Places to stay near Galena Cellars Vineyard

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, 226 reviews

Galena Getaway

Peaceful, pet-friendly ($50 fee per reservation) vacation home in the Galena Territory. 3 bedrooms, 3 bathrooms, two living rooms, 2 wood fireplaces, screened in porch, upper level porch, deck, firepit, access to owner's club (pool, exercise room and game room), marina and 24 miles of hiking trails. Sleeps up to ten people. (Please ensure your guest count is accurate when you make your reservation. The guest count can be updated if needed. Inaccurate reservations will be charged accordingly. )

FamilyValueCleanliness

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.

4.97 out of 5 average rating, 143 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.

FamilyLocationPool

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, 136 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.

LocationFamilyHospitality

4.98 out of 5 average rating, 150 reviews

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.

LocationFamilyCleanliness

A spacious living area features vaulted wood ceilings and a stone fireplace, creating a warm focal point. Cozy seating arrangements include plush sofas and armchairs, accompanied by decorative blankets. Large windows allow natural light to flood the space, showcasing wooded views outside.

4.98 out of 5 average rating, 206 reviews

Family Fall! Hot Tub•Fire In/Out•Game Room•3 Kings

Relax, unwind, & explore at this Fall Retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and fall/winter adventure!

ValueLocationDecor

A bright bedroom features a spacious bed covered with a dark throw blanket. A large window seat, adorned with cushions, offers views of the street. A small table and chair sit nearby, with hardwood flooring and elegant decor enhancing the room's character.

4.98 out of 5 average rating, 364 reviews

Ulysses Suites, Suite 202

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213-217 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 202 is a gorgeous studio with a huge window seat looking over Main Street.

ValueLocationQuiet

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, 137 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.

ValueFamilyCheck-in

4.98 out of 5 average rating, 249 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

LocationValueAmenities

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, 265 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!

LocationFamilyLaundry

4.93 out of 5 average rating, 287 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.

FamilyValueGetting around

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.

5.0 out of 5 average rating, 106 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!

FamilyValueSleep quality

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, 170 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.

LocationValueAir conditioning

Popular amenities for holiday rentals near Galena Cellars Vineyard

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with wifi

4.99 out of 5 average rating, 253 reviews

A living area features a blue sofa paired with two light-colored armchairs. A round wooden coffee table sits in the center, complemented by a decorative object. The room is well-lit by two matching lamps and showcases a unique mirror above the sofa, set against a textured brick wall.

Apartment in Galena

Elle & Becks' Second Floor Suite

LocationFamilyCleanliness

4.9 out of 5 average rating, 201 reviews

The kitchen features a spacious island with four industrial-style bar stools. Modern pendant lights hang above, illuminating the dark cabinetry and white subway tile backsplash. A stainless steel refrigerator and microwave are visible, contributing to the contemporary design.

Apartment in Dubuque

Modern Loft Overlooking Downtown

LocationFamilyRiver

Apartment in Downtown Dubuque

The living area features modern furnishings with a dark gray couch adorned with decorative pillows. A natural wood coffee table complements the space. The open kitchen is equipped with stainless steel appliances, granite countertops, and wooden shelving displaying dining ware, all illuminated by warm overhead lighting.

Montana House #302 - The Luxurious Downtown Stay

LocationFamilyGetting around

4.94 out of 5 average rating, 215 reviews

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.

Lake Links Loft in Galena, Illinois

FamilyLocationGetting around

4.86 out of 5 average rating, 22 reviews

5.0 out of 5 average rating, 54 reviews

The living area features a light-colored sofa paired with a circular glass table, situated on a vibrant area rug. Floor-to-ceiling sliding glass doors offer views of the balcony and the Mississippi River. Natural light enhances the space, creating a welcoming ambiance.

Apartment in Bellevue

Gorgeous Riverview condo on the Mississippi

FamilyLocationComfort

4.95 out of 5 average rating, 82 reviews

A vibrant living area features a blue sofa and a colorful accent rug adorned with floral patterns. Multiple seating options, including stools in red, green, and blue, surround a coffee table. Natural light streams through two large windows, brightening the space.

Apartment in Hanover

Where Time Stands Still ~ Near Galena

LocationValueDecor

5.0 out of 5 average rating, 7 reviews

Apartment in Galena

Amazing Golf Views! Close 2 Driving Range! Pools!

FamilyLocationAmenities

Superhost

The exterior of the Long Bay Point Condo is shown, featuring a blend of warm wood tones and natural landscaping. A welcoming entrance with a covered porch leads into the property, surrounded by large windows that reflect the building's spacious design. A mature tree provides shade.

Apartment in Galena

Long Bay Point Unit C11 The Galena Territory

LocationIndoor spacesPool

4.84 out of 5 average rating, 38 reviews

Family-friendly house rentals

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, 140 reviews

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

LocationValueCleanliness

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, 106 reviews

Golden Meadows Escape: A Luxurious Country Retreat

FamilyValueBack garden

4.93 out of 5 average rating, 105 reviews

The lake house is situated on a sloping hillside, surrounded by trees. A stone pathway leads down to the water's edge, where a private dock can be seen. The calm lake reflects the blue sky and scattered clouds, creating a serene setting.

Home in Apple River

The Ho Hum East on Apple Canyon Lake

ValueFamilyTV

A spacious living area features soft seating arranged around a circular glass coffee table. A large window allows natural light to fill the room, with a view of the outdoors visible. A stone fireplace and wall-mounted television enhance the cozy atmosphere.

4.94 out of 5 average rating, 200 reviews

The Beauty on Belden: Owners' Club access & more!

FamilyLocationHeating

5.0 out of 5 average rating, 106 reviews

5 Min to Owners Club | Hot Tub & Bunkhouse

LocationValueHiking

4.98 out of 5 average rating, 133 reviews

Serene 2-King Golf Villa | Fireplace + Spa Nearby

FamilyValueCheck-in

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, 181 reviews

Galena Territory - Pets - Fireplace - Pool Access

FamilyValueCondition

The exterior view showcases a spacious two-story home with a screened porch and a large backyard. Seating is arranged around a fire pit, surrounded by green lawn. The property is complemented by trees and stone landscaping, with ample windows reflecting natural light.

4.97 out of 5 average rating, 161 reviews

Hot tub/Game Room/Fire Pit/Across street from Pool

LocationFamilyBack garden

Apartment rentals with air conditioning

A stylish entryway is highlighted by a decorative sign featuring the name 'Miss Kitty's Calhouse Suites.' A cozy ambiance is created with a blend of exposed brick and soft green walls, accompanied by modern cabinetry and tasteful wall art.

4.93 out of 5 average rating, 630 reviews

The VIP Room at The Cathouse Suites, Dogs OK w/$$

ValueLocationCheck-in

A decorative sign reading 'Dawson's Remise' is illuminated in warm tones, framed in black wood. Next to it is a textured pillow featuring a geometric red and black pattern, adding a modern touch to the setting.

4.99 out of 5 average rating, 434 reviews

Dawson's Remise Luxury Accommodation

ValueFamilyLayout

The exterior of a colorful two-story home is presented, featuring patriotic flags adorning the front porch. Decorative pillars and a lattice design enhance the entrance. Two stone lion sculptures are positioned at the base of the steps, adding a distinctive touch to the welcoming facade.

4.9 out of 5 average rating, 215 reviews

Nine Star Suites - 1 Block to Main Street!

ValueLocationWifi

4.98 out of 5 average rating, 447 reviews

Suite Victory #2 On Main St w/Reserved Parking

ValueLocationSkiing

An expansive recreational area features warm wooden flooring and exposed brick walls. Comfortable seating arrangements include a sectional sofa and armchairs. A pool table is positioned center stage, with a wall-mounted television nearby. Large windows allow natural light to fill the space, creating an inviting ambiance.

4.94 out of 5 average rating, 471 reviews

Gameroom in Galena

ValueFamilyOutdoor spaces

The spacious bedroom features a large, plush bed draped in a green quilt, complemented by wooden nightstands. Soft lighting is provided by stylish pendant lamps. A decorative area rug adds warmth to the floor, while a doorway leads to a well-appointed bathroom visible in the background.

4.96 out of 5 average rating, 184 reviews

Downtown Galena Luxury Penthouse W/ Parking

LocationValueWalkability

4.95 out of 5 average rating, 113 reviews

A inviting living area is presented, featuring a floral-patterned sofa and a deep red armchair. A wooden side table with a lamp is positioned near the sofa, with a round dining table set nearby. Light from windows illuminates the space, accentuating the simple woodwork.

Flat in Shullsburg

Historic Building in the Heart of Shullsburg

FamilyLocationCondition

An open living area features a light-colored sectional sofa paired with a rustic coffee table. A dining table with black chairs is visible, along with modern kitchen appliances and cabinetry. Natural light flows through large windows, enhancing the inviting atmosphere of the space.

4.95 out of 5 average rating, 390 reviews

Downtown Gem for Two

FamilyLocationAir conditioning

Other great holiday rentals near Galena Cellars Vineyard

4.91 out of 5 average rating, 100 reviews

Best View. Huge Hot Tub. King Beds. Amenities.

LocationFamilyNearby

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, 124 reviews

Jackson Ready Properties

FamilyValueBiking

4.95 out of 5 average rating, 152 reviews

The open-concept living area showcases a cozy couch accented by a decorative rug. A mounted television is positioned on a wooden feature wall. A dining table is visible in the background, accompanied by modern kitchen amenities and large windows that allow natural light to illuminate the space.

Townhouse in Galena

Hook Wine And Sinker - Golf, Shop, Pools, & Relax

FamilyLocationParks

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, 613 reviews

Beautiful Miner's Cottage in a Garden

ValueLocationDecor

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, 209 reviews

Awesome Lodge in Galena Territory

ValueLocationCheckout

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, 208 reviews

Galena home close to Main St with parking and deck

FamilyLocationAmenities

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, 326 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

LocationValueCondition

A spacious 7-seat hot tub is situated on the back patio, surrounded by lush greenery. The bubbling water and soft glow of market lights create a serene atmosphere, providing a perfect spot for relaxation amidst nature.