Vacation rentals in Upland

4.93 out of 5 average rating, 171 reviews

The exterior of the home features a cozy cabin-style design set among tall trees. A covered balcony overlooks the yard, while lush greenery surrounds the property. A well-maintained pathway guides to the entrance, highlighting the inviting atmosphere of this pet-friendly retreat.

Chalet in Twin Peaks

Clubhouse Lodge 3 BR w/ Romantic Master Suite

*Pet-friendly home nestled in the trees, this lovely 3 bedroom detached single family home with private front and back yards. Relax in the romantic Master Suite with private balcony a views of the surrounding trees. Escape the city within an hour's drive & unwind amongst nature with all the comforts of home. Eat alfresco in one of the multiple outdoor entertainment areas. Enjoy all the amenities of home while having a Mountain Experience. Self check-in *Pets must be requested in reservation

4.98 out of 5 average rating, 57 reviews

A modern kitchen showcases white cabinetry and sleek countertops. Included are a refrigerator, microwave, and coffee maker, with a small dining area featuring two wooden stools. Natural light enters through a window, enhancing the bright atmosphere.

Guesthouse in Whittier

The Backyard Retreat

Bright, private, 2-bedroom guesthouse with high ceilings & excellent A/C in every room. Located in a family-friendly suburb of LA, near Disneyland and Knott’s Berry Farm! There is one queen size bed in each of the bedrooms. Unit is ompletely separate from the main residence with its own outdoor space, and dedicated workspace for remote work. Near Biola University & Whitter College. Sleeps a max of four people. Please note: no smoking inside or outside Airbnb (tobacco/cannabis/other).

4.95 out of 5 average rating, 306 reviews

A Cozy Cabin in Lake Arrowhead

Come stay at IRONWOOD CABIN. A COZY mountain getaway in LAKE ARROWHEAD. Enjoy BBQ-ing, sipping wine by the FIRE PIT and watching the SUNSET from the LARGE DECK above the trees with a beautiful view. Come to Ironwood Cabin and enjoy the mountains, air and nature. The bedrooms are large and the beds are new and incredibly comfortable. Just 10-15 minute drive to historic Arrowhead Village and very close to Blue Jay Village. Everything you need is here to relax and unwind. (3 portable AC units).

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

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.

A charming cabin exterior is framed by tall trees, showcasing a sloped roof and large windows. The entrance features a green door, with a pathway of stone leading to it. Newly astroturfed yard is visible, adding a touch of greenery to the inviting surroundings.

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.

A charming cottage exterior is depicted, featuring a white facade with gray shingles. Two inviting chairs are positioned on the brick walkway, leading to the front door adorned with a decorative wreath. Lush greenery surrounds the property, enhancing its welcoming appearance.

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.

The interior space features a high-beamed ceiling with a rustic chandelier. A stone fireplace serves as a focal point in the living area, surrounded by seating and a television. A dining table with wooden chairs and white accents is positioned in the foreground.

4.86 out of 5 average rating, 552 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.

A warm and inviting living area showcases wood-paneled walls and a textured area rug. A stylish coffee table is centered beneath a modern light fixture. A stone fireplace is framed by shelves, and comfortable seating is arranged to create a cozy atmosphere.

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.

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.

A tranquil lakeside view features calm waters reflecting a clear blue sky with scattered clouds. The shoreline is lined with lush green trees and charming homes. In the foreground, several boats are anchored at a dock, enhancing the serene nautical atmosphere.

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.

4.93 out of 5 average rating, 408 reviews

An open living space features high vaulted ceilings and ample natural light. A staircase leads to the loft area. A dining table and kitchen are visible, with a comfortable couch and decorative poufs arranged on a patterned rug.

Cabin in Running Springs

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Upland vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Upland's top sights

Pomona College6 locals recommend

Montclair Place14 locals recommend

Rancho Santa Ana Botanic Garden16 locals recommend

The Claremont Colleges18 locals recommend

Some Crust Bakery3 locals recommend

Claremont McKenna College3 locals recommend

Other great vacation rentals in Upland

Cabin in Green Valley Lake

A spacious balcony features a suspended swinging chair, inviting relaxation. The wooden deck is adorned with natural light filtering through trees, enhancing the open feel. Sturdy railings provide safety while maintaining unobstructed views of the surrounding forest.

4.94 out of 5 average rating, 141 reviews

Cozy Cabin Steps from the Forest - sleeps 8

Apartment in Atwater Village

A modern lobby space features a sectional sofa in rich purple, paired with yellow accent chairs. Artwork with abstract designs adorns the walls above a sleek dark wood console. Large windows provide natural light, and plants add a touch of greenery to the welcoming atmosphere.

4.8 out of 5 average rating, 5 reviews

Cozy 2BR w/pool/gym/parking/hot tube

4.93 out of 5 average rating, 103 reviews

A cozy outdoor seating area features a circular fire pit surrounded by modern wicker furniture with soft cushions. String lights hang above, illuminating the space. A grill is positioned nearby, with a large grassy yard providing a peaceful backdrop, ideal for evening gatherings.

Home in Rialto

Cozy modern home with huge yard!Perfect getaway!

5 out of 5 average rating, 3 reviews

A spacious kitchen features modern appliances, including a stainless steel refrigerator and a large island with bar seating. Sleek cabinetry and a tile backsplash enhance the design. Adjacent, a dining area with a wooden table and chairs is illuminated by ceiling lights, creating an inviting space.

Home in Anaheim

David's Vacationland 2BR

4.98 out of 5 average rating, 134 reviews

A comfortable living room featuring a stylish gray sofa with light-colored cushions, a black coffee table, and a cozy yellow accent chair. Light streams through the sheer curtains, illuminating the textured stone wall and creating a relaxed atmosphere.

Home in Bixby Knolls

Calming Sanctuary near attractions/beaches and LAX

An open-concept living area features a high cathedral ceiling with exposed wooden beams. Large windows provide abundant natural light and views of the surrounding trees. A comfortable sofa and stylish coffee table are positioned near a dining table, while sliding glass doors lead to an outdoor deck.

4.91 out of 5 average rating, 148 reviews

Beautiful A-Frame Cabin Retreat: Hot tub & Theater

4.91 out of 5 average rating, 67 reviews

Home in Crestline

Majestic Escape LakeView, Pet friendly & Hot tub