Vacation rentals in Stockport

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Top-rated vacation rentals in Stockport

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

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Top guest favorite

A comfortable living area features two leather sofas adorned with plaid throw blankets. A coffee table with a wooden top and black metal frame is centered between them. Natural light filters in through two windows, illuminating the warm wood paneling on the walls.

Home in Keosauqua

Riverview Cottage in Keosauqua

Overlooking the Des Moines river, this inviting cottage offers the perfect getaway for a hunting retreat or girl’s weekend. Built in 1870 and thoughtfully restored in 2024, it offers a modern kitchen with an oversized island, spacious living room, and two cozy bedrooms with custom made barn doors. Situated in the heart of Keosauqua, you’ll be walking distance to restaurants, shops, and city park. Enjoy an afternoon fishing at Lake Sugema or exploring the historic Villages of Van Buren County.

FamilyLocationAccess

4.95 out of 5 average rating, 39 reviews

Guest favorite

Home in Fairfield

Fillmore’s Retreat

Welcome to the Fillmore Retreat. Enjoy a beautiful kitchen fully stocked with essential cookware & all new appliances , plus a bathroom featuring a double vanity & tiled shower/tub combo. Sleeps up to 5 guests across 3 bedrooms: (1 king, 1 queen, and 1 twin). Relax in the comfortable living spaces or work remotely with the dedicated office desk. For added comfort & cleanliness, the home features an Aurabeat sanitizing air purifier, and all windows are equipped with blinds for privacy & comfort

LocationFamilyComfort

5.0 out of 5 average rating, 7 reviews

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

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.

LocationTVGetting around

5.0 out of 5 average rating, 12 reviews

Top guest favorite

The exterior of the house features a single-story white structure with a gray roof, framed by a grassy yard dotted with yellow dandelions and purple wildflowers. Large windows and a welcoming front porch enhance the home's inviting appearance.

Home in Farmington

Poppy's Place. Handicap ramp/private garage entry.

This beautiful, spacious daily rental house offers the ultimate connected or socially distanced experience while exploring the historic Villages of Van Buren County. Located 2 mi. from Shimek State Forest, .5 mi. from the Des Moines River, a block from Hwy 2 & the general store. Ideal for reuniting with friends or family, for couples seeking a romantic get-away, tourists, contract/construction workers, & business travelers. Whirlpool tub, full modern kitchen & private garage parking with ramp.

LocationFamilyWalkability

4.94 out of 5 average rating, 140 reviews

Guest favorite

A cozy living room is presented, featuring a dark sofa with two pillows and two light blue armchairs. A wooden coffee table is centered on a richly patterned rug. Soft light from a floor lamp and table lamp complements the natural light coming through a nearby window.

Home in Fairfield

Crescendo Chalet

Keep it simple at this peaceful and centrally-located home. Perfectly situated walking distance to the MIU Campus, Everybody's and walking trails, our cozy and beautifully appointed, East facing chalet will have you starting each day with a smile on your face. With off street parking, this single story home features a fully equipped kitchen and laundry with dedicated ironing board. Perfect for short or long stays. The home is renovated but old - uneven flooring and imperfect finishing work.

LocationValueCleanliness

4.89 out of 5 average rating, 80 reviews

Guest favorite

A spacious living area features a combination of orange and gray sofas arranged around a central coffee table. Large windows allow natural light to fill the room, while a flat-screen TV is mounted on the wall, and a stylish mirror reflects the inviting atmosphere.

Loft in Fairfield

Luxury Downtown Loft | Rooftop + Sauna | Sleeps 12

One of the only places in Fairfield designed specifically for groups—this downtown loft lets you stay together, relax on a private rooftop patio, and unwind in the sauna or jacuzzi tub, all just steps from the town square. Whether you're visiting for a wedding, event, work trip, or weekend getaway, this is the ideal place to stay and sleep up to 12 in comfort. Walk downstairs to the town square, bars, wine bar, boutique, and restaurants. Unwind on the rooftop patio and enjoy the sunset!

LocationFamilyLayout

4.82 out of 5 average rating, 77 reviews

Top guest favorite

The spacious kitchen features dark wood cabinetry and a large granite island, equipped with modern stainless steel appliances. A stylish dining area with white chairs and a long table is visible in the background, alongside decorative plants and warm lighting.

Loft in Fairfield

Penthouse Luxury + Hot Tub Private Roof Deck + EV

Welcome to our Luxury Downtown Loft—where industrial chic meets traditional design. Relax and unwind as you watch the stars from your PRIVATE Hot Tub located on the rooftop deck. Catch an amazing sunset while playing games from the grass turf area. Hang out and cook your favorite food in our designer kitchen. Need to work? We have blazing fast Internet. At 1,500 square feet, you'll enjoy luxuries of a full-size home plus you're only 1 minute from downtown Fairfield.

FamilyValueBathroom

4.96 out of 5 average rating, 101 reviews

Guest favorite

A wooden staircase with sturdy railings leads to a lofted sleeping area, made of warm-toned timber. A cozy bed with patterned linens is visible, along with high wood ceilings illuminated by soft lighting. Plush seating is situated nearby on the ground level.

Cabin in Keosauqua

River's Edge Cabin-Riverfront Acres/DISH/WiFi

This cabin is nestled by the bridge across from Pittsburgh, Iowa, just a few miles west of Keosauqua. Accommodations not only include the cabin, but also 1.5 acres of flat, riverfront land to play, relax and enjoy nature. A screened porch with seating overlooks the Des Moines river. Guests can also enjoy the outdoor fire ring. The amazing wildlife along the river is absolutely beautiful. If you enjoy the outdoors, hunting, fishing and nature, this is the cabin for you!

LocationFamilyTV

4.87 out of 5 average rating, 190 reviews

Guest favorite

A spacious living area is furnished with a light-colored sofa adorned with patterned pillows. Two armchairs are positioned beside a round coffee table on a richly colored area rug. A long dining table with elegant chairs is visible in the background, creating an inviting setting.

Apartment in Fairfield

Luxury 1st Floor Apt Near Square

Experience the best of Fairfield at this stunningly remodeled apartment in an 1858 farmhouse. You'll be just a few minutes walk to Fairfield Square with its unique art, cafe, and dining scene. The master bedroom features a sliding door to a covered porch overlooking a larger patio ready for a party. Walk the beautiful grounds with an organic garden and orchard. Help yourself to produce in season. I enjoy meeting and interacting with my guests as they wish.

FamilyLocationAccuracy

4.96 out of 5 average rating, 28 reviews

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

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.

LocationValueAmenities

4.91 out of 5 average rating, 70 reviews

Guest favorite

Guesthouse in Mount Pleasant

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.

LocationFamilyAmenities

4.91 out of 5 average rating, 144 reviews

Guest favorite

A charming cottage with a metal roof and exterior featuring light-colored siding. The entrance is framed by two sets of stairs leading to a covered porch, which is flanked by windows adorned with red shutters. Green grass and landscaped areas surround the home.

Home in Keosauqua

Droptine Cottage

A back road get-away in Iowa's best deer country. Featuring all the comforts of home with 2 bedrooms (1 queen & 1 full/twin bunk bed). Relax outside on the deck or by the firepit. Perfect for a group of hunters, fishermen or a family visiting the Villages! Included TV, DVD, Washer & Dryer, Wi-Fi, Charcoal & Gas Grills. Daily or weekly rentals available.

FamilyLocationBackyard

4.93 out of 5 average rating, 245 reviews