
Holiday houses in Highland
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Top-rated holiday rentals in Highland
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Riverfront Boho Penthouse-Loft•Jacuzzi•Balcony
The perfect place to unwind! Master room boasts a super comfy king bed, a stylish built-in wall dresser, cozy fireplace, as well as a riverfront balcony. The Loft is great for lovers of Boho style, queen bed w/ ample space to stretch out for yoga as well as a private crow’s nest balcony! 3rd bed(twin) can be found in a repurposed library room. Take a dip in the jetted jacuzzi tub w/ a sunset view! A full kitchen awaits your cooking needs! Large private dressing/makeup room is a favorite!
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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!
LocationFamilyIndoor spaces

Cozy House in a Great Area
This charming 2-bedroom home is beautifully decorated with great amenities including high-end appliances, well appointed furnishings, and is equipped with high-speed Wifi. It is located in a great area that is close everything while having easy interstate access, but also within walking distance to a salon and neighborhood pub. You will love your stay with us, because we have taken the time to ensure that it is not only clean and comfortable, but that you also have all of the amenities of home.
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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.
LocationFamilyAir conditioning

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!
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The Historic Savannah Reporter Venue
The First Floor 1800 square foot space provides a Great Room perfect for entertaining and stretching out. Set right off the Savannah Square you have a blend of retail and residential neighborhoods nearby for comfortable walks. Four Bedrooms offer space for family members to have privacy while sharing a large common living space. Known to locals as the "Reporter Building" this was built in 1892 to house the newspaper printing press and was converted to living quarters in the last 20 years.
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Loft C in downtown St. Joseph
This amazing property is located in the heart of downtown St. Joseph and is within walking distance of coffee shops, local dining and shopping. This 1 bedroom loft apartment is located on the 2nd story of the building with great views of the historic downtown. There is street parking on both sides of the building, keypad entrance with personal code, free WiFi and YouTube TV. The living room has a sofa bed, couch, love seat and ottoman, full kitchen with bar seating and a spacious bathroom.
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Rustic Waterfront 2 BR Cabin Stunning Sunset View!
Take it easy in this rustic cabin duplex. Enjoy a huge yard on both sides of the house, a large concrete patio, grill, and many places for a riverfront fire. There is a train that passes by the distance of 2 blocks away and blows its horn, but not to worry, while inside, the horn is hardly noticeable thanks to the multi-layered, sound deadening windows. Enjoy the hammock, hanging swing chair, or the porch swing. 2 bedroom, Wifi, central heat/air, full kitchen, coffee maker, etc!
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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.
LocationFamilyWalkability

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.
FamilyValueHospitality

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
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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.
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Popular amenities for Highland holiday rentals
Other great holiday rentals in Highland

A 3-bedroom 2nd floor atop local diner.
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Cozy Cactus Retreat 4bd/2bth St Joe/Savannah area
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Falls City Gathering Home
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Red Rock Loft | *Pet Friendly Hunters Dream*
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The Grain Bin at Big Lake
LocationFamilyHospitality

Timber Creek Cabin
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Cabin at Spring Meadow Farm
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Sleeps 1-3 ~ Clean, Stylish, Close to BC
LocationFamilyIndoor spaces
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