Entire home
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Photo gallery for Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.





Reviews
9.8 out of 10
Exceptional
5 bedrooms2 bathroomsSleeps 12
Popular amenities
Rooms & beds
5 bedrooms (sleeps 12)
Bedroom 1
2 Queen Beds
Bedroom 2
1 Single Bed
Bedroom 3
1 King Bed
Garage Apartment
2 Queen Beds
Owner Suite
1 King Bed
2 bathrooms
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Toilet · Shower only
Garage Apartment Bathroom
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
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!
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!
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- Kitchen
- Air-conditioning
- Outdoor space
- Parking available
10.0 out of 10, Exceptional, (88 reviews)
House Rules
Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
Events allowed: family gatherings and birthday parties
Small family gatherings are fine.
Pets
No pets allowed
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
About the area
Galena
Located in Galena, this holiday home is in a rural area and on the waterfront. South Chesapeake City Historic District and Middletown Historic District are local landmarks, and some of the area's activities can be experienced at Sassafras Harbor Marina and Granary Marina. Spend some time exploring the area's activities, including winery tours.

Galena, MD
What's nearby
- Toal Park - 14 min walk - 1.2 km
- Sassafras Harbor Marina - 15 min walk - 1.3 km
- Granary Marina - 2 min drive - 1.7 km
- Skipjack Cove Yachting Resort - 2 min drive - 1.8 km
- Duffy Creek Marina - 2 min drive - 1.8 km
Getting around
Restaurants
- Royal Farms - 7 min drive
- Kitty Knight Inn - 10 min walk
- Twinny's Place - 2 min drive
- Galena Pizzaria - 3 min drive
- Fish Whistle at the Granary - 3 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
1 December 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Oct 2025
10/10 Excellent
Dori L.
1 December 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Dori L.
Stayed 2 nights in Nov 2025
10/10 Excellent
Ken K.
18 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ken K.
Stayed 7 nights in Aug 2025
10/10 Excellent
Levi M.
25 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome house
Levi M.
Stayed 6 nights in Jul 2025
10/10 Excellent
Julie S.
12 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Julie S.
Stayed 2 nights in Jan 2026
10/10 Excellent
will u.
9 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
will u.
Stayed 3 nights in Jun 2025
10/10 Excellent
Pat K.
9 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful scenic getaway
Pat K.
Stayed 4 nights in May 2025
10/10 Excellent
Regina L.
27 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Regina L.
Stayed 2 nights in Oct 2025
10/10 Excellent
Mary G.
25 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great home!
Mary G.
Stayed 7 nights in Jun 2023
10/10 Excellent
Stephanie R.
20 May 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay!
Stephanie R.
Stayed 2 nights in May 2024
10/10 Excellent
Lisa M.
12 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacation
Lisa M.
Stayed 5 nights in Aug 2024
10/10 Excellent
JEFF C.
22 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay!!
JEFF C.
Stayed 6 nights in Jul 2023
10/10 Excellent
Nancy L.
9 August 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best family vavation!
Nancy L.
Stayed 7 nights in Jul 2022
10/10 Excellent
maggi W.
4 September 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely retreat on the river
maggi W.
Stayed 3 nights in Aug 2023
10/10 Excellent
linda u.
2 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Birthday Getaway
linda u.
Stayed 5 nights in May 2023
10/10 Excellent
Jennifer W.
8 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing Retreat!
Jennifer W.
Stayed 3 nights in May 2025
10/10 Excellent
Anne S.
10 October 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fall Weekend Getaway
Anne S.
Stayed 2 nights in Oct 2022
10/10 Excellent
Dwight B.
25 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Secluded with a view!!
Dwight B.
Stayed 4 nights in Aug 2024
10/10 Excellent
Garrett A.
12 September 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
We are definitely coming back!
Garrett A.
Stayed 2 nights in Sep 2022
4/10 Poor
Thomas W.
14 July 2024
Liked: Location
Disliked: Listing accuracy
Outside pictures need to be updated
Thomas W.
Stayed 7 nights in Jun 2024
10/10 Excellent
Diane S.
20 August 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing family get together!
Diane S.
Stayed 1 night in Aug 2022
10/10 Excellent
Ebonie L.
30 November 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Highly recommend this rental!!!!
Ebonie L.
Stayed 4 nights in Nov 2022
10/10 Excellent
Janet S.
21 November 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful venue for family reunion
Janet S.
Stayed 3 nights in Nov 2022
10/10 Excellent
Arlene S.
3 October 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Place to Stay
Arlene S.
Stayed 2 nights in Sep 2022
10/10 Excellent
Jaren
28 July 2022
Liked: Communication
Jaren
Stayed 7 nights in Jul 2022
About the host
Hosted by Ruth Gilbert
Our family loves this home away from home but we don’t use it enough lately w kids getting older so we've decided to share it with you to make some of your own memories! If you appreciate details of a simple and beautiful all American Home then this place is for you to get away from it all. 2 min drive to 2 waterfront dining establishments. Less than a 20 minute drive to Chesapeake city. Less than 20 minute drive to Chestertown. Less than a 20 minute drive to the hustle and bustle of suburban in Middletown for franchise shopping and more dining chain and locally owned dining establishments. Enjoy visiting local antique stores. Visit a local winery. Check out the boats on the marina - you can kayak or paddleboard there or drive over in two minutes by car. Take a nice walk up the lane to stretch your legs before taking a nap on the porch. Enjoy beautiful sunsets on the water while sipping wine from the Adirondack chairs. Let the kids roast marshmallows over the fire pit. Motor boat rental may be available at local marina nearby. We provide three standup paddleboard’s a double kayak and two single kayaks.
Why they chose this property
We were tired of the sand, sunburn, traffic and crowds! Less than two hours from Philadelphia. One hour from Wilmington. Beautiful shade trees. If you’re tired of the beach and just want to disconnect away from the hustle and bustle of retail and traffic- then book now. A great place to bond with the kids and reduce screen time. Reconnect with your spouse and experience the simpleness of the good old days!
What makes this property unique
Off the beaten path and perfect if you are tired of the beach scene. Step away from the commercialism, traffic and hustle and bustle of the beaches - this is a nice change.
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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