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.

Hot Tub, 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.

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.

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena

Nestled along a serene, tree-lined road, you'll discover this charming brick and timber resort. Embracing a lodge-like design, it offers tranquil and stylish accommodations that exude comfort and sophistication. Welcome to Wyndham Galena Resort, featuring a delightful 1BR King Suite that invites you to unwind and relax. With its spacious layout and thoughtful amenities, this retreat promises a memorable stay.

Liberty Living - A grand, comfy woodland retreat!

Take a break and unwind at this peaceful oasis. Escape to this warm and cozy home in The Galena Territory. The home is surrounded by trees in a cul de sac offering a secluded and private feel. Plenty of room to spread out in over 4,800 sq ft of space. Several outdoor seating areas to enjoy nature and the fresh air. The Country Store (grocery items and small deli) is very close in proximity.

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, IL, 1 Bedroom S #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 - Special Needs: King in master, queen Murphy bed in living area. Grab bars and roll under sink. Jetted tub in bathroom. Maximum occupancy 4.