North Upper Street vacation rentals
We found 130 vacation rentals — enter your dates for availability
Discover a selection of vacation rentals in North Upper Street that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll have the best amenities for spending time at your home away from home, such as WiFi and cable TV. You're sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.
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Find the best place to stay - North Upper Street

Upscale downtown Lexington townhome
Sleeps 10 · 5 bedrooms · 4+ bathrooms

Elegant & Historic 1805 Thomas January Hemp House
Sleeps 9 · 3 bedrooms · 2 bathrooms

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Sleeps 3 · 1 bedroom · 1 bathroom

Mid-Century 3 BR In Heart of Downtown Lex
Sleeps 6 · 3 bedrooms · 2 bathrooms

Graffiti Art Haus - Walk to Central Bank Arena
Sleeps 4 · 1 bedroom · 1 bathroom

Historic Mansion in Downtown Lexington.
Sleeps 6 · 3 bedrooms · 3+ bathrooms
Top rated rentals - North Upper Street

50th Reunion Getaway
Lovely property with 3 en suites. Great location near good restaurants and UK Ropp Arena. House is well equipped with all the amenities necessary for your stay. Property manager is pleasant and easy to deal with. Highly recommend this property
Kathy b.
Stayed Oct 2024

Keeneland trip
The unit is nice inside. There are some shared spaces which is unusual for VRBO. The owner was using the back deck with family which was fine with us since we were going out but something to be aware of. If we planned to grill out that night it would have been a little awkward. They do have 2 beautiful dogs which we enjoyed meeting and petting.
Todd C.
Stayed Apr 2024
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
How much does it cost to rent a vacation home in North Upper Street?
Prices for vacation rentals in North Upper Street vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in North Upper Street to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for North Upper Street vacation house rentals?
You can find great discounts on house rentals in North Upper Street on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any North Upper Street vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in North Upper Street with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in North Upper Street?
A long-stay vacation rental in North Upper Street is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit North Upper Street for a vacation rental?
The best time to visit North Upper Street is during the peak season from March to May, when visitors can enjoy the vibrant setting and pleasant weather. This period is characterized by blooming flowers and mild temperatures, typically ranging from the mid-50s to the low 80s Fahrenheit, making it ideal for outdoor activities and sightseeing. As you stroll through the charming streets, you'll find various local events and festivals that showcase the community's rich culture and hospitality.July is also a popular month for visitors, with warm weather and a lively environment, great for those looking to immerse themselves in the local scene. However, if you prefer a quieter experience while still enjoying the region's beauty, consider planning your trip in October. This month offers lovely fall foliage and comfortable temperatures, allowing you to explore local parks and historical sites without the crowds.Regardless of when you choose to visit, North Upper Street provides a friendly setting and plenty of opportunities for adventure and relaxation.
How early should I book a North Upper Street vacation rental?
Book your North Upper Street vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in North Upper Street, Kentucky, United States of America?
In North Upper Street, Kentucky, visitors can enjoy a range of attractions that reflect the area's rich culture and history. The neighborhood is close to the University of Kentucky, where you can explore the beautiful campus and visit the UK Art Museum, showcasing a diverse collection of artworks. The nearby Lexington Cemetery, known for its stunning landscapes and historic monuments, offers a peaceful setting for a reflective stroll.Additionally, the vibrant downtown area is just a short distance away, featuring a variety of shops, restaurants, and live music venues. The Lexington Opera House and the historic Kentucky Theatre are popular spots for those interested in performing arts. For a taste of local culture, the Lexington Farmers' Market provides fresh produce and crafts, typically held in the warmer months.
Can I change or cancel my North Upper Street home rental booking on Vrbo?
To find North Upper Street vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.
Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the North Upper Street vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.
If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.
Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.
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