled much, but since it’s autumn, there were some bees and wasps around the immediate area, and the garage unit was a bit buggy. We’d still happily return!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Nancy L.

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

Best family vavation!

Breathtaking view! The home is beautiful, inviting, and comfortable. My family thoroughly enjoyed the amenities especially the kayaks. There is so much to do around the area or you can just relax and take in the beauty. The owner is very responsive to questions and provided great info on local dining and activities. We're definitely returning again!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

linda u.

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

Birthday Getaway

What a fantastic home with an awesome view! 9 lifelong friends celebrated our 65th birthdays. We especially enjoyed the screened in porch and fire pit. The place was immaculate! Thank you for providing such a comfortable home for us to celebrate and relax.
Stayed 5 nights in May 2023
Verified

10/10 Excellent

Anne S.

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

Fall Weekend Getaway

Charming home in a lovely, peaceful setting on the river. Super convenient location. We walked to breakfast place. Just a three minute drive to nice restaurant on the Marina. Great starting point to visit Chestertown and spend time with family in the area. Hosts were very accessible by text for minor issues.
Stayed 2 nights in Oct 2022
Verified

10/10 Excellent

Garrett A.

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

We are definitely coming back!

I can't believe what a gem of a place this house is. We searched for a place near Middletown (20 min) for a quick weekend with family. We were blown away by the character and location of the house. Rita & Brian made this home so inviting. There was plenty of room for our family of 8 with space left over. The view from the screen porch was peaceful, and the property itself was well maintained. The house was well stocked and met all of our needs. We are making plans to visit again, we loved it that much!
Stayed 2 nights in Sep 2022
Verified

10/10 Excellent

Diane S.

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

Amazing family get together!

We had an amazing time at this house!! The property is absolutely beautiful and the owner was extremely attentive to all of our needs! This house was unbelievably stocked with all the little odds and ends that you always need and have to buy when getting together in a large family setting. It was all there for us! Well stocked kitchen with enough plates for everyone! Salt and pepper…so many times we have to go purchase shakers for another meal! Even coffee pods for the k-cup! The owner goes above and beyond to make the stay special!! We used the kayaks and had a great time. Paddle boards were provided but we aren’t coordinated enough! Beds were amazingly comfortable! TVs everywhere, but we were having family fun and didn’t have time to watch. It was great to have a master bedroom on the first floor for my mom who struggles with the steps and the apartment over the garage provided a little extra privacy for my nephew. I have recommended this facility to my friends and family and highly recommend to all who read this review!!
Stayed 1 night in Aug 2022
Verified

10/10 Excellent

Ebonie L.

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

Highly recommend this rental!!!!

I was looking last minute for a rental to host Thanksgiving this year and I stumbled across this gem. I could not believe that it was available so I was very skeptical about what I would find when I arrived. I have had a bad experience before so I was hoping that this wouldn't be a repeat. And it was not. From the very beginning, even before I booked, the host was responsive and very friendly. I was even more surprised when I arrived, the house is very comfortable and the property is breathtaking. During my stay, she was very willing to answer our questions even though I felt bad asking because it was a holiday. I appreciated everything that she did to make our visit enjoyable. I can't wait to book it again!
Stayed 4 nights in Nov 2022
Verified

10/10 Excellent

Janet S.

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

Wonderful venue for family reunion

This property is beautiful. Situated right on the river, it has great views. Lots of space to spread out and have kids run around. Well stocked kitchen and comfortable beds with plenty of bedding and towels. Ruth was a pleasure to deal with and quick to respond. Highly recommend this property!
Stayed 3 nights in Nov 2022
Verified

10/10 Excellent

Arlene S.

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

Wonderful Place to Stay

Our family so enjoyed staying here. There was plenty of room to spread out. It was so cozy and relaxing. It felt like home. The screened in back porch that overlooked the river was our favorite hang out place. The house was well supplied with everything you might need as well as some nice touches that you don't find at most places. The owner was always very quick to respond to any questions and went out of her way to make sure you had everything you needed. She was great! I am really hoping we have the opportunity to make a repeat visit.
Stayed 2 nights in Sep 2022
Verified

10/10 Excellent

Jaren

Liked: Communication
Stayed 7 nights in Jul 2022