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.

Spacious/hot tub/games/firepit

Bring the family to this great place with lots of room for fun. Spacious home features living areas along w/downstairs game room. 2 fireplaces, outdoor hot tub, firepit or barbeque grill. Six bedrooms, each w/TV & bath. 5 bedrooms furnished w/kings & 6th bdrm w/2 queens. Wireless internet. Fully furnished kitchen. Screened porch. Owners Club guests can enjoy amenities (swimming pools, tennis, exercise room, bball). Lake Galena/Marina/Shenandoah Riding Center/golf all nearby.

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.

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!

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.

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

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.

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.

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.

Galena, IL, 1 Bedroom #1

I can accept a 1-night stay for a weekend night (Friday or Saturday) if the date is within 2 days of stay date. One Bedroom: King in master, queen Murphy bed in living area. Jetted Tub in bathroom. Max occupancy 4.