Holiday rentals with a pool in Jackson County

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.

Secluded Treehouse w/great views from every room!

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.

Comfortable retreat w/sounds of nature! Firepit

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. Dog Friendly, Firepit

Tower House | Heated Pool, Sauna, Hot Tub + Views

Tower House sits on its own hilltop in The Galena Territory, home to the area's only heated private saltwater pool, plus a cedar sauna, hot tub, fire pit, and a glass observatory tower in a certified Dark Sky community. Sunset views from every window. Four bedrooms and multiple living areas, generously equipped and spacious enough that groups stay together without feeling crowded. Minutes to downtown Galena and Chestnut Mountain. Guests say it feels like a five star boutique hotel.

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.

Brand New Luxury Home on The General's 17th

⛳ Overlooking the 17th hole of The General ⛳ Brand-new luxury construction ⛳ Sleeps up to 10 guests ⛳ Private cul-de-sac setting ⛳ Garage game room with ping pong 🏓 ⛳ Arcade machines & rec room 🎮 ⛳ Fire pit under the stars 🔥 ⛳ Large deck & patio with golf views ⛳ Chef's kitchen & designer furnishings ⛳ Fast WiFi & Smart TVs 📺 ⛳ 6 Guest Passes to Territory amenities 🏊 ⛳ Minutes to golf, trails, marina & Owners' Club ⛳ Family friendly - pack 'n' play included

10 Goldenrod

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!

Summer in Galena | Hot Tub, Fire Pit & 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.

Galena - 1BR Condo

This spacious one-bedroom resort suite measures approximately 750 square feet. You will enjoy a king bed in the master bedroom and one queen Murphy bed in the living room. Additional amenities include a full kitchen and dining area, washer/dryer, fireplace, and a whirlpool. Maximum occupancy is four. Private sleeping area sleeps two.

Studio Suite @ Club Galena Resort

You'll have a great time at this comfortable place to stay. You’ll come upon the brick and timber edifice of this resort along a quiet, tree-lined road. The lodge-like design offers peaceful accommodations draped in style and comfort. Second only to Chicago as the most-visited destination in Illinois, Galena is a vacation dream.

King beds, Fire places, Game Room, Dog friendly.

Wonderful Galena Territory home with 4 bedroom/3 bathroom (2700 sq ft) where you, your family and/or friends can enjoy everything that Galena has to offer. Spacious home with plenty of room to entertain and gives you the opportunity to enjoy your vacation or golf get away to its fullest.

Galena Resort Condo w/ Pool, Hot Tub & Balcony

***Condo: Studio Condo w/ Queen murphy bed in living area. - kitchen that includes a two-burner stovetop, microwave, and small refrigerator, limited counter space - gas fireplace - jetted tub in bathroom - cable TV - A/C - Balcony -maximum occupancy 2.