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Holiday houses in Oswego

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Top-rated holiday rentals in Oswego

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.
Home in Naperville
4.85 out of 5 average rating, 179 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Guest favourite
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, 174 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 favourite
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
4.98 out of 5 average rating, 274 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.

Guest favourite
Guesthouse in Oswego
4.91 out of 5 average rating, 110 reviews

The Loft-Rustic Retreat and Sauna

This unique space features a beautiful relaxing yard space and easy walking distance to downtown Oswego.. If you need a place to work quietly or stay overnight this is the ideal location to get rest and relaxation, as well as, enjoy the local tranquilities. Antique shopping, River adventures, Bike trails, and more! The Fox River Trail is a few blocks from the Loft and goes North all of the way up to Algonquin. Along the trail is the River where you can tube, kayak, canoe, fish…

Guest favourite
A spacious living room features a large sectional sofa and two blue upholstered chairs, arranged around a black coffee table on a light area rug. A flat-screen TV is mounted on the wall, flanked by shelves with decorative items. Natural light enters through large windows with sheer curtains.
Home in Oswego
4.91 out of 5 average rating, 159 reviews

Cozy 4-bedroom ranch - minutes from everything

Relax and have fun with the whole family at this peaceful place to stay. It is located within walking distance from US Route 34 in the middle of shopping centers such as Meijer, Jewels, Target, Walmart, great restaurants, bars, entertainment, hair and nail salons, gas stations, etc. There are 5 beds (1 king and 4 queens plus a queen-size air mattress and a twin pull-out bed) and 3 couches waiting for their guests. The house is cleaned and sanitized before every reservation.

Superhost
A modern two-story house features a light, neutral exterior with decorative shutters. The inviting front yard is well-maintained, including colorful shrubs and a manicured lawn. A garage door is visible on the right side, and tall trees frame the property against a clear blue sky.
Home in Naperville
4.86 out of 5 average rating, 169 reviews

California King Bed | Fast Wi-Fi | 75" Smart TV

Our 3bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful, quiet neighborhood. Built w/ cathedral ceilings, there is plenty of space for 10 people to sleep comfortably (6 beds & several comfy couches), as well as 3 smart TVs, an indoor fireplace, a gas grill & large yard (including outdoor games), a desk space, & more. Enjoy close access to main roads & large stores (Costco, Walmart, hardware stores, etc.)!

Top Guest favourite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Apartment in Warrenville
4.94 out of 5 average rating, 129 reviews

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

Top Guest favourite
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
4.95 out of 5 average rating, 83 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 favourite
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, 556 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.

Guest favourite
Home in Oswego
4.9 out of 5 average rating, 20 reviews

Luxury Riverfront Retreat w/ Game Room + Fire Pit

Welcome to Dovehill, a luxury riverfront escape where comfort, connection, and adventure meet. Perfect for families, friends, and group getaways, this elegant 3-bedroom, 3-bath home offers direct access to the Fox River, resort-style amenities, and expansive outdoor living — all set against the peaceful backdrop of nature.

Guest favourite
The exterior of a renovated two-story farmhouse is showcased, featuring a fresh gray facade and white trim. Large windows offer natural light, and a wraparound porch is accessible. Lush green grass surrounds the home, complemented by trees in the background beneath a partly cloudy sky.
Home in Oswego
5 out of 5 average rating, 10 reviews

Private 8 Acre Retreat Near Wedding Venues

Escape the city in this newly renovated 2800 sf farm home placed on a park like 8 wooded acres — complete with stainless kitchen, fire-pit, game room and plenty of space for family or friends. Ideal for families, groups, remote workers, or anyone craving peace + comfort just outside the suburbs.

Guest favourite
Apartment in Aurora
4.78 out of 5 average rating, 119 reviews

Aurora Apt with garage, fast wi-fi and laundry

This home has everything you need, 4k smart TV, 1 car garage, yard, laundry inside unit, full kitchen, comfortable king size bed and a sofa bed. There is also high speed internet available, you will feel like you're right at home.

Popular amenities for Oswego holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Oswego

Guest suite in Montgomery
4.92 out of 5 average rating, 78 reviews

Beautiful Basement Studio By The Fox River

Top Guest favourite
Home in Montgomery
4.96 out of 5 average rating, 26 reviews

5 bdrm 7 bed 2.5 bth Ranch w Fenced Yard Sleeps 10

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
4.65 out of 5 average rating, 176 reviews

Convenient Studio Apartment in Oswego | Fast WIFI

Home in Oswego
4.78 out of 5 average rating, 108 reviews

Moxie - w/ Game Room- 4 Kings, Sleeps 15

Guest favourite
Home in Naperville
5 out of 5 average rating, 9 reviews

Elegant 4BR Tudor Retreat — Spacious, Peaceful!

Guest favourite
Apartment in Downtown Naperville
4.87 out of 5 average rating, 193 reviews

Comforts of home in downtown Naperville

A comfortable living area features a dark couch with yellow accent pillows. A small side table holds a tray and tissue box. A desk with a chair is positioned near a window, and a wall-mounted television displays various apps.
Apartment in Oswego
4.75 out of 5 average rating, 72 reviews

Studio| 2 min drive to Downtown Oswego

Top Guest favourite
Home in Yorkville
5 out of 5 average rating, 9 reviews

Private Riverfront: Kayak-Fire Pit-Near Water Park

Frequently Asked Questions

  • What are the best places to stay in Oswego?

    Oswego has a range of stays, including private homes in quiet neighborhoods and options near downtown. Stays around historic and residential areas often provide easy access to local shops, cafes, and green spaces.

  • What are the best things to do in Oswego with kids?

    Families often explore local parks, join fun programs at the Oswego Public Library, or enjoy play areas and community centers around town. Outdoor festivals and seasonal events are frequently suggested for younger visitors.

  • What are some of the best things to do in Oswego?

    Explore the art displays in Oswego’s downtown, stroll along Hudson Crossing Park’s waterfront, or learn local history at the Little White School Museum. Outdoor concerts and food festivals bring the community together seasonally.

  • How is the weather in Oswego?

    Oswego experiences cold winters around 13–33°F (-10–1°C) with snow, while summer days are warm, reaching 80–82°F (26–28°C) and often humid. Spring and fall bring mild temperatures and changing foliage, so packing layers is helpful.

  • When is the best time to visit Oswego?

    Late spring through early fall is often recommended for milder weather, lively festivals, and outdoor activities. Winter brings cold temperatures and snow, creating a quieter atmosphere for those who enjoy a slower pace.

  • What are the best places to visit in Oswego?

    Visitors frequently explore Hudson Crossing Park, walk the Fox River Trail, or browse exhibits at the Little White School Museum. The downtown area is also known for local shops and welcoming cafes.

  • What are some hiking trails in Oswego?

    The Fox River Trail is often recommended for walking, running, or biking along scenic river views and natural areas. Other local parks have shorter paths and loop trails suitable for a relaxed outdoor experience.

  • What are some family activities we can do in Oswego?

    Families can picnic and play at local parks, discover hands-on history at the Little White School Museum, or attend seasonal events together. Community pools and ice skating are also popular activities depending on the season.

  • What are some of the best day trip ideas from Oswego?

    Visitors often take day trips to nearby forest preserves, historic towns, or larger cities known for museums and shopping. Popular choices include exploring scenic state parks or discovering family attractions just outside Oswego.

  • Are there any pet friendly accommodations available in Oswego?

    You can find pet friendly stays in different Oswego neighborhoods, including near parks and residential areas. Many hosts welcome pets, and some offer fenced yards or easy access to nearby walking trails.

  • What are some local tips for visiting Oswego?

    Locals suggest exploring the downtown farmers’ market, trying homemade treats at small bakeries, and visiting area parks early for a peaceful experience. Weekends tend to host seasonal events, so check community calendars for updated offerings.

  • What is Oswego known for?

    Oswego is known for its charming downtown, historic sites like the Little White School Museum, and community events that celebrate local art and music. The area is also recognized for natural spaces around the Fox River.

  • What are the best hidden gems to explore in Oswego?

    Oswego has tucked-away art murals, community gardens, and small batch coffee shops that are favorite local discoveries. Some visitors also enjoy peaceful paths along lesser-known areas of the Fox River.

  • What are the best foods to try in Oswego?

    Oswego has a variety of dining with frequently suggested options including classic American comfort foods, locally made pizza, and family-run bakeries. Seasonal farmers’ markets highlight fresh produce and regional specialties.

  • What should I bring for a trip to Oswego?

    Pack weather-appropriate layers, as temperatures change across seasons, and bring walking shoes for park trails or the downtown area. A reusable water bottle and sun protection are useful, especially for outdoor activities.

  • What is the nightlife in Oswego like?

    Oswego’s nightlife has local bars, breweries, and casual restaurants where people gather for live music or trivia nights. Some venues feature outdoor patios, especially during warmer months.

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