Holiday rentals 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.
Guest house in New Lebanon
4.97 out of 5 average rating, 229 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.
Flat in Centerville
4.9 out of 5 average rating, 320 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, 302 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
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.'
Guest house in Centerville
5 out of 5 average rating, 246 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
Home in Dayton
4.93 out of 5 average rating, 194 reviews

Great Location | Historic Oregon District

Welcome to our cozy 1-bedroom duplex, blending mid-century charm with modern comfort in Dayton’s historic Oregon District. Perfect for a weekend getaway or extended stay, this inviting first-floor space offers a comfy queen bed, fully equipped kitchen, and a cozy living room. Enjoy easy access to local attractions and unwind in the warm, welcoming atmosphere after exploring all that Dayton has to offer. #1bedroom #superhost #Airbnb #budgetfriendly #dayton #cozy #easyaccess #DaytonOH

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.
Flat 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
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.
Guest house in Dayton
4.97 out of 5 average rating, 153 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
A bright living room features a comfortable gray sofa and an accent chair beside a wooden coffee table. Natural light fills the space through multiple windows, highlighting the modern decor and a flat-screen TV mounted on the wall. A stylish ceiling fan adds to the ambiance.
Townhouse in Dayton
4.96 out of 5 average rating, 713 reviews

The Riverview Townhome, Downtown Skyline View

Exciting, fun, and cozy townhome built in 1883 with tranquil views of the downtown skyline and the Great Miami River in a charming, historic district near downtown The RiverScape Metropark, The Levitt Pavilion, and multiple bars/restaurants are within walking distance. The excitement of the vibrant Oregon District is also within minutes, whether walking or driving. Both WPAFB and Wright State University are an easy 10-15 minute drive!

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.

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, 146 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!

Superhost
A warm living room is showcased with a vintage-style sofa and chairs arranged around a central coffee table. A patterned rug covers the floor, and natural light enters through two windows, creating a relaxed ambiance.
Cottage in Dayton
4.79 out of 5 average rating, 418 reviews

The Surf Shack in South Park

Close to downtown, Miami Valley Hospital and University of Dayton. This surfers paradise offers a bright and cozy place to rest and relax. Close to coffee shops, local breweries, and in the summer time surfing. Dayton has standing waves you can surf and this adorable bungalow is an homage to the sport. Please enjoy your stay!

Top guest favourite
A charming single-story home with a welcoming front porch illuminated by warm string lights. Stone and wood accents enhance the exterior, while well-maintained landscaping features green plants and autumn leaves. The inviting entrance includes two chairs for relaxation.
Home in Dayton
4.95 out of 5 average rating, 172 reviews

The Cozy Corinth

Welcome to The Cozy Corinth! A peaceful escape from the hustle and bustle of everyday life. Conveniently located just a short drive from downtown Dayton. Note: Please, no parties or events! We are located in a small, quiet neighborhood and cannot accommodate parties or events. Thanks for your understanding.

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