Best Vacation Homes in Highland
New
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
Parking
Kitchen
Air Conditioner
Internet
US $214/Night
7 Nights - US $1,495
House
10.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
3196.88 ft²
- Parking
- Internet
Pet Friendly
Child Friendly
US $571/Night
7 Nights - US $3,999
Bed & Breakfast
10.0(27 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Balcony/Terrace- Internet
US $279/Night
7 Nights - US $1,954
New
House
9.6(18 Reviews)
4 Bedrooms
3 Baths
8 Guests
3195 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $506/Night
7 Nights - US $3,542
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
3 Guests
602.78 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $127/Night
7 Nights - US $891
New
Condo
2 Bedrooms
1 Bath
3 Guests
1250 ft²
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $194/Night
7 Nights - US $1,355
New
Condo
2 Bedrooms
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $119/Night
7 Nights - US $836
New
Apartment
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $110/Night
7 Nights - US $770
Highland Luxury Rentals
Bed & Breakfast
5 Bedrooms
5 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,824/Night
7 Nights - US $12,766
Apartment
1 Bedroom
1 Bath
1 Guest
- Air Conditioner
- Internet
Security/Safety
US $636/Night
7 Nights - US $4,453
House
6.6(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
1300 ft²
Private Pool- Parking
Pool- Balcony/Terrace
US $462/Night
7 Nights - US $3,236
Cottage
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $460/Night
7 Nights - US $3,220
Hotel
8.6(1002 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $330/Night
7 Nights - US $2,307
House
3 Bedrooms
2 Baths
6 Guests
1302.43 ft²
- Parking
- Pool
- Balcony/Terrace
- Internet
US $322/Night
7 Nights - US $2,254
Hotel
9.0(430 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $321/Night
7 Nights - US $2,247
Hotel
8.9(148 Reviews)
8 Baths
369.56 ft²
Oceanfront- Breakfast
- Parking
- Pool
US $316/Night
7 Nights - US $2,210
Highland Pet Friendly Vacation Rentals
House
9.4(6 Reviews)
1 Bedroom
1 Bath
4 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $191/Night
7 Nights - US $1,337
US $189/Night
7 Nights - US $1,324
Apartment
9.0(770 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $140/Night
7 Nights - US $981
House
10.0(28 Reviews)
3 Bedrooms
2 Baths
7 Guests
Hot Tub- Parking
- Pool
- Balcony/Terrace
US $274/Night
7 Nights - US $1,916
Hotel
8.9(31 Reviews)
2 Baths
522.05 ft²
- Private Pool
- Breakfast
EV Charge Station- Parking
US $209/Night
7 Nights - US $1,463
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $316/Night
7 Nights - US $2,213
House
3 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $395/Night
7 Nights - US $2,764
House
10.0(1 Review)
4 Bedrooms
6 Baths
12 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $947/Night
7 Nights - US $6,628
Highland Large Vacation Homes
House
10.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $260/Night
7 Nights - US $1,821
House
8.8(6 Reviews)
5 Bedrooms
3 Baths
14 Guests
22604 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $705/Night
7 Nights - US $4,938
Other
10.0(6 Reviews)
6 Bedrooms
5 Baths
17 Guests
- Private Pool
- Pool
- Air Conditioner
- Internet
US $1,015/Night
7 Nights - US $7,102
House
5 Bedrooms
3 Baths
13 Guests
3365 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $620/Night
7 Nights - US $4,339
House
10.0(1 Review)
6 Bedrooms
7 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $954/Night
7 Nights - US $6,678
House
4.8(29 Reviews)
8 Bedrooms
5 Baths
6 Guests
5000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $721/Night
7 Nights - US $5,047
House
7 Bedrooms
4 Baths
22 Guests
4500 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
US $579/Night
7 Nights - US $4,055
House
15 Bedrooms
1 Bath
30 Guests
15000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $300/Night
7 Nights - US $2,100
Why Choose Rent By Owner for your Highland Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Highland
When should you plan your Vacation Rentals stay?
Timing your visit to this destination can greatly enhance your experience, as the region offers distinct seasonal attractions and weather patterns that cater to a variety of interests throughout the year.
Peak Season Highlights
Spring (March to May)
During springtime, the area experiences pleasant weather that is ideal for exploring outdoor activities and enjoying the scenic beauty.
Average Temperature Daytime: 60-75°F - Nighttime: 45-55°F
Fall (September to November)
Autumn brings stunning foliage and comfortable temperatures, making it a perfect time for outdoor adventures and experiencing the region’s natural charm.
Average Temperature Daytime: 65-70°F - Nighttime: 50-55°F
Off-Season Highlights
Summer (June to August)
The warm summer months attract visitors seeking outdoor recreation and leisurely activities, often leading to busier travel periods overall.
Average Temperature Daytime: 80-85°F - Nighttime: 60-65°F
Winter (December to February)
In winter, the cooler temperatures and occasional snow create a quieter atmosphere, ideal for those looking for a peaceful retreat in this destination.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Weekly Weather Forecast for Highland
How to Book Your Highland Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Highland
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor lounging areas with comfortable seating to relax under the sun.
- Take advantage of private or shared patios perfect for dining al fresco with scenic views.
- Make the most of landscaped gardens or yards that provide a peaceful setting for outdoor activities.
- Utilize outdoor grills or barbecue facilities for enjoyable cookouts in the fresh air.
- Benefit from access to outdoor recreational spaces, such as walking trails or bike paths nearby.
- Relax by a private pool or hot tub, ideal for unwinding after exploring the region.
- Discover outdoor sports amenities like tennis courts or basketball hoops available at some properties.
Top Attractions Around Highland
What attractions are nearby?
While staying in this charming area, you can enjoy a variety of outdoor activities and scenic attractions just moments from your Highland vacation rentals in Maryland.
Family Activities
- Adventure Park USA: Experience family-friendly fun at this amusement park, offering rides, go-karts, and entertainment suitable for all ages in the region.
- Gathland State Park: Explore scenic trails, picnic areas, and historical sites nestled within this natural preserve, perfect for outdoor family outings in this destination.
- Highland Community Center: Participate in engaging recreational activities, arts and crafts, and sports programs designed to entertain children and parents alike here.
- The Maryland Agricultural Education Center: Discover farm exhibits, interactive displays, and seasonal events that educate and entertain your family in the local area.
Adult Activities
- Exploring local history at the Howard County History Center: Discover the area's rich heritage and fascinating exhibits to deepen your appreciation of the region.
- Enjoying outdoor pursuits at Centennial Park: Engage in relaxing walks, picnics, or sports within this scenic park situated nearby, offering a peaceful retreat in the area.
- Shopping and dining in downtown Columbia: Experience the vibrant local scene with diverse restaurants, boutique stores, and entertainment options that reflect the region's charm.
- Participating in cultural events at local community centers: Attend workshops, performances, and festivals that showcase the area's lively arts and culture scene.
Highland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Guidelines: Familiarize yourself with any regional regulations or guidelines to ensure a smooth and trouble-free stay in this area.
- Plan Nearby Activities: Take advantage of this destination's local attractions and outdoor spaces to make the most of your visit here.
- Choose Convenient Accommodation: Select a vacation rental that offers easy access to key sites and amenities, enhancing your overall experience in the region.
- Pack Smart for the Climate: Prepare appropriate clothing based on the area's weather patterns to stay comfortable during your stay here.
Transportation Options
- Washington Metro & MARC Train: Providing convenient rail options, this regional transit system connects the area to Washington D.C. and surrounding communities, making it easy for you to explore nearby attractions.
- Bus Services: Local bus routes serve the region, offering affordable transportation that allows you to navigate Highland and its vicinity comfortably.
- Car Rentals: Numerous car rental agencies operate in the area, giving you the flexibility to drive at your own pace while exploring Highland and neighboring destinations.
- Taxi and Rideshare Services: Modern taxi companies and rideshare apps are readily available here, providing quick and reliable transportation for day trips or evening outings.
Local Customs Options
- Southern Hospitality:** You may notice the warm and welcoming attitude of locals who value politeness and friendliness, reflecting the area's deep-rooted Southern hospitality.
- Community Celebrations:** Participating in seasonal festivals and parades is a common tradition here, showcasing the region’s strong sense of community spirit.
- Local Cuisine Etiquette:** When dining out or sharing meals, expect an emphasis on generosity and good manners, which are integral to the area's social customs.
- Respect for Nature:** There is a notable appreciation for outdoor activities and environmental preservation, encouraging visitors to engage respectfully with the natural surroundings of the region.
Highland Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Highland?
There are a lot of options in Highland. If you plan on staying in the Highland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland:
- Rancher, pets welcome, Wash/Balt/Annplis family friendly Pool table, deck, river
- Inn at Mary's Land Farm
- Cozy Private Apartment in Columbia King Bed Free Parking
- Nature Getaway w/On-Site Trails, 17 Mi to DC!
- Bright spacious 5 bedroom home, Easy Access DC/Baltimore/Annapolis
- Private ground-level studio suite
- Cozy Private Apartment in Columbia -King Bed
- Private Basement Studio with Patio in Columbia, MD
- Residence Inn Fulton at Maple Lawn
- Nature Getaway w/On-Site Trails, 17 Mi to DC!
2. Which vacation homes in Highland are best for families?
If you are looking for a family-friendly vacation home in Highland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland:
3. How many Rentbyowner vacation rentals are available in Highland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 90 in the Highland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Highland.
4. What is the cancellation policy for vacation rentals in Highland, Maryland?
Cancellation policies vary by property. You should review the specific cancellation terms listed on the property’s page or contact the owner directly to understand your options before booking.
5. How do I find pet-friendly vacation rentals in Highland, Maryland?
Pet-friendly options are available in this area; you can filter your search to include properties that allow pets and check the listing details for any restrictions or additional fees.
6. Are there specific check-in and check-out times for rentals here?
Check-in and check-out times are set by each property owner. Be sure to review the listing details or contact the host directly to confirm the designated times for your stay.
7. What amenities are typically included in Highland vacation rentals?
Amenities vary per property but often include essentials like Wi-Fi, parking, and kitchen facilities. Detailed information about amenities is available on the property listing page.
8. How can I ensure my reservation is secure when booking in this region?
Booking through a reputable platform offers secure payment methods and verified listings. Always read reviews and communicate with the owner if you have any concerns before confirming your reservation.
Highland Top Rated Vacation Rentals
Hotel
9.6(162 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $270/Night
7 Nights - US $1,890
US $145/Night
7 Nights - US $1,012
Other
10.0(77 Reviews)
1 Bedroom
1 Bath
5 Guests
576 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $658/Night
7 Nights - US $4,609
Apartment
10.0(27 Reviews)
2 Bedrooms
1 Bath
2 Guests
1035 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $241/Night
7 Nights - US $1,686
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1320 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $203/Night
7 Nights - US $1,421
House
8.8(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Breakfast
- Parking
- Pool
US $389/Night
7 Nights - US $2,723
Apartment
4.0(1 Review)
1 Bedroom
2 Baths
4 Guests
1100 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $254/Night
7 Nights - US $1,779
Apartment
1 Bedroom
2 Baths
4 Guests
1100 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $237/Night
7 Nights - US $1,662
