Family-friendly holiday rentals in Ashtabula

Sip+Shop+Snuggle this winter @ The Harbor Haven

⭐️⭐️ Welcome to Harbor Haven ⭐️⭐️ Escape to this stunning townhome in Ashtabula Harbor! Enjoy a short walk to the beach, yoga, delicious restaurants, charming shops, and a brewery. This home is thoughtfully designed with all the amenities you need for a comfortable getaway. Spend your days kayaking or fishing on Lake Erie, or explore nearby wineries and covered bridges. Spire Institute is also a short drive away! The Harbor Haven offers the perfect blend of adventure, comfort, and convenience!!

Lakeside Retreat

Welcome to our Lakeside Retreat! Our 1 bedroom, 1 bath getaway located next to Saybrook Park in a cabin community. Only a 5 minute drive to GOTL, a 7 minute drive to historic Ashtabula Harbor and a 15 minute drive to Spire Institute. Short drive to many local wineries. Window air conditioner in the bedroom! Walkway to the lake with beautiful sunset views. 21 and over please. No smoking and no pets! Community gazebos. Laundry facilities available. Construction may be going on near the cabin.

BOHO Bungalow Lake Erie-Wine/GOTL & BULA

Step into the spacious and relaxing 2BR 1Bath boho getaway nestled in a tranquil and picturesque area in the heart of Ashtabula County. Explore GOTL, Historic Ashtabula Harbor, Ohio Wine Country, and much more, or lounge the day away around the fire pit in the private backyard! ✔ 2 Comfortable Queen Bedrooms ✔ Spacious Living Area ✔ Fully Equipped Kitchen ✔ Backyard (BBQ, Fire Pit, Back deck) ✔ Front Porch with Lake View ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Free Parking- 2 cars See more below!

Quaint open room with bathroom on horse farm

A quaint cowboy decor room on a working horse farm . Great over night room in the country but minutes from town. Full bathroom, fridge, microwave queen size bed. . Rooster lets you know when dawn is approaching . Great stop over if hauling horses . Picnic area at top with grill. Arabian horses dot the pastures. Covered bridge on the road and within minutes of wineries, Lake Erie, Historical Ashtabula harbor. Room is small but comfortable without the noise of a hotel. Wifi but no TV .

Chardon Loft

Large private 2nd floor studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix. No cable channels. The furnace is nontraditional. It is not located in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

Cherry Hill House

A quiet, old farmhouse with plenty of space for outdoor activities. Perfect for hunters and fishermen visiting the area or a place to stop that is just 7 minutes from the interstate. We kept the nostalgic style of your grandparents (or parents!) with a few updates for comfort. This is a very simple country house, if you are looking for a hotel stay, this is not it. This house is old and the layout is not modern, and it is not fully updated, so please keep this in mind as you decide to book.

Harbor Retreat, 15 min to Geneva!

Welcome to The Retreat on Bridge Street! Bring your family & friends to relax in this cozy townhouse! Located in the historic Ashtabula harbor, you’re right in the heart of all the fun. Walk across the lift bridge for a kayak or boat rental to experience a day on the water. Or you can walk to dinner and stop at all of the unique shops on the street. We are also walking distance to Walnut Beach! Just six miles away from Geneva on the Lake, and 15-20 minutes from Ohio’s wine country!

Cozy Cabin in Kinsman

This is a western themed, open concept cabin. The cabin is the upper level of a barn-like structure, separated from our home by a large patio. It has a Loft and a Sleep n’ Play Hideaway for children. (The double bed inside the Hideaway is suitable for teens and even adults.) Our cozy cabin is perfect place for either a couple, a few friends or a family. It is also a wonderful place for a retreat or a place to work away from home or the office. (See photos for clarity of layout.)

Cozy winery getaway with hot tub!

Relax in this cozy country garage apt. in Grand River Valley. The first stop on your winery tour is just 4 minutes away with over 30 more to explore. Visit nearby Lake Erie, Thompson Ledges, Geauga Park District Observatory, or a covered bridge. Kitchenette w/ mini fridge, microwave, Keurig & sink. Quaint bath w/ stand up shower Private keycode entry Electric fireplace King size bed Rustic wood rockers & table Pet friendly Shared access to hot tub, back yard fire pit & patio

Riverview Country Cabin

Take it easy at this unique, tranquil getaway nestled atop a scenic ridge of the Ashtabula River. Get away from it all and enjoy your morning coffee inside the cozy cabin with views that stretch up and down and across the river. Or bask in the beauty of nature outside on the custom-made porch swing. Keep an eye out for the local bald eagles as they soar above the river daily, right outside your door! This custom built cabin is the perfect quiet getaway!

Harbor House

The Harbor House is located in the heart of the Ashtabula Harbor and with a few steps you will be on Bridge Street. Our newly renovated house has 2 Bedrooms, a den (sleeps 6), 1 bathroom, a living room, a dining room, and a kitchen equipped with a stove, refrigerator, and dishwasher for your convenience. Relax in the private backyard on the large covered deck for your outdoor living. Thank you, Tammie and Kevin.

Beautiful House walk to everything downtown!

Beautiful Restored Century home right in downtown Conneaut. Groceries, Gym, Restaurant/Bar, Rock Church and many more within 0-2 blocks! 2 Bedroom with Comfortable Queens, a HUGE Bathroom, Large Kitchen and Basement Bar! Minutes from Lake Erie Beaches/ Marina and restaurants. Our house is meticulously cleaned and sanitized between guests. This is a standalone house with its own private entrance.