We took the list of America’s best small towns and cozy vacation spots then set out to find the best vacation homes from those towns. We will compile our findings throughout a series of posts on our website. For simplicity, each post will have 7-8 homes.
Click on the name of each rental home to check on pricing and availability of each. These are definitely homes to wow and brag to your family and friends about!
Part one of Amazing Vacation Homes From America’s Best Small Towns can be found HERE!
Beach Cottage– St Simon’s Island, Georgia
When you think of that delightful, relaxing beach and island life, I am SURE the first place that comes to mind would be…GEORGIA? Well if it wasn’t, you may want to reconsider! St Simon’s Island is a beautiful and relaxing island that provides all the relaxation, scenery, restaurants, and shopping…but WITHOUT the crazy crowds that come with the more popular beach or island destinations.
Popular activities on St Simon’s Island include golfing, horseback riding, guided trolley tours, and biking. For those that prefer their activities to be water related, there is fishing, kayaking, whale watching, and of course beach time! There are numerous dining opportunities throughout the island and shoppers will be delighted with all the local shoppes!
To fully take in that island life, you need to stay at an island cottage! This newly built coastal cottage boasts 4 bedrooms and 4 baths. It will sleep up to 10 guests. We are a huge fan of the brightly lit open floor plan. You walk in and it just feels like vacation! The first floor also has a screened in porch with a swinging day bed! There is another screened in porch in the back of the home!
The master suite is located on the first floor. The three guest bedrooms are all located upstairs. One of the upstairs bedrooms is the “kids haven” with super cool bunk sets and cute decoration! The kitchen is well appointed with stainless steel appliances. It is properly stocked for the occasional meal cooked at home.
The perfect vacation starts with the perfect vacation home. This beach cottage certainly fits that bill. To see pricing and availability, click the name of the home above. To see all of the amazing homes in St Simons Island, click HERE.
Bourbon Luxe Estate– Bullitt County, Kentucky
As you head out of Louisville, KY and follow the signs for the Kentucky Bourbon Trail, you will find no shortage of quaint, historic towns along the way. The bulk of the bourbon distilleries are found in a triangle roughly formed between Louisville, Lexington, and Bardstown.
Since this is a family-centric travel site, we obviously recognize that there needs to be things for the kiddos to do too! This part of Kentucky doesn’t disappoint. Horse riding and trails are everywhere. There are plenty of lake and rivers for fishing and boating opportunities. Kentucky is also known for its amazing caves!
So where do you stay? I am not sure if there is a more amazing home than the Bourbon Luxe Estate! This 6 bedroom/4 bath home sleeps up to ten. The home sits on 22 acres and has its own trail system. The estate is bordered on three sides by the Bernheim Forest.
The home itself is over 5500 sq/ft of living space. There are so many places to unwind and relax. There are games and even a piano in the lounge area. We love the three story “silo” that is now living space! Outside, there are several patios, decks, and courtyard for further relaxation. We love the pond with dock!
The Bourbon Luxe Estate makes a perfect home base when wandering the Kentucky Bourbon Trail and surrounding countryside. It is fairly centrally located among the most popular distilleries. To see pricing and availability, click the name above. To see a larger selection of homes along the Bourbon Trail, click HERE.
Pilot House– Astoria, Oregon
Astoria, OR is a Victorian era town located right at the mouth of the Columbia River. Being the oldest settlement west of the Rocky Mountains, Astoria is known just as much for its history as it is for its rugged beauty. But is Astoria a good location for family vacation? YES!
Oregon’s north coast area is dotted with many small towns, each with its own unique look and feel. In Astoria itself, you have the Columbia River Maritime Museum with its walk on warships and tug boats. Climb the 125 foot tall Astoria Column for 360 degree views of the area. Be sure to buy a balsam glider at the shop at the base to throw off the top! The beaches are large and wide providing plenty of room to roam and run. In nearby Seaside, visit the historic Funland Arcade. Visit the shops on Broadway, including the many treat shops! There are also many museums and aquariums to keep the kids entertained.
It’s no surprise that nautical activity is what made Astoria a key seaport. Many of the area homes and hotels are perched high on the bluffs, offering great views of where the Columbia River meets the Pacific Ocean. But the Pilot House literally sits ON the Columbia River, offering the most up close views of this busy river port.
Pilot House take up the second floor of an actual working river pilot house. The river pilots live and work out of the first floor of the building and dock their tugs to the pier below. Because you are in the middle of the action, you literally have views of the river all around you from nearly every window in the home. Despite the commercial nature of the building, the Pilot House home had the feel of a 4 Star hotel with luxury and high end appointments to make you feel warm and at home.
Click the name of the home above to get availability and pricing for Pilot House. To see all of Astoria’s great vacation rentals, click HERE.
Seven Springs House– Dorset, Vermont
The towns of Dorset and Manchester, Vermont both reflect life in the Green Mountains region. Peaceful. Outdoorsy. Local artisans. World-class restaurants. Skiing. Hiking. Cycling. Horses. Quaint towns. Mountain views. Adventure…
What we love about this area is how they are truly four season vacation locations. There truly is not a bad time of the year to visit depending on what interests your family. We found so many wonderful vacation rentals, all of which would make for a great home base for your Green Mountains vacation. One really stood out for us: Seven Springs House!
This home boasts 5 bedrooms and 6 baths. It will sleep up to 12 guests. The home sits on 70 acres. You will find natural meadows, wooded areas, and two ponds. The house is designed in a contemporary style with high end finishes. You will fall in love with the massive floor to ceiling stone fireplace. The gourmet kitchen will be a bonus for the chef in the family!
The outdoor decks and patios are gorgeous. The beautiful landscaping surrounding the stone patio sets the frame for the mountain views in the distance. We love how the upper deck uses glass rails to allow unobstructed views. The ponds will be refreshing for those summer days!
Seven Springs House is an amazing home base for your Dorset, VT and Green Mountains vacation. After a long day exploring, skiing, fishing, shopping, hiking, or biking…we can’t think of a better way to rest and admire the area. Click the name of the home above for pricing and availability. To see all of the AMAZING Dorset and Manchester vacation rentals, click HERE.
Rock Haus– Eureka Springs, Arkansas
Eureka Springs is an eclectic small town nestled into the Ozark Mountains of Northwest Arkansas. There are no shortages of activities when visiting this area, so there is bound to be something for everyone in your family. Here are some of the biggest attractions.
The entire downtown area of Eureka Springs is on the National Register of Historic Places. Buildings have an interesting mix of Victorian, Romanesque, Queen Anne, and others. Main Street is a one mile stretch of shoppes and restaurants. All local, no chains! Downtown also hosts plenty of festivals and parades throughout the year.
Visitors can also take boat tours of picturesque Beaver Lake. Dine on the historic Eureka Springs & Northern Arkansas Railway. Visit one of the nations more respected big cat preserve. Relax in one of the areas famous hot springs. If you get tired of being above ground, then head to one of the areas caves and explore underground. Enjoy some art…downtown is home to several art galleries displaying the works of the areas many artists. And lastly, enjoy many of the areas hiking, biking, kayaking, and swimming opportunities!
With an area that has so much diversity in things to do, they also have a ton of diversity in vacation homes. Lake homes, river homes, modern, historic Victorian downtown homes, and more. But we found this gem…The Rock Haus!
The Rock Haus was built to mimic and authentic European stone cottage. Built with local Ozark limestone, this home will certainly make a memorable vacation. Rock Haus is a 3 bedroom and 2 bath home that will sleep up to six. Not only does the exterior have the appearance of a European cottage, but the interior does as well. The entire home is wonderfully decorated. The home sits on 25 country acres with hiking paths for a rural feel, yet is only a 4 minute drive to downtown!
We love Rock Haus for its uniqueness and amenities. The convenience to area attractions is a huge bonus too. No wonder the home has been reviewed 195 times with all perfect five stars! To see pricing and availability, click the name of the home above. To see all of Eureka Springs vacation homes, click HERE.
Ulysses S. Grant Home– Galena, Illinois
Galena, IL will challenge everything you THINK you know about Illinois. When most people hear Illinois they either think about Chicago or the rest of the VERY flat farmlands that make up the bulk of the state. But tucked into the far northwest corner of the state you will find rolling hills, bluffs, rivers, and the historic city of Galena. Galena is full of wonderful shopping and dining. The surrounding areas have ancient Native American mounds.
The majority of Galena is listed on the National Register of Historic Places. Located on the Galena River just a short distance from the Mississippi River, Galena was once one of the busiest port cities along the Great River. Many of the homes and businesses in the downtown area of Galena are the same buildings from 1860’s and earlier. These buildings are all very well preserved and in most cases look today as they did 150+ years ago.
Ulysses S Grant, who was a Union Civil War General and then the 18th President of the United States lived in Galena prior to the Civil War. His home has been meticulously restored to its 1860’s splendor with decor from that period. Modern conveniences such as internet and central air and heat have been added in a way to not detract from the historic appearance of the home. It is not often to be able to be able to stay in a home that was lived in by a former US President, let alone one that is over 160 years old!
A vacation to Galena is one that would be filled with long lasting memories. Staying in the home of Ulysses S Grant would simply be the icing for this vacation! To see rates and availability of the Ulysses S Grant home, click the name of the home above. To see the full list of other historic homes in Galena, IL, click HERE.
The Cottage at Dark Horse Estate– Franklin, TN
Located just 21 miles south of Nashville, you will find a town that couldn’t be any different that the party atmosphere of Music City. Franklin’s main draw is its 16 block downtown area which is listed on the National Register of Historic Places. The historic downtown is full of historic, Victorian era buildings, a central town square, and plenty of shoppes, restaurants, distilleries, and more.
Take a trolley tour to visit local historical places, wander inside sprawling mansions, take in a concert at one of many theatres or venues, and more. For outdoors enthusiasts, look forward to enjoying hiking, mountain biking, fishing, horseback riding, kayaking and more at several local nature preserves.
A great vacation deserves great lodging. And it doesn’t get much better than the Cottage at Dark Horse Estates. The home is a 3500 sq/ft, 3 BR/2BA home that will sleep up to 7. The home is located on the grounds of Dark Horse Recordings, which has seen the likes of Taylor Swift, Tim McGraw, Matchbox 20, Keith Urban, and more wander these same grounds!
This home is truly amazing and impressive, both inside and out. The main foyer with the grand piano is truly impressive. The stone, glass, and wood design work just oozes class. There is no wonder so many star musicians have chosen to stay here while recording at the studio just steps away!
To see pricing and availability of The Cottage at Dark Horse, click the name above. There are many more beautiful homes in the Franklin area. Check them out HERE!
We hope you have enjoyed this list of some of the BEST vacation homes from some of America’s BEST small towns. The next selection of homes will be featured in an upcoming article in the very near future! Hopefully some of these homes will light that spark and get you to plan and book your vacation!
