Holiday rentals in Upland

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Top-rated holiday rentals in Upland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Santa Ana

4.92 out of 5 average rating, 193 reviews

Charming Private Casita-Spacious Patio-Near Disney

Newly built, private one bedroom, one bathroom unit with large outdoor patio. It is fully furnished and fully stocked with kitchen appliances and items to cook at home. Minutes away from downtown Santa Ana, this home is nearby to all of which OC has to offer: Disneyland, Knott’s, Newport & Huntington Beach, South Coast Plaza, Angel Stadium and more! Please note that although the unit is attached to a main house, there is a separate entrance and there is no direct contact with the owner.

Guest favourite

Chalet in Running Springs

4.98 out of 5 average rating, 215 reviews

100 Mile View:Your Romantic Stay

As you relax on the deck, a million city lights twinkle beneath the spectacular sunset. You're conveniently close to Lake Arrowhead, the "Alps of Southern California" This retreat, nestled on a cliff's edge, offers expansive views from Mt. Baldy to Catalina Island on clear days. It’s the perfect spot for a much-needed family vacation, or a romantic time together. For reservations, please provide the age categories of all guests during booking; this is essential for approval. Thank you

Guest favourite

Home in Lake Arrowhead

4.91 out of 5 average rating, 67 reviews

Lake Front Modern Luxury

Magnificent 2800sqft, 4 bedroom, 5 bath, 3 level PERMITTED vacation rental luxury home nestled in gated community. Extensive lake trail system for hiking and wonderful trails available through San Bernardino Park system. Short distance to Arrowhead Village with multiple restaurants, bars and shopping. The yard is beautifully maintained complete with two lawn sides, BBQ, and lounging areas. There are multiple balconies allowing you to splendor over the beautifully landscaped grounds.

Top guest favourite

Home in Lake Arrowhead

5 out of 5 average rating, 23 reviews

Arrowhead Cabin Located next to Village & Lake

Located 5 minute walking distance to Arrowhead Village. Quick access to Stater Brothers, village shops, weekend entertainment, restaurants and the lake. Perfect cabin for connecting in a peaceful environment with friends and those you love. Newly astroturfed yard, surrounded by a grove of trees. Unique art decorates the house, with new beds and comfortable furnishings. Always kept clean and up to date. The perfect get away, to reconnect with each other, yourself and nature.

Superhost

Flat in Santa Ana

4.75 out of 5 average rating, 4 reviews

Stunning 1BR Beach Retreat: Gorgeous Views Await

Experience coastal living at its finest in this charming 1-bedroom apartment with breathtaking views of the bay. Perfect for a romantic getaway or solo retreat, the space features a cozy living area, fully equipped kitchen, and a comfortable bedroom with ocean-inspired decor. Enjoy your morning coffee or evening wine on the balcony as you take in the stunning scenery. Located just minutes from the beach, dining, and shopping, this is your ideal escape by the sea!

Guest favourite

Home in Lake Arrowhead

4.98 out of 5 average rating, 104 reviews

The Maple Cottage: family cabin by @themaplecabins

Located in Palisades neighborhood, The Maple Cottage is a charming, family friendly cottage outfitted with stylish decor and all the comforts of home your family needs for the perfect mountain getaway. Enjoy the lake trail accessible from the cottage. The home is surrounded by massive oak trees that you can sit under on the patio while enjoying your morning coffee. At night you can sit under the giant canopy of oak trees with the kids roasting marshmallows.

Superhost

Cabin in Lake Arrowhead

4.86 out of 5 average rating, 551 reviews

Cozy Pine Cottage – Walking Distance to the Lake

Step back in time at Cozy Pine Cottage, a beautifully restored two-story 1930s-style cabin thoughtfully upgraded with all the modern comforts you need. Tucked away in a peaceful, scenic setting, this charming retreat is ideally located—just a short walk to Lake Arrowhead Village, Lake Arrowhead Brewing Co., and picturesque mountain trails. Whether you're here to relax, explore, or reconnect, Cozy Pine Cottage offers the perfect mountain escape.

Superhost

Home in Lake Arrowhead

4.89 out of 5 average rating, 121 reviews

Whispering Pine Boho, AC, Dog Friendly, In Village

Located in Lake Arrowhead Village, Whispering Pine Lodge features 4 bedrooms, 2 baths, gourmet kitchen, great room, deck with BBQ & fire pit, fireplace, AC, high-end furnishings, appliances, and home entertainment. Newly remodeled and professionally decorated 3 level home sleeps 8 with parking for 2 vehicles. Dog friendly. 2-minute drive to village. Combined marketplace total of 190+ Five Star guest reviews from online travel agencies.

Top guest favourite

Cabin in Lake Arrowhead

4.99 out of 5 average rating, 252 reviews

Mile High Haus, by @To_Dwell_Here

Will it be the views or the architecture that wows you more? Both are stunning. This premier property (built in 2019 by the mountain area's top builder) is unmatched in all Lake Arrowhead. We cannot wait for you to fully escape real life by grilling on the deck, reading by the wood burning Malm fireplace, swinging in the hammock, or soaking in the tub. Before you even depart, you'll be planning you next getaway to the Mile High Haus.

Guest favourite

Home in Lake Arrowhead

4.81 out of 5 average rating, 108 reviews

Lake Home in the Pines with a Dodger History

Prior home of the Fred Claire family (Dodger General Manager). This home is nestled on a quiet lane in the heart of the forest, this tri-level beauty epitomizes the warmth and beauty of Lake Arrowhead with casual elegance and refined details. Location! Location! 5 min drive to The Lake, Village, Beach, Lake trail, Sky Park and great restaurants. This is an all season vacation rental with warm summer days, and snow in the winter.

Guest favourite

Cabin in Running Springs

4.93 out of 5 average rating, 408 reviews

Rocky Top Retreat- Amazing Views!

You will love the peacefulness of this cozy hilltop cabin. This cinder block home sits in a quaint Arrowbear community just up the hill from a seasonal lake. Trees & large boulders abound on the property, provide surroundings you are sure to appreciate. Situated between Lake Arrowhead & Big Bear you are just a short drive to either. Relax on the front deck or enjoy the serenity of the back patio with amazing views.

Guest favourite

Home in Lake Arrowhead

4.94 out of 5 average rating, 117 reviews

Stunning A Frame, Great room, Loft, AC, In Village

Located in Lake Arrowhead Village, Treetop Cabin features 3 bedrooms, 2 baths, gourmet kitchen, great room, deck with BBQ & fire pit, fireplace, AC, high-end furnishings, appliances, and home entertainment. Professionally remodeled and decorated 2 level home sleeps 8 with parking for 2 vehicles. Dog friendly. 2-minute drive to village. 300+ Five Star guest reviews from online travel agencies.