Vacation 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.

Family · Location · Indoor spaces

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.

Location · Value · Getting around

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

Location · Family · Outdoor spaces

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.

Value · Family · Amenities

Historic Macon Luxury Lodge with updated decor

Nestled in the heart of town, our Historic Macon Lodge has everything you need to relax and feel like you have escaped into nature. 3 bedrooms, 2.5 bathrooms, with 2 stone fireplaces and large glass windows. There is a spacious backyard with a fire pit and breathtaking wooded walking trails to a nearby historic Grotto. This Lodge is perfect for romantic couples and families with small children. There will be no parties, groups or gatherings allowed. Please acknowledge in your message

Value · Location · Layout

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!

Family · Value · Cleanliness

Dublin Bungalow

This unique place has a style its own. Totally renovated, open floor plan, large marble fireplace with 65” TV. Large island open to living room, good for gathering of friends and family. The location is a walking distance to Dublin Country Club. Four bedrooms, two master suites , one king size bed, three queen size beds, and one sofa bed; accommodating a total sleep of up to 10 people. Both master suites have 55” TV. Wi-Fi is available. Good location, 10 minutes from downtown Dublin.

Location · Family · Layout

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.

Location · Value · Indoor spaces

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.

Family · Location · TV

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.

Family · Location · Bathroom

Cozy Wooded Cabin w/ Tub, Rain Shower & Pergola

Fall Tiny House Hideaway! 🍂 Escape to this Milledgeville gem in a quiet retreat just 5 mins from downtown. Embrace the crisp autumn air with cozy evenings by the fire pit or relaxing under the pergola. Indoors, soak in the luxury tub with a Smart TV, or step outside for a rinse in the private outdoor rain shower under the stars. Perfect for couples or friends looking to sneak away, connect, and enjoy the season!

Location · Value · Amenities

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.

Value · Location · Check-in