Holiday rentals with a pool in Jackson County

4.62 out of 5 average rating, 34 reviews

The exterior of the cabin features a white facade with a green metal roof. Windows allow natural light, and the surrounding tall grass adds a rustic charm. A gravel pathway leads to the entrance, enhancing the cabin's secluded setting.

Ranch in Elizabeth

The Cabin at The Ranch, Galena, aka The Love Shack

Newly renovated, private romantic cabin with high end appliances, granite kitchen and bath counters, knotty alder doors. Located on 500 acre working cattle ranch and commercial wine grape vineyard. Wildlife abounds: Bald Eagles, coyote, bobcat, deer, pheasant, raccoon, and turkey. Close to The General golf course. Hayride and vineyard tour available. Use the amenities of GTA Owner’s Club. See adjacent Sister property The Lodge at The Ranch, airbnb.com/h/thelodgeattheranch, for groups up to 12.

A modern bathroom features dual circular mirrors above elegant stone sinks. The spacious walk-in shower is equipped with multiple showerheads and glass walls, enhancing the contemporary design. Soft lighting is provided by sleek sconces on the walls.

4.57 out of 5 average rating, 23 reviews

Modern Home - Sauna, Steam Shower & Chef's Kitchen

Escape to this 4,000 sqft retreat, perfect for family gatherings or groups. Unwind with a private hot tub, sauna, steam shower, and two fireplaces. Indulge Your Inner Chef: Prepare culinary delights in the gourmet chef's kitchen, then challenge your friends to a foosball or poker game. The GTA Awaits: Enjoy full access to all GTA amenities, a pool & recreation complex, lake & marina, and over 25 miles of scenic trails. Downtown Galena & Chestnut Mountain Ski Resort are both 10 minutes away.

Guest favourite

The exterior of a modern wooden home is showcased, surrounded by lush greenery. Large windows bring natural light into the space, and a gravel pathway leads to the entrance. The sloped roof adds character, while a patio area is visible, providing a welcoming entry.

5 out of 5 average rating, 5 reviews

Comfortable retreat w/sounds of nature!

Relax with the family at this wonderful nature's retreat. If you are planning a family trip, or just a weekend with friends memories are waiting to be made at this cozy home in the woods. Swimming, horseback riding, zip lining, boating, hiking, skiing & many other activities. Downtown Galena is a short drive away. Relax with a our jetted 2 pp bathtub and spacious walk in shower, Roku TV’s, wood fireplace, 4bdrm, 4.5 bath, fully stocked kitchen. deck/gas grill. WIFI. Pet Friendly, no cats

Guest favourite

A warm living area features a brick fireplace with a mounted television above it. Large skylights and windows allow natural light to fill the space. A coffee table stands at the center, adorned with decorative items, complemented by comfortable seating and a vibrant area rug.

4.96 out of 5 average rating, 107 reviews

Secluded Treehouse, w/great views, close to Hwy 20

Enjoy the many charms of this one of a kind Tuscan style treehouse with different levels showcasing spectacular views. This home has every amenity and personal touch of home to make your stay relaxing and memorable. Conveniently located approximately 1 mile off Highway 20 in the Galena Territory, backing up to hole 13 on The General Golf Course. Set back off the main road you will enjoy privacy without sacrificing convenience and access to the many amenities offered during your stay.

5 out of 5 average rating, 26 reviews

The cabin exterior reveals a wooden facade with a welcoming porch highlighted by rocking chairs and potted plants. A barbecue grill stands ready for outdoor cooking. The surrounding landscape features greenery and trees, creating a tranquil setting.

Cabin in Elizabeth

Cedar Cove Cabin, Private Beach near Galena

Cedar Cove Cabin, nestled amongst the woods and a newly structured pond you’ll wake up feeling like you’re in the north woods! A luxury cabin amongst a wooded retreat on 50 acres, pond to swim and fish, beautiful surroundings , trails, and so much more! Welcome to your perfect vacation home! As you drive down the lane to our Cedar Cove Cabin you will instantly feel that you are leaving your busy, hectic daily life and you have entered a place of serene getaway.

A spacious home is situated on a gently sloping landscape, framed by mature trees. The exterior features a combination of stone and wood elements, with a welcoming front porch and large windows that enhance natural light. A paved driveway leads up to the property.

5 out of 5 average rating, 76 reviews

Stunning 5 bdm home on The General in Galena Terr!

No MGMT Fees! Enjoy all that Galena Territory and Jo Daviess County has to offer! Nearly 5k sq ft with 5 bdrm/5.5 baths and located on the number one handicap hole on The General golf course with views of holes 12, 13, 14, 15 and 16! A one-of-a-kind location on over 2 acres of land. About 20 min from Downtown and Chestnut Mtn! Minutes from golf, hiking, horseback riding, boat rentals, fishing, indoor/outdoor pool, fitness center and game room at the Owner's Club!

A charming red house is nestled among autumn foliage, showcasing shades of orange and yellow. The entrance features a covered porch with seating for relaxation. Surrounding greenery and a gently sloping lawn add to the inviting exterior of the home.

10 Golenrod

Stunning 5R/5.5BA BIG Retreat in The Galena Territory! Pool Table! Firetable! This stunning 5 bedroom/5 ensuite FULL bath Galena Territory resort home has a large screen porch and deck. This home is designed to accommodate ten guests in beds. Two additional guests are allowed, but there is no sofa sleeper. NEW!! We now have a large fire table on the back deck. Enjoy gathering around a warming fire without the inconvenience of wood. We provide propane. Have fun!

4.96 out of 5 average rating, 124 reviews

A spacious dining area features a large wooden table surrounded by black chairs. A living space is visible in the background with comfortable seating, large windows, and a sleek gas fireplace. Natural light fills the room, highlighting the open and airy layout.

Holiday home in Galena

Fall Escape | Hot Tub, Fire Pit & Galena Views

Welcome to Shenandoah Ridge—our thoughtfully designed 4-bedroom, 4.5-bath vacation rental tucked into the woods of The Galena Territory. Spacious, peaceful, and full of cozy touches to help you unwind. Whether you’re here for a family getaway, group trip, remote work retreat, or just time in nature, you’ll find everything you need to feel at home. Just 7 minutes to the Owners Club and 15 minutes to downtown Galena—close to the action, but still calm and quiet.

4.88 out of 5 average rating, 8 reviews

An indoor pool area is presented, featuring a smooth pool surface reflecting large windows that allow natural light to flood the space. Comfortable seating is arranged along the poolside, and a stone accent wall adds texture to the environment.

Flat in Galena

Galena 1 Bdrm Condo Resort

Large 1 Bedroom condo at a resort condo development in beautiful, Galena,Illinois ❤ Free Parking. Free Internet ❤ ★ If reserving a FRIDAY OR SATURDAY there is a 2 night minimum unless request is made last minute (3 days before check in)★ ★24 hour reception★ ★Calendars updated daily★ ★Multiple Units/Room Sizes Available★

An aerial view showcases the home nestled among lush greenery. The structure features multiple levels, with large windows and a spacious deck visible, blending seamlessly into the surrounding trees. A pathway leads from the deck into the dense foliage.

5 out of 5 average rating, 79 reviews

Secluded Country Dream with all the fun!

You'll make lasting memories in our newly appointed stylish retreat located in The Galena Territories! Whether you come to Galena to shop, ski, golf or just soak up the sun, Owl's Stay has all the essentials needed to relax, have fun, and spread out with your loved ones.