Holiday rentals with a pool in Lake 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.

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.

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

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.

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

Newly Renovated. Gorgeous Retreat!

Newly Renovated. Gorgeous Retreat w/seasonal waterfall view! *This home has Large flat screen TV's in Living Room and Both BDRMS. All new kitchen cabinets, Side by Side Refrigerator with Ice Maker, Electric Stove, Microwave, and includes Dishwasher, Keurig Coffee pot, Regular 12 c coffee pot. New Flooring through out, and new Furniture.. Relax by the electric fireplace indoor or the backyard firepit. NO SMOKING IN UNIT New windows coming in the near future. Minimum 2 night stay

Family Fun! Hot Tub•Fire Pit•Game Room•3 Kings!

Ultimate Family Escape in Galena Territory! Unwind, explore, and make memories at this chic, spacious cabin! Sip coffee on the deck as deer wander by, soak in the hot tub, and gather around the fire pit for s’mores. Relax on the screen porch or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball. Adventure awaits—book your perfect getaway today! Family fun!-Hot tub-Fire pit-3 king beds-Game room

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

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.

Spacious, King Beds, Pool steps away, Near 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 🔹No guests above or below you 🔹Steps to semi-private pool 🔹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

King Loft | Fireplace | Arcade Game | Pool Access

Escape to this cozy 1-bedroom cottage retreat in The Galena Territory—perfect for slowing down, reconnecting, and enjoying everything Galena has to offer. ✨ HIGHLIGHTS • King loft bedroom with skylight ✨ • Wood-burning fireplace 🔥 • Retro arcade game + puzzle collection 🎮 • Access to Owner’s Club (pool, fitness center & more) • Fast WiFi • 12pm check-in & check-out • ~10–15 minutes to downtown Galena • Cozy, romantic cottage feel

*Covered Hot Tub * 2 Fire Tables * Massive Deck*

Relax at Rolling Hills Retreat, featuring a covered private hot tub, two fire tables, a huge upper deck, and a screened-in porch—perfect for outdoor living year-round. Enjoy Owner’s Club access with indoor/outdoor pools, pickleball, fitness center, marina, hiking & more. Every bedroom has a private bath for comfort and privacy. Dog-friendly, peaceful wooded setting just minutes from Galena.