House holiday rentals 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, 132 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

ValueLocationBackyard

4.98 out of 5 average rating, 141 reviews

* 10 min Walk to Main Street*Stocked kitchen*

Take a step back in time in this 1840s era home! Newly renovated with an eye to maintaining it's vintage charm, this house fits right into Galena's historic character. Grab your morning coffee on the side porch swing. Take the 10 min walk to Main Street for shopping and lunch. Relax in the light filled living room or fully stocked kitchen. Or, enjoy front porch rockers. Be sure to keep an eye out for some historic surprises in the house. NOTE: There are a lot of stairs to the side porch entry.

LocationValueBathroom

The charming craftsman-style house features a welcoming front porch with brick accents and a porch swing. A well-manicured garden with vibrant foliage adds a touch of color, while tall trees provide a natural backdrop. The entrance is framed by large windows, enhancing natural light.

4.95 out of 5 average rating, 203 reviews

Galena home close to Main St with parking and deck

Charming four-bedroom house located 2 blocks from Galena's Main St. Fully-equipped kitchen, dining room, living room, and laundry room. Direct TV and WiFi are also available. One bedroom is on the main floor, 3 are upstairs. The home has a large front porch with a porch swing. There is also a deck with lots of seating built into the back hillside which is shaded in the afternoon. Two concrete off-street parking spots between the house and deck are available for guests. Easy self-check-in.

ValueLocationWi-Fi

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.

4.9 out of 5 average rating, 118 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.

ValueFamilyQuiet

The exterior of a spacious home is displayed, featuring a wraparound deck and large windows that allow ample natural light. Outdoor seating options, including blue chairs and a stone fire pit, are positioned on a grassy area surrounded by mature trees.

4.95 out of 5 average rating, 202 reviews

Awesome Lodge in Galena Territory

Bring the whole family to our Galena home for fun, games, and making memories! Located 1.3 miles from the Owner's Club in The Galena Territory, enjoy many amenities and everything Galena has to offer! 15 mins to downtown! 3 bedrooms and 3 full bathrooms, the house is equipped with great Wi-Fi and key cards to access Territory amenities! There is tons of space to spread out across 3 floors . Enjoy the game room, hot tub, three seasons room, deck, and outdoor space in this awesome home!

ValueFamilyBathroom

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, 130 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.

FamilyValueNearby

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, 259 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!

LocationValueCondition

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.

LocationFamilyRiver

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, 604 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!

LocationFamilyQuiet

A stone lion statue is positioned prominently at the entrance of a brick building. The lion faces forward, with its detailed mane and features clearly visible. Green-framed windows can be seen flanking the entrance, which is marked by a decorative door above a number.

4.98 out of 5 average rating, 167 reviews

Galena RowHouse - Downtown with parking included!

Built in 1846, the Galena RowHouse is one of the oldest guest homes in Galena. Although it was built over 175 years ago we have taken time to provide beautiful and modern updates with out destroying the historical integrity. The home is in downtown Galena with a beautiful view of the Fever River and near many walking paths, including Grant’s Home. Live like a local during a stay at the family-friendly Galena RowHouse. Free parking provided for your entire stay.

LocationValueBiking

A round dining table is set outdoors with four yellow plates, each topped with a drink garnished with olives and celery. A bottle of cocktail mix rests beside the glasses, surrounded by textured placemats. Lush greenery provides a natural backdrop.

4.89 out of 5 average rating, 124 reviews

Quiet Yet Close/Steps to Pool/Paths, Pet Free Home

Cozy Tranquility on Walnut, Galena IL Entire Home Vacation Rental, 1 Bed, 2 Bath, 4 Person Occupancy This adorable, recently remodeled and refurnished, 1 bedroom/2 full bath townhome is ready to welcome and embrace you any time of the year! Situated with seasonal views of the North Golf Course, and just a short distance from the driving range makes it a great choice for golfers... it's charm and central location make it an ideal choice for everyone!

FamilyValueWalkability

4.97 out of 5 average rating, 106 reviews

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

FamilyLocationHot tub

Popular amenities for Galena house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A charming gray house is set against a backdrop of colorful autumn foliage. The front porch features a red door, framed by shrubs and well-maintained landscaping. A clear blue sky provides a bright contrast to the warm tones of the trees.

4.96 out of 5 average rating, 319 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

ValueLocationAccuracy

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, 220 reviews

Galena Getaway

ValueFamilyKitchen

4.9 out of 5 average rating, 136 reviews

Modern Home w/Amazing Views, Hot Tub, Game Room

LocationValueLayout

An outdoor deck features comfortable seating arrangements, including wicker chairs and a coffee table. Large windows in the background allow natural light to fill the adjacent indoor area while showcasing the surrounding greenery.

4.98 out of 5 average rating, 213 reviews

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

LocationValueHiking

A hot tub is positioned outdoors, with bubbling water visible, offering a view of lush greenery and rolling hills in the background. The scene is framed by a tree, creating a serene and inviting atmosphere for relaxation.

4.97 out of 5 average rating, 102 reviews

Where the Hot Tub Faces the Fairway

ValueLocationPool

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!

LocationValueCheckout

4.98 out of 5 average rating, 125 reviews

Spacious, King Beds, Pool steps away, Near Golf

FamilyValueTV

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, 121 reviews

Lake Views | Hot Tub | Nature Retreat | Movie Room

LocationFamilyCheck-in

Weekly house rentals

Superhost

5 out of 5 average rating, 4 reviews

Golf Sim~Hot Tub~Arcade~4 Kings |The Augusta House

FamilyLocationPool

An inviting screened porch features a wooden coffee table surrounded by comfortable seating with black and white cushions. Natural light filters through the surrounding trees, creating a peaceful ambiance in this private outdoor space.

4.91 out of 5 average rating, 92 reviews

Quiet and Peaceful

LocationFamilyDecor

4.99 out of 5 average rating, 228 reviews

The exterior of the revitalized car wash features a striking white facade with bold red accents. A vintage black truck is parked on the grass, while two bright red chairs sit invitingly near the entrance, adorned with a retro-style sign pointing towards the inn.

Home in Shullsburg

The Car Wash Inn A Unique Stay

ValueFamilyAmenities

An open living space features a modern kitchen with stainless steel appliances and a spacious island. A staircase with wooden railings leads to a second-level area illuminated by large windows. The dining area includes a long table and comfortable chairs, creating an inviting atmosphere.

4.94 out of 5 average rating, 90 reviews

Cozy retreat in Galena Territory

FamilyLocationHospitality

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, 214 reviews

The Downtown House - 1820s home steps from Main St

ValueLocationComfort

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, 115 reviews

Jackson Ready Properties

FamilyLocationCheck-in

5 out of 5 average rating, 28 reviews

Pleasant View School

FamilyLocationHospitality

5 out of 5 average rating, 55 reviews

The Owl House

LocationValueKitchen

Private house rentals

5 out of 5 average rating, 7 reviews

Hearth & Haven | A Peaceful Country Escape

FamilyIndoor spacesCleanliness

Superhost

A cozy bedroom features a wooden bed frame with a patchwork quilt displaying nature-themed designs. Two decorative pillows rest on the bed. A wooden dresser displays decorative items, and the wall is adorned with subtle forest-themed decorations. Ample closet space is available with wooden sliding doors.

4.95 out of 5 average rating, 38 reviews

Deerview

FamilyLocationSleep quality

A spacious yard features a circular stone fire pit surrounded by four metal chairs. The house stands in the background, showcasing a classic architecture with a hipped roof and a front porch. Green grass and trees provide a natural setting under a clear blue sky.

4.97 out of 5 average rating, 72 reviews

Summer deals*hot tub*dog friendly*5 stars*arcade

FamilyLocationCleanliness

4.85 out of 5 average rating, 95 reviews

Tower House | Heated Pool, Sauna, Hot Tub + Views

LocationFamilySkiing

A cabin nestled among the trees features a wooden exterior with green siding. Steps lead to the entrance, bordered by lush foliage. The surrounding forest is dotted with young leaves and greenery, creating a serene natural setting.

4.98 out of 5 average rating, 56 reviews

3 Greenwood Trail The Galena Territory

ValueFamilySleep quality

An open living space showcases original hardwood floors and exposed brick walls. A comfortable sofa faces a wall-mounted TV, while a dining table accommodates six. Soft lighting is provided by a unique chandelier, and natural light filters through large windows, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 47 reviews

Luxury Historic Tower House

FamilyLocationAmenities

A comfortable living area is presented with two plush blue armchairs and a coffee table featuring a geometric design. A flat-screen TV is mounted above a modern fireplace. Natural light pours in through large windows with sheer curtains, offering a view of the outdoor space.

4.98 out of 5 average rating, 49 reviews

The Galena Getaway | Townhouse in Galena Territory

ValueFamilyView

A cozy sleeping area features a spacious bed with a light quilt, accompanied by two bedside tables. Elegant lamps cast a warm glow, while a large piece of wall art depicting an autumn tree adds a touch of color. Natural light filters through a window adorned with wooden blinds.