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!
Coppola– Healdsburg, California
Located in Sonoma County, Healdsburg is a lesser known known destination when it comes to vineyards and wine tasting. But while it may not have the name recognition, its certainly does NOT lack in natural beauty, wine tasting, shopping, dining, and outdoor activities!
Located along the Russian River, the Healdsburg area offers plenty to do. Some of the most popular activities when visiting Healdsburg include antiquing, art galleries, casinos, kayaking, cycling, breweries, horseback riding, dining, hot air balloon rides, spas, and of course…WINE TASTING!
After a long day being out and about, you deserve an exceptional place to sleep and rest your feet. We loved the look and convenience of Coppola! This 4 bedroom and 2 bath homes will sleep up to 8. The home is bright with plenty of places to rest and enjoy family or friends.
A huge draw for this home is actually OUTSIDE the home. The large and spacious yard is great for sitting and enjoying the outdoors. An oversized picnic table is perfect for outdoor dining. There is a bocce ball court. And check out that bar with garage door that opens to the yard. Did you catch that pool table??
While there is so much to do and see when visiting Sonoma County, don’t you think your lodging see be equally awesome? We do, and a stay at Coppola meet those needs. Click the name above to see pricing and availability. See more Healdsburg vacation rentals HERE. Does Healdsburg meet the standards for one of America’s best small towns? We think so!
Blue Chair Key– Cedar Key, Florida
Cedar Key takes everything you think you know about Florida vacation towns and turns it upside down. No hustle, bustle, or partying here! What you get in Cedar Key is a quaint, hometown feel with tons of hospitality.
Cedar Key is a fantastic for outdoor lovers. Uncrowded beaches, nature preserves, and plenty of excellent fishing abound! It is island living at its best! For those that aren’t fishing fanatics, Cedar Key offers a lovely downtown area with plenty of shopping, dining, and drinking options.
Blue Chair Key is the perfect home for families with varied interests. For the non-outdoorsy folk, downtown is a short golf cart ride away! For those that are info fishing, this home sits right on the water and has its own dock and fish cleaning station. Talk about fresh caught dinner!
The home itself is a cute 2BR/1BA cottage that will sleep four. It has a perfect nautical theme that goes with the island atmosphere of Cedar Key. Check out the porthole windows! The back deck that leads to the dock is huge and comes complete with tables and comfy Adirondack chairs. The home also has an available golf cart that can be rented at a discounted rate.
Blue Chair Key is a great choice for an island vacation. To see rates and availability, click the name above. To view other Cedar Key cottages, click HERE. You can see why Cedar Key is one of America’s best small towns!
Panoramic Lake Views– South Haven, Michigan
South Haven is a beautiful town in Western Michigan. Nestled along the shores of Lake Michigan, South Haven offers an amazing vacation for families with varied interests. Some of the popular things to do in South Haven are fishing, boating, beaches, ATV parks, horseback riding, wineries, shopping and more. Downtown South Haven has amazing dining options and is very walkable.
South Haven was a favorite vacation location for myself and many of my friends from my days in Chicago. We loved renting a boat, fishing, and relaxing on the gorgeous beaches. In the evenings, we would head downtown. We were always impressed by the variety of restaurants, breweries, and more. It wasn’t hard to find live music playing somewhere. At night, we would head back to the house where we would sit outside and listen to the waves crashing the shore. It was nearly perfect!
Our recommended home for South Haven is pretty stellar. It is a 3200 sq/ft home with 4 BR/5BA and will sleep up to 12 of your family members or close friends. There are tons of windows allowing in plenty of natural light. The whole home has a tasteful nautical theme, fitting as the home sits right where the Black River meets Lake Michigan. The chefs kitchen is great for those that somehow find a way to get tired of South Haven’s dining scene.
Our favorite draw are the lake views!! You can see endless lake views from many rooms in the home. But that upstairs deck is AMAZING! There are so many places to sit and relax while enjoying the company of family and friends.
South Haven is a vacation recommendation we can make from personal experience. There is a nice blend of small town hospitality with big city dining and entertainment. South Haven definitely qualifies as one of America’s best small towns. Click the name above for pricing and availability. To see dozens of other South Haven homes in all price ranges, click HERE.
The Train Depot– Frederick, Maryland
Frederick, MD really makes for a pretty perfect vacation location. You are less than an hour from Washington, DC, Baltimore, and Gettysburg. The city of Frederick’s downtown area is a designated Arts and Entertainment District. The entire city is surrounded by mountains, so the views are stunning!
There is NO SHORTAGE of things to do when visiting Frederick. There are historic battlefields. Limitless outdoor activities. The Appalachian Trail passes nearby. Restaurants with nearly every cuisine possible. Wineries, breweries, and distilleries. Beautiful and historic architecture. You want it? Frederick has it!
When visiting a historic town such as Frederick, shouldn’t you stay somewhere historic? How about the second oldest train depot in the US? The train depot has been converted into a luxurious vacation rental with high end furnishings and a great kitchen. What’s better? It is literally in the middle of all the action. You can walk to many restaurants, cafes, and shopping!
Frederick is absolutely deserving of its place on our list of America’s best small towns. Click the name of the home above to find pricing and availability. There are dozens more homes around Frederick. To see them, click HERE.
Willow Tree Retreat– Damascus, Virginia
Damascus, VA just may end up being the smallest town on our list of America’s best small towns! Boasting just 700 full time residents, Damascus claims the title of being Trail Town USA. That’s because this small town sits right at the crossroads of two of the best trails in the country (the Virginia Creeper Trail and the Appalachian Trail). Five more trails are nearby.
This town has made its livelihood on the trails systems. The city has more bike shops (5) than gas stations (3)! There are hiking outfitters, cozy cafes, a small diner, and a brewery and distillery after a long day of hiking or biking.
Willow Tree Retreat is an authentic 4 BR/2BA log cabin. The homes sits on 4 acres, so your family will have plenty of peace and privacy. The wrap around porch has plenty of seating after a long day of hiking or biking. We love the cozy living room with country décor. The stone fireplace is perfect for cool mountain evenings. The Creeper Trail is within walking distance from the home.
For lovers of hiking, biking, canoeing, kayaking, fishing, and general outdoor adventures, Damascus, VA definitely deserves to be on our list of America’s best small towns! Click the name of the home above for pricing and availability. For more Damascus homes, click HERE.
White Rabbit– Fredericksburg, Texas
Fredericksburg is an amazing choice for America’s best small towns. There is just so much to do there all year long. In Winter, Fredericksburg does Christmas as well as anywhere, due to the town’s strong German heritage. As Spring rolls around and wildflowers bloom, people from around the country descend upon the Hill Country to take in bluebonnets, Indian Paintbrush, and dozens of other varieties that adorn the hills and fields. Summer brings out families on vacation to shop, eat, explore, and enjoy Central Texas hospitality. As Fall hits, so does Oktoberfest, again a nod the area’s German heritage.
While Fredericksburg is a family favorite, the area has also gained a reputation for being a great place for a girl’s getaway! There are numerous wineries in the area highlighting some of Texas’ best vintages. Couple that with some old time country dance halls, outstanding dining options, and over 150 shops along Main Street, you can’t go wrong!
White Rabbit is a highly recommended vacation rental whether you are traveling with family or friends. With 4 bedrooms and 3 baths, there is plenty of room for all. This house just FEELS like Texas, with the rustic décor and the inviting backyard area. The backyard entertaining area almost feels like you having your own beer garden (which Fredericksburg has plenty) like the Ice Houses that Central Texas is famous for. We love everything about this house!
If you have never been to Fredericksburg, now is the time to plan a trip. To see pricing for this home, click the name above. To see a selection of other amazing Fredericksburg vacation rentals, click HERE. We are 100% positive you will agree that Fredericksburg is one of America’s best small towns.
Hood River Home– Hood River, Oregon
Hood River, OR is another small town that is geared toward the outdoors enthusiast, but in reality has so much to offer anyone looking for a beautiful mountain vacation. This area is known for kayaking, white water rafting, fishing, mountain biking, skiing, and hiking. But what about the non-action sports enthusiast?
Lucky for you, Hood River has those that prefer a more relaxing vacation covered also. There are numerous wineries, breweries, coffee roasters, and cafes. They have art galleries, abundant shopping, and outstanding dining. Spas and salons are in abundance. Hood River checks all the marks!
With so much to do, you need an amazing home to come back to after a long day being a tourist. Check out the views you get from this 4BR/5BA home will sleep up to ten. There are plenty of tall, wide windows that give guests beautiful views of downtown Hood River, the Columbia River, and the mountains in the distance. The rooms are large, giving all guests plenty of space to relax and unwind after a long day. There are several decks for outdoor viewing too!
We think Hood River deserves its spot on our list of America’s best small towns. To get pricing and availability of this gorgeous vacation rental, click the name above. To see all Hood River homes, click HERE.
Search for your own rental in any of America’s best small towns in the search box below!