Vacation rentals in Winfield

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Top-rated vacation rentals in Winfield

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

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Top guest favorite
A rustic home with a wooden exterior is surrounded by greenery. Red Adirondack chairs are positioned near a circular firepit on the grassy lawn. Trees provide a natural backdrop, while a clear sky with wispy clouds adds to the tranquil setting.
Home in Fairfield
5 out of 5 average rating, 8 reviews

Prairie Sunsets

Unwind in this peaceful and utterly private oasis. Thirty two acres of pristine prairie and stunning sunsets. Built using Stapatyaved principles that promote alignment with natural law, this home feels nourishing and harmonious. New bamboo floors, granite countertops, soothing color palette. Lounge in a hammock, relax by the firepit, explore the 2 mile walking trail, look for our resident owl in one of the two classic barns. Or have an adventure or meal in eclectic Fairfield, just 5 miles away.

Guest favorite
Cottage in Carthage
4.96 out of 5 average rating, 479 reviews

Private Lakefront Romantic Cottage w/Swimspa&sauna

This cozy cottage is for couples looking to escape from it all and regenerate on many levels. You'll have your very own steam shower ....check out the company description.... . "Featuring 10 acupuncture jets, sunken tub and a high efficiency steam engine, the 608P steam bath is designed to greatly increase your spa experience. Indulge yourself in a state of complete relaxation". You'll also enjoy the comfy bed, fully stocked kitchen, private deck and access to a Swimspa and sauna 100 ft away.

Top guest favorite
Two horseback riders are positioned on a grassy hill overlooking a tranquil pond. The clear water reflects the surrounding greenery, enhancing the serene rural setting. The landscape features rolling hills, contributing to a peaceful country experience.
Farm stay in Riverside
4.92 out of 5 average rating, 385 reviews

Farm stay close to Iowa City, IA

15 min.-Iowa City, 5 min- Riverside Casino, & 35 min-Eastern Iowa Airport, Cedar Rapids, IA. Comfy beds, living room sectional pulls out to queen hide a bed, 32 acres, horseback riding (sm. fee)*, winter fun, & fishing pond. First 2 guests pay base price, then 3rd thru 10th guests pay an extra 30.00 EACH. NO PARTIES on our farm. We live on property in a separate home. Dogs welcomed (must be kenneled when you leave property). We have an oven and cookware in kitchenette. *contact for details.

Top guest favorite
A screened porch features a round table surrounded by four chairs, all with green cushions. Natural light streams through the screens, showcasing views of a tranquil lake framed by colorful autumn foliage.
Guesthouse in Berwick
4.98 out of 5 average rating, 261 reviews

Private Guest Lake House On 37 Acres In Country

Private guest lake house, located next to main house, on private lake in the country. 2 bedroom, 1 full bath, full kitchen, washer and dryer and large attached screen porch. Private 37 acres of woods and prairie. Fishing and walking trails. Great window views of lake, woods, prairies and river valley. Please note, this guest house is located 1 mile down a county maintained gravel road. 25 minutes from Galesburg, IL, 20 minutes from Monmouth, IL and 35 minutes from Macomb, IL.

Guest favorite
A bright living area features a large window with flowing curtains, allowing natural light to embrace a cozy seating arrangement. A patterned rug lays beneath a wooden coffee table, complemented by a yellow accent chair, a teal side table, and a plant in the corner.
Home in Mount Pleasant
4.97 out of 5 average rating, 35 reviews

Charming Modern 1950s Mid-Century Ranch

Enjoy a nostalgic experience at this centrally located home that was built in 1954. My wife and I have furnished it with a touch of modern mid century charm. There is ample parking in front of the house and we are across the street from Hy-Vee grocery. At the opposite end of the house in what was the original garage is my one chair salon called Headlines. It has a separate entrance and please be assured that you will not be disturbed by the business activity. We look forward to your visit!

Top guest favorite
Yurt in Washington
5 out of 5 average rating, 23 reviews

Rustic Ridge Retreat

Enjoy a private hot outdoor shower under the stars at this beautiful 24-ft yurt on a peaceful Iowa homestead. Elevated deck with a grill, fire table, sectional and sweeping prairie views. Inside - a giant skylight dome over a plush queen bed, sofa bed, kitchenette, WiFi, and air conditioning. XL Games (Tetris tumble, etc). No running water, but we supply fresh Culligan jugs, a clean flushable porta-potty with sink and light, plus the new outdoor shower. Free YMCA day pass per day. Max 4.✨

Guest favorite
A spacious home is visible with a combination of brick and siding exterior, featuring multiple gables and a large covered porch. A manicured lawn extends toward a serene pond, enhancing the natural surroundings. Clear blue skies contribute to the relaxing outdoor atmosphere.
Home in Morning Sun
4.9 out of 5 average rating, 262 reviews

Buckman's Bed and Breakfast (5 Bedrooms+)

Enjoy the comfort and welcoming atmosphere of a home built to entertain family & friends. There are 5 guest bedrooms rooms: Room 1-King bed, sofa bed & recliner Room 2-Queen & sofa bed Room 3-Twin beds & convertible sofa Room 4-Queen & sofa bed Room 5-King & recliner Rooms 1,2 &5 have in suite bathrooms. Bathroom for room 4 is next door. Rooms 2 &3 share an inner door; ideal for parents with children. Breakfast is included. To book a room instead of the house, see separate listings.

Top guest favorite
The exterior of the Milk House features a red structure with gray siding, adorned with a triangular window and a decorative sun motif. A small porch with a welcome sign opens to a gravel path lined with flower planters. A chair and table are set for outdoor relaxation.
Farm stay in Iowa City
4.98 out of 5 average rating, 422 reviews

The Milk House at Lucky Star Farm

The Milk House is a unique space located in the countryside, between Iowa City and Kalona. This 700 square foot home has ample parking and room for four adults. The house is well appointed with a full kitchen, two luxurious queen beds, wifi and a Smart TV. Guests are invited to explore our 20-acre working farm with lots of livestock and two friendly dogs. It's a perfect blend of rural living with the perks of beautiful Iowa City 15 minutes away. Come unwind at Lucky Star Farm!

Guest favorite
A single-story home features a light-colored exterior with blue shutters and a covered porch. The driveway provides space for parking, leading to a one-car garage. Surrounding greenery includes a neat lawn, and trees are visible behind the house, contributing to a quiet residential setting.
Home in Washington
4.94 out of 5 average rating, 107 reviews

Be at Home in Washington, Iowa

Be at Home on South Avenue B in Washington, Iowa! This cozy yet spacious home is centrally located in Washington just blocks from shopping, dining & coffee on the square or just over 1 mile to the Washington Wellness Park and trailhead of the Kewash Trail. Our home offers two bedrooms and one full bath with laundry. Bedroom 1 has a king bed and sitting area while bedroom 2 can be configured with 1 king or two twin beds allowing flexibility for your stay.

Top guest favorite
The cottage exterior showcases a welcoming entrance with a white staircase leading to the front door. A small patio area features a pair of black chairs and a table, surrounded by well-maintained landscaping and a grassy yard under a clear blue sky.
Home in Wayland
5 out of 5 average rating, 10 reviews

Cozy Cottage

Enjoy a cozy stay in a private cottage nestled in on a beautiful tree-lined street. Wayland is a small, friendly community in Southeast Iowa. It’s just a short drive—10 miles north to Washington, 20 miles south to Mt. Pleasant (County Seat), or 40 miles to Burlington, Iowa City, or Ottumwa—offering small-town living with nearby city amenities. We are available to assist you with any needs, as we live right in Wayland. We look forward to your visit.

Top guest favorite
A cozy living area is furnished with two patterned armchairs and a textured sofa. A neutral coffee table is centered on a colorful area rug, which features stripes in various shades. Natural light enters through the windows, accentuated by light drapes and wall decor.
Apartment in Mount Pleasant
4.92 out of 5 average rating, 62 reviews

Great location! Close to downtown.

Welcome! Come and enjoy a stylish, cozy, and tranquil stay at this centrally-located apartment. Just one block from the vibrant downtown area, you'll be close to charming restaurants and unique shops. It’s also a short distance from the train station and grocery stores. This newly remodeled apartment has been thoughtfully designed with your comfort in mind, offering a perfect retreat where you can relax and truly feel at home while you're away.

Guest favorite
A bright and spacious bedroom features a comfortable bed with a layered blanket, complemented by decorative pillows. A fan hangs from the ceiling, and artwork adorns the wall above the bed. A small desk and chair are visible in the corner, providing a work area.
Guesthouse in Mount Pleasant
4.91 out of 5 average rating, 136 reviews

The Vernon Street Guest House - Suite 2

Built in 1900 and renovated in 2022, Suite 2 shows little signs of the once quirky old space. Completely private, with all the amenities, it boasts a spacious bedroom, 1 bathroom, a fully equipped kitchen, dining area, living room with a desk for workspace, and a laundry room. While you're here, we hope you are able to relax and enjoy the well lit deck along with a cup of freshly roasted coffee, which we are happy to have provided.

Popular amenities for Winfield vacation rentals

  1. Airbnb
  2. United States
  3. Iowa
  4. Henry County
  5. Winfield