Vacation rentals in Montgomery County

Guesthouse in New Lebanon

4.97 out of 5 average rating, 215 reviews

Cottage on a working market garden

Studio cottage with full bath and self-catering kitchen with pots and pans, etc., queen sized bed with fresh linens and towels provided. This cottage is on a working market garden. Maximum occupancy two adults. We do have a small bed that could be added to accommodate a small child about 6 years and under. WE WILL ACCEPT SOME PETS, BUT NOT ALL. We are one mile from grocery shopping. Local roads ideal for cycling. Thirteen miles west of Dayton. Price includes fresh flowers and vegetables from the garden during the season. One cat on the property. Cottage has ceiling fan and good air circulation and a window air-conditioner during the warmer months. There is a TV that streams Apple TV and Kanopy in the cottage, and excellent WIFI access. National Air Force Museum in Dayton is only 20 miles/ 30 minutes away. University of Dayton is 14 miles/ 20 minutes from the cottage. Dayton International Airport is 21 miles/ 26 minutes away. Your hosts are a hospitable couple who enjoy meeting new people. If no one else is booked after you, we can be more flexible with the check-out time.

4.96 out of 5 average rating, 315 reviews

Bungalow in Dayton

South Park Guest House

Historic South Park guesthouse. Built as the center of 3 sisters, this 1920 shotgun cottage and its neighbor to the right were bought by me, a neighborhood activist, who stripped them both down to the studs. What you'll find is a mix of historic, modern, and mid-century modern, with vaulted ceilings with skylights in both the bedroom and the spacious bathroom, and safe, snug, and quiet thanks to the insulation, new windows, new doors, and Berber carpet. Owned by a Certified Service Disabled Vet.

4.87 out of 5 average rating, 125 reviews

Apartment in Dayton

Cozy &Affordable | Oregon District Area | King Bed

Ideal for business travelers, students, & couples, this cozy one bedroom in Dayton’s historic Oregon District offers comfort & convenience. Enjoy fast WiFi, a dedicated workspace, smart TV, and a fully equipped kitchen, everything you need for work or relaxation. Located just steps from top dining, shops, & downtown, it’s perfect for work trips, extended stays, & relocations. Blending modern amenities with historic charm, this walkable neighborhood stay truly feels like a home away from home.

4.97 out of 5 average rating, 137 reviews

Barn in Beavercreek

Quaint 1 bedroom barn cottage with lots of privacy

Welcome to the Cranberry Cottage! Enjoy the rustic barn experience while enjoying modern conveniences of this sweet romantic cottage. You'll feel like you're a million miles away from the hustle and bustle while you enjoy coffee on your own private deck. Walk up the path and cross the road and you can enjoy 150 acres with walking trails at Mount Saint John. Drive just 2 miles and you'll be close to the finest shopping and dining experiences at the Greene Mall. Come enjoy this unique experience.

Guesthouse in Centerville

5 out of 5 average rating, 221 reviews

The Carriage House in Uptown Centerville

The Carriage House is designed with couples in mind—a private escape just for two. Tucked in the heart of Uptown Centerville, you’ll be only steps from shops, local restaurants, & a scoop (or two) of Graeter’s Ice Cream. Whether you’re here for a romantic weekend, visiting family, or simply looking to unwind, this is the perfect place. Built in 1897 & thoughtfully renovated in 2017, the Carriage House blends historic charm with modern comfort making it one of Centerville’s favorite hidden gems.

4.97 out of 5 average rating, 189 reviews

Oak Street Place in Historic South Park District

This is a one of a kind stay located in the heart of the historic South Park district. This unique property used to serve as several different types of businesses including a barbershop, grocery store and church. The space has now been completely remodeled into a stunning open concept home full of history and character. With ship lap walls and vaulted ceilings with original exposed beams, it looks like it could have been on an episode of HGTV’s Fixer Upper! Come stay at Oak Street Place!

Superhost

4.86 out of 5 average rating, 148 reviews

* Cozy 2 bedroom home with 2 TV’s *

Relax & unwind alone, or with your family in our cozy home! Fast WiFi Fully stocked coffee bar. Conveniently located 10 minutes from the Dayton Airport, and 14 minutes to downtown Dayton. 11 minutes to Rose Music Center. Restaurants and shopping within walking distance, and Metroparks bike trail at the end of our street. Pets are welcomed for an additional fee PER PET. Unique quirks about our little home: the ceiling coming down the steps is lower, and the bathroom is a jack-and-jill.

4.94 out of 5 average rating, 223 reviews

Meet-n-Sleep Edwardian Guest House

Combine business with slumber - and bring your baby along! This guest house is designed with work/business meeting space on the ground floor, but is also a fully equipped home with sleeping quarters upstairs. Sleeps 2-3, seating for 8. 1 standard bed & crib/twin airbed option in 2nd BR. There's a large deck out back with a picnic table and grill. NOTE: We only accept guests whose Airbnb verification includes a government issued photo ID for the primary guest who will be in residence.

4.9 out of 5 average rating, 113 reviews

Lovely Eclectic Duplex - Peaceful Neighborhood

Kick back, relax, and feel right at home in this recently renovated duplex. Located in an adorable and quiet neighborhood, this unique space is comfortable, clean, artfully decorated, and has a calm and soothing atmosphere. Includes updated appliances, a laundry room, a toilet bidet, a workspace, and smart TVs. Just 6 miles from Dayton Airport and an easy drive to downtown, restaurants, eateries, and shopping malls. It will be my pleasure to host you.

4.97 out of 5 average rating, 123 reviews

Guesthouse in Dayton

NEW Oregon District Cozy Downtown Towhome

This guest townhouse is in the heart of the Oregon District, right next to all of Dayton’s best food & nightlife/events! The space is quaint and perfect for groups of 1-4, in a historic neighborhood, and incredible for quaint getaway. Please be aware that the other side of the home is also rented for guests, so while the spaces are completely separate, you may hear noise from other bookings. Please reach out if there are any issues. Come stay with us!

Superhost

4.85 out of 5 average rating, 265 reviews

Cozy 2BR | Fenced Yard & Fire Pit | Walk to UD

Relax in this charming two-bedroom bungalow, nestled in historic South Park, just minutes from the Oregon District and Dayton’s best dining and nightlife. Enjoy all the comforts of home with a washer/dryer, a fully stocked kitchen, and a private fenced backyard - perfect for evening drinks around the fire pit! Centrally located only a short walk or Uber to UD, Miami Valley Hospital, and Downtown Dayton.