4 Weekend Vacations for Two That Will Cost You $1,500 (or Less)

When was the last time you responded to your coworker with enthusiasm when asked if you had big weekend plans? Can you even remember the last time you had an exciting answer Monday morning when asked how your weekend went? If your answers are fuzzy and out of focus, it’s time for you to get away.

We’re here to help you plan a weekend trip with your special someone, sibling, or best friend that won’t leave you smashing your piggy bank.

We think the perfect mini-vacation means an arrival at your destination in time for dinner Friday night, enjoying Saturday, and sleeping in Sunday before heading back home for work Monday. And, of course, we want to help you save money, so each of these trips will cost you and your guest $1,500 or less.  We also segmented them by time zone so you don’t have to worry about traveling across the country. All the research is here, so all you have to do is choose your adventure and start booking.

1. For Eastern Time Zoners: Check out St. Michaels, Maryland

St. Michaels, Maryland, is a historic destination town located about an hour and a half from both Baltimore and Washington, D.C. The cozy bed-and-breakfast-filled village is popular among history buffs, outdoor enthusiasts, and anyone looking for a quiet getaway.

weekend vacations_dock in st michaels, maryland

Where to Stay:

Just a mile from the historic downtown district you’ll find the St. Michaels Inn. It’s one of the few local inns open year-round, and it happily boasts about its outdoor pool and butterfly garden. You’ll have cable and Wi-Fi during your stay and can enjoy a complimentary hot breakfast before heading home on Sunday.

What to Do:    

When you arrive on Friday, get yourself checked in to the hotel and find some dinner. Choose a local spot like St. Michaels Crab & Steakhouse and create an exquisite meal for two. Split the New York Strip, then add-on a half-dozen Cherrystone Clams on the half-shell and a half-dozen oysters for a surf-and-turf experience you’ll not soon forget.

Get started early Saturday with breakfast at the hotel and then stroll through downtown visiting the local boutiques and art galleries. If you’re interested, check out the Chesapeake Bay Maritime Museum which has both indoor and outdoor attractions related to the region’s commerce, trade, navigation, fisheries, and waterfowl.

Once you’re done at the museum, you can snag lunch somewhere like Ava’s Pizzeria and Wine Bar located just blocks from the museum. Share an appetizer of mussels and a brick oven-baked pizza before embarking on your next leg of the adventure.

For fun, think about checking out at least one of the local wineries, breweries, or the distillery. The St Michaels Winery can be found in an old mill, and tastings are available daily. Once you’re done tasting, you can pick up your favorite in a bottle as a souvenir to take home.

After you’ve sampled the local wares, learn more about local history by taking a Patriot cruise. The narrated historical tour traverses the waters of the Miles River, which is part of the Chesapeake Bay Estuary. You’ll see historic homes and wildlife and, if you’re lucky, you could catch workers harvesting oysters, clams, or crabs.

Once your tour is complete, finish off the day by having dinner right by the dock at The Crab Claw. Try a local favorite like the Crab Imperial for dinner or try something lighter like the Rockfish ‘n’ Chips.

After the entire day filled with activities and a stomach full of seafood, you’ll be ready to hit the hotel for a good rest. The hotel will prepare breakfast on Sunday, and you can plan for a new week at work while dazzling your coworkers with your newfound knowledge of the Chesapeake Bay’s history.


We suggest choosing a flight into the Baltimore/Washington International Thurgood Marshall Airport. Round-trip flights from Miami to Baltimore cost about $200, and the expense to fly from John F. Kennedy International Airport in New York is about $150 per person.

Once you arrive in Baltimore, you’ll want to rent a car to travel the rest of the way to St. Michaels. Book in advance to find the best deals and ensure your rental car agency of choice will have the car you’ve selected. For this trip, we used National’s online option for pricing.

Trip Total: $1,222 out of $1,500

  • Flight: $406
  • Car rental: $251
    • Extra Tank of Gas: $30
  • Hotel with Taxes and Fees: $242
  • Meals, Including Gratuity:
    • Friday Dinner: $65
    • Saturday Lunch: $50
    • Saturday Dinner: $65
  • Activities:
    • Museum: $30
    • Winery with Souvenir Bottle: $30
    • Patriot Cruise: $53
  • Leftover Budget for Incidentals, Additional Activities, and Souvenirs: $278

2. For Central Time Zoners: Visit Emporia, Kansas

Considered by some to be a “flyover state,” Kansas is located directly in the middle of the country. People who’ve visited or lived there often call it the Heartland. Either way, if you’re interested in finding out about what it’s like to live amid the Great Plains and experience the wide-open spaces, you’ll find the answers here.

La Quinta Inn & Suites by Wyndham Emporia_emporia kansas

Where to Stay:

You’ll want to select a hotel in Emporia, Kansas, then simply drive to visit the rest of the region. Emporia will put you within minutes of all the attractions and restaurants in the area.

When you’re looking for both comfort and affordability, try the La Quinta Inn & Suites by Wyndham Emporia. You’ll have free Wi-Fi with a pool and fitness center. If you enjoy traveling with a furry best friend, they’re also welcome at this location.

What to Do:

For Friday night, book a sunset tour of the prairie on horseback. You’ll have to drive about 45 minutes from Emporia to catch the tour, but you’ll experience the prairie like you’ve never seen it before. The entire tour takes about two hours and you’ll learn about everything that makes the Flint Hills region special.

You’ll surely be ready for dinner after the tour. Try something like Keller Feed and Wine while you’re in Cottonwood Falls. The menu changes weekly, the local children help grow ingredients, and you’ll have a memorable experience. Look out for the prime rib special and pizza. Try a side dish or two and top it all off with dessert to keep the munchies at bay until Saturday.

Get your fill of the hotel’s complimentary breakfast before you start your Saturday adventures. Start off in Emporia at the David Traylor Zoo, and spend an hour getting to know the regional fauna. Then make a stop by Red Rocks, the home of the William Allen White family, to discover how they made their mark on both Kansas and U.S. history.

By the time you’ve filled your brain full of Kansas history, lunchtime will have arrived. If you’re headed out to the prairie for the afternoon, grab some food to go from a local Emporia spot called J’s Carryout. You’ll find all your drive-in-style favorites ready to go—like the pork tenderloin, footlong coneys, and onion rings. Don’t forget to load up on the napkins!

Fill the rest of your day with hiking and exploring at the Tallgrass National Preserve, which protects nearly 11,000 acres of natural tallgrass prairie land. While at the preserve, you’ll step back in time and hike on rustic trails, see a wild buffalo herd, and visit a historic ranch—the Springhill Ranch House֫.

Head back to Emporia for dinner and experience real Kansas-style barbecue. Bobby D’s Merchant St. BBQ claims “it’s all ‘bout da meat,” and when you check out the menu, you won’t doubt it. Try the meat trio dinner to taste several choices or pick one of your favorites. Starters, sides, and desserts round out the menu and all of it is priced to please.

With all the outdoor action this trip includes, there’s no doubt you’ll rest well Saturday night before eating breakfast and heading back to your normal routine.


If you’re flying in, you’ll want to choose the Kansas City International Airport. The cost of a round-trip flight from Dallas comes to a little more than $200 per person. From Kansas City, you’ll drive about 130 miles to reach Emporia, or a little more than two hours.

The rental car should be fairly inexpensive if you’re picking it up from the airport Friday afternoon and returning it Sunday afternoon. The rental fee from Enterprise was just over $100, plus the cost of fuel.

If you choose this trip, you’ll be covering a bit less than 500 miles in the rental vehicle over the weekend, so you should expect to stop for gas more than once.

Trip Total: $1,465 out of $1,500 budget

  • Flight: $448
  • Car Rental: $110
    • Gas: $75
  • Hotel with Taxes and Fees: $180
  • Food, Including Gratuity:
    • Friday Dinner: $50
    • Saturday Lunch: $30
    • Saturday Dinner: $60
  • Activities:
    • Sunset Tour of the Prairie with Tip: $250 per person
    • Zoo/Red Rocks Tour: $12
    • Tallgrass Prairie National Preserve: $0
  • Leftover Budget for Incidentals, Additional Activities, and Souvenirs: $35

3. For Mountain Time Zoners: Discover Estes Park, Colorado

Estes Park, Colorado, draws people in like moths to a flame. Whether you dream of dominating the trails hidden inside Rocky Mountain National Park or discovering beauty among the art studios and galleries clustered along Elkhorn Avenue—this place has something for every type of traveler.

weekend vacations_Best Western Plus Silver Saddle Inn_estes park, colorado

Where to Stay:

Get a comfortable room at a great price when you choose the Best Western Plus Silver Saddle Inn. You’ll be less than four miles from the entrance to the Rocky Mountain National Park and you’ll be able to enjoy free breakfast and a fitness center, not to mention the incredible mountain views.

What to Do:

If you’ve planned your trip with care, you can check into your hotel and head to the First Friday Art Groove. As one might guess from the name, the art galleries and shops stay open late for art socials and artist events on the first Friday of each month. The entire community is invited—tourists too—and the mood is festive and fun.

You’ll be ready to sit down and enjoy some dinner once you’ve experienced all the incredible art Estes Park has to offer. Luckily, near your hotel, you can find authentic New York-style pizza at Antonio’s Real New York Pizza. Choose from mouth-watering options like the Sicilian pepperoni pie or the Godfather while you relax on one of two patios. If you’re a beer lover, one of their 14 beers on tap is bound to be one to hit the spot.

After crashing for the evening and then feasting on the hotel’s complimentary breakfast, it’s time to experience more of Estes Park. Start the day by visiting Dick’s Rock Museum, an Estes Park official historical landmark. Originally Cy’s Rock Museum, it’s a unique place with an eclectic blend of gems and minerals on display. You’ll be able to see and purchase all kinds of agates, petrified woods, butterfly geodes, and other exotic minerals.

After the museum but before heading to Rocky Mountain National Park, grab a quick bite for lunch along the way. Try something like Bird & Jim, where the food is locally sourced and provides a pure, mountain-dining experience. Share a couple of dishes so you can taste it all, like the provisions and pickle jar charcuterie board and the summer squash lamb lasagna, if it’s in season.

After you’ve tasted the local menu, head on over to Rocky Mountain National Park. Scheduling a guided tour of the Rocky Mountains is an incredible experience no one should miss. However, booking the Rocky Mountain National Park Photo Safari through Yellow Wood Guiding takes the experience to a whole new level. Not only will you get to experience the Rocky Mountains in a way you never have before, but you will be provided with an experienced photographer as a guide for a 3.5- or 4-hour private tour (depending on the season). All the equipment and snacks are included.

Once your photo safari comes to an end, saddle up to a reserved table at SEASONED – An American Bistro. Try a couple of small plates and share an entrée or two like the dish called “That’ll Do Pig” featuring braised, applewood-smoked pork belly.

With a full weekend of activities, you’re sure to want to sleep in Sunday before making the trek home. You’ll have plenty of stories and photos to make all your social media followers jealous.


The journey to Estes Park isn’t the most direct. Your best bet is to fly into Denver International Airport. As an example, a round-trip flight from Billings, Montana, costs less than $200 per person. You’ll then need to pick up a rental car to continue the trip to Estes Park.

If you book a rental car online with Hertz for pickup at the Denver airport, you have the option to save money by paying in advance. However, for this trip, we chose to pay at the time of pickup since weekend trips often get rescheduled. It would cost about $349 to rent a small car for the weekend using this option.

The drive from the Denver airport to Estes Park is about 76 miles and takes an hour and a half. The trip from the airport and back uses about half your initial tank of gas in an average economy rental car, so you’ll probably need to refill before returning it.

Trip Total: $1,476 out of $1,500 budget

  • Flight: $376
  • Car Rental: $349
    • Gas:  $30
  • Hotel with Taxes and Fees: $266
  • Food, Including Gratuity:
    • Friday Dinner: $60
    • Saturday Lunch: $75
    • Saturday Dinner: $120
  • Activities:
    • First Friday Art Groove: $0
    • Dick’s Rock Museum: $0
    • Guided Photo Tour with Park Fee: $200
  • Extra Budget for Incidentals, Additional Activities, and Souvenirs: $24

4. For Pacific Time Zoners: Experience Leavenworth, Washington

If you love the idea of visiting a quaint Bavarian village, but can’t manage to get out of the country, a weekend in Leavenworth, Washington, might do the trick. You can wander the boutiques in downtown Leavenworth, which was created to mimic the Swiss Alps, and find authentic nutcrackers and cuckoo clocks.

weekend vacations_Howard Johnson by Wyndham Leavenworth_leavenworth, washington

Where to Stay:

Spend your weekend at the Howard Johnson by Wyndham Leavenworth. It’s located just minutes from skiing in Steven’s Pass and boasts a heated outdoor pool with breathtaking views of the surrounding mountains. This pet-friendly hotel also offers complimentary breakfast and free Wi-Fi.

What to Do:

When you get to town and get settled, it’s definitely going to be time for dinner. To help you get into the spirit of the neighborhood, why not try München Haus? With a selection of old-world style German sausages hand-selected for quality, you’ll be hard-pressed to find a more authentic Bavarian experience without traveling across an ocean.

On Saturday morning, don’t forget to grab the complimentary breakfast from the hotel as you head out to Steven’s Pass for a day of skiing. The trip takes about 45 minutes, but you’ll spend the entire day on the slopes.

Even if you’re a beginner and don’t own a single piece of skiing gear, you can get a guided, small group lesson with rental gear included for about $150 per person. Your lesson will last about three hours and you’ll have time to grab lunch somewhere like the Tye Creek Deli before trying out the beginner slopes on your own for the afternoon.

Once you’re exhausted from the slopes and ready to head back to Leavenworth, you’re surely already thinking about dinner. If you’re not interested in Bavarian-style fare, try something like the Watershed Café. It’s a Pacific Northwest farm-to-table restaurant inspired by the food available with the turn of each season.

After a full day and a full belly, you’ll likely be ready to call it a night. It won’t be long before you’ll be headed home Sunday with stories of how you learned to ski and now dream of moving to the mountains.


If you’re planning to fly, the Seattle-Tacoma International Airport is the closest to Leavenworth. A sample round-trip flight from San Diego cost about $150.  You’ll need a rental car, but if you reserve an economy car from Alamo, the price is less than $200 for the weekend.

The drive from the airport will take about two and a half hours, so you’ll likely need to get a couple of tanks of gas after factoring in the round-trip drive to Stevens Pass on Saturday.

Trip Total: $1,487 out of $1,500 budget

  • Flight: $314
  • Car Rental: $192
    • Gas: $60
  • Hotel with Taxes and Fees: $349
  • Food, Including Gratuity:
    • Friday Dinner: $75
    • Saturday Lunch: $75
    • Saturday Dinner: $120
  • Activities:
    • Stevens Pass Ski/Snowboard Daily Lift Tickets: $302
  • Leftover Budget for Incidentals, Additional Activities, and Souvenirs: $13

Things to Keep in Mind

There are a zillion details to consider when you’re planning any sort of vacation, and that includes weekend getaways. We hoped to provide you with as much detailed information as possible, but since we don’t know where you’ll be starting your vacation from, it wasn’t always possible. Therefore, we have a few things you’ll want to keep in mind as you go through each vacation.

  • We picked a city in each time zone in an attempt to make at least one of the options close to any starting destination.
  • A random weekend was used in our research—which was approximately three months into the future at the time. We used that weekend for all pricing and availability for flights, hotels, and rental cars.
  • The airfare is the cost of one roundtrip flight, which is then doubled for the two people going on the trip, and assumes both people are starting in the same city.
  • The cost of fuel for your rental car is figured at the national average rate ($2.50 per gallon), assumes you’re driving an economy car with the average-sized fuel tank (12 gallons), and assumes it gets the average miles per gallon for an economy car (24.7) which will take you almost 300 miles. This means each tank of gas is assumed to cost about $30 and each mile you drive costs $0.10.
  • Each of the trips could be more or less expensive depending on how you plan it—what time of year the trip is planned, how you travel to and from the destination, how many people are sharing expenses, etc. This is a guide, meant to help you plan a fabulous getaway, and not meant to be a promise of any specific pricing.
  • We chose the economy car option from among the top-rated rental car agencies available in each city.

It’s our mission to make your travel experiences simple and transparent. Whether we’re helping you find inspiration for your next destination or taking you to a hotel website to book your chosen room directly, you won’t get the runaround from us. Start searching for your next great adventure at Roomkey.com today.