
Vacation rentals in Highland
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Top-rated vacation rentals in Highland
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Antebellum Cottage in Downtown St. Joseph, Mo.
5miles from MO Western!This charming cottage is a rare piece of history located in the historic Museum Hill District of St. Joseph MO. This delightful cottage is one of the oldest built homes in the district. Home was built in the 1860's & was the starter home for many newlywed couples during this era. Location of property is just a short stroll from downtown shops, restaurants & bars. If you are a historical enthusiast or just need a couples retreat this unique piece of history is a must stay!
4.92 out of 5 average rating, 497 reviews
Homey Cottage with Sunroom & Smart TV!
Quiet but vivid, this remote Highland home is a brilliant choice for a getaway where solitude is king. Although the property is away from the hubbub of crowds, it’s still only 1 block from Highland Community College and an easy drive to the Four State Lookout to enjoy the Missouri River. Bursting with character and guest-ready amenities, this 1-bedroom, 1-bathroom vacation rental boasts a sunroom that lets guests unwind without a breeze and a laundry room that doubles as privacy for a 2nd bed.
4.98 out of 5 average rating, 53 reviews
The Grain Bin at Big Lake
Stay in a beautiful remodeled grain silo on a secluded lake. This retreat blends cozy design, stunning views, and endless outdoor fun. Just 90min from Omaha or Kansas City, the silo is perfect for couples, families, or small groups. Rise to splendid sunrises, wind down with blazing sunsets and enjoy enchanting star gazing. Full access to kayaks, paddle boards and a lily pad all included. Bring your boat, jet ski or ATV with private boat slip. The Lake and nearby trails are built for adventure!
4.97 out of 5 average rating, 61 reviews
Hidden Pearl Inn&Vineyard-serene cottage retreat
You won’t want to leave this charming one-of-a-kind place conveniently located on 28acres less than a mile from town. This French inspired cottage rests atop a hill overlooking vineyard and valley views. Wake up to the sun rising over the vineyard from the comfort of your balcony, or view the best sunsets from various vantage points. We offer all the amenities to help you & your spouse or friend group escape the busyness of life while you take in all that our serene property has to offer!
4.99 out of 5 average rating, 153 reviews
The Nest(Tiny House) Private, Self Check-In, Wi-fi
400 sq. ft "tiny house" on edge of woods on private property with neighbors in view. Rural setting. Outside: green space and trees! Inside: cozy, cute, modern, and pleasing color palette. Well-lit spacious parking in driveway next to sidewalk leading to your patio. Here for a long weekend, wedding, or work? Perfect! 25-30 minutes to Atchison, Weston, & the K.C. Airport. Less than 5 minutes to St. Joe, gas, and food. Read on for more information regarding setting and amenities.
4.98 out of 5 average rating, 230 reviews
The Farmhouse: Cozy, Quiet Getaway
Enjoy this cozy country home in Oregon, Missouri. Located about a mile off I-29, this is the perfect place to stay for reunions, family visits, or even a weekend getaway. This is a quiet area with local restaurants nearby. St. Joseph is about 20 minutes away. Free wi-fi is included, along with a full kitchen including Keurig coffee maker, dish washer, garbage disposal and pots and pans. The house also includes a smart TV so you can bring your favorite streaming device.
4.97 out of 5 average rating, 144 reviews
Riverfront 2 BR Jacuzzi Cabin w/ Sunset Balcony
Forget your worries in this spacious 2 bedroom cabin located on the 2nd floor of this riverfront building! Enjoy a glass of wine in the jacuzzi while watching the river water pass by. Nestled just outside of town… a few blocks away, find new mountain bike trails. 2 miles away sits a casino, boat ramp, boat dock, conservation center, and a new riverwalk path that provides a peaceful path to historic downtown St. Joseph! Museums, great food, and amazing sunsets await you!
4.89 out of 5 average rating, 242 reviews
The Elm House
Three bedrooms, two bathrooms, dining room, kitchen hardwood floors throughout living area, Corner lot with privacy fence on the south and the west side. Easy access to grocery store, gas station, beauty salon, library, church, restaurants. Extended Stay guests (booked for a week or more) will enjoy significantly reduced rates (falling within GSA per diem guidelines). Your group, or family can enjoy small town life while relaxing with all the comforts of home
4.93 out of 5 average rating, 321 reviews
Charming home in small town
Relax with the whole family, including your fur family, at this peaceful place to stay in Sabetha, KS. We have completely renovated this home to make your stay as easy and comfortable as possible. The kitchen is fully stocked and ready to enjoy. The master features a king sized bed with lots of pillows to choose from. A dedicated office space surrounded by windows to brighten up your day in the office. The second bedroom offers a comfy queen size bed.
4.96 out of 5 average rating, 183 reviews
Gracious Farmhouse with Beautiful Views
Gracious farmhouse on beautiful working farm offers opportunity for families to disconnect from city life. The farm has been in our family for 160 years; the house was built by our grandfather; Lewis & Clark camped on the land. The house is simply but comfortably furnished; all the mattresses are new. Enjoy family meals either in the dining room or on the enclosed porch. Doug and Bill farm the land so you may see them coming down the road.
4.94 out of 5 average rating, 110 reviews
Hippie Hills - Cozy Country Lodging and a Hot Tub
Like a storybook, but with Wi-Fi, a hot tub, and a hospitality crew. Dogs Taco, Ally, and Bullet greet you at your car, frisbee in tow and zero chill. Donkeys Slim and Shady expect breakfast negotiations, while cats Potato and French Fry judge from afar. Horses Pieces and Jasper love head scratches. Historic Weston is 5 minutes away with shops, wineries, and charm. After exploring, unwind in hot tub under the stars. LGBTQ friendly
4.93 out of 5 average rating, 403 reviews
Quiet Cabin Getaway
Take a break and unwind at this peaceful getaway. This two room cabin is the perfect spot to recharge and find some peace. There is a pond so there are lots of opportunities to see wildlife throughout the day and in every season. There is no WiFi or TV so you will be as unplugged as you want to be as there is cell service. You are about a mile from town on blacktop road after you make it up about a half mile of gravel driveway.
4.94 out of 5 average rating, 31 reviewsPopular amenities for Highland vacation rentals
Other great vacation rentals in Highland

Atchison 1870 Farmhouse
5.0 out of 5 average rating, 37 reviews
Red Rock Loft | *Pet Friendly Hunters Dream*
5.0 out of 5 average rating, 15 reviews
Cabin at Spring Meadow Farm
5.0 out of 5 average rating, 59 reviews
Lemon House
4.8 out of 5 average rating, 71 reviews
Updated home w/ BIG yard, game room, coffee nook!
4.97 out of 5 average rating, 77 reviews
Beauty on Berkshire
4.94 out of 5 average rating, 53 reviews
Newly Remodeled 3BR Near Scenic Overlook
5.0 out of 5 average rating, 16 reviews
3 beds/2 bathrooms/1 shower/Ranch home/3+acres
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