Vacation rentals with a pool in Lake Galena

4.96 out of 5 average rating, 142 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.

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An outdoor deck features a spacious hot tub surrounded by a wooden railing. Nearby, two wooden benches and a table provide additional seating. Sunlight filters through the surrounding greenery, casting a natural warmth on the deck.

4.97 out of 5 average rating, 126 reviews

Lake Views | Hot Tub | Nature Retreat | Movie Room

Looking for nature? Come immerse yourself in nature at this private oasis. • 3 bed/3.5 bath (7 adults comfortably w/max 8 guests) • 12 mins to downtown Galena • Outdoor hot tub • Grill & dining space on upper deck • Seasonal views of Lake Galena • Lounge/Movie room with pool table, electric fireplace & smart TV • Full Kitchen w/fridge, oven, microwave, dishwasher, keurig coffee machine, air fryer, instant pot, & crockpot • Upstairs family room with smart TV, fireplace, & board games

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A spacious living area is highlighted by a cozy seating arrangement featuring colorful chairs and a comfortable sofa. Natural light fills the room through large windows, while a fireplace and a wall-mounted TV create a central focal point. Decorative items and warm wooden accents enhance the welcoming feel.

4.97 out of 5 average rating, 115 reviews

Townhome in Galena Territory w/ Pools, Lake, Gym

Escape the hustle of everyday life by treating yourself to a world of relaxation. Wake up with a nice cup of coffee on the back porch as you take in the fresh air and prepare for your day. The toughest decision you'll have to make is what activity to partake in (hiking, swimming, boating, skiing/snowboarding, golfing, horseback riding, exploring downtown Galena). End the day by watching a movie using the TVs equipped with Roku or browsing the internet using the free high speed internet.

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4.93 out of 5 average rating, 210 reviews

A cozy seating area is highlighted by a mounted television displaying a serene landscape. A stone fireplace, with glowing flames, adds warmth to the space. A green sofa is complemented by soft faux fur throws. Small side tables and potted plants enhance the inviting decor.

Tiny home in Galena

Tiny Home with Resort Pool Access-Fire Pit-Kng Bed

Enjoy the cozy setting of this romantic nature retreat at The Hygge Haus. Hygge ("hooga") is about taking time away from the daily rush to be together with people you care about to relax and enjoy life's quieter pleasures. Come hygge in our cozy house meant for two, wrap in a fuzzy blanket by a fire. Feel contentment in sharing a cozy meal at the table, talking on the chaise built for two. Enjoy access to the Owner's Club pools & fitness center. A serene getaway to reconnect and relax.

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4.99 out of 5 average rating, 245 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

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4.91 out of 5 average rating, 100 reviews

Cabin in Galena

Best View. Huge Hot Tub. King Beds. Amenities.

Frogmore Cabin is more than a stay—it’s a true Galena Countryside experience. A log lodge, where a million-dollar view meets rustic chic interiors that balance luxury with creature comforts. Guests call it unforgettable. We call it home. - 2 King Master Suites, and 3 other sleeping rooms all with views -Large Hot Tub- professionally cleaned between each guest - Pool table, corn hole, arcade - Fire pit - Prime Location: close to Downtown Galena - FULL Guest Access to owner club.

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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.

4.95 out of 5 average rating, 148 reviews

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. Whole home Golf Near Lake Galena 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

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The villa is a three-level structure, featuring a wood siding exterior and multiple windows allowing natural light. A spacious deck extends from the upper level, surrounded by green grass and mature trees, contributing to a peaceful outdoor setting.

4.92 out of 5 average rating, 123 reviews

Sunny Farmstead: Owners' Club access, golf nearby!

Welcome to Farmstead: a quiet and comfortable villa nestled within the heart of the Galena Territory. This home features 3 KING beds, a wood burning fireplace, bumper pool table, child bunk beds, dart board, and a closet full of games. Property is 10min from downtown Galena. Booking Sunny Farmstead also gives you access to the Owners' Club (4 minute drive) which features indoor and outdoor heated pools, basketball courts, game room, tennis courts and more.

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4.98 out of 5 average rating, 131 reviews

Wooded 2 King BR~Fireplace~Near Spa, Trails, Golf

🔹2 King bedrooms & 2 full baths on separate levels 🔹Modern, fully equipped kitchen 🔹Peaceful wooded end-unit 🔹Private deck with grill & seating for 4 🔹Wood-burning fireplace with supply of firewood 🔹Full club amenities, including fitness center 🔹3 Smart TVs 🔹Computer workspace 🔹Lake access 🔹Paved walking trails nearby 🔹2 min to golf, driving range & spa 🔹12 min to downtown Galena 🔹15 miles to Chestnut Mountain, zipline & ski

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4.88 out of 5 average rating, 118 reviews

Hot Tub | Fireplace | Screened Porch | Pool Access

Escape to this cozy 2-bedroom retreat in The Galena Territory—perfect for relaxing, reconnecting, and enjoying everything Galena has to offer. ✨ HIGHLIGHTS • Private hot tub + outdoor fire tables • Screened-in porch surrounded by nature • Wood-burning fireplace • Access to Owner’s Club (pool, fitness center & more) • Smart TVs + fast WiFi • 12pm check-in & check-out • 11 minutes to downtown Galena

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A spacious living area features a navy blue sectional sofa and a modern brown armchair. Large windows provide views of the surrounding greenery. A round, marble coffee table is centered in the room, with a fireplace beneath a mounted television, creating a cozy environment.

4.95 out of 5 average rating, 152 reviews

Cozy Galena Townhome

This renovated 2-story, 2-bedroom townhome plus loft is located in the Galena Territory, a 6800-acre resort area with beautiful rolling hills, 24 miles of walking trails, golf courses, and amenities. Located in the Creekwood townhomes, it's less than a 4-minute drive to the Country Store, Highlands Restaurant, and Thunder Bay Falls. Kick back and relax in this calm, modern space.

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The cozy living room features two brown leather sofas facing a stone fireplace. A wooden coffee table with rustic decor sits in the center, complemented by a large television mounted on the wall. Inviting natural light streams in through the windows, enhancing the warm atmosphere.