Holiday rentals with a pool in Jackson County

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Top-rated rentals with a pool in Jackson County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Superhost

Home in Galena

4.89 out of 5 average rating, 28 reviews

Expansive 5b6ba Countryside Home

Come enjoy your home-away-from-home with a private forest on a serene 2.12 acres. This home is perfectly designed for guests to spend quality time with family, friends, or colleagues in large, open concept common spaces and then discreetly escape to recharge into your own space/bedroom. The kitchen is professional grade and fully stocked to help you impress others with your cooking techniques OR to hire a professional. Each bedroom has with a private bathroom and towels of the highest quality.

Superhost

Home in Galena

4.65 out of 5 average rating, 17 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.

Superhost

Home in Galena

New place to stay

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

Home in Galena

4.96 out of 5 average rating, 98 reviews

Secluded Treehouse w/amazing views & private trail

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.

Top Guest favourite

Home in Elizabeth

4.96 out of 5 average rating, 46 reviews

Cliffside Cottage, Breathtaking Views near Galena

Cliffside Cottage, a secluded wooded retreat located on 50 acres with breathtaking views, a pond to swim, fish, wooded trails, and so much more! A perfect destination to get away from it all while being in close vicinity to so many amenities. The cottage, conveniently located just off Highway 20. Only a 15 minute drive from Eagle Ridge/Galena Territory, and only 20 minutes from Chestnut mountain and historic downtown Galena that offers museums, boutiques & restaurants!

Guest favourite

Home in Galena

5 out of 5 average rating, 71 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!

Superhost

Home in Galena

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!

Guest favourite

Holiday home in Galena

4.96 out of 5 average rating, 105 reviews

Hot Tub Retreat|Summer Nights · Fall Colors Await

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.

Superhost

Apartment in Galena

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.

Superhost

Condo in Galena

4.6 out of 5 average rating, 5 reviews

Tranquil Retreat: Cozy Studio @ Wyndham Galena

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. Wyndham Galena Resort |Queen Bed Studio w/ Balcony • Size: 417 - 450 • Kitchen: Mini • Baths: 1 • Accommodates: 2 Guests • Beds: Queen Murphy Bed - 1

Superhost

Apartment in Galena

4.91 out of 5 average rating, 46 reviews

Studio Unit @ Galena Condo Resort

Studio Unit 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★

Top Guest favourite

Home in Galena

5 out of 5 average rating, 73 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.