Holiday rentals in Stockport

Carriage House - Historic Louden Hay Trolley + EV

Welcome to our Historic Carriage House - where you can enjoy a luxurious stay surrounded by famous Louden Hay Trollies that were invented here in Fairfield! Relax and unwind while surrounded by curated vintage decor on a plush leather sofa. Hang out and cook your favorite food in our designer kitchen with quartz countertops. Freshen up while standing on heated marble bathroom floors. Located 1 block off the town square with quick access to parking, restaurants and shops. EV Charger outside.

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.

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

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.

A Stone's Throw

Take a break and unwind at this peaceful country home just outside of city limits. A Stone's Throw from the interchange of highway 1 and highway 34, as well as the hospital and all that Fairfield offers. This charming cottage has a spacious living room complete with a murphy bed that folds into a desk during the day and has a barn door to close it off as an extra bedroom at night. Enjoy the stocked kitchen, grill on the deck or sit on the porch and soak in the charm of this country cottage.

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.

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!

Spring/Summer Cabin - Kayak - Hunting -River Views

Come enjoy a great getaway at our spacious cabin on the Des Moines River in Keosauqua, Iowa. Enjoy year round river views. We have everything you need to recharge - porch dinning, grill, fire pit & amazing views! Love to fish, kayak, boat, golf, or hunt? You can do it all here. We also have a boat ramp about 300 yards from the cabin. We are a minute drive from the famous Van Buren county that has multiple unique things to offer. Come relax and enjoy the great outdoors!

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!

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.

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.

Nauvoo Halfling House

Live like a Halfling in this fantasy getaway five minutes from historic Nauvoo Illinois! This bermed home is tucked into a hill in a small wooded glen, perfect for anyone looking to connect with nature or hibernate through the winter.