It’s fun to learn the history of where you’re staying for vacation, and it creates a deeper connection to your surroundings that many tourists miss. Spending a few nights in a historic dwelling is even better because you can take a true step back in time and open your eyes each morning to sights enjoyed by generations past.
Historic doesn’t mean outdated, however. When these historic homes were built, many were on the cutting edge of amenities for their day. You’ll enjoy that same feeling today in historic vacation home rentals that are fully modernized.
Many are more affordable than you might think. Some are similar in price to a nice motel room. Others have a steeper price tag, but accommodate a large number of people. Click through to see which of these affordable rentals, all available through the rental site HomeAway, might be on your travel bucket list.
1. Harlem, New York, N.Y.
With history dating back to the 1660s, Harlem offers plenty of history to explore when you visit New York City. Immerse yourself in gospel music, the Civil Rights movement, and the roots of cabaret, jazz and blues.
Located in Upper Manhattan, Harlem features luxurious brownstone homes that were once home to key figures during the Civil Rights era and Harlem Renaissance. Composer W.C. Handy, pianist Eubie Blake and prizefighter Harry Wills were just three of many famous residents on Striver’s Row.
Get a taste of Harlem’s good life in a 1,500 square-foot brownstone duplex. Enjoy the best of modern living with historic charm in a two-bedroom, two-bath townhome with private balconies off each bedroom and a private garden terrace. The home is adjacent to the former home of Oscar Hammerstein II, of Broadway musical fame.
2. Makawao, Island of Maui, Hawaii
Maui’s beaches, Molokini snorkeling crater and championship golf courses lure visitors to the Hawaiian island for a relaxing vacation. Although beach house rentals might be tempting, find great deals in Maui’s upcountry on the slopes of Mt. Haleakala. Miles of rolling ranchlands offer sweeping views over verdant grasslands and ocean.
Experience the island from this unique perspective with a stay in a historic home that was the retirement home of Haleakala Cattle Ranch’s first ranch manager. The ranch dates back to 1888, while construction on the home began in 1916.
The home features an 85-foot lanai that lets you bask in Hawaii’s mild climate. Spacious and screened-in, the lanai provides room for lounging, dining and even snoozing. The 3,500-foot home has four bedrooms and encompasses views of the ocean, pasturelands and orchards.
3. Hōlualoa, Island of Hawaii, Hawaii
Hawaii’s Big Island isn’t just the state’s largest island, it’s also the most diverse. You’ll find green semiprecious stones at Papakolea Beach and black sand at Punalu’u Beach, as well as towering active volcanoes and a crown of lush rainforest. It’s the ideal place to headquarter your Hawaiian vacation.
The island brims with historic sites as well. See lava rock carvings at Puako Petroglyph Archaeological Preserve or visit Pu’uhonua O Hōnaunau National Historical Park, where native Hawaiians would seek refuge during battle.
The mountainside ranch house in Hōlualoa dates back to 1895. Bedrooms overlook the ocean or mountain. In the morning, stroll through a spacious yard that features old plantings of banana, pineapple, avocado and other fruit trees. Or, follow a path through a 60-year-old coffee orchard that leads to Kona Blue Sky Coffee.
4. Waimanalo, Island of Oahu, Hawaii
Waimanalo is tucked on Oahu’s southeast coast, just 15 miles from Waikiki but worlds away from tourist crowds. Its soft, sugar-white sands are ideal for a barefoot stroll alongside the turquoise water that rolls into the shore. Part of Waimanalo’s charm is that it’s not overcrowded. L&L Hawaiian Barbecue, Dave’s Ice Cream and Honolulu Nuts & Ukulele Company roll out everything your taste buds need. Its off-the-beaten track location puts you in the perfect position to visit lesser-known sightseeing spots in Hawaii.
Stay in a historic Hawaiian home that backs up to the powdery beach. Known as “Hale Pohaku,” or “house of stone,” this 2,000-square-foot home is listed on Hawaii’s Register of Historic Homes. It greets you with traditional stone exterior flanked by tropical plants. Swim, snorkel and boogie board just steps away from the house, explore 5 miles of beach, or relax inside with sweeping views of the Pacific.
5. Scotch 80s, Las Vegas, Nev.
Home to internationally renowned entertainers, casino tycoons and other prominent Las Vegas types, the Scotch 80s has been a hip neighborhood to live since the 1950s. The area features ornate architecture, lush landscaping and one-acre estates off the Strip, making it a natural for visitors who want to see how Vegas’s upper crust lives.
Find out for yourself by renting this historic vacation home. A fully stocked chef’s kitchen, outdoor fire pit, swimming pool, expansive cabana and spacious entertaining areas let you enjoy every facet of stylish Vegas living.
Learn More: Las Vegas Vacation Secrets Only Insiders Know
6. Mount Dora, Orlando, Fla.
Orlando is best known as home to family theme parks such as Walt Disney World, Universal Studios and SeaWorld. But the city and surrounding communities have a historic side as well, and there are inexpensive things to do in the area. The city of Mount Dora in the northwestern part of the metro area dates back to the 1880s. It overlooks Lake Dora and is home to one of the state’s three freshwater lighthouses.
One lodging option is a vintage Mount Dora home, built in 1888. Wood floors, a clawfoot tub and charming sunroom take you back to yesteryear, while high-speed internet, flat screen TV and modern appliances make sure you don’t miss out on modern living. The home is just a block from the lake, where you can linger to watch the sunset.
7. Glen Ellyn, Chicago, Ill.
Chicago is an architecture lover’s paradise. Heralded as the city that changed architecture forever, Chicago was the birthplace of the skyscraper. Four of the country’s tallest buildings are located in Chicago, along with other notable works of architecture such as the Robie House by Frank Lloyd Wright and the Merchandise Mart, a two-block Art Deco structure that was once the world’s largest office building.
Stay in a historic Victorian home that recalls the days when Chicago’s city skyline rose only 10 stories tall. The home is in the village of Glen Ellyn, located 29 miles due west of downtown, in a leafy neighborhood full of historic buildings. Modern updates, combined with period décor, let you enjoy the best of both eras.
8. Old Town, San Diego, Calif.
San Diego might be synonymous with SeaWorld, its famous zoo and its miles of sandy beaches, but the city’s Old Town section enjoys its position as the birthplace of California. Home to the first permanent Spanish settlement, Old Town offers a rich history going back to 1769.
Stay in a historic Victorian home overlooking Old Town San Diego. Built in the early 1800s, the private one-bedroom, one-bath unit is fully modernized and sleeps four.
9. Bayview-Hunters Point, San Francisco, Calif.
San Francisco is a history lover’s dream, with Spanish roots dating back to around the same time the Declaration of Independence was signed on the other side of the continent. The city is well known for its Victorian houses, iconic Golden Gate Bridge and historic Chinatown community.
What you might not expect, though, is a castle. Tucked away in the Bayview-Hunters Point area about a block from India Basin, the Albion Castle was built in 1870 as a home and brewery. Its six-story tower is made of stones that once were a cargo ship’s ballast and its depths house stone tunnels leading to 10,000-gallon cisterns that provide fresh spring water, now filtered by modern means.
Enjoy a stay within its stone walls where modern conveniences combine with rustic royal decor.
10. Seaport, Key West, Fla.
If you want to head south to escape winter, Key West is as far south as you can drive by car in the U.S. Its Old Town neighborhood in the western part of the city brims with historic architecture built by seafaring captains who sailed into the deep port to resupply with fresh water. Unique architecture — called “conch-style” because conch shells were an original building material — characterizes Old Town neighborhoods. Houses have deep porches and are set on stilts to thwart the tropical heat and moisture.
Experience life in a graceful conch home when you rent a vacation home in the historic Seaport neighborhood. Fine detailing and craftsmanship include heart pine walls, an intricately carved staircase and open beam ceiling. A pool and private yard make it the perfect place to hang out. Gather a group of friends — the home’s seven bedrooms sleep 14 people — making it both affordable and elegant.
11. French Quarter, New Orleans, La.
The French Quarter is renowned for jazz, Bourbon Street bars, its Mississippi riverfront and six-block French Market, among other things. French Creole architecture lines the picturesque streets, which feature graceful brick buildings flanked by cool courtyards and decked out with ironwork railings.
You don’t have to look from the outside. Stay in a French Quarter vacation rental and gaze down from your private balcony to the street below. Gas lanterns light the private courtyard. The 1838 Creole home is fully renovated with modern conveniences, but its brick walls, exposed wood ceilings and antique appointments let its historic charm shine through.
12. Logan Circle, Washington, D.C.
There’s perhaps no destination in the U.S. filled with more historic attractions than the nation’s capital. From the National Mall to a host of monuments and museums, your days in the city will be a history buff’s delight.
Gaze across the city from the rooftop garden of a historic D.C. vacation rental home. The three-story home was once a Civil War hospital and the former rectory of St. Augustine’s Church. You’re perfectly positioned to visit the trendy 14th Street Corridor, visit nearby monuments or even head over to the White House a few miles away.
13. Ansonborough, Charleston, S.C.
Founded in 1670, there’s oodles of history to explore in the city of Charleston. Head to one of the city’s oldest neighborhoods, Ansonborough. Experience history as you visit the Old Slave Mart Museum, the Aiken-Rhett House Museum, Fort Sumter and antebellum homes. Or pick up some souvenirs at the Charleston City Market, a fixture in the city since the early 1800s.
Spend the night in a renovated 1820 carriage house in Ansonborough. The two-story brick house has soaring open-beam ceilings, modern amenities and lushly landscaped outdoor living spaces.
14. Dock Square, Kennebunkport, Maine
Before being a retreat for the extended Bush family, Kennebunkport was a bustling fishing village. Before that it was hunting ground for Native Americans for more than 11,000 years. Discover the area’s rich history at the Museum in the Streets, a series of self-guided tour panels that let you delve into Kennebunkport’s past at your own pace. Stop by the Brick Store Museum from Tuesday through Sunday to view displays and exhibits and download the History Hopper app to go even more in-depth.
Stay at the historic Old River House off Dock Square. The 1848 mansion was completely renovated in 2010, offering modern luxury coupled with 19th-century craftsmanship. The house backs up against the Kennebunk River and has 10 bedrooms, making it ideal for an extended family reunion.
15. Forsyth Park, Savannah, Ga.
Graceful antebellum homes, cobblestone squares and enormous live oak trees draped in Spanish moss make Savannah the epitome of Southern living. Forsyth Park is a 30-acre green space and surrounding neighborhood in Savannah’s historic district. The Park was a drilling site for Confederate soldiers and today houses an immense fountain and Confederate monument.
Experience the neighborhood’s spacious ornate porches when you spend the night at the restored Italianate Mansion. Gaze out floor-to-ceiling bay windows or stare into the flames dancing in the marble fireplace. The home is fully modernized but filled with historic touches like pine heart floors and grand staircase.
16. West End, Nashville, Tenn.
Nashville is famous for country music, but when it’s time to leave the neon honky tonks behind, head for the city’s West End. Give your ears a rest and delight your eyes at the Parthenon, a full-scale replica of the real thing in Athens, Greece. The building dates to Tennessee’s 1897 Centennial Exposition and presently serves as the city’s art museum.
Stay in the penthouse apartment of the neighborhood’s most luxurious apartment building. The Gladstone Building was designed in 1923 by Charles Ferguson, a prominent local architect. Access the Elizabethan revival building’s penthouse by a grand staircase sweeping up to the third floor.
17. Jackson, Wyo.
Whether you want to golf, fish, hike or visit a national park, there are few places better to do all four options than in Wyoming, with a view of the Grand Teton mountain range. Jackson is only a few miles from Grand Teton National Park and is less than an hour’s drive away from Yellowstone National Park, a great place to visit if you have kids.
Don’t be surprised if you look out your floor-to-ceiling windows and see a moose looking back at you when you stay at the Director’s Cabin at Golf Creek Ranch. The cabin was home to a National Parks Service director for more than two decades. The fully modernized cabin also has a view of the mountains from every room in the house.
18. Moab, Utah
Moab is the gateway to outdoor recreation in Utah’s red rock country where mountain bikers, off-road enthusiasts, and hikers set off into colorful canyonlands. It’s the perfect stop for a summer road trip. The settlement was the primary crossing in 1830 of the Colorado River along the Old Spanish Trail that ran from Santa Fe, N.M. to Los Angeles. Its roots go back before its settlement to traders who passed through the area as early as 1765.
Stay in a historic trading post that’s been converted to a fully modernized vacation home. Exposed adobe brick and Southwestern decor embrace the building’s history while fully modern upgrades deliver modern convenience.
19. Mars Hill, Weaverville, N.C.
Just 15 minutes away from the Blue Ridge Parkway, Weaverville brims with North Carolina mountain charm. Explore its quaint downtown to discover art galleries, antique stores and boutiques tucked away in buildings dating to the early 1800s.
Stay at Grace House, a 1917 home tucked into 14 forested acres in the prestigious Mars Hill neighborhood. The home once rang with the laughter of 15 children and cheery spaces including sun rooms and porches are sure to bring a smile to your face. Eight gas fireplaces, beadboard walls and a farm-family sized dining room might hearken back to yesteryear but they live side by side with a complete range of modern amenities.
20. Glen Ellen, Santa Rosa, Calif.
Old growth redwoods meet California wine country in the town of Glen Ellen tucked just outside the eastern edge of the Santa Rosa metro area. The village was home to author Jack London, author of “The Call of the Wild.” Take an inspiring hike through London’s old estate, now Jack London State Historic Park. You needn’t be a literary fan to discover hidden treasure in this picture-perfect small town: Wineries, spas and old growth forest roll out memorable vacation adventures.
Tuck away for your stay in a historic guest house on the slope of Sonoma Mountain just outside the village. Discover the Sonoma wine country lifestyle in a historic 1898 bungalow that was built as part of Bruning’s Summer Resort that operated in the area until 1915. Discover vineyards, berry bushes and gardens. Gather fresh eggs for breakfast and enjoy picking seasonal fruit.
21. Northeast Coconut Grove, Miami, Fla.
Coconut Grove’s freshwater springs made it a natural stopping place for ships to resupply long before the first settlers put down roots in the area. It’s the oldest continually inhabited part of the Miami area and swells with Mediterranean Revival architecture dating back to the late 1800s.
Stay in a piece of Coconut Grove’s elegant history at Villa Valentino, built in 1910. The exotic Mediterranean revival estate goes on and on, accommodating up to 24 guests in the main home and three guest houses.