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 spacious living area is equipped with a comfortable leather sofa and contemporary wooden furniture. A large television is mounted on the wall, while a stylish round coffee table sits in the center. Natural light enters through two windows, enhancing the neutral color palette.
Bungalow in Dayton
4.96 out of 5 average rating, 330 reviews

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.

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, 321 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.

Superhost
Flat in Huber Heights
4.83 out of 5 average rating, 180 reviews

Rest & Connect! Wi-Fi, WSU, WPAFB, Ext-Stay, Pets

Bright, beautiful, comfortable 2-bedroom apartment for friends, families. Small pets welcome! Relax & enjoy your time together watching Roku Tv or playing some provided board games! Coffee & tea are provided! Close to Hollywood Gaming, WPAFB, Air Force Museum, Miami Valley Hospital, Wright State & University of Dayton. 18 Amazing Parks! I'm always available to you to ensure a 5 star stay! Note: Strict cleaning and sanitizing measure are in place to ensure the health and safety of our guests.

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, 303 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, 248 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 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, 151 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 charming yellow cottage is presented with a vibrant blue door, decorated with a festive wreath. Lush greenery surrounds the home, featuring neatly trimmed bushes and a well-kept lawn. A soft path leads to the welcoming entry, while a wooden fence offers a sense of privacy.
Home in Dayton
5 out of 5 average rating, 104 reviews

Yellow Bird Cottage; Cozy, Clean, Downtown

Tranquil and exceptionally clean solar powered home on a cul-de-sac in a quaint and safe historic neighborhood near downtown Dayton. It is excellent proximity to many events, bike paths, rivers and highways. Nearest restaurants, coffee, clubs, bars and river are 5-15 min walk. Grandveiw Hospital-.3 mile Dayton Art Institute-.3 mile Victoria Theater and Schuster Center- .7 miles Oregon District-1.2 miles UD-3.3 miles National Museum of the Air Force-13 miles

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, 156 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 spacious living area features a light-colored sectional sofa adorned with patterned cushions. A wooden side table stands nearby, and various plants add natural elements. Sunlight filters through sheer curtains, enhancing the bright ambiance of the room.
Home in Dayton
4.95 out of 5 average rating, 195 reviews

Well-Styled · King Bed · Fast Wi-Fi · Top Location

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
A spacious living area is highlighted by large windows that allow natural light to fill the room. A black sofa and a unique black chair are positioned around a round wooden coffee table. A decorative fireplace and built-in shelving add charm to the space.
Loft in Dayton
4.91 out of 5 average rating, 172 reviews

The Loft on 5th w/hot tub in the Oregon District

Enjoy your stay in the heart of Dayton's entertainment district. This beautiful building built in 1870 is right on the main strip, seconds away from breweries, pubs, bars, and restaurants in and around the Oregon District. Minutes away from the University of Dayton and Miami Valley Hospital. Located just east of I-75 and north I-35. A short 15 minute drive to WPAFB.

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!

Popular amenities for Montgomery County holiday rentals

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