Vacation rentals in Montgomery

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Top-rated vacation rentals in Montgomery

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Top guest favorite
A spacious glass sliding door opens to a patio with outdoor seating overlooking a serene body of water. A fire pit is positioned on the concrete surface, surrounded by four chairs, while trees and grass frame the peaceful view.
Guest suite in Oswego
4.95 out of 5 average rating, 19 reviews

Live it up on the Lake.

Very modern setup in your own walkout lower level of a house. All the amenities and steps away from nature too! Sunrise wake up calls if you want, or remain shrouded in seclusion until you are ready to make your coffee and walk outside to the beautiful sounds of nature. Just a mile away from everything you need. Walmart, Meijer, Sam's club, a veritable bevy of restaurants and more...a few miles away from the Fox Valley Mall. A few miles away from Historic Naperville. C'mon out! Stay with us.

Top guest favorite
A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.
Guest suite in Saint Charles
5 out of 5 average rating, 302 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

Superhost
A modern kitchen features dark cabinetry complemented by granite countertops. Stainless steel appliances, including a refrigerator and stove, are present. Two bar stools with circular bases are positioned near the countertop. Pendant lights hang above the island, adding functional illumination to the space.
Apartment in Aurora
4.82 out of 5 average rating, 102 reviews

AT YOUR SERVICE! Downtown Aurora River Facing Gem

Welcome to your cozy retreat in the heart of Downtown Aurora! This charming 1-bedroom apartment is perfect for up to 2 guests and offers a peaceful river view. The unit is complete with a full kitchen & is pet-friendly. Located steps from Hollywood Casino, Paramount Theatre, RiverEdge Park, and the scenic Riverwalk, you'll have easy access to local attractions. Stroll to restaurants, shops, and entertainment, making this the perfect base for exploring all that Downtown Aurora has to offer.

A cozy sleeping area is highlighted by a spacious bed adorned with decorative pillows. Soft blue accents are provided by a throw blanket and curtains. A standing lamp offers gentle lighting, and a mirror reflects the room's calming colors.
Condo in Montgomery
4.64 out of 5 average rating, 83 reviews

*Cozy Farmhouse apartment/FastWiFi/Hulu/UTubeTV

Pet-Friendly. (Pet fees apply). Beautiful cozy Farmhouse Theme Apartment with tons of amenities. ➢ Fox River 2 blocks away, Aurora University & Aurora Casino- 7 min drive. ➢ Raging Waves Waterpark - 15 min drive. ➢ Fast Wi-Fi 300Mbps ➢ Free parking in the designated indoor garage for 1 compact-size car, plus 2 more in the driveway. ➢ 4k HDTV w Roku, YoutubeTV, and Disney+ included. ➢ Located in Downtown Montgomery Traveling with kids? We have: ➢ Pack'n Play Portable Playard & High chair

Top guest favorite
A single-story ranch home is presented with a dark blue exterior and white shutters. A neatly trimmed lawn and concrete pathway lead to the front door. Flanking the entrance, small shrubs add greenery, while a tall evergreen tree stands nearby.
Home in Montgomery
4.87 out of 5 average rating, 156 reviews

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Top guest favorite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Apartment in Aurora
4.99 out of 5 average rating, 203 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Superhost
A light-filled living area is presented with a soft blue couch and a glass coffee table atop a textured rug. A comfortable armchair complements the seating arrangement. French doors lead to an outdoor deck, enhancing the connection with nature.
Townhouse in Yorkville
4.79 out of 5 average rating, 154 reviews

Riverfront Townhome in Downtown Yorkville

➢ Everything is sanitized/washed/cleaned after every guest ➢ Right on Fox river ➢ Raging Waves Waterpark - 4.1mi ➢ Yak Shack (Canoe & kayak rental) - 0.8mi ➢ Saw Wee Kee Park - 6mi ➢ Fast, Dedicated Wifi ➢ Free parking in attached garage for 2 compact-size cars + additional free parking onsite. ➢ 3 Smart TVs (Living Room, Bedrooms) ➢ Fully equipped + stocked kitchen / bathroom / laundry ➢ Located Downtown Yorkville ➢ Pack 'n Play ➢ High chair ➢ Kurig coffee maker ➢ King size beds

Guest favorite
Home in Aurora
4.82 out of 5 average rating, 11 reviews

4 bedrooms 2.1 bath, Basement - Aurora, Naperville

Location, Location, Location. Four bedrooms. Great-sized home. Strategic location near I-88, Chicago Outlet mall, Rush-Copley Hospital, and new Shopping strips, near RT 59 train station. Full English basement, Light & bright w/9ft ceilings & large windows. Great deck for your outdoor enjoyment. Oswego 308 Schools & onsite park. Your family will be close to everything when you stay at this centrally-located place. It’s 7 beds, up to 10 people includes the basement.

Top guest favorite
The cottage exterior is surrounded by lush green grass and mature trees, providing a peaceful setting. A pathway leads to the inviting porch with pleasant lighting. The sunset casts a warm glow, enhancing the tranquil atmosphere of the setting.
Home in Big Rock
5 out of 5 average rating, 20 reviews

Riverside Cottage

Peaceful two bedroom cottage newly refurbished. Plenty of outdoor space, woods streams and walking trails nearby. Tucked out of the way of busy roads or city life but only a short drive to all the amenities of civilization. Keep an eye out for deer, ducks, beavers, hawks and other scenic wildlife out the back window/patio. There’s even a couple bald eagles that live nearby. Consider a longer stay to take advantage of discounts on 2, 4 or 7 night stays

Top guest favorite
A functional kitchen area features wooden cabinetry and modern appliances. Ample countertop space is complemented by tile flooring. A small dining table with chairs is positioned near a window, allowing natural light to illuminate the space. A doorway leads to a cozy bedroom.
Guest suite in Oswego
4.96 out of 5 average rating, 74 reviews

1 Bed w/ Full Kitchen A Mile From Downtown Oswego

Enjoy a stay within walking distance of 3 parks and about a mile from downtown Oswego and its quaint shopping area. Nestled in the middle of a great neighborhood, you'll feel safe and be able to enjoy a quick getaway or an extended stay. If you're interested in visiting Chicago, we're close enough for day trips to the city (about 45 miles) but far enough to save some money. You'll definitely have a great time here!

Top guest favorite
A tranquil lake scene is depicted, featuring autumnal trees reflecting vibrant hues of yellow, orange, and red in still water. The grassy shoreline enhances the serene environment, while neighboring greenery contributes to the picturesque landscape.
Guest suite in Naperville
4.96 out of 5 average rating, 478 reviews

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

A cozy living area features a dark seating arrangement with a patterned throw, complemented by a wall-mounted television. A spacious bed with decorative pillows is positioned in the background, with an air conditioning unit and a colorful wall art piece adding character to the neutral-toned space.
Apartment in Oswego
4.62 out of 5 average rating, 162 reviews

Convenient Studio Apartment in Oswego | Fast WIFI

• Fast, Dedicated Wifi • 1 Queen Size Bed, 1 Twin Size Sofa Bed • 4k HDTV w Roku, Apple TV 4K, Youtube TV • Onsite parking for 1 vehicle • Fully equipped + stocked kitchen with Keurig coffee & Tea • Desk • Basic toiletries • Vivint security system + keypad entry

Popular amenities for Montgomery vacation rentals

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