Holiday houses in Stockton

The Ho Hum East on Apple Canyon Lake

The Ho Hum East is a beautiful lake house with private dock on pristine Apple Canyon Lake! The house is named in honor of my grandparents who ran the Ho Hum Motel in Denison, Iowa :) A place to unwind, de-stress, and have some family fun! The house features all brand new mattresses in 3 bedrooms plus flex space; master bedroom with queen bed, guest bedroom with 1 queen and 1 twin, loft bedroom with 2 queens, pull out couch in living room, and 2 couches in the loft that pull out into twin beds.

Family · Location · Kitchen

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.

Family · Value · Hospitality

Family Friendly Modern Farmhouse 42 Private Acres

PRIVATE FARM FOR YOU! 42 acres of woods, prairie and pastures surround a renovated 1880s farmhouse nestled in a private valley outside Elizabeth, IL. Breathtaking views, fishing pond, canoe, hiking trails, fire pits, screened in porch and acres of rolling prairie make for the perfect getaway. Pets welcome (add. fee applies). 20 min. from Galena & 2 hrs from Chicago. Family friendly, we provide everything for kids of all ages including pack-n-play, height chair, games, activities and more.

Location · Family · Outdoor spaces

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.

Location · Family · Condition

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.

Value · Location · Laundry

Family Fall! Hot Tub•Fire In/Out•Game Room•3 Kings

Relax, unwind, & explore at this Fall Retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and fall/winter adventure!

Location · Family · Sleep quality

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

Value · Family · Air conditioning

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

Family · Location · River

Pool Table + Ping Pong | Fireplaces | Hot Tub

Escape to this spacious 4-bedroom, 5-bath luxury retreat in the Apple Canyon Lake community—perfect for relaxing, reconnecting, and enjoying time together with beautiful lake views and incredible gathering spaces throughout the home. ✨ HIGHLIGHTS • Stunning wraparound stone fireplace 🔥 • Basement game room with pool table, ping pong, foosball + darts 🎯 • Huge wall of windows + soaring ceilings • Large Smart TVs + fast WiFi • Minutes to golf + dining ⛳ • 12pm check-in & check-out

Family · Indoor spaces · Checkout

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

Family · Location · Layout

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.

Location · Family · Accuracy

The Farmhouse

Relax by yourself, with friends or the whole family at this peaceful country spot -limited cellular. Explore Jo Daviess county in the northwest corner of Illinois and surrounding areas staying in a recently renovated country ranch style house located on a 150 year old working farm. Perfect get away from the fast pace busy life for those who want to take a quiet break, history buffs, explorers, and making lasting memories with family or friends.

Location · Value · Comfort