
Holiday rentals in Boston
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Top-rated holiday rentals in Boston
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Cabin on Lake Nichols
Enjoy a comfortable retreat in a historic 1930s cabin overlooking a 350-acre private lake. This fully renovated farmhouse features its original beadboard. The historic touches, combined with all the modern amenities, make this the perfect destination for those seeking to enjoy a getaway into nature and fishing experience. The lake is loaded with largemouth bass, catfish, speckled perch, bream, and bluegill and is only otherwise available by very limited membership. See more on IG @lake_nichols
4.97 out of 5 average rating, 345 reviews
Edgewood Cottage
Whether you're in town for an event or looking for a getaway, you'll feel cozy, comfortable, and right at home in this historic cottage. Built in 1916, the home offers historic charm and modern amenities. With more than 1,600 sq. ft. and three bedrooms, there's room for the whole family! There's a huge fenced-in yard and Macintyre Park is just half a block away. The front porch and back deck offer serenity under the pines. Or take a 3 minute drive to experience all that downtown has to offer.
4.93 out of 5 average rating, 209 reviews
Hollybourne Cottage
Welcome to Hollybourne Cottage, a cozy, quiet getaway in the heart of Thomasville. Perfectly located just a short drive from charming local shops and exceptional dining, this elegant retreat offers the best of Southern charm! Beautiful MacIntire Park is only a short walk away, or settle in for a relaxing evening with games, TV, or a dedicated desk space, ideal for remote work. Whether you're visiting for a weekend escape or an extended stay, you'll feel right at home at Hollybourne Cottage.
5.0 out of 5 average rating, 26 reviews
Charber Farm Cabin
A tranquil retreat nestled at the back of a 20-acre Pinetree farm. Here, you’ll experience the calming sounds of nature, with the occasional rooster crowing and the gentle mooing of cows in the distance. A few times a day, you can enjoy the picturesque sight of a train passing by, adding a touch of nostalgia to the setting. Whether you're enjoying a morning coffee on the porch or unwinding at sunset, the peaceful rhythm of the farm life invites you to slow down and reconnect with nature.
5.0 out of 5 average rating, 45 reviews
Cozy cabin in the Georgia pines! Retriever kennels
No neighbors on 30 acres of woods in the beautiful town of southern charm, Boston Georgia, 20 minutes from downtown Thomasville Georgia. A modern but retro cabin in the pine forest with all the modern luxuries including full kitchen, gas indoor fireplace, outdoor natural fireplace, outdoor shower, very comfortable beds, fast WiFi, smart TV. A great hideaway from the craziness of life. NON-SMOKERS ONLY! NEWLY ADDED FOUR COVERED RETRIEVER KENNELS 6x6x10 FT. I WILL BE BOW HUNTING NOV-JAN.
5.0 out of 5 average rating, 61 reviews
Lakeview Privacy in the Heart of Thomasville
Sparkling clean, comfortable, very nice, established neighborhood 1 mile from the trains/noise of Downtown Thomasville. Cul-de-sac street, walk to Cherokee Lake, Rose Garden or downtown. Outside deck/arbor with seating for grilling, having coffee or watching the sunset overlooking garden & small residential lake. Open floor plan, lots of natural light, cathedral ceiling. Fully stocked kitchen, 3 BR, 2 queen, 1 single. 2 full baths. Garage/remote.private, tasteful and friendly. No pets,
4.98 out of 5 average rating, 63 reviews
The Shed-King Bed-Boho - Cabin- Grand Piano- WiFi
The Shed is located in a sprinkle of country, splash of city, Thomasville, GA. The Shed hosts a king bed and a combined kitchen living room space with a pullout Queen couch. You can spend your evenings outside on the patio with a fire or explore the beauty of historic downtown only 5 minutes away! A private 2 room guest house with a unique modern flare. No contact, keyless entry on arrival and a cozy, safe, clean space for your get away! We look forward to hosting you!
4.97 out of 5 average rating, 554 reviews
Bobwhite Bungalow - Thomasville, GA
Experience timeless Southern elegance at the Bobwhite Bungalow, a 2-bedroom sanctuary nestled in one of Thomasville’s historic neighborhoods. Inspired by the area’s legacy as “quail hunting heaven” this escape blends comfort with sophistication for the discerning traveler. Whether you’re seeking a romantic getaway, a stylish retreat, or a cozy base for your family to explore Thomasville’s rich history, the Bobwhite Bungalow offers convenience wrapped in Southern charm!
4.95 out of 5 average rating, 66 reviews
The Jerger - Amazing loft in the heart of downtown
Experience everything historic downtown Thomasville has to offer all within walking distance - including the Ritz Amphitheatre, award winning restaurants and locally curated shops. The Jerger sits atop what was once Georgia's oldest jewelry store (Jerger Jewelers) and is now a working leather shop, SouthLife Supply. Its mid-century modern design boasts custom high end finishes, 200 year old heart pine floors, exposed brick walls and a breath taking view downtown.
5.0 out of 5 average rating, 66 reviews
Remodeled Farmhouse!
Take it easy at this unique and tranquil getaway. Recently remodeled farmhouse; close to Thomasville, Moultrie, Valdosta. Pet friendly. Want to get out in the country to the peace and quiet but be close to cities listed above. Book this beautiful farmhouse in Pavo, Georgia and enjoy the country life. Nestled by the fields and beautiful view; that is what you will find. Two bedroom; 1 bath, 3 beds and plenty of parking. King bed, twin and full size
4.95 out of 5 average rating, 63 reviews
Home Sweet Bookings
Home Sweet Bookings at Ariana's Place in a rare gem located in the perfect spot in Thomasville, Ga. We have put so much love and dedication into making this home feel like your home. Ariana's Place has fast WIFI, HUGE washer and dryer, full kitchen with all pans and utensils, Large televisions in each room, and a huge deck for entertaining. Stay one night or stay longer. We want this stay to be a memorable one.
4.97 out of 5 average rating, 102 reviews
small town living
Enjoy the laid back. simple, life of a small southern town. Our old house with hardwood floors, nice comfortable furniture, and vintage decorating choices is perfect for a leisurely get away or business. Great stay for travel nurses or others working temporarily in the area, or just a layover during travels. An air mattress and pack and play are also available. We do allow pets with a pet fee and rules.
4.96 out of 5 average rating, 380 reviewsPopular amenities for Boston holiday rentals
Other great holiday rentals in Boston

Award-Winning Private Victorian Suite + Golf Cart
5.0 out of 5 average rating, 58 reviews
Covey Cottage
5.0 out of 5 average rating, 27 reviews
The Turner House - Farm views in Moultrie!
4.99 out of 5 average rating, 89 reviews
Lakefront 2 Bedroom Cottage with Indoor Fireplace
5.0 out of 5 average rating, 36 reviews
Magnolia Bloom: office, large deck, self check in
4.93 out of 5 average rating, 45 reviews
Jewel Box Cottage
4.94 out of 5 average rating, 18 reviews
Private Lake Retreat | Kayak, Fish + Trail Walk
4.97 out of 5 average rating, 32 reviews
Renovated, rare, peaceful home
4.82 out of 5 average rating, 28 reviewsDestinations to explore
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- Florida State University
- Madison Blue Spring State Park
- Alfred B. Maclay Gardens State Park
- Wild Adventures
- Doak Campbell Stadium
- Fred O. Drake Park at Lake Ella
- Story Lake
- Cascades Park
- Tom Brown Park
- Edward Ball Wakulla Springs State Park
- Tallahassee Automobile Museum
- Suwannee River State Park
- Backwoods Crossing





