Highland places to stay

Book unique places to stay, houses, and more on Airbnb

Top-rated places to stay in Highland

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

Tiny home in San Bernardino

4.87 out of 5 average rating, 261 reviews

#1 Cozy Tinyhouse "Route 66" container- private

Peaceful, rural neighborhood- No Smoking property, NO animals allowed due to health conditions. Right in the center of all: 1.5 hour or less to Santa Monica, Venice Beach, Huntington Beach, less than 2 hours from San Diego, 3 hours to Las Vegas, 5 min from the world famous motocross track, Glen Helen Amphitheater, Route 66, and hot spot for paragliding is close by. CozyTiny Container home is private, with all comforts. Peaceful, calm at the foot of the mountains with 1 dedicated parking spot.

Mar 15 – 22

G$19,010 GYD per night

Guest favorite

Guesthouse in Yucaipa

4.98 out of 5 average rating, 124 reviews

Yucaipa's Cottage on a Hill

Welcome to our quiet country cottage located on top of a hill overlooking the canyon and City of Yucaipa. With all the amenities you'll need during your stay, you will feel right at home. Less than five minutes to the freeway, your home away from home will be the perfect place to rest your head at the end of the day. The Cottage is the central location to LA, the beaches, Disneyland, Palm Springs, San Diego and the mountains. And if you don't want to leave, there's plenty to do right here!

Jul 9 – 16

G$26,919 GYD per night

Guest favorite

Guesthouse in Redlands

4.99 out of 5 average rating, 276 reviews

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

Located in beautiful South Redlands near Prospect Park, this detached cottage has its own private and inviting fenced backyard, nicely landscaped with comfortable patio furniture. Inside you will find separate living and bedroom spaces, charming decor, Heating/A/C, Cable TV, WIFI, kitchenette with microwave, Keurig coffee maker and compact refrigerator, fine linens, comfortable queen sized bed, and newer bathroom. Conveniently located near Downtown Redlands, University of Redlands and ESRI!

Dec 29 – Jan 5

G$27,485 GYD per night

Guest favorite

Guesthouse in San Bernardino

4.82 out of 5 average rating, 147 reviews

Guesthouse Surprise W/Loft

This private and stylish guest house is perfect for group trips or the single traveler. Will sleep 4 adults and 1 kid with a Q bed, Q leather sofa fold out and a D futon. Quality bedding and pillow top mattress are very comfortable. K-Cups of coffee are provided along with bath sheets. Work at the desk or watch the game on the 50" big screen. Close to Yaamava Casino, Glen Helen Amphitheatre, Crestline, and three major hospitals. It's quiet and peaceful. Smoke outside only. Ice-cold A/C

May 18 – 25

G$22,177 GYD per night

Guest favorite

Guest suite in Redlands

4.88 out of 5 average rating, 352 reviews

(2) Downtown Redlands Retreat: Cozy Master Suite

This is a nice master bedroom, converted to a guest suite. The room has a private entrance, and private bathroom. Walls were recently torn down & made sound proof so as to not disrupt our guest with noises inside the house. This house has a lot of history, it’s over 120 years old. It’s perfectly situated about a minute away from the freeway is a central locations, in the beautiful & historic city of Redlands. Security cameras recording at all times all around the outdoors of the property.

May 27 – Jun 1

G$19,979 GYD per night

Guest favorite

Apartment in Redlands

4.93 out of 5 average rating, 101 reviews

2-BDR attached apt in rural Redlands neighborhood.

We are located in the So Cal Inland Empire, 1 mile off the 10 freeway. We are near University of Redlands, Historic Downtown Redlands, numerous restaurants, as well as Oak Glen apple farms. We are 60 miles or less from Palm Springs, Disneyland, Casinos, Big Bear or Mountain High skiing and not far from Los Angeles and San Diego. It's a semi-quiet neighborhood with beautiful views of the local mountains. You will have a clean bedroom, bathroom, and a full kitchen and living room area.

Aug 11 – 18

G$21,602 GYD per night

Guest favorite

Guest suite in Redlands

4.98 out of 5 average rating, 199 reviews

Amazing Large 1 Bedroom, No Chores Home

Bring the whole family to this wonderful place in the heart of Loma Linda. The bedroom has its own retreat with a sleeper sofa for the kids or friends. Within a couple of miles you have Loma Linda University and Loma Linda VA. A couple miles East and you are in Downtown Redlands where you have entertainment, plentiful restaurants, and nightlife. Or enjoy the peaceful citrus trails this beautiful neighborhood offers which lead you to large parks where you can enjoy a picnic.

Sep 20 – 27

G$29,155 GYD per night

Guest favorite

Guesthouse in Fontana

4.95 out of 5 average rating, 106 reviews

The Blue Cabin

Relax at this unique, tranquil, and comfortable mini home in our backyard. Surrounded by a beautiful garden with a wide variety of succulents and a relaxing pool. With a space to enjoy reading or listening to music. Equipped with microwave, Keurig coffee machine, mini refrigerator, toaster, blender, washer/dryer, and tableware. The mini home has air conditioning and heating system for comfort and a smart TV. (SPACE EQUIPPED ONLY FOR 2-3 PEOPLE *no more than 3 fit*)

Aug 2 – 9

G$27,904 GYD per night

Guest favorite

Guest suite in Riverside

4.97 out of 5 average rating, 671 reviews

PARADISO RETREAT with VIEWS - DOWNTOWN RIVERSIDE

Step inside this beautiful, private guest suite with large patio to enjoy spectacular views. Just minutes away from Downtown Riverside and direct access to Mount Rubidoux many hiking trails. Due to COVID-19, we are taking extra care to disinfect the Suite between reservations with our enhanced cleaning routine. We are within 1 hr drive to : * Palm Springs * Hollywood * San Diego * Laguna Beach * Joshua Tree National Park * Indio/Coachella * Big Bear Ski Resort

Sep 28 – Oct 5

G$23,208 GYD per night

Guest favorite

Guesthouse in Redlands

5.0 out of 5 average rating, 179 reviews

"Garden of Eden" Farmstyle Private Back House

Located in beautiful South Redlands near Prospect Park, this detached studio with private entrance will give you all the cozy farmhouse vibes you are looking for! Inside you will find a charming farmhouse decor with a Redlands theme. There is a separate living and bedroom space, heating/AC, newly renovated kitchen with a refrigerator, stove, oven and microwave, comfortable full size bed, fine linens and a large bathroom.

Jul 21 – 28

G$26,303 GYD per night

Guest favorite

Guesthouse in Redlands

4.95 out of 5 average rating, 120 reviews

Industrial Modern Studio blocks from Downtown

Brand new, modern studio with vaulted ceilings and lots of natural light. Our property is 1.5 miles away from Downtown Redlands located in a quiet neighborhood off of the historic Olive Avenue. We have provided a full-sized kitchen, laundry facilities, and walk-in shower. During your stay, you may be greeted by our golden retriever Cedar. He is a service animal and trained as a therapy dog and would love to say hi!

Aug 1 – 8

G$32,254 GYD per night

Guest favorite

Guesthouse in Highland

4.96 out of 5 average rating, 225 reviews

Serene Escape Tiny House Living with pool access

Close to dining , hiking, shopping, movie theaters, National Orange Show Event Center NOS, Yaamava Resort and Casino, and some nightlife. You’ll love my place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. Our place is good for couples, solo adventurers, and business travelers. Perfect little getaway! I have another listing-click on my photo to view.

Feb 16 – 23

G$19,065 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Highland places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Highland

Guest favorite

Home in Lake Arrowhead

4.93 out of 5 average rating, 322 reviews

Romantic Mountain cabin with full AC & EV charging

May 4 – 11

G$22,478 GYD per night

Superhost

Guest suite in Redlands

4.92 out of 5 average rating, 158 reviews

Redlands Peaceful One Bedroom Suite w/Access to a

Nov 7 – 14

G$29,868 GYD per night

Superhost

Home in San Bernardino

4.89 out of 5 average rating, 106 reviews

Hidden Casita with Jacuzzi, newly remodeled.

Dec 31 – Jan 7

G$38,306 GYD per night

Superhost

Cabin in Crestline

4.84 out of 5 average rating, 223 reviews

Your Favorite Cozy Modern Little Cabin! 🏞

Nov 10 – 17

G$26,173 GYD per night

Guest favorite

Cottage in San Bernardino

4.94 out of 5 average rating, 269 reviews

Adorable Cottage, base of Beautiful Mountains

Aug 10 – 17

G$34,954 GYD per night

Guest favorite

Guesthouse in Riverside

4.98 out of 5 average rating, 181 reviews

BRAND NEW CALIFORNIA COTTAGE

Feb 28 – Mar 7

G$27,399 GYD per night

Guest favorite

Cabin in Running Springs

4.96 out of 5 average rating, 161 reviews

Cozy A-Frame Cabin Nestled In The Mountains

Jul 18 – 25

G$29,449 GYD per night

Guest favorite

Cabin in Rimforest

4.91 out of 5 average rating, 551 reviews

1930 Cozy One Bedroom Lake Arrowhead Cabin

Aug 1 – 8

G$17,296 GYD per night

Show all

Other great vacation rentals in Highland

Guest favorite

Guesthouse in San Bernardino

4.87 out of 5 average rating, 54 reviews

B&G Studio Space Guesthouse

Nov 21 – 28

G$21,675 GYD per night

Superhost

Apartment in San Bernardino

4.89 out of 5 average rating, 18 reviews

SB Beautiful Stay

May 23 – 30

G$20,867 GYD per night

Guest favorite

Guest suite in San Bernardino

4.99 out of 5 average rating, 94 reviews

All New cozy SUITE in Arrowhead Country Club!

Sep 16 – 23

G$24,838 GYD per night

Superhost

Guesthouse in Redlands

4.85 out of 5 average rating, 41 reviews

Peaceful Detached Studio

Jul 1 – 8

G$18,477 GYD per night

Guest favorite

Apartment in San Bernardino

4.95 out of 5 average rating, 61 reviews

Amber Cove - Gorgeous 1-bedroom luxury apartment

Sep 17 – 24

G$27,566 GYD per night

Guest favorite

Home in Mentone

4.93 out of 5 average rating, 43 reviews

Sasvari Inn - A Home Away from Home

Jun 25 – Jul 2

G$22,357 GYD per night

Guest favorite

Guesthouse in San Bernardino

5.0 out of 5 average rating, 13 reviews

Private Casita - Near NOS Events Center | Yaamava

Jun 14 – 21

G$32,044 GYD per night

Guest favorite

Home in Highland

4.96 out of 5 average rating, 27 reviews

Cactus Casino- w/game room-next to Yaamava Casino!

Oct 2 – 9

G$87,708 GYD per night

Show all

Quick stats about vacation rentals in Highland

Total rentals
60 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
3.2K reviews
Nightly prices starting at
G$4,180 GYD before taxes and fees

Frequently Asked Questions

How much does it cost to stay in house rentals in Highland?
Experience the best of Highland with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Highland?
Yes! Work meets play with ease at over 20 house rentals in Highland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Highland?
Make yourself at home in Highland by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in East Highlands, and over 240 vacation rentals in North Redlands.
Do house rentals in Highland have wifi?
Absolutely! We offer over 40 house rentals with wifi in Highland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Highland have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Highland. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Highland?
Four-legged friends are welcome in Highland. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Highland?
Highland has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Highland?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Highland places to stay

Top-rated places to stay in Highland

Vacation rentals for every style

Cottages

Houses

Cabins

Popular amenities for Highland places to stay

Other great vacation rentals in Highland

Home in Lake Arrowhead

Guest suite in Redlands

Home in San Bernardino

Cabin in Crestline

Cottage in San Bernardino

Guesthouse in Riverside

Cabin in Running Springs

Cabin in Rimforest

Other great vacation rentals in Highland

Guesthouse in San Bernardino

Apartment in San Bernardino

Guest suite in San Bernardino

Guesthouse in Redlands

Apartment in San Bernardino

Home in Mentone

Guesthouse in San Bernardino

Home in Highland

Quick stats about vacation rentals in Highland

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

How much does it cost to stay in house rentals in Highland?

Are there house rentals with a dedicated workspace in Highland?

Where should I stay in Highland?

Do house rentals in Highland have wifi?

Do house rentals in Highland have air conditioning?

Are there pet-friendly vacation rentals in Highland?

Are there family-friendly house rentals in Highland?

What are the most popular amenities for House Rentals in Highland?

Destinations to explore