Holiday houses in Montgomery County

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Top-rated holiday rentals in Montgomery County

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Top Guest favourite
The exterior of the studio cottage is seen, featuring white siding and red shutters. A walkway leads to the entrance, bordered by vibrant flower pots. Plants are hanging from the front, and a grill area is visible in the background among greenery.
Guesthouse in New Lebanon
4.97 out of 5 average rating, 227 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.

Top Guest favourite
A light-colored couch is centered in the living area, complemented by a striped blue cushion. A glass coffee table rests on a patterned rug. A floor lamp and a side table fill the space, while a landscape painting adorns the wall, adding a touch of nature.
Apartment in Centerville
4.9 out of 5 average rating, 319 reviews

Apt 1: Octopus Garden in Uptown Centerville

This apartment is a twin to our 'Pilot Lounge' airbnb located across the hall. Two adults can sleep in a dedicated bedroom on a queen bed while your third guest sleeps on a twin roll-away bed. The kitchen is equipped for basic cooking with a fridge, Keurig, oven, microwave and toaster plus tableware. 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. Free parking is available in the adjacent public lot.

Top Guest favourite
The guesthouse is nestled among lush greenery and trees, offering a serene view of the white exterior. Vibrant foliage surrounds the structure, while various plants and gardens enhance the natural landscape, creating a tranquil atmosphere.
Cottage in Dayton
4.98 out of 5 average rating, 301 reviews

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.

Top Guest favourite
A modern living area features a dark gray couch adorned with colorful pillows, paired with a mid-century chair. Natural light enters through two windows, illuminating the stylish rug while a round mirror reflects the space. A flat-screen TV is mounted on the wall, accompanied by a decorative console.
Home in Dayton
5 out of 5 average rating, 150 reviews

Modern Historic House in the heart of South Park

Check out this stylish and modern home in the Historic South Park District centrally located in Dayton Ohio. Located on the best street in this trendy neighborhood where you can enjoy a view of the park from the porch. Built in 1880 this newly revamped home has an open concept full kitchen, 2 bedrooms and 2 full baths. Wood flooring and 12-foot ceilings throughout. Close to downtown, Miami Valley Hospital and the University of Dayton. Within walking distance to shopping, dining and much more.

Top Guest favourite
An inviting living area features a large brown leather sofa, a patterned area rug, and a decorative coffee table atop wide plank wood floors. A cozy corner chair and a lamp add warmth, while the back wall showcases a mural with 'Centerville Carriage.'
Guesthouse in Centerville
5 out of 5 average rating, 243 reviews

The Carriage House in the Heart of Uptown

The Carriage House. Historic Charm with Modern Comfort. Built in 1897 and fully renovated in 2017, the Carriage House blends timeless character, with modern style & comfort, making it one of Centerville’s true hidden gems. Just steps from Uptown local restaurants, coffee shops and a scoop (or two) of Graeter’s Ice Cream. It’s perfectly located for your stay. Whether you’re planning a romantic weekend, visiting family, or simply looking to relax, this cozy retreat is the ideal place to unwind.

Guest favourite
A charming blue house features a welcoming front porch with wrought iron railings. Large windows allow natural light to fill the space. A well-maintained lawn and a driveway are visible in front, alongside a detached garage positioned to the side.
Home in Dayton
4.89 out of 5 average rating, 500 reviews

Air Force Museum Getaway! WPAFB & Downtown too...

The best place to stay when visiting the National Air Force Museum. It's open year round, entrance is free, and you even can walk there if you want :) You will also be very close to all the Wright Patterson AFB entrances and only 5 minutes to Wright State University, only 10 minutes to the Nutter Center (for watching various shows) and Downtown Dayton - including the Oregon District, University of Dayton, Schuster Center, Miami Valley Hospital, and others. Perfect for vacation or work!

Guest favourite
A modern living area features exposed brick walls, complementing a spacious grey sofa and a patterned armchair. A round coffee table sits on a striped rug, while a television cabinet and hanging light fixtures add to the elegant ambiance. The kitchen area is visible in the background.
Apartment in Dayton
4.93 out of 5 average rating, 149 reviews

Historic & Eclectic Apt in the Heart of Huffman!

A new space inviting you to experience all that Historic Huffman and the surrounding neighborhoods have to offer! Located in a 140 year old building, this recently renovated unit has been given new life and is ready to welcome you to the Gem City. If you're here for business, visiting friends, or attending a wedding at The Lift or one of downtown's many venues, this centrally located space is a great place to kick-back and relax. Please read House Manual prior to booking. Thank you!

Top Guest favourite
A cozy living area is presented with hardwood flooring and neutral-colored walls. A flat-screen television is positioned near a window with sheer curtains. A small plant adds a touch of greenery beside a comfortable couch, complemented by an accent chair and side table with a lamp.
Apartment in Dayton
4.91 out of 5 average rating, 117 reviews

Root2Rise Quiet, Clean, Prime Location, 2 bedroom

Enjoy your own two-bedroom, first floor apartment in a quiet four-unit building. It is modestly decorated, squeaky clean and cozy. This location could not be more convenient! Walking distance to two grocery stores, retail shopping, and The Fraze Pavilion. Ten minute drive to Kettering Hospital, Miami Valley Hospital, downtown Dayton and University of Dayton. 15-20 minute drive to the Wright Patt Air Force base. Furnished and equipped with everything you need.

Top Guest favourite
The living area features a genuine leather sofa positioned across from a dark wood entertainment unit. Two upholstered armchairs are situated near arched windows, adorned with floral curtains. The walls are decorated with distinctive Gucci wallpaper, and a light rug complements the hardwood flooring.
Guesthouse in Dayton
4.97 out of 5 average rating, 151 reviews

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!

Top Guest favourite
Home in Dayton
4.95 out of 5 average rating, 195 reviews

Beautiful Design, King Bed. Near it All. Fast Wifi

Welcome to La Belle Verde, a Guest Favorite in Dayton’s Historic St. Anne’s Hill. Built in the late 1890s, this home rests on a quiet, tree-lined street in one of Dayton’s most historic neighborhoods, it’s only minutes from downtown, the Oregon District, UD, and Miami Valley Hospital. Inside, history and comfort come together in 10-foot ceilings, windows that pour in natural light, and greenery that brings the home to life.

Top Guest favourite
The exterior of Carillon Cottage features a striking blue facade with white trim, set against a backdrop of lush greenery. The structure displays a classic gable roof, with multiple windows allowing for natural light. A stone wall borders the front garden, which is accentuated by small, neatly trimmed hedges.
Home in Dayton
4.99 out of 5 average rating, 114 reviews

Carillon Cottage - Modern Comfort & Vintage Design

Carillon Cottage is a historic home featuring modern comfort with vintage design. This family-friendly and spacious house, which was originally built in 1905 and fully renovated in 2023, is filled with details highlighting the rich history of Dayton, Ohio. Enjoy the curated display of local photos and elegant furnishings with classical touches. We look forward to hosting you!

Guest favourite
A well-appointed kitchen and living area is showcased, featuring a black sectional sofa with a soft throw. Light wood flooring complements the white cabinetry and modern appliances, including a microwave and a stove. A stylish wall featuring intricate tile patterns adds character.
Home in Dayton
4.91 out of 5 average rating, 144 reviews

Petite Paradise: Tiny Home Vibes! Great Location!

Tiny Home! Enjoy 420 sq home, a private fenced-in yard for your furry friends! Relax on the spacious sun deck or take advantage of the large side yard—ideal for running and playing with your dog. Plus, unwind by the cozy fire pit with provided wood and a swing for ultimate relaxation. Perfect for pet owners and nature lovers alike!

Popular amenities for Montgomery County holiday rentals

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