Holiday houses in What Cheer

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Top-rated holiday rentals in What Cheer

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

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Guest favourite
Home in Oskaloosa
4.95 out of 5 average rating, 147 reviews

Sunny Cottage: FirePit, by Prairie & Wooded Trails

This bright, cheerful two bedroom home with full service kitchen, vaulted open living area, smart Weber grill, fire pit and private backyard is tucked away in a quiet neighborhood with easy access to a 14 mile paved recreation trail, nearly 1700 acres of forests, wetlands, prairies and parks to explore, local winery with dine in nights, cheese farm, museums and active art community. Guests will have easy access to the home with keyless entry. You'll find yourself rested, refreshed and reignited!

Top Guest favourite
An open kitchen area features a blend of modern appliances and industrial design, highlighted by exposed brick walls. A long wooden island with two stools invites social dining. Natural light pours in through large windows, enhancing the warm atmosphere.
Loft in Williamsburg
4.95 out of 5 average rating, 276 reviews

Brickhouse Loft- East Side

This loft is situated above a small town bustling coffee shop, also overlooking the park in the town square. The space is the perfect combination of old historic charm with a modern urban flair with plenty of natural sunlight streaming through the front windows. The kitchen flows seamlessly into the living room where there are multiple seating options. The bedroom and living room have smart TVs if you want to use your own streaming site. The spa inspired bathroom has numerous amenities included.

Guest favourite
An inviting interior showcases a spacious living area with wooden beams and a cozy couch. A colorful area rug lies on the polished floor, while the kitchen features dark cabinets and modern appliances. Light floods the space through large windows, enhancing the cabin's rustic charm.
Cabin in Malcom
4.98 out of 5 average rating, 215 reviews

Bison Ranch*Cabin*Hot Tub with Huge Views

Come to the place where the buffalo roam! Relax in our beautiful handcrafted cabin with one full bedroom and two oversized lofts. Take a stroll on a 1.6 mile trail to view America’s National Mammal. 3 miles from I-80. Stay connected with our reliable wifi or unplug to enjoy the sounds of nature from the wrap around deck and firepit. Bring your own food to grill or purchase bison burgers from our onsite retail store. Close to dining and recreation! Stunning sunsets at Sunset Hills Bison Ranch!

Top Guest favourite
Home in Pella
4.99 out of 5 average rating, 149 reviews

Historic Dutch Cottage • Walk to Central • Firepit

The Rock House • Historic• Walk to Central College• Fire Pit Stay in a true piece of Pella history. The Rock House was built in 1856 by Dutch homesteaders and has been beautifully restored with modern comforts. This cozy 2-bedroom cottage sits next to Central College and is just minutes from downtown shops, bakeries, and the famous Vermeer Windmill. Perfect for couples, small families, Central College visitors or a cozy Pella getaway, the home blends historic charm with a peaceful retreat.

Top Guest favourite
A spacious living area features a large sectional sofa with decorative cushions, complemented by a round leather ottoman and a rattan chair. Two beds are positioned along one wall. Natural light brightens the room through multiple windows with blinds, enhancing the welcoming environment.
Apartment in Brooklyn
4.99 out of 5 average rating, 115 reviews

The Attic on Front

Welcome to your home away from home in the heart of historic Brooklyn, Iowa! Located on the second floor of a downtown building, this space includes a full kitchen, office nook, bathroom, and a large living area with sleeping quarters. Enjoy beautiful downtown views, just steps from the Michael J. Manatt Community Center and Brooklyn Opera House. Centrally located between Des Moines and Iowa City, with easy access to I-80, this is the perfect spot to experience Brooklyn's charm and history.

Top Guest favourite
The exterior of a remodeled house is adorned with warm white lights, highlighting the entrance. A porch with two chairs is visible, alongside decorative plants and stones. The landscape features a welcoming pathway leading to the front door, surrounded by winter foliage.
Cottage in Pella
4.99 out of 5 average rating, 408 reviews

The Strawtown Cottage - in downtown Pella

Completely remodeled 1865 original Strawtown Store of Pella conveniently located in one of the best small towns in Iowa. Three blocks to downtown Pella, 1 1/2 blocks to West Market Park, 2 blocks to Central football, baseball and softball complex. Enjoy the cottage charm with two private bed and bath suites, a family room with dining, full kitchen, front and side porch, laundry and large back yard. Off-street parking in the back. Luxury sheets on queen beds await after your adventures.

Guest favourite
A cozy bedroom features a spacious bed covered with a decorative blanket. A piece of wall art adds visual interest. Natural light enters from a nearby window, illuminating the warm wood flooring. A small bedside table holds a lamp and a rug lies at the foot of the bed.
Home in Deep River
4.92 out of 5 average rating, 26 reviews

My Place on Main

Take it easy at this unique and tranquil getaway. We offer a quiet and cozy place on Main St. in Deep River , Iowa. It's great for couples , windmill workers, hunters or travelers just looking for something a little different. We are located just 9 miles off of I-80 between Des Moines and Iowa City. Only 12 miles from the WhatCheer Flea Market . Diamond Lake is only 8 miles away . Poweshiek Co has lots of beautiful country to explore. Lots of wonderful places to eat, close by too.

Guest favourite
A spacious studio apartment with an open floor plan is highlighted. Two reclining sofas are arranged around a coffee table, while a dining area features a table with white chairs. Natural light enhances the overall space, which is finished with modern flooring.
Apartment in Oskaloosa
4.94 out of 5 average rating, 208 reviews

Downtown Oskaloosa Square

Brand new in 2021! 650 sf studio apartment in downtown Oskaloosa. Located on 3rd floor of commercial building, across the street from the iconic bandstand and Oskaloosa square. Elevator access to private 3rd floor. 10 foot ceilings, washer & dryer in unit, (2) 50" smart tvs with high speed wifi and cable tv included. Nectar memory foam Queen mattress, double reclining sofa. Plenty of closet space and furnishings for long stays. Professional property management office on main floor.

Top Guest favourite
Home in New Sharon
5 out of 5 average rating, 44 reviews

Niland Nook

Relax with the whole family at this wonderful 3 bedroom, 2 bath house nestled in the farming countryside. Whether you're in the cozy living room, sitting out in the screened in porch, or spending time in the backyard....this house has all the amenities to make your stay an enjoyable one. Cows and calves can be seen for that added country experience. Several local attractions and nearby activities are just 15 minutes away in Oskaloosa, Iowa. Just a short 27 miles from Interstate 80.

Guest favourite
A spacious living area features a black leather couch and a wooden coffee table on a textured area rug. Light wood flooring complements the neutral walls. In the background, a kitchen with dark cabinetry and bar seating is visible, enhancing the openness of the space.
Loft in Montezuma
5 out of 5 average rating, 91 reviews

Monte Lofts, on the square. No Cleaning Fees!

Welcome to Monte Lofts in downtown Montezuma. This spacious, newly remodeled loft features a private, secured entrance, a huge, fully stocked kitchen with stainless steel appliances and a laundry room with front load washer and dryer. The bedroom features a large walk in closet and its own entrance to the laundry room and full bathroom. The living room, with floor to ceiling windows offers a great view of the historic downtown Montezuma square.

Top Guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A spacious island with a light marble countertop is complemented by four wooden bar stools. Two stylish pendant lights hang above the island, enhancing the bright and airy atmosphere of the space.
Loft in Williamsburg
4.94 out of 5 average rating, 108 reviews

Stellapolis Lofts - The Evans

Modern + Historic Evans Suite combines "old brick charm" with modern comfort in this spacious 1300sqft unit located on the Square in Williamsburg where you'll be overlooking the bustling downtown and park. Just two minutes off I-80 you'll be close to: - Williamsburg Outlets - 2 minutes - Fireside Winery - 10 minutes - Amana Colonies - 15 minutes - Iowa Hawkeyes (University of Iowa, UIHC, Kinnick Stadium & Carver Arena) - 25-30 minutes

Top Guest favourite
The exterior of the Retreat is showcased, featuring a well-maintained house with light-colored siding and a red front door. A manicured lawn surrounds the home, complemented by trees and shrubs. A two-car garage is visible on the left side of the image.
Home in Marengo
4.99 out of 5 average rating, 134 reviews

The Retreat at Fireside Winery

Welcome to your home away from home, thoughtfully designed for comfort and convenience. Located just steps from Fireside Winery and a short drive to Williamsburg, the historic Amana Colonies, and Iowa City, our retreat offers the ideal setting for both relaxation and exploration. Spend your days discovering local charm and your evenings unwinding in comfort.

Popular amenities for What Cheer holiday rentals