Holiday rentals with a pool in Jo Daviess County

The exterior of the home is showcased, highlighting a multi-level structure surrounded by lush greenery. Large windows reflect warm indoor lighting, and a spacious deck is visible, featuring Adirondack chairs positioned near the lawn, offering ample space for relaxation and outdoor enjoyment.

4.96 out of 5 average rating, 109 reviews

Treehouse! Hot Tub • Fire-pit • Spacious

🌲7 minutes to Owner's Club 🌲10% Weekly Discount 🌲3 BRDM+3.5 BTH (all ensuite) 🌲Secluded + Spacious on 2-acre lot 🌲Hot tub! 🌲Smokeless firepit (wood provided)🪵 🌲Year-round community indoor pool & seasonal outdoor pool 🏊‍♂️ + zero entry kiddie pool 🌞 🌲Open concept main level 🌲Games & puzzles for all ages 🧩 🌲Axe throwing game 🎯 🌲Large connect 4 game & jenga 🌲New & fully equipped kitchen 🍽️ 🌲Kid & Dog friendly 👧🏼🐶 🌲Seasonal valley views 🌲Gym access 🌲High-speed internet

4.98 out of 5 average rating, 165 reviews

Wooded Villa with Resort Access, Fireplace, K Bed

⭐King bed with plush bedding in a peaceful, private setting ⭐Wood-burning fireplace — perfect for cozy evenings together ⭐2-minute drive to the North Golf Course, driving range, & Stonedrift Spa ⭐Wooded nature views & tranquil surroundings for a relaxing escape ⭐Just 12 minutes to downtown Galena — excellent shopping, dining, & sight-seeing ⭐Access to Owner’s Club amenities including indoor pool & fitness center ⭐15 miles to Chestnut Mountain Skiing ⭐2 Full bathrooms & newer full size sofa bed

4.95 out of 5 average rating, 185 reviews

The inviting main living area features a high wooden ceiling with exposed beams, a stone fireplace at the center, and ample seating options. Natural light floods in from large windows, illuminating cozy furnishings and warm earth tones throughout the space.

Cabin in Galena

Family Winter Fun! Hot tub-Fireplace-Game room!

Escape to our cozy luxe cabin in Galena Territory, the perfect retreat for fall! Start your mornings sipping coffee by the gas fireplace, then warm up each evening in the hot tub! Enjoy friendly competition with arcade games, board games, air hockey, and darts. With 8 amenity cards, you can access the owner’s club for swimming and exercise including indoor pickle ball-rackets and balls at the house! Experience relaxation and adventure in this tranquil haven—your unforgettable getaway awaits!

A charming exterior view of the house is showcased, featuring a welcoming front porch with white railings and two rocking chairs. Lush greenery surrounds the home, and a stone pathway leads to the entrance. Sunlight filters through the trees, casting gentle shadows on the lawn.

4.95 out of 5 average rating, 156 reviews

Galena Territory - Pets - Fireplace - Pool Access

Inquire about exclusive local discounts. Loved by guests for its cleanliness, location, and value, this spacious 3BR, 3.5BA home is perfect for families traveling together or groups of friends. This Galena Territories retreat is steps away from the Owners Club, Marina, and championship golf courses. Unwind in two comfortable living areas and enjoy private en-suite baths in every bedroom. Surrounded by wooded views, this home offers ample space to relax, recharge, and reconnect with nature.

4.98 out of 5 average rating, 131 reviews

The living area features a comfortable sofa and a rustic coffee table atop a circular rug. A stone fireplace serves as a focal point, complemented by a vibrant artwork of a rooster above it. Natural light floods in through large windows, providing views of the outdoor patio.

Townhouse in Galena

Farmhouse Chic|Fireplace|View|Peloton|Near Town

Are you searching for a serene and idyllic countryside escape in a winter wonderland? Look no further. Our elegantly appointed farmhouse-inspired townhome is located in the picturesque Galena Territory, boasting an array of amenities such as indoor/outdoor swimming pools, a fitness center, game room, tennis courts, 20+ miles of hiking trails, a private lake and more. Surrounded by verdant hills, the home offers a peaceful retreat while being only 20 min from Chestnut Mountain Ski Resort.

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.

4.97 out of 5 average rating, 115 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.

A comfortable living area is featured with two spacious sofas and a round coffee table. A wall-mounted television is positioned above a stylish fireplace, with large windows showcasing views of grassy landscapes. Soft textiles and decorative art add a welcoming touch.

4.95 out of 5 average rating, 103 reviews

*King Bed*, *Fire Pit Table* & *Stunning Views*

Welcome to The Golf View, where relaxation and fun collide! This 1-bedroom, 2-bath abode is perfect for a romantic getaway or a golfing adventure with pals. Whip up a culinary masterpiece in the fully-equipped kitchen, chill out with some vintage tunes on the mezzanine loft, or binge-watch your favorite shows on the 50" Smart TV. Outside, unwind on the deck or get cozy around the fire pit table for some unforgettable nights. Book your stay now and get ready for a hole-in-one experience!

4.99 out of 5 average rating, 204 reviews

The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.

Treehouse in Galena

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

4.95 out of 5 average rating, 263 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

A round dining table is set outdoors with four yellow plates, each topped with a drink garnished with olives and celery. A bottle of cocktail mix rests beside the glasses, surrounded by textured placemats. Lush greenery provides a natural backdrop.

4.91 out of 5 average rating, 112 reviews

Quiet Yet Close/Steps to Pool/Paths, Pet Free Home

Cozy Tranquility on Walnut, Galena IL Entire Home Vacation Rental, 1 Bed, 2 Bath, 4 Person Occupancy This adorable, recently remodeled and refurnished, 1 bedroom/2 full bath townhome is ready to welcome and embrace you any time of the year! Situated with seasonal views of the North Golf Course, and just a short distance from the driving range makes it a great choice for golfers... it's charm and central location make it an ideal choice for everyone!

4.88 out of 5 average rating, 146 reviews

An aerial view of the living room is displayed, showcasing a dark leather sectional couch positioned around a textured area rug. A wooden coffee table is centered in the space, while a flat-screen television is positioned next to a large stone feature wall. Natural light fills the room through large windows.

Villa in Galena

Spring Creek Sanctuary-2BR-Owners’ Club Access

Welcome to Spring Creek Sanctuary! This 2BR/2BA condo in Galena Territory offers comfort and nature. Relax by the wood-burning fireplace, cook in the modern kitchen, or unwind on the private deck with wooded views. Enjoy Owners’ Club amenities—pools, fitness, game room, tennis—plus nearby golf, trails, and Lake Galena. Just 15 minutes to historic downtown Galena, shopping, dining, and wineries!

An outdoor deck features comfortable seating arrangements, including wicker chairs and a coffee table. Large windows in the background allow natural light to fill the adjacent indoor area while showcasing the surrounding greenery.