4 Best Vacation Rentals With Pool Near Galena, Illinois - Updated 2024

Contributing Writer
| 3 min read

Tucked away amidst the lush green hills of northern Illinois, the charming city of Galena offers the ideal blend of historical architecture and modern attractions. Whether you are an active, outdoorsy traveller who loves nature or someone who enjoys cosy coffee shops and boutique stores selling handmade baubles, Galena has something for you.

Active travellers can enjoy a visit to Chestnut Mountain Resort, featuring year-round adventures such as river cruises, ziplining, biking and skiing in the winter. Shop till you drop for accessories, unique home décor and souvenirs in downtown Galena’s unique boutique retail stores, such as At Home in Galena. Downtown Galena also has some of the best bars and pubs, such as Galena Lion’s Den speakeasy.

One of the perks of visiting a town like Galena is the amazing vacation rentals available, complete with leisure amenities for unlimited fun! For options, read on to find the best vacation rentals with pool near Galena, Illinois!

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on June 02, 2024.

1. Cosy woodland studio situated close to Galena (from USD 145)

Enjoy complete tranquillity and privacy away from the busy downtown in this lavishly appointed studio. Featuring a cosy fireplace, an indoor hot tub and a sparkling swimming pool, this charming condo offers everything a couple or solo traveller may need during their stay. Aside from swimming, you can play pool basketball or rest on any of the poolside loungers.

You can also enjoy use of the barbecue facilities for a fun cookout, a fitness room to start your day with the perfect workout and a gaming room with foosball. The home also features a functional kitchen where you can prepare your favourite meals.

Stayed at this property?
Galena, Illinois, United States
30.97 km (19.3 mi) from National Mississippi River Museum & Aquarium
319 reviews   Wifi Available
Entire guest suite 2 Beds 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
they got a grill outside by the pool which was awesome
the condo was cozy and relaxing
the room was very clean coffee and water were provided and the location was great for our purposes
the bed feels like a cloud
it was a lovely stay it was the perfect getaway for a day and the jacuzzi/pool was great
very clean and would stay again
the room (really a condo) is large and very clean
cozy condo- everything was clean
accommodations were spacious and extremely clean
a little confusing between rules of air bnb/host versus the site but really great room
it was close to our venue and close to the beautiful historic galena
we loved the secluded location as well
nice quiet location just outside of town in the territory
this was a perfect location as it was right next door
this is a great place to stay in a lovely location
Read more reviews

2. Comfortable two-bedroom condo situated in a well-appointed building (from USD 170)

Situated very close to the town of Galena, this two-bedroom condo offers use of amenities that you can enjoy in a typical hotel. You have access to a hot tub, an indoor swimming pool, a gaming room with ping pong and pool, and a small on-site fitness centre. The delightful pool area receives plenty of sunlight and features many loungers and pool towels.

The condo itself has two cosy bedrooms and can sleep up to six guests. It includes plenty of thoughtful perks such as complimentary toiletries, linens, laundry facilities and cookware. The home also features WiFi at an additional charge, perfect for remote working or streaming movies.

Stayed at this property?
Galena, Illinois, United States
31.11 km (19.4 mi) from National Mississippi River Museum & Aquarium
28 reviews   Superhost Wifi Available
Entire serviced apartment 3 Beds 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
very clean and comfortable accommodations
very nice and clean condo
place was very clean and just as described
plenty of space very clean great game room for kids and a pool
the suite itself was incredibly clean the beds were so comfortable and the staff was great
resort staff very courteous and the host easy to communicate with
the staff there were all very friendly
great place for a retreat of any kind
the deli next door is delicious and within walking distance
the resort was great and not too far from main street
the perfect place to come back to after a day of skiing at chestnut mountain
great place to stay if you’re looking to visit galena
great place for a modified local-ish spring break
Read more reviews

3. Wonder Bear Lodge (from USD 1088)

Experience luxury living amidst quaint woodlands in this seven-bedroom wooden cabin located just 35.41 kilometres (22 miles) away from Galena. The rental includes access to the nearby swimming pool and marina. Moreover, it comes with a private pool if you enjoy intimate swimming sessions. The fenced swimming facility is situated on a deck and offers fun floats.

Enjoy an impressive list of leisure options, including two gaming rooms, a private two-person jetted tub in the master bedroom and a cosy porch to relax in. The cabin also offers high-speed WiFi and a study nook if you wish to work remotely. Plan a movie night with your loved ones, with a large-screen Roku TV, and a s’mores night with the outdoor fire pit.

Stayed at this property?
Stockton, Illinois, United States
50.42 km (31.4 mi) from National Mississippi River Museum & Aquarium
lodge 15 Guests 7 Bedrooms 6 Bathrooms

4. Spacious log cabin situated on private property (from USD 1199)

Perfect for family reunions or hobby retreats, this sprawling log cabin can sleep up to 17 guests. It is situated on a secluded private property with plenty of walking trails and ponds for outdoorsy guests to enjoy.

The cabin itself features impressive amenities for your enjoyment, such as a pizza oven, a tiki bar and a fully equipped kitchen to prepare all your meals. Enjoy challenging each other to a game of pool or foosball. The living area is perfect for socialising, with relaxed seating and a cosy fireplace.

However, the highlight of this cabin is the sprawling outdoor swimming pool, along with the nearby deck chairs to sunbathe on. The heated pool is 65 feet (19.81 meters) long and overlooks lush greenery.

Stayed at this property?
Fulton, Illinois, United States
86.6 km (53.9 mi) from National Mississippi River Museum & Aquarium
PRIVATE VACATION HOME 17 Guests 5 Bedrooms 5 Bathrooms

Experience a rejuvenating stay neat Galena

With so much to do and explore in the lovely city of Galena, you are sure to end up exhausted at the end of the day. Treat yourself to an amazing vacation rental so you can enjoy a dip in the pool in the evenings, with your favourite beverage and people to keep you company. So what are you waiting for? Start planning your itinerary and look forward to a carefree stay!

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Being a military kid, Shamika has lived and travelled all over India, and her nomadic childhood has fueled an immense hunger and fascination for new cultures and languages (she's a polyglot!)...Read more

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