Holiday rentals in Toomsboro

Spacious lakefront home. Super location! Deep H2O.

Spacious home on quiet deep-water cove, great for swimming. Put your boat in just .2 mile away & dock it here. Ample outdoor space, with 3 decks & terraced yard. Eat on the screened-in porch, grill out for dinner. HUGE master w/ door to a deck. Enormous kitchen. Two additional BR & large rec room w/ two twins. Double lot feels very private, but you're close to everything! 2 min to Dollar Gen; 6 to Kroger; 8 to downtown. I will consider two-night stays during non-peak months. Message a request.

Adorable 1-bedroom guesthouse on the river

Guesthouse at TURKEY HILL COTTAGE Relax in this calm, stylish woodland retreat just 6 miles off 1-16 on the Oconee River. Dublin is 15 min. away, VA Hospital & Fairview Park Hospital 20 min. Southern Pines Rec. prk, 12 min. Extra large bedroom with queen bed and loft. Can accommodate at least 4 adults, 2 children. Full kitchen with bar. Amenities include internet, cable, VCR, HVAC. All linens, dishes, & cookware provided. Apartment located above separate garage. Community boat ramp available.

Waterfront Retreat • Sleeps 14 • Game Room • Gym

Private waterfront retreat minutes from downtown Dublin. Step back to the good old days at The Dublin House, thoughtfully decorated to complement its authentic mid-century features with nostalgic artwork and even a record player. • 12-acre private property • Stocked 4-acre fishing pond • 4 king bedrooms + bunk room • Sleeps 14 in beds / up to 18 guests • Game room + home gym • Canoe, fishing & fire pit • 3.5 bathrooms • Ramp entry + accessible primary bath • Perfect for family & group getaways

Granny’s House-3/2- 25ish min Milledgeville/Dublin

Welcome to Granny’s House; your peaceful and comfortable retreat. This charming 3-bed, 2-bath home is designed with families in mind and comfortably sleeps 7(up to 9) see notes on beds. The warm and inviting atmosphere makes Granny’s House feel like home. The layout includes two separate living spaces, giving your group plenty of room to spread out. The home is furnished with comfort and practicality in mind. Granny’s House is the perfect place to relax, reconnect, and make lasting memories.

Best Dam View at Sinclair! Big Water Pets Welcome

Lovely sunrises & moon views. 5 min to downtown, 2 min from The Club at Lake Sinclair & DG. Sleeps 6-8 people, (air mattresses/beds) Perfect for entertaining with outdoor dining areas. Fire pit with lots of seating. Big views of water & nearby sandbar, across from an island with beachfront space. Tons of amenities you may need, including a pack-n-play. For the hot-natured, white noise lovers we have large floor fans! Kayaks & paddleboards on site & Rubber Dockie that will entertain the kids.

Luxe Lakefront: Spa, Kayaks, Pickleball & Theater

🌅 Secluded + 180° Big Water Sunset Views ✔ Private Dock: Kayaks, Paddleboards, & 2023 Pontoon Boat* ✔ Luxe KingBR: Balcony + Lake-View Spa Bath & Rain Shower ✔ 3-Tier Deck: Spa, Firepit, Hammock, & Lakeview Lounge ✔ 85” theater, Life-Size Jenga, 4-square, Retro Arcade, Cornhole, & Board Games ✔ Private Playground, Pickleball, & Basketball courts ✔ Chef’s Kitchen: Fully Stocked + Coffee Bar ✔ Outdoor Dining for 16 w/ Lakeview BBQ Area ✨ Your Stunning, Secluded Lakehouse Escape Awaits!

Renovated 1928 cottage on a former asylum campus

Into the macabre? Stay on the campus of what once was the largest mental asylum in the world. Stay in a fully renovated craftsman, 1920's cottage situated on the corner of a large pecan grove, across from the Central State Hospital infirmary. Walking, driving or trolly tours are available to learn all about the history of one of the nation's oldest and largest institutions for the mentally ill. Note: Buildings are closed to the public. There are no tours inside buildings.

Harts Ford Farmhouse

Harts Ford Farmhouse is quaint, peaceful and roomy. It's surrounded by farmland in the heart of Middle Georgia. The house was built in 1900 and has been in our family for 4 generations. Guest can enjoy the many amenities including use of full house, outdoor fire pit, lounge chairs, outdoor grill, outdoor dining area, large yard for parking. It's family friendly for playing games, walking, and peaceful large front porch with rockers to star gaze into the night sky.

Lake Escape

Relax with the whole family at this peaceful place to stay. This home offers a place to get away and enjoy the views from your own private secluded lake. The house includes a king size bed with 2 additional bedrooms and 2 bathrooms. Enjoy the large patio with gas grill and plenty of outdoor space to explore. Bring your fishing pole and enjoy catching bass off of the new dock in the stocked lake. This house is the perfect place to get away and enjoy the outdoors.

Lakefront Retreat with Pool and Room For Everyone!

Welcome to your perfect getaway on the shores of Lake Sinclair! This stunning six-bedroom, 4.5-bath lakefront home offers breathtaking views, a private pool, and unbeatable convenience—just minutes from downtown Milledgeville, shopping, dining, golf, and more. Whether you’re here for a family vacation, a friends’ getaway, or a relaxing retreat, this lakefront paradise has everything you need—including a private pool house for those who value their own space.

Cottage at the Blue Goose

The Cottage at the Blue Goose is the perfect space to relax or work remotely. It's surrounded by established gardens full of perennials and native plants. From the front porch rocking chairs enjoy watching the the hummingbirds dart from flower to flower. The Cottage also has a Southern style screened in porch with haunt blue ceiling and lots of comfortable seating. Parking is under the lighted breezeway connected to the cottage.

The Farmhouse

Peaceful farm house cottage. Enjoy a weekend in the country just a few minutes from Milledgeville, and a short drive to Dublin or Macon. Safe, warm, and cozy. You and your family will enjoy chickens crowing in the distance, watching horses graze from the front porch, and the spacious yard providing plenty of safe, secure parking.