Vacation rentals in Charter Oak

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Top-rated vacation rentals in Charter Oak

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Guest favorite

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

4.92 out of 5 average rating, 51 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 favorite

A wooden dining table with four chairs is positioned on polished dark hardwood flooring. Natural light enters through a window, illuminating the space. An archway leads to a cozy sitting area, which features a floral-patterned sofa and soft curtains, complemented by a brick chimney.

Home in Moorhead

5 out of 5 average rating, 42 reviews

Queen Anne Cottage - Early 1900

Follow us on FB at The Cottage In Moorhead This early 1900’s, 1000 sq ft Queen Anne Cottage, sleeps 6, and is located in the heart of the Loess Hills. The home features: 2 bed/2 bath, stocked kitchen, dining room, living room/sofa sleeper, 50”smart tv, and WiFi. Unique features include: original pocket doors, corded/weighted window sashes, and antique pieces. Step back in time while enjoying the modern conveniences of central heat/AC, appliances, luxury bedding, and high speed internet.

Top guest favorite

This historic cottage features a blue exterior with white trim and a charming front porch. Rocking chairs are positioned on the porch, surrounded by lush greenery and colorful flower beds. The two-story structure is set back from the pathway, offering a welcoming appearance.

Home in Woodbine

4.99 out of 5 average rating, 78 reviews

Victorian Cottage steps from historic downtown

Historic cottage renovated top to bottom. Steps from the Brick Street Historic District & Downtown Woodbine. A perfect getaway - whether you're celebrating a family event or just want to escape the hustle and bustle of everyday life. Large open basement hosts tv and relaxing. Three kings (master on main level with ensuite bath), two queens, full kitchen and 3 full baths. Relax in a rocker on the porch, rejuvenate with a hike in the Loess Hills, or cruise one of three Iowa Scenic Byways.

Guest favorite

A spacious studio apartment features a cozy seating area with a yellow couch and armchair, complemented by large windows that allow natural light. The full kitchen and dining area are visible in the background, along with wooden beams highlighting the ceiling.

Guest suite in Dunlap

4.94 out of 5 average rating, 228 reviews

Hilltop Studio Apt.

Located one hour from Omaha in the scenic Loess Hills of Iowa, this newly remodeled studio apartment above the garage has a large deck and a beautiful valley view overlooking my hometown. With a queen bed, a pull-out sofa, full kitchen, shower in bathroom, laundry, and gas fireplace, the apt. is attached by an elevated deck to the main house, my childhood home, (which my husband and I call our "Hilltop Hospitality House"). We are excited to welcome gracious guests to this lovely space.

Guest favorite

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

4.98 out of 5 average rating, 217 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 favorite

A two-story house with a blue exterior is featured alongside an oversized garage. A spacious driveway leads up to the front deck, surrounded by green trees and open land. The structure provides ample outdoor space under a clear blue sky.

Home in Moorhead

4.91 out of 5 average rating, 58 reviews

Heart of the Loess Hills

A perfect oasis for a getaway into the country. Totally updated family retreat. Perfect for families, hunters and couples! Enjoy the tranquil country views from the front deck. Brand new fridge, couches, tables, chairs, beds, firepit, grill and all guest linens, paint, carpet etc. Features oversized 3+car garage, and huge yard. Excellent spot for hunters, or anyone wanted to escape city life. Take a moment to view every single star in the sky. Beautiful furnishings to enjoy.

Top guest favorite

A welcoming living room features two brown leather sofas and two blue armchairs arranged around a small table. Natural light filters through large windows, highlighting a decorative rug on the floor. A ceiling fan and lamps add functional yet stylish elements to the space.

Home in Ida Grove

5 out of 5 average rating, 19 reviews

Holly's Cottage

Bring the whole family, girlfriends, work buddies to this newly renovated home with lots of room. Whether you need extra space for family for a wedding, family gathering, the holidays or want to impress clients or out-of-town employees with a stylish space for their home away from home, this home has it all! Our newly remodeled home backs to the park and is located in a great neighborhood. If you're looking for a homey feel where one or more families can stay, this is it!

Top guest favorite

A welcoming living area is shown, featuring a light-colored sofa and armchair arranged around a wooden coffee table. Natural light flows in through large windows, and a television is mounted on the wall. A door leads to an outdoor space, enhancing accessibility.

Home in Denison

5 out of 5 average rating, 20 reviews

Fort Purdy Home

Bring the whole family to this great house with lots of room for fun. This has been my family home for almost 4 decades and our children were raised here. It has been entirely remodeled and upgraded most recently in 2019 with all new flooring, kitchen, kitchen appliances, and bathroom updates. Great corner lot, plenty of parking, high end appliances, and plenty of room to hang out! It’s a great place to hang out, entertain, or just visit the amenities of Denison

Top guest favorite

An inviting front porch features two chairs placed beside a small table. A potted plant adds a touch of greenery near the entryway, which is highlighted by a round, decorative door with an oval window. The exterior is framed by a clean, beige siding.

Home in Dunlap

5 out of 5 average rating, 68 reviews

O’Connor House on Court Street

The O'Connor House on Court Street is perfect for family trips or business travelers! Located in the heart of Dunlap Iowa, this home features 2 bedrooms (one with king bed & one with queen bed, plus additional twin air mattress), pack-n-play & high chair, bathroom with tub/shower combo, onsite washer & dryer, dedicated office area, fully-equipped kitchen, and comfortable living room. All the amenities of home and more! The perfect place to kick back and relax!

Guest favorite

A comfortable living area is presented with a plush sofa and two recliners. Soft lighting from the lamps creates a cozy ambiance. A wooden side table holds a small plant and a decorative sign. A large window allows natural light to enrich the space.

Apartment in Harlan

4.9 out of 5 average rating, 71 reviews

Cozy Modern 1 bedroom apartment

Forget your worries in this spacious and serene space. You'll enjoy the privacy this apartment offers amid small town living. Close to historic downtown Harlan, where restaurants and unique shopping adventures await! Beautiful full kitchen with granite countertops opens up to a full living space. Private bedroom with desk/office space, with large full size bathroom. Unit even includes private laundry room!

Guest favorite

The kitchen area features dark cabinetry and granite countertops, complemented by stainless steel appliances. Ample natural light streams in, highlighting a large island with seating and a double sink, while a decorative rug adds a touch of warmth.

Home in Lake View

4.94 out of 5 average rating, 100 reviews

Cheerful two bedroom lake home.

This stylish place to stay is perfect for group trips. Master bedroom with small private bath; including a bonus room. Guest bedroom with 4 beds for kids or large family. Second bathroom with shower/bathtub. Spacious vaulted kitchen living room with tons of seating for lake views, binge watching favorite series, or watching the cook make the magic happen. 7 Day stays or longer receive 30% discount!

Guest favorite

A bright living area is furnished with two light-colored sofas adorned with decorative pillows. A dark wooden coffee table is positioned in front, complemented by a textured area rug. A wall-mounted television is visible, and natural light filters through a window with dark blinds.

Home in Ida Grove

4.91 out of 5 average rating, 127 reviews

Cozy like home! Fully Furnished

Experience the feeling of home in this warm and cozy 2-bedroom rental. With accommodations for up to 4 people, in a quiet neighborhood close to downtown Ida Grove. Relax or visit all our Castletown has to offer. You will be close to a movie theater, bowling alley, skating rink and local shopping. Also you will have a 7 mile walking trail that can take you out to beautiful Moorehead Park.