Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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Guest favourite
A charming barn-style home is surrounded by lush greenery, showcasing vibrant flora along the walkway. A spacious deck is accessible from the side, while large windows provide natural light to the interior. The structure displays a blend of warm red siding and wooden accents.
Farm stay in Castana
4.91 out of 5 average rating, 75 reviews

Grandma's House at Jordan Valley

Come and relax in the peaceful surroundings of this rural destination. Nestled on the outskirts in the popular Loess Hills of western Iowa the views of nature are sure to inspire. We have built our very roomy home to resemble a barn. Having raised our 13 children here we have some empty space. Grandpa and Grandma's apartment is a very inviting homey atmosphere for any one passing through or planning a lengthier stay in our area you will be happy with our family friendly accommodations & price.

Top guest favourite
A spacious deck extends along the water's edge, offering a serene view of the lake and surrounding landscape. Comfortable seating areas are visible, complemented by a sandy shoreline in the foreground. The sky is bright with scattered clouds, creating a relaxed outdoor atmosphere.
Cabin in West Point
4.96 out of 5 average rating, 23 reviews

Eagle's Nest Secluded Retreat

Large beautiful home overlooking 250+ acre lake/wetland. Abundant residential and migrating waterfowl, including geese, ducks, pelicans and bald eagles provide for a birdwatchers delight. Wild turkeys and whitetail deer will be your neighbors. A short walk on our 800 acre property gets you to the banks of the Elkhorn River. Five bedroom house sleeps 14 comfortably. Large kitchen seats 10. Two separate living areas with TV's. Ample space for a large family getaway in northeast Nebraska.

Guest favourite
A large window frames a view of the river and surrounding landscape. Trees provide greenery, while a seated area is visible on the patio, along with a picnic table. The scene is bright, showcasing clear skies and serene water.
Home in Tekamah
4.85 out of 5 average rating, 27 reviews

Retreat & Relax @ The River at 673

Relax with the whole family at this peaceful property or make it an off-the-grid couple's retreat. This riverside home is the perfect place for a fishing getaway, a guys or girls' trip, a book club or quilting weekend, or a family river vacation. Enjoy our fully equipped kitchen and eat at the dining room table that seats 6, or dine alfresco and enjoy the river views and firepit. You can also relax in the above-ground pool from June to mid-Sept. or, at the end of the day, enjoy the spa bath.

Top guest favourite
The A-frame exterior of the house is showcased against a twilight sky, with warm lights glowing from within. A striking red door stands at the center, flanked by large windows and a sloping roof nestled among trees.
Chalet in Benson
5 out of 5 average rating, 107 reviews

Dahlia House (A-Frame, Sauna, Wood Fired Hot tub)

Dahlia House is a modern A-frame retreat for two in the heart of Omaha’s Benson Creative District. Thoughtfully curated, as featured in Architectural Digest, it features many unique touches and amenities — sauna, wood-burning hot tub, etc. — to help you find what exactly what you need, and to leave rejuvenated. Please note: Each stay is curated with great care, and we have a firm cancellation policy. Dahlia House hosts two registered guests only, and no unapproved visitors are permitted.

Guest favourite
The living area features a spacious layout with a comfortable seating arrangement including a sofa and two reclining chairs. A wooden coffee table centers the area, while a large window allows for natural light. Soft curtains frame the window, and a simple rug provides comfort on the concrete floor.
Guest house in Scribner
4.91 out of 5 average rating, 11 reviews

The Bunk House

Take it easy at this unique and peaceful accommodation. Located 8 miles from West Point, 7 miles from Snyder, and 6 miles from Scribner, this location offers a short drive to surrounding communities. Less than a mile away is Dead Timber State Recreation area with walking trails and lakes. The Bunk House is located on the same place the hosts live. Covered parking in the shed is available. Sleeping spaces include one queen size bed, a couch, and a queen size air mattress if needed.

Guest favourite
Two repurposed grain bins are situated on a landscaped area, featuring a small patio with seating arrangements. A vibrant flower bed is placed adjacent to the patio, and a gravel pathway leads to the entrance. Lush greenery surrounds the structure, creating a serene environment.
Tiny home in Missouri Valley
4.97 out of 5 average rating, 230 reviews

Grain Bin Getaway

Nestled at the foot of the Loess Hills, this repurposed grain bin is a sight to see. Every inch of the inside has been customized for a relaxing and luxurious experience. Conveniently located just 30 minutes from downtown Omaha, as well as within a quick drive to numerous state parks. There is even an external electrical hook up for campers. Finally, our grain bin includes 20 acres of the Loess Hills to explore. We recommend hiking to the top of the ridge for sunset. It's breath taking.

Top guest favourite
A cozy room features a spacious bed with a striped comforter and decorative pillows. A comfortable couch sits beside a bedside table and lamp, creating a welcoming area. A dresser is positioned against the wall, and soft lighting gives the space a warm feel.
Flat in Papillion
4.95 out of 5 average rating, 338 reviews

Coastal Retreat Getaway, Secluded, Off 370/I-80

Step into a private and cozy space. Relax watching TV in bed or on the couch. This place is part of our walk out basement, so you may hear day to day living upstairs. For your safety there is a Ring camera installed at the entrance and will light up the entryway when it’s dark. Parking is on the well lit public street. Easily walk up our dedicated Airbnb sidewalk, no steps, walk around to the back of the house. You’ll be in a serene space that makes you feel right at home.

Top guest favourite
A bright living area presents large windows allowing natural light to fill the space. Comfortable teal sofas and a wooden coffee table create a casual atmosphere. A dark wood TV stand supports a flat-screen television, while a soft rug lies underneath, adding texture to the floor.
Guest house in Blackstone
5 out of 5 average rating, 224 reviews

The Hidden Garden at Blackstone

Newly renovated second floor of a carriage house located on a historic property in the popular Blackstone District. Shares an acre of land with the main house, built in 1892 and occupied by the owners. Although situated in the middle of the city, the unit feels secluded from its urban environment and looks out onto a garden surrounded by trees, shrubs and flowers and is in walking distance to many restaurants and bars in both the Blackstone District and Midtown Crossing.

Guest favourite
A spacious living area features a modern, curved orange sofa complemented by a round coffee table with a plant centerpiece. Natural light floods through large windows, highlighting the decorative art pieces on the walls and the open layout connecting to the dining area.
Home in Old Market
4.97 out of 5 average rating, 143 reviews

Old Market Eclectic Townhouse – Walk to Everything

This townhome has the style, amenities and location perfect for an unforgettable getaway in Omaha. Located in Omaha's quaint Old Market you'll be just steps away from the best restaurants, bars, shopping and entertainment Omaha has to offer. The main level is a fun, cozy hang out space complete with a gas fireplace. The upstairs bedrooms are spacious. The best part – a large rooftop patio with views of downtown Omaha. The space also includes a two-car heated garage.

Top guest favourite
An open living area features warm wooden floors and a cozy wood-burning fireplace centered in the wall. A large TV is mounted above the fireplace. Comfortable seating arrangements and a dining table are visible, complemented by natural light from nearby windows.
Home in Fremont
4.92 out of 5 average rating, 111 reviews

Cheerful home with indoor Fireplace & King beds

We have a unique older home in a nice neighborhood. This home has 2 bedrooms with king sized beds, a sofabed, queen air mattress and a pak-n-play. A wood burning fireplace gives the home a cozy warmth during the winter months. Outdoor fire pit as well as a gas barbecue are available for use in the large, fenced back yard. Fully stocked kitchen should have most everything you'd need to prepare and serve a nice meal. We look forward to hosting you.

Top guest favourite
The cottage showcases a charming exterior with a mix of brick and textured siding. Decorative gables frame the roof, while a distinct red door marks the entrance. A manicured lawn extends in front, bordered by neatly trimmed shrubs and trees, offering spacious outdoor views.
Home in Fremont
4.94 out of 5 average rating, 18 reviews

Fremont Farm Cottage

Forget your worries in the spacious and serene property. The cottage sits on an acreage nestled among farmland with flowing field views. Built in the 1920’s the cottage underwent full renovation in 2024. It maintains it 1920’s character while offering a large kitchen, 3.5 beautiful bathrooms and a large family room with ping pong and foosball tables. Paved access to Highway 275 makes Fremont a quick 7 minute drive and West Omaha a 25 minute drive.

Guest favourite
The exterior of a two-story cottage features a combination of white and red-brown shingles. A covered porch with wooden columns is visible, along with large windows that allow light into the interior. A well-maintained pathway leads to the entrance, bordered by decorative stone.
Home in Wayne
4.95 out of 5 average rating, 172 reviews

D'Brick House in Wayne

D'Brick Cottage is located across from Wayne State College in Wayne, NE. This recently renovated 2-bedroom house offers a comfortable place to get away. Includes indoor fireplace, equipped kitchen with all appliances and conveniences, plus laundry in the basement. The perfect place to get some rest for traveling employees, visiting family, or just because. SPECIAL NOTE: The basement contains an apartment that is rented separately.

Popular amenities for Oakland holiday rentals

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