Holiday rentals with a pool in Galena

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, 133 reviews

Treehouse! 3BR Ensuites• Secluded•Hot Tub•Fire Pit

🌲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

LocationFamilyWalkability

A modern living area features a stone accent wall with a wooden mantel above a sleek fireplace. A large smart TV is mounted above the mantel, displaying options for streaming. A cozy chair sits beside a bookshelf filled with decor items.

4.97 out of 5 average rating, 188 reviews

Adorable Settlement home, views of lake/waterfall

Views of the waterfall and lake Galena in the fall, winter and spring. This home was just fully remodeled. All new furniture, flooring,cabinets and bathrooms. You will have access to 6 proxy cards to enter into the Owners Club. Parking is on site, WI-FI, all smart TV's to login into your NetFlix acct. Each of the bedrooms has their own private bathroom. The kitchen is stocked with mostly everything you need. Towels, linens, throw blankets, coffee, creamer provided. Toilet paper, paper towels too

FamilyValueIndoor spaces

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.

4.98 out of 5 average rating, 127 reviews

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.

LocationValueCheckout

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.

4.96 out of 5 average rating, 138 reviews

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.

LocationFamilyBackyard

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, 131 reviews

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.

ValueLocationPool

4.99 out of 5 average rating, 236 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

ValueLocationSkiing

Guest favourite

A spacious living room features a stone fireplace as a focal point, surrounded by large windows offering natural light. A comfortable sofa is complemented by two leather chairs. A dark coffee table sits in the center with decorative items, creating a cozy gathering space.

4.82 out of 5 average rating, 119 reviews

Log Home/Firepit/Game Room/Hot tub

Relax with the whole family at this peaceful log home. Located in the Galena Territory. 3 bedroom (2 kings) (2Twins located in lower level family room), 3 baths w/futon and sofa sleeper in loft area, sleeps up to 10. Hot tub, pool table, ping pong/air hockey, arcade game, main level family room with wood fireplace and lower level family room. Very Spacious and quiet, wooded surrounding, firepit. Access to the resort amenities which is a short drive away as well as downtown Galena.

FamilyValueWalkability

Guest favourite

4.94 out of 5 average rating, 279 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.

ValueLocationSleep quality

A cozy living area features a stone fireplace as the focal point, surrounded by large windows that provide views of the woods. A comfortable armchair and modern lamp are positioned nearby, while a TV and a stack of firewood add to the inviting ambiance.

4.97 out of 5 average rating, 196 reviews

Family Fall! Hot Tub•Fire In/Out•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

FamilyValueWalkability

An outdoor seating area is arranged around a central fire pit on a spacious deck. Comfortable chairs with decorative pillows face the fire, surrounded by a plaid rug. Lush green hills are visible in the background, enhancing the tranquil outdoor setting.

4.98 out of 5 average rating, 100 reviews

Golden Meadows Escape: A Luxurious Country Retreat

"This home is flawless! From the serene, private location to the abundant amenities, our trip was perfect. My kids especially loved the theater room and gaming console." – Sadie Golden Meadows Escape offers the perfect blend of tranquility and entertainment, with easy access to everything Galena has to offer. This beautifully designed home rests on a spacious 2+ acre lot, ensuring endless peace and family fun. "A taste of luxury with all the charm of the countryside" – Matt

ValueLocationSleep quality

A spacious home is situated on a gently sloping landscape, framed by mature trees. The exterior features a combination of stone and wood elements, with a welcoming front porch and large windows that enhance natural light. A paved driveway leads up to the property.

5 out of 5 average rating, 102 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!

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