Midwest

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The Best Places to Stay in the Midwest

The Midwest is dotted with charming farmers markets, classic American eateries, and some of the friendliest folks you’ll ever meet. Whether you’re enjoying a color tour of the Great Lakes or experiencing Americana across the Plains states, the Midwest is worth the trip.

This Month’s Featured Properties

2025 Guest Loyalty Award
Glenlaurel, A Scottish Inn and Getaway Cottages
Rockbridge, OH
Hocking Hills' Scottish-inspired luxury inn. Escape the ordinary for a romantic experience like no other! Glenlaurel, A Scottish Inn & Cottages is situated on 140-acres in the heart of Ohio's Hocking Hills. The adult-onl
Double Reward Points
The Oakwood Inn Okoboji
Spirit Lake, IA
Guests awaken to gorgeous morning views of the expansive gardens & oak savannah after a refreshing night's rest at this elegant Lake Okoboji Hotel. The adults-only inn near Okoboji, Iowa offers sumptuous accommodations,

Stays in the Midwest

30 properties

All Stays

2024 Quality Assurance Award
The Hotel Saugatuck
Saugatuck, MI
The Hotel Saugatuck is a thoughtfully curated, adults only, boutique hotel designed for couples seeking an elevated yet relaxed retreat. Guests enjoy serene, private accommodations with king beds, spa inspired baths, fir
Prairie Guest House
Fishers, IN
Set on two acres in Fishers, Indiana, Prairie Guest House is a mid-1800s Gothic farmhouse offering 10 guest suites, an early-1900s cottage, and a barn backdrop used for weddings, retreats, and micro-events - with the opt
2025 Guest Loyalty Award
Glenlaurel, A Scottish Inn and Getaway Cottages
Rockbridge, OH
Hocking Hills' Scottish-inspired luxury inn. Escape the ordinary for a romantic experience like no other! Glenlaurel, A Scottish Inn & Cottages is situated on 140-acres in the heart of Ohio's Hocking Hills. The adult-onl
2024 Best Craft Lodging Property Award
Cherry Ridge Retreat
New Plymouth, OH
Cherry Ridge Retreat combines the privacy and beauty of a woodland paradise with the comforts and amenities of a 5 star vacation destination. Secluded hot tubs, private pool, miles of trails, and fishing ponds are just s
Goldmoor Inn and Resort
Galena, IL
We invite you to be our guest at the historic Goldmoor Inn, the only Galena bed and breakfast located high above the banks of the Mississippi River with stunning views of the river. The Goldmoor bed and breakfast is loca
Double Reward Points2024 Innkeeper of the Year Award
Jail Hill Inn
Galena, IL
Jail Hill Inn is a boutique luxury inn located one block from downtown historic Main Street, prominently situated overlooking Galena and its stunning countryside. This 140-year-old building once served as the county jail
The Leland Lodge
Leland, MI
The historic Leland Lodge will celebrate its 100th anniversary in 2027. Located in the lakeside village of Leland, in the heart of Leelanau County, the Lodge's 18 recently renovated rooms, three rustic cottages, and two
Frederick Stearns House
Detroit, MI
Frederick Stearns House offers nine individually designed rooms and suites with king beds, private bathrooms and modern comforts. Wi-Fi, private parking, all-day coffee and tea, shared lounges and gardens are included. C
ALEO
Detroit, MI
Tucked in Detroit's Little Village, ALEO is a boutique bed & breakfast offering four design-forward suites in a restored rectory. Steps from The Shepherd art space and Father Forgive Me bar, guests enjoy a serene stay im
2025 Sustainability Champion Award
Goldberry Woods
Union Pier, MI
Experience Michigan's premier Farm-To-Table B&B. Creative homemade breakfasts feature ingredients grown on our organic farm and orchard. Kayak, bike, or hike our 30 acres of woods along our river. Relax in one of the inn
Double Reward Points2024 Guest Loyalty Award
The Welsh Hills Inn
Granville, OH
Award-winning, relaxing, romantic boutique Inn in the heart of the historic, New England-like Village of Granville's idyllic Welsh Hills countryside. Spacious, beautifully appointed guestrooms, luxurious linens, en-suite
Double Reward Points
The Oakwood Inn Okoboji
Spirit Lake, IA
Guests awaken to gorgeous morning views of the expansive gardens & oak savannah after a refreshing night's rest at this elegant Lake Okoboji Hotel. The adults-only inn near Okoboji, Iowa offers sumptuous accommodations,