Holiday rentals in Montgomery County

Guest house in New Lebanon

4.97 out of 5 average rating, 201 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, 301 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.

4.98 out of 5 average rating, 129 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.

4.99 out of 5 average rating, 291 reviews

Cottage in Dayton

The Blue Heron Guest House

Whether you are traveling solo for work, or for recreation with your family, our lovely two bedroom, 1200 square foot guest house is ideal. One of two houses on the property (we live in the other) designed and built in 1920 as a summer residence for a local family. These 5.5 acres of park-like setting are situated on the serene Stillwater River. Tucked away, in the midst of the suburbs, surrounded by trees, gardens and the sound of birds, this gem of a place is a perfect home away from home.

4.89 out of 5 average rating, 284 reviews

Flat in Centerville

Apt 1: Octopus Garden in Uptown Centerville

This apartment is a twin to our Apt 2: Pilot Lounge located across the hall. Two adults can sleep in a dedicated bedroom on a queen bed while your child sleeps on an air mattress (the 2nd bed) in the living room. The kitchen is equipped for basic cooking with a fridge, Keurig, oven, microwave and toaster. There's a 42" TV paired with an apple TV loaded with multiple apps. Alexa provides info and light control. Two window a/c keep the place cool. Parking is available in the adjacent public lot

4.93 out of 5 average rating, 108 reviews

Flat in Dayton

BRIGHT~AIRY Loft - near Downtown/UD/UVM

Bright, open upstairs apartment in circa 1860 federal style building with high ceilings and lots of natural light. Located a 3 minute walk from Miami Valley Hospital in Historic South Park. Close to the University of Dayton, shops on Brown Street, Interstate 75, the Oregon District and Downtown Dayton. South Park is one of the most popular neighborhoods in Dayton. Walk or bike anywhere. The unit below is currently undergoing work, some noise is to be expected. Only during daytime hours :)

4.95 out of 5 average rating, 121 reviews

Luxury & Wellness

Discover a sanctuary of wellness and luxury in the heart of Dayton, Ohio. Our exclusive three-bedroom, two-bath home is not just a place to stay, it's an immersive bio-hacking experience designed to rejuvenate your mind, body, and soul. Here, health technology isn't just an amenity, it's a way of life offered to our guests at no extra cost. You have seen celebrities like Joe Rogan embrace these technologies on social media, and now it's your turn to experience their transformative power.

4.93 out of 5 average rating, 177 reviews

Guest suite in Dayton

The Wayside

This listing is a suite with a living room, kitchenette, bathroom and bedroom. The living area also has a sleeper sofa for additional sleepers. It has a separate entrance, private parking, and an outside patio area with accessibility to a hot tub, beautiful yard with playground, and close to the Greene shopping area . In the refrigerator will be water along with coffee, tea and a few snacks. Whole house generator installed- no fear of power loss.

Guest house in Centerville

5 out of 5 average rating, 194 reviews

The Carriage House in Historic Uptown Centerville

Welcome to the Carriage House. Walk to shops, restaurants, ice cream & more! Whether you're staying for a fun weekend, romantic get away, work or visiting family and friends- the Carriage House is the perfect place. The Carriage House was built in 1897 & underwent a complete renovation in 2017. With its open style concept & 12 ft ceilings, it has taken on a whole new role as one of Centerville's coziest getaways, in the heart of Uptown.

4.86 out of 5 average rating, 254 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.

4.97 out of 5 average rating, 177 reviews

Updated home in Dayton with low fees!

This unique home in Dayton is loaded with charm. It has been updated in all of the right places to maintain its original character while providing all of the amenities you desire. You'll get quartz countertops, new appliances, high-end mattresses, brand new wood bedframes, and a sit-in front porch. Whether you are here for work or play, this home will be a great "home away from home".

4.94 out of 5 average rating, 195 reviews

Tiny home in Dayton

Stillwater Riverfront Stay in La Casita Cardinal

🏡Welcome to La Casita Cardinal, a cozy 320 sq ft A-frame nestled along the serene Stillwater River, offering over 450 ft of scenic riverfront. Tucked behind main homes on a tranquil lane near the historic Buckhorn Tavern, this peaceful hideaway is ideal for couples, solo travelers, and nature enthusiasts.

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Popular amenities for Montgomery County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Montgomery County

4.88 out of 5 average rating, 57 reviews

Flat in Dayton

*{Spacious 2-Bedroom Gem in the heart of it all!}*

DavidRating, 5 stars2 weeks ago

Great stay! Needed a quiet place to stay for a few days and was not disappointed. Megan is super responsive and everything is as advertised. Highly recommend if you’re in the area!

Bungalow in Dayton

4.75 out of 5 average rating, 344 reviews

The Gemini Bungalow- Your peaceful and cozy pad

ChrisRating, 5 stars2 weeks ago

Very clear on everything! Very good host! Very clean house very peaceful if you want a peace of mind by yourself this is the place to be. The area is very peaceful area! This house looks better in person! Will be booking again soon!!

4.96 out of 5 average rating, 56 reviews

Home in Vandalia

Cozy and Convenient 3 bedroom

PatriciaRating, 5 stars2 days ago

The house is as described and the furniture is comfortable which I have found not to be in many AB&Bs. Victoria responds quickly and all our needs were promptly addressed. We would have been comfortable living in this home. Victoria is an A+ host.

5 out of 5 average rating, 59 reviews

Cottage in Dayton

Rest Haven Cottage: Dayton's Cozy 3-Acre Hideaway

NatalieRating, 5 stars4 days ago

I can’t say enough amazing things about this cottage! It was by far the best airbnb I’ve ever stayed at! Pictures don’t do the cottage justice & it is stacked with absolutely everything you need. You will not be disappointed & I cannot recommend this place enough!

5 out of 5 average rating, 33 reviews

Tiny Home fit for a King: Perfect for Couples!

AvaRating, 5 stars2 weeks ago

I chose this place last minute due to work needing to be done in my home. I stayed for a couple days. The place was clean, comfortable and had all the amenities I needed.

5 out of 5 average rating, 83 reviews

Carillon Cottage - Modern Comfort & Vintage Design

SarahRating, 5 stars2 days ago

Beautiful home that was clean and cozy. Perfect location as we were down for UD alumni weekend and it was less than 5 minute drive to campus.

Superhost

5 out of 5 average rating, 3 reviews

Cozy Bungalow near UD & downtown

JenniferRating, 5 stars2 weeks ago

Such a beautiful home located in a wonderful location; easy highway access, quiet neighborhood, minutes from downtown and University Of Dayton, lots of night life in the area and great dining. The home was exactly what the host described, very clean and loved the interior. The kitchen/dining area was beautiful and had plenty of space. Would definitely book again!