Holiday houses in Stockton

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Top-rated holiday rentals in Stockton

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Top Guest favourite
Home in Stockton
4.93 out of 5 average rating, 29 reviews

Hudson Hotel

Located in picturesque Stockton, Illinois, this 4-bedroom home boasts numerous updated features including a new kitchen and bathrooms. Ideal for family getaways, group trips, or business stays. Situated conveniently within walking distance of essential amenities such as a grocery store, gas station, local restaurants, bars, and a town pool, it ensures convenience and accessibility. Nearby attractions include the charming towns of Galena, Dubuque, and Freeport, enhancing the appeal of your stay.

Guest favourite
The living area features a comfortable sofa, accented with pillows, and a pair of ottomans. Two windows allow natural light to fill the space, adorned with sheer red curtains. A television is positioned on a wooden stand, accompanied by decorative plants and framed artwork.
Home in Bellevue
4.8 out of 5 average rating, 128 reviews

Mississippi River house has everything you need

Your family will be close to everything when you stay at this centrally-located place. The river is right across the street and so is the walkway the walkway will take you all the way to the other end of town beautiful walk along the river. Richmond‘s café Great place for breakfast. The brewery has igloos to sit in outside just two blocks from the guest house. The river park will be lighted for Christmas right across the street all the way through the end of town Great place to be this holiday

Top Guest favourite
An inviting firepit area features two black Adirondack chairs positioned around a circular stone firepit. The A-frame cabin is seen in the background, softly illuminated by decorative lights, surrounded by trees at dusk.
Cabin in Elizabeth
4.97 out of 5 average rating, 104 reviews

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Top Guest favourite
A wooden swing hangs from a tree in a lush green field, gently swaying in the breeze. In the background, the log home is set atop a hill, showcasing its wrap-around deck and panoramic views of the surrounding landscape under a clear blue sky.
Guesthouse in Stockton
4.98 out of 5 average rating, 395 reviews

HighviewCountry Escape-log home-family farm w/view

Whether you want a staycation or just a weekend away, we have the place for you! Quiet secluded setting, with spectacular view, on one of the highest hilltops in Illinois! Morning sunrises are exceptional. Evening sunsets are breathtaking. Starry nights are amazing. Something in every season! Not far from Galena and other small towns that offer charm, restaurants and shopping. Our rental is fully independent and has everything that you need for your getaway. Please see all photos.

Guest favourite
The modern living space features a grey sofa with a patterned throw pillow, positioned near a wooden coffee table. A dining area with two black chairs is visible, alongside an open kitchen that includes stainless steel appliances and dark cabinetry. Natural light brightens the room.
Apartment in Galena
4.99 out of 5 average rating, 158 reviews

Ulysses Suites, Suite 302

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213 to 217 S. Main Street. The location is walking distance to all the best restaurants and shops. We have 7 suites and a beautiful lobby that are modern and luxurious, with lots of historical character as a nod to its previous existence as the Grant Hotel from 1895 to 1933. Suite 302 is an ADA accessible unit located on the 3rd floor and can be attached to Suite 301.

Top Guest favourite
The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.
Treehouse in The Galena Territory
4.99 out of 5 average rating, 214 reviews

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Top Guest favourite
A charming exterior view of the house is shown, featuring a welcoming porch with wooden seating. The deck extends from the entrance, surrounded by greenery and trees, providing a connection to nature and a peaceful retreat.
Cabin in Savanna
4.97 out of 5 average rating, 371 reviews

Cozy, Secluded Cabin -A Peaceful Getaway Location!

Located just a half mile from town, but secluded enough to be a private hilltop house retreat. The deck overlooks downtown with a backdrop of the Mississippi River! Enjoy the outdoors hiking at the Palisades State Park with miles of trails just a short drive away, kayak or fish one of the many rivers or lakes, stroll through downtown for antique and gift shopping, or visit a nearby winery. After a day of adventures, relax in the spa tub or enjoy a glass of wine on the private deck.

Guest favourite
Tiny home in Stockton
5 out of 5 average rating, 14 reviews

A-Frame Cabin Retreat

Escape to tranquility in this stylish A-frame cabin nestled in the woods just 20 minutes from historic downtown Galena, IL. Whether you're sipping coffee on the deck, cozying up by the fire pit, or exploring historic Galena, this unique cabin is your perfect year-round getaway. Thoughtfully designed with a blend of rustic charm and modern comfort, the cabin is ideal for couples, small families, girl’s weekends, or solo travelers seeking peace, privacy, and a touch of adventure.

Top Guest favourite
A blue A-frame house is showcased, surrounded by greenery. The brick walkway leads to a cedar deck, framed by landscaping. Windows are visible on the sides, allowing natural light to fill the interior.
Chalet in Elizabeth
4.92 out of 5 average rating, 373 reviews

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

Guest favourite
A calm view of the Mississippi River is presented, featuring smooth water reflecting trees along the bank. The scene is framed by greenery and a gravel path leading toward the river, with a soft gradient of colors in the sky at dusk.
Home in Bellevue
4.93 out of 5 average rating, 103 reviews

Kick Back and Relax at this River Front Property!

This river front home is the perfect getaway to relax! With 3 bedrooms, 2 and a half baths, and a screened in porch overlooking the Mississippi River - this home is great for families, couples and/or a friends trip! This home is a on a quiet, private gravel road outside of the quaint, small town of Bellevue, IA, which has so much to offer! Enjoy watching the river go by and the spectacular sunrises from the many amazing views this home has to offer!

Guest favourite
A spacious outdoor deck is featured, surrounded by lush greenery. Several chairs and a table are positioned for seating, with large windows of the cabin visible in the background, allowing natural light to illuminate the interior.
Tiny home in Thomson
4.88 out of 5 average rating, 498 reviews

Cozy Cabin on the Mississippi River

This cabin is located on the serene backwaters of the Mississippi. It is the perfect destination for a weekend getaway, or ideal spot to rent for fishing tournament‘s or duck hunting. This cabin is situated next to pool 13, and there is plenty of space for multiple vehicles and boats to park. Only half a mile away from the loading dock and close by to an Illinois State Park, our cabin allows Guests to enjoy nature in a relaxed setting.

Top Guest favourite
The exterior of the revitalized car wash features a striking white facade with bold red accents. A vintage black truck is parked on the grass, while two bright red chairs sit invitingly near the entrance, adorned with a retro-style sign pointing towards the inn.
Home in Shullsburg
4.99 out of 5 average rating, 210 reviews

The Car Wash Inn A Unique Stay

Enjoy a unique stay inside a beautifully revitalized single bay 1950s car wash. Only minutes away from historic downtown Shullsburg. This space has been thoughtfully designed to retain it's industrial charm with a nostalgic ambiance, while offering modern amenities for a comfortable stay. ~20 miles to Galena, IL ~25 miles to Mineral Point, WI ~25 miles to Dubuque, IA ~ATV Trail Access with large parking area

Popular amenities for Stockton holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Jo Daviess County
  5. Stockton