Holiday rentals with a pool in Jo Daviess County

A tranquil vacation home is set in a lush green landscape. The house features a screened-in porch and multiple balconies, surrounded by a wooden fence. Mature trees provide shade, and the inviting lawn enhances the serene outdoor environment.

4.93 out of 5 average rating, 218 reviews

Galena Getaway

Peaceful, pet-friendly ($50 fee per reservation) vacation home in the Galena Territory. 3 bedrooms, 3 bathrooms, two living rooms, 2 wood fireplaces, screened in porch, upper level porch, deck, firepit, access to owner's club (pool, exercise room and game room), marina and 24 miles of hiking trails. Sleeps up to ten people. (Please ensure your guest count is accurate when you make your reservation. The guest count can be updated if needed. Inaccurate reservations will be charged accordingly. )

4.98 out of 5 average rating, 109 reviews

A well-maintained cabin is set amid lush greenery, featuring a stone accent facade. The exterior includes a two-car garage with a vibrant teal door, and a welcoming porch with blue chairs inviting relaxation. Spacious lawns surround the cabin, enhancing the natural setting.

Cabin in Galena

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Unwind in our comfortable Galena Territory cabin with 3 bedrooms, 3 full baths and sofa sleeper. EV Charging outlet in garage. Strong Eero boosted Wi-Fi; Roku streaming on every floor. Stone wood burning fireplace. Three-season room with scenic sunrise and wooded views. Lower-level walkout to patio with hot tub, fire pit and beautiful stargazing. Minutes away from the Lake Galena Marina, golf, tennis, pool, and fitness center. 15 mins from Chestnut Mountain and historic downtown Galena.

4.96 out of 5 average rating, 130 reviews

A custom log cabin is framed by lush greenery and manicured landscaping. The warm wooden exterior features multiple gabled roofs and large windows. A stone pathway leads through the vibrant garden, creating an inviting approach to the entrance.

Cabin in Galena

Private, Galena Log Cabin

This custom log cabin is the perfect getaway for friends & family seeking the solitude of the Galena Territory and fine dining and shops just 10 minutes away on Galena's Main Street. Each of the 3-levels offers an owner's suite with bath. Cozy up to 2 fireplaces, grill on the deck, or make 'smores at the firepit. The cabin has high speed, fiber internet and the lower-level walkout features a 55” flat screen TV. Guests can access swimming pools & pool tables at the Owner's Club 7 minutes away.

4.99 out of 5 average rating, 134 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, 117 reviews

Secluded Treehouse, w/great views, new luxury bath

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, 104 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, 212 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

4.94 out of 5 average rating, 266 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.

4.95 out of 5 average rating, 125 reviews

The open-concept living area showcases a cozy couch accented by a decorative rug. A mounted television is positioned on a wooden feature wall. A dining table is visible in the background, accompanied by modern kitchen amenities and large windows that allow natural light to illuminate the space.

Townhouse in Galena

Hook Wine And Sinker - Golf, Shop, Pools, & Relax

Relax with the whole family at this peaceful getaway. A beautifully renovated, 3 bedroom / 3 bathroom townhome located within The Galena Territory in Galena, Illinois. This home is a perfect, peaceful getaway that sleeps up to eight (8) people comfortably. Whole home Golf Lake Self Check in WiFi Coffee Oven Dishwasher Grill BBQ accessories Washer/Dryer Free parking Board games Exercise equipment Pool table Deck Outdoor dining Child friendly Pack 'n play Pickleball set

4.97 out of 5 average rating, 149 reviews

A spacious dining area features a large wooden table surrounded by black chairs. A living space is visible in the background with comfortable seating, large windows, and a sleek gas fireplace. Natural light fills the room, highlighting the open and airy layout.

Holiday home in Galena

Hot Tub & Fire Pit | Galena Spring Escape

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.

4.94 out of 5 average rating, 137 reviews

A charming red cottage is nestled among tall aspen trees. A winding stone pathway leads to the entrance, which features a wooden door and large window. Lush greenery surrounds the house, enhancing the tranquil forest setting.

Holiday home in Galena

Aspen House - A Secluded Getaway In Nature

Relax with your loved ones at the peaceful Aspen House. A Miner's Cottage nestled in a beautiful stand of aspen trees = a quiet retreat just for you! The property is surrounded by protected wooded green space with the Taylor Run trail adjacent on the northwest side. The Owners Club, pools & lake are accessible by hiking/ 5 minute drive. Enjoy bird watching, fishing, hiking and picnicking without driving anywhere!