Holiday rentals with outdoor seating 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, 121 reviews

Spacious Treehouse: Hot Tub • Fire pit • Games

🌲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

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, 185 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

4.96 out of 5 average rating, 133 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.

A tri-level house with a muted gray exterior features multiple large windows. A front porch with railings is visible, inviting relaxation. Surrounding greenery and a neatly maintained yard contribute to the peaceful setting. The sloped roof adds character to the home.

4.91 out of 5 average rating, 108 reviews

Cozy Wooded Tri-Level In Galena Territory

Relax with friends or the whole family at this wooded and peaceful place to stay in the Galena Territory.Cozy Tri-Level with 3 comfortable bedrooms and 3 baths. Tvs in 2 bedrooms as well as large tvs in the living room and downstairs rec room.Fireplace in living room area.Sit outside and enjoy the scenery on the front porch or back screened patio.Only 6 miles to Downtown Galena .Guests are welcome at Lake Galena,the Owners Club,Restaurants,Pools and Trails.Six Free passes are included.

4.97 out of 5 average rating, 116 reviews

An inviting firepit area features two black Adirondack chairs positioned around a circular stone firepit. The A-frame cabin is seen in the background, softly illuminated by decorative lights, surrounded by trees at dusk.

Cabin in Elizabeth

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

4.99 out of 5 average rating, 226 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

This historic brick home features multiple windows reflecting a classic architectural style. A stone garage, designed with modern doors, complements the house. Lush greenery surrounds the property, enhancing its natural appeal. A paved driveway leads to the garage, showcasing an inviting approach to the entrance.

4.96 out of 5 average rating, 250 reviews

1842 Bavarian Brew House

Nestled in charming and historic Galena this beautiful home was built in 1842 by brewer Peter Specht from Bavaria. The cellar operated as his brewery and tavern while living in the home above. The house was extensively renovated in 2008. It remains full of character and charm, but now boasts an abundance of modern comforts. A quiet private patio and yard are the perfect spot for a morning coffee or a glass of wine. All within a few walkable blocks to Main Street, the heart of Galena!

The charming two-story miner's cottage features a welcoming front porch adorned with historic American flags. Lush greenery surrounds colorful flower beds, enhancing the outdoor space. The stone and white clapboard exterior reflects classic architectural elements within the Galena National Historic District.

4.96 out of 5 average rating, 600 reviews

Beautiful Miner's Cottage in a Garden

This 1840's miner's cottage in the heart of Galena is only 3 blocks from beautiful, historic and fun Downtown Galena Main Street, but is far enough to have quiet times in the quarter acre yard of perennial gardens as well the expansive 2 story front porch, and 3rd porch off the kitchen, with gas grill. The house sits on a corner lot in the Galena National Historic District. The bathroom and kitchen are newly remodeled and the entire house is designer decorated. Beautiful!

A spacious living area features a contemporary black sofa set, complemented by a sleek area rug. Exposed brick walls and wooden beams create a cozy atmosphere. A well-equipped kitchen is visible in the background, enhancing the open layout. Natural light floods in from large windows.

4.96 out of 5 average rating, 102 reviews

Suite Victory #3 On Main St w/Reserved Parking

Suite Victory #3- Beautifully renovated apartment on Main St. right where you want to be with Reserved Parking. Dining, entertainment, and shopping just outside your door. Open floor plan with beautiful views of downtown Main Street. King bed. Double sink vanity and large walk-in shower. Kitchen has island, quartz countertops, and new appliances. Stackable washer and dryer within the unit. Above Charlie’s Place Eatery on Main Street. MAX 2 PEOPLE. NO DOGS ALLOWED.

4.9 out of 5 average rating, 110 reviews

Cabin in Galena

Hot Tub l Fire pit I Chestnut Mt I 6 bed I 10 ppl

Escape to your own spacious mountain retreat just 8 miles from historic downtown Galena! 2 min to Chestnut Mountain. Enjoy a brand-new hot tub, fire pit with free wood, gas BBQ, and patio—perfect for summer nights or crisp fall days. Spend your days hiking, golfing, shopping, or taking scenic wine tours. In fall, explore vibrant foliage, festivals, and local charm. After your adventures, relax in comfort and style with plenty of space for the whole family.

A spacious living area is highlighted by large windows allowing natural light to fill the room. A round dining table with orange chairs complements a cozy seating arrangement near the fireplace, featuring a stylish couch and armchairs. Decorative elements enhance the contemporary aesthetic.

4.99 out of 5 average rating, 150 reviews

Ulysses Suites, Suite 201

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213 to 217 S. Main Street. The location is walking distance to all the best restaurants and shops. We have 7 suites and a beautiful lobby that are modern and luxurious, with lots of historical character and texture as a nod to its previous existence as the Grant Hotel from 1895 to 1933. Suite 201 is located on the 2nd floor.

4.88 out of 5 average rating, 106 reviews

Hot Tub | Fireplace | Screened Porch | Pool Access

Escape to this cozy 2-bedroom + loft 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

Popular amenities for outdoor seating rentals in Galena

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A living area is showcased with hardwood flooring, featuring a spacious sofa and two patterned armchairs. A coffee table is positioned centrally, surrounded by two end tables. Natural light is welcomed through large windows, complemented by decorative wall art.

5 out of 5 average rating, 209 reviews

The Downtown House - 1820s home steps from Main St

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

Superhost

An open living area showcases a bright red sofa with decorative pillows, positioned next to a glass-top coffee table. The wooden staircase leads to an upper level with a railing, while large windows invite natural light and offer views of the surrounding greenery.

4.81 out of 5 average rating, 104 reviews

House 3bd/3bth- indoor pool -close to chestnut mnt

A spacious outdoor area showcases a well-maintained patio with stone pathways and seating arrangements. The property features a modern two-story structure with a welcoming entrance, surrounded by greenery and decorative landscaping. A grill is positioned nearby for outdoor cooking.

4.99 out of 5 average rating, 103 reviews

Jackson Ready Properties

A spacious living room features two light-colored sofas arranged around a central coffee table on a textured area rug. A large fireplace serves as a focal point, framed by tall windows that enhance natural light, with views of the wooded outdoors visible beyond.

4.91 out of 5 average rating, 131 reviews

Serene Escape in The Galena Territory

A charming exterior view of the house is showcased, featuring a welcoming front porch with white railings and two rocking chairs. Lush greenery surrounds the home, and a stone pathway leads to the entrance. Sunlight filters through the trees, casting gentle shadows on the lawn.

4.94 out of 5 average rating, 167 reviews

Galena Territory - Pets - Fireplace - Pool Access

The house features a sloped green lawn leading to a light-colored, two-story structure with a metal roof. A wraparound porch is visible, adorned with a welcoming wreath. A small outdoor table displays colorful pumpkins, highlighting the natural surroundings.

4.95 out of 5 average rating, 111 reviews

Stagecoach Valley Getaway

4.99 out of 5 average rating, 216 reviews

A welcoming living area features a comfortable sofa and a wooden coffee table. Large windows provide a scenic view of the landscape and river, allowing natural light to fill the space. A TV is mounted above a stone fireplace, creating a cozy atmosphere.

Home in Dubuque

Home by the River

Apartment rentals with outdoor seating

4.84 out of 5 average rating, 238 reviews

A cozy bedroom is presented with a spacious bed dressed in white linens and accented by a blue decorative pillow. A bedside table with a lamp provides soft lighting. Dark curtains frame the window, enhancing the restful ambiance.

Flat in Dubuque

Historic oasis next to spa in downtown Dubuque

A spacious bedroom is presented with a large, upholstered king size bed layered with a white quilt. A pair of bedside lamps, a decorative bench, and an armchair with floral accents are featured, complemented by soft wall colors and warm natural light from the nearby window.

4.96 out of 5 average rating, 72 reviews

Suites at 414 - Suite 2

4.9 out of 5 average rating, 242 reviews

The kitchen features wooden cabinetry with ample storage space and stainless steel appliances. A granite countertop provides a functional workspace, and a decorative backsplash enhances the room's design. Natural light is accessible through a nearby window, accentuating the warm wood tones.

Flat in Dubuque

Impressive Private 2BR Suite w/Parking Univ. Area

4.93 out of 5 average rating, 138 reviews

A cozy sleeping area features a spacious bed with blue and white bedding. Natural light enters through the dark window treatments, illuminating the wooden dresser and nightstand. Coordinating wall art adds subtle character to the serene gray walls.

Flat in Dubuque

Tom's place

4.95 out of 5 average rating, 60 reviews

A cozy living area is highlighted by a sectional sofa adorned with yellow accent pillows. A wall-mounted television is positioned above a dark furniture unit that features decorative items. Soft carpet covers the flooring, contributing to a welcoming atmosphere.

Flat in Scales Mound

Updated Unit w/Panoramic Views

4.9 out of 5 average rating, 415 reviews

A contemporary living room features a comfortable gray sofa with a textured throw draped over it. Exposed brick walls create a warm backdrop, while a ceiling fan provides airflow. A flat-screen TV is mounted above an electric fireplace, enhancing the room's cozy atmosphere.

Flat in Downtown Dubuque

Drake House: City View with Private Hot Tub

A comfortable living area features a dark leather sofa positioned in front of a rustic wooden table. A vase with dried flowers adds a touch of decor. In the background, a spacious bed is visible, set against a soft blue wall.

4.88 out of 5 average rating, 382 reviews

Fever River View Master Suite

The historic building features a blend of brick and stone elements, showcasing decorative windows with green shutters. A welcoming porch is supported by decorative railings, while vibrant tulips in shades of yellow and red flourish in the landscaped garden along the base.

4.88 out of 5 average rating, 105 reviews

Albert's Glen King, Abes Spring Street, Downtown

Apartment rentals with outdoor seating

4.93 out of 5 average rating, 14 reviews

Apartment in Galena

The Cozy Lake Stay You've been Craving - Fireplace

Apartment in The Galena Territory

4.86 out of 5 average rating, 21 reviews

2 King Beds | Game Area + Foosball | Pool Access

Apartment in Jo Daviess County

A bright living space is showcased, featuring large windows that invite natural light. A stone fireplace is positioned against the wall, complemented by a wooden mantel with artwork above. A television stands on a stand nearby, and a cozy seating area is arranged for relaxation.

4.82 out of 5 average rating, 17 reviews

Lake Links Loft in Galena, Illinois

Apartment in Jo Daviess County

An entryway is shown, featuring a covered structure with a wooden floor and gently sloping roof. Snow is visible on the ground and rooftops, while shrubs and bare trees surround the area, indicating a serene and wintry atmosphere.

4.93 out of 5 average rating, 14 reviews

Long Bay Point Unit C5