Pet-friendly holiday rentals in Galena

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, 219 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. )

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, 130 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

A comfortable living area features a spacious sofa and armchair, with a wooden coffee table at the center. A fireplace is positioned beneath a decorative mirror, and a TV sits against a wooden cabinet. Large windows offer views of the surrounding greenery.

4.96 out of 5 average rating, 115 reviews

Verdant Vacation Getaway: Owners’ Club Access!

Our home is a green, botanical-themed townhome in the heart of the Galena Territory, carefully curated to reflect the diversity of plants you will find in the natural surroundings of the area. There are two ensuite bedrooms and a full kitchen featuring stainless steel appliances. The living room sofa converts into a queen sized bed for more sleeping options. Our home can accommodate a maximum of 6 overnight guests (assuming 1 or 2 people on the sleeper sofa). Located near golf course and trails!

A modern living room features a comfortable seating arrangement with a light gray sofa and armchair. A large window allows natural light to fill the space, while a flat-screen TV is mounted above a cozy fireplace. Built-in shelves are neatly arranged with books and decorative items.

4.98 out of 5 average rating, 105 reviews

Inviting & Bright | Firepit Sauna Hot Tub & Games!

Golfer? Inquire for(e) for details on our Golf Packages. Welcome to The Overlook, your perfect home away from home during the upcoming summer season in the Galena Territory. This contemporary three-bedroom, two-and-a-half-bathroom home is the ideal retreat for a relaxing and fun-filled vacation. Enjoy the firepit under starry skies, sweat it out in the sauna, soak in the hot tub, or challenge your friends to Pac-Man or foosball. Perfect for families and couples alike. Dog-friendly with a fee.

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, 129 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.

A spacious living area is highlighted by a large sectional sofa in warm tones. Natural light pours in through skylights, illuminating wooden floors. A dining table with multiple chairs is visible, alongside a well-equipped kitchen in the background, creating an inviting and open atmosphere.

4.91 out of 5 average rating, 158 reviews

Hot Tub Retreat • Firepit • 3BR/3BA • Dogs OK

Cozy, Private Retreat with Hot Tub & Firepit Welcome to The Nest—a cozy, peaceful escape tucked into the woods of The Galena Territory. ✔ Spotlessly clean, peaceful wooded setting ✔ 3 bedrooms & 3 bathrooms — ideal for groups • ✔ Private Hot tub • Fire pit • Dog-friendly ✔ Discounted golf available at Eagle Ridge ✔ 12 minutes to Downtown Galena ✔ Access to Galena Territory Amenities • Indoor/Outdoor pool • Fitness Center • Pickleball • Lake Galena & Marina • Shenandoah Riding Center

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

4.82 out of 5 average rating, 117 reviews

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.

Cabin in Galena

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.

4.98 out of 5 average rating, 185 reviews

Cute & Cozy King Suite Villa ~ Steps to Pool

⭐ Bright, open villa with king suite ⭐ Fully equipped kitchen & wooded views ⭐ Private deck with gas grill overlooking woods ⭐ Dedicated loft workspace perfect for remote work ⭐ Full bath on each level for maximum convenience ⭐ Steps to semi-private neighborhood outdoor pool ⭐ Indoor pool & fitness center access ⭐ Lake access & paved walking trails ⭐ 2 min to golf, driving range & spa ⭐ 12 min to Downtown Galena ⭐ 15 miles to Chestnut Mountain Resort (skiing, zipline & river views)

An electric fireplace is positioned below a large flat-screen TV mounted on a stone mantel, which adds texture to the living space. A comfortable armchair is shown with a patterned upholstery, and natural light filters through nearby windows, illuminating the inviting decor.

4.97 out of 5 average rating, 205 reviews

Newly Renovated. Gorgeous Retreat!

Newly Renovated. Gorgeous Retreat w/seasonal waterfall view! *This home has Large flat screen TV's in Living Room and Both BDRMS. All new kitchen cabinets, Side by Side Refrigerator with Ice Maker, Electric Stove, Microwave, and includes Dishwasher, Keurig Coffee pot, Regular 12 c coffee pot. New Flooring through out, and new Furniture.. Relax by the electric fireplace indoor or the backyard firepit. NO SMOKING IN UNIT New windows coming in the near future. Minimum 2 night stay

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, 603 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!

4.96 out of 5 average rating, 113 reviews

An aerial view of a spacious cabin is displayed, showcasing large glass windows and a broad deck. A cozy fire pit with colorful chairs surrounds the outdoor area, and string lights are visible, enhancing the serene atmosphere amidst lush greenery.

Cabin in Galena

Upscale 5KingBed 5Bath HotTub Cinema FirePit Views

Perched atop a private hill in The Galena Territory, Maya's Galena Cabin is a luxury retreat with breathtaking panoramic valley views. Sleeping up to 12 guests, it features five private King suites, a hot tub, theater, game room, steam showers, cozy fireplaces, and designer gathering spaces. Just minutes from historic Downtown Galena, wineries, championship golf, hiking, boutique shopping, and exclusive Owners' Club amenities, it's the perfect upscale escape.

Popular amenities for Galena pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 28 reviews

Entire Home|Fireplace|Views|Firepit

4.96 out of 5 average rating, 106 reviews

A charming house exterior is framed by greenery, featuring a welcoming front porch with steps leading up to a glass door. Lush grass surrounds the home, and sunlight filters through the trees, highlighting the inviting entrance.

Home in Dubuque

Welcoming 2 bedroom house in the heart of Dubuque

4.99 out of 5 average rating, 222 reviews

The exterior of the home is showcased from an aerial view, displaying multiple levels, porches, and a well-maintained yard. Surrounding greenery and neighboring homes are also visible, illustrating the neighborhood's charm and the property's prominent position.

Home in Downtown Dubuque

Beauty on the Bluff

4.98 out of 5 average rating, 111 reviews

The kitchen features a dual sink with modern fixtures, surrounded by elegant cabinetry. A coffee maker and various kitchen tools are arranged on the countertop. Natural light filters through multiple windows, highlighting a potted plant on a small stand.

Home in Dubuque

Blufftop Charmer

Superhost

A tranquil lakeside view is captured at sunset, with silhouettes of trees framing the water. A small dock and a picnic table are visible, while canoes are lined up along the shore, providing a peaceful setting for relaxation.

Home in East Dubuque

4.88 out of 5 average rating, 429 reviews

A MUST SEE! 2BR Lakefront Home w/ Boats & More!

4.8 out of 5 average rating, 142 reviews

The living area features a comfortable sofa, accented with pillows, and a pair of ottomans. Two windows allow natural light to fill the space, adorned with sheer red curtains. A television is positioned on a wooden stand, accompanied by decorative plants and framed artwork.

Home in Bellevue

Mississippi River house has everything you need

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, 174 reviews

Galena Territory - Pets - Fireplace - Pool Access

4.97 out of 5 average rating, 38 reviews

Pet Friendly/Beautiful Bluebirds/Star Studded Sky!

Pet-friendly home rentals with a pool

A spacious living area features a large sectional sofa adorned with decorative throw pillows. Large windows allow natural light to illuminate the space, presenting views of the wooded surroundings. A mounted television is positioned above a cozy fireplace, enhancing the room's inviting atmosphere.

4.85 out of 5 average rating, 33 reviews

Galena escape, golf, dogs, pool, games

Home in Jo Daviess County

A spacious living area features a circular wooden dining table surrounded by four black stools. A comfortable brown sofa faces a modern stone fireplace, with a large television mounted above. Natural light floods in through sliding glass doors that lead to a wooded view.

4.98 out of 5 average rating, 57 reviews

Cozy Galena Retreat | Trails, Pool & Eagle Ridge

Superhost

A hot tub filled with bubbling water is situated in a serene outdoor setting, surrounded by lush trees. The warm light of the setting sun filters through the branches, creating a calming atmosphere for relaxation.

4.55 out of 5 average rating, 71 reviews

6BR Galena Territory Amenities | Private Hot Tub

Townhouse in The Galena Territory

4.92 out of 5 average rating, 12 reviews

Golf Theme | Pet Friendly | King Bed | Fireplace

The living area features a comfortable sofa and a rustic coffee table atop a circular rug. A stone fireplace serves as a focal point, complemented by a vibrant artwork of a rooster above it. Natural light floods in through large windows, providing views of the outdoor patio.

4.97 out of 5 average rating, 154 reviews

Farmhouse Chic|Fireplace|View|Peloton|Near Town

A bright living area features a comfortable seating arrangement in light tones, with a wooden coffee table at the center. Windows with natural light provide views of the surroundings. A dining space is seen in the background, complemented by a ceiling fan and wooden beams.

4.97 out of 5 average rating, 181 reviews

Resort Townhome: Close to Lodge, Pool & Gameroom

4.89 out of 5 average rating, 64 reviews

Charming 3B3B | Access to indoor and outdoor pools

4.89 out of 5 average rating, 134 reviews

The exterior of the cabin features a welcoming wooden facade complemented by a front porch with a railing. A well-kept garden with various flowers rests by stone steps leading up to the entrance, surrounded by lush greenery and natural elements.

Cabin in Galena

Serenity Cabins - A rustic, yet upscale cabin!

Private, pet-friendly home rentals

5 out of 5 average rating, 23 reviews

A spacious kitchen features wooden cabinetry and a large island with dark countertops. Pendant lights hang from a sloped ceiling, illuminating the area. Modern appliances are included, with plenty of natural light entering through multiple windows.

Home in Elizabeth

Hell's Branch Cabin

Superhost

The exterior of the tree house is softly illuminated at night, showcasing large windows that reveal the warmth inside. A red-lit sauna entrance is visible on the side, while a cozy fire pit is situated nearby, inviting relaxation in the serene outdoor setting.

4.8 out of 5 average rating, 44 reviews

The Tree House

4.87 out of 5 average rating, 31 reviews

A charming exterior of a two-story townhome is depicted, featuring a welcoming front porch with chairs. Light yellow siding complements the surrounding greenery, and large windows allow natural light to enter the interiors.

Townhouse in Dubuque

Impressive three bedroom on historic Fenelon Place

4.93 out of 5 average rating, 58 reviews

A secluded log cabin is set against a clear blue sky, surrounded by greenery. A gravel path leads to the inviting entrance, with a spacious porch decorated with rustic seating. A detached barn adds to the scenic rural charm of the property.

Cabin in Hazel Green

Secluded cabin near Galena.

A charming red cottage is nestled among tall aspen trees. A winding stone pathway leads to the entrance, which features a wooden door and large window. Lush greenery surrounds the house, enhancing the tranquil forest setting.

Holiday home in Galena

4.9 out of 5 average rating, 146 reviews

Aspen House - A Secluded Getaway In Nature

4.94 out of 5 average rating, 84 reviews

A wooden ramp leads up to the accessible front porch, surrounded by trees. The view shows a quiet street with white houses across the road. The grassy area adjacent to the ramp is well-maintained, providing a pleasant entrance to the property.

Home in Bellevue

Large 1 Bedroom that's Handicap Accessible

5 out of 5 average rating, 78 reviews

The exterior of a charming red barn is framed by blossoming trees, providing a vibrant contrast to the greenery. Multiple windows allow natural light to enter, and warm light from a nearby lamp adds to the welcoming atmosphere of the property.

Barn in Dubuque

Annabel Lee Barn ~ A Getaway of Warmth & Charm!