
Holiday rentals in Galena
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Top-rated holiday rentals in Galena
Guests agree: these stays are highly rated for location, cleanliness and more.

Wooded Villa with Resort Access, Fireplace, K Bed
⭐King bed with plush bedding in a peaceful, private setting ⭐Wood-burning fireplace — perfect for cozy evenings together ⭐2-minute drive to the North Golf Course, driving range, & Stonedrift Spa ⭐Wooded nature views & tranquil surroundings for a relaxing escape ⭐Just 12 minutes to downtown Galena — excellent shopping, dining, & sight-seeing ⭐Access to Owner’s Club amenities including indoor pool & fitness center ⭐15 miles to Chestnut Mountain Skiing ⭐2 Full bathrooms & newer full size sofa bed

1129#3 / Ken’s place-cute / Free Parking
This is one of the best locations to be in downtown Dubuque. Few blocks access to Highway 61, Highway151 and Highway 20. Right on the farmers market (May through October). Five Flag Center, Art museum, Millwork district, Restaurants, Breweries and Coffee house all with in walking distance. You’ll have: - premium pillows - Memory foam queen mattress. - Smart TV. High speed Internet - Keurig Coffee maker - Regular & decaf coffee and tea - One off street parking You’ll absolutely love it here.

Cute Galena Townhouse - Close to Resort and Spa
Location, location, location!! Forget about your worries in this nicely updated townhome. Close to everything Galena has to offer! ~0.5 mile away: -Eagle Ridge Resort -Stonedrift Spa -North Golf Course -East Golf Course -tennis courts ~1.5 miles away: -South Golf Course -Owners Club with indoor/outdoor pools, basketball court, gaming lounge ~2.0 miles away: -Thunder Bay Falls ~3.5 miles away: -The General Golf Course ~7 miles away: -Downtown Galena ~13 miles away: -Chestnut Mountain

Suite Victory #2 On Main St w/Reserved Parking
Suite Victory #2 (facing Main St.) Beautifully renovated apartment on Main St. right where you want to be with Reserved Parking. Dining, entertainment, and shopping just outside your door. Large open floor plan with beautiful views of downtown on the corner of Main Street and the old cobbled Perry Street. King bed. Double sink vanity and large walk-in shower. Kitchen has oversized island, quartz countertops, and new appliances. Full size washer and dryer within unit. MAX 2 PEOPLE. NO DOGS.

*Hot tub-Fire-3 king beds-Game room*Winter fun!*
Relax, unwind, & explore at this winter 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 winter adventure!

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

The Brick Apartment Main Street Galena
Hello! Welcome to our beautifully-renovated apartment, conveniently located on the north end of Galena’s historic Main Street. This unit is above Big Bill’s coffee shop, and boasts exposed original brick from the historic Logan House Hotel, hardwood floors, a kitchen (range, refrigerator, microwave, sink), and beautiful views of our historic town! Only feet from restaurants, shopping, and night life! Check out all our listings at Airbnb.com/p/galenaapartments ( copy & paste into URL)

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!

Ulysses Suites, Suite 203
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 203 is almost 1400 square feet and is located on the 2nd floor.

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!

Home by the River
Situated alongside the Mississippi River, wildlife abounds in every season. With eagles nesting nearby, there is always something new to see from the beautiful sunrises, cruise ships passing by, and watching the commerce of the barges and railroad right out the front window! This home has been recently refurbished and sits at the edge of our 15 acres. You can see us and visit with us if you like, or you can maintain privacy 10 acres away!

Dawson's Remise Luxury Accommodation
Enjoy a luxurious stay in our remise ("carriage house"), complete with authentic Art Deco and Industrial furniture and design. We took great care in ensuring top notch craftsmanship and amenities, so as to create an inviting environment that you won't want to leave! Hidden away off the quaint and historic Park Avenue, you'll enjoy a quiet and restful stay whilst within walking distance to Main Street Galena and all it has to offer.
Popular amenities for Galena holiday rentals
Other great holiday rentals in Galena

Entire Home|Fireplace|Views|Firepit

The Calico Room at The Painted Cat Bed & Breakfast

The Ranch, a lot more than just a place to sleep.

Historic Linen&Stone Inn (Unit 6) Walk to Downtown

Whirlpool Suite on Main Street Galena

Comfy, end unit, on Golf Course!

The Drey: A Winter Getaway In the Treetop Canopy

Galena Cabin on 20 Acres: 5 Mi to Downtown!
When is the best time to visit Galena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $228 SGD | $225 SGD | $217 SGD | $215 SGD | $229 SGD | $240 SGD | $240 SGD | $235 SGD | $242 SGD | $249 SGD | $235 SGD | $235 SGD |
| Avg. temp | -7°C | -5°C | 2°C | 9°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 2°C | -4°C |
Frequently Asked Questions
What are the best places to stay in Galena?
Galena has unique accommodations in its historic downtown and scenic hilltop neighborhoods, where travelers can immerse themselves in the town's 19th-century character. Many stays are situated near local shops, galleries, and dining.
What are the best things to do in Galena with kids?
Families often explore interactive history sites, hands-on museums, and stroll through Galena's parks. Kids can enjoy outdoor activities such as river walks and gentle nature trails, while seasonal events welcome visitors of all ages.
What are some of the best things to do in Galena?
Explore Galena's Main Street with its locally owned shops and galleries, visit historic homes and museums, and take in views from surrounding parks. Outdoor experiences, local tastings, and river activities are frequently suggested.
How is the weather in Galena?
Galena has cold, snowy winters with average lows near 11°F (-12°C), while summers are warm and humid around 80°F (27°C). Spring and fall bring mild weather with increasing or decreasing rainfall, making layers a comfortable choice year-round.
What are the best places to visit in Galena?
Explore the Ulysses S. Grant Home, Galena History Museum, and stroll along Main Street for architecture, shops, and galleries. Grant Park is frequently suggested for relaxing and taking in views of downtown.
What are some hiking trails in Galena?
Galena has local hiking paths in parks and natural areas around town, including Grant Park and routes near the Galena River. Nearby preserves also provide trails with views of wooded hills and prairies.
What are some family activities we can do in Galena?
Families can join guided tours of historic sites, browse interactive museum exhibits, or relax with picnics in local parks. Seasonal activities, such as carriage rides and riverboat outings, are frequently suggested for all ages.
What are some of the best day trip ideas from Galena?
Explore nearby state parks, scenic byways, and historic small towns with artisan shops and local food. Riverfront recreation areas and vineyards in the region are also popular for a day's adventure.
Are there any pet friendly accommodations available in Galena?
Many hosts in Galena welcome pets, especially in neighborhoods near parks and walking paths. It is a good idea to check each listing for pet amenities and any specific house guidelines.
What are some local tips for visiting Galena?
Wear comfortable shoes to explore Main Street’s historic brick sidewalks and hillside neighborhoods. Sampling local specialties and joining a guided tour can add depth to your visit, especially during special events or markets.
What is Galena known for?
Galena is known for its well-preserved 19th-century downtown, significant Civil War history, and scenic rolling hills. The town is frequently associated with Ulysses S. Grant, who lived here before his presidency.
What are the best hidden gems to explore in Galena?
Artisan studios, quiet side streets with preserved architecture, and small local markets are often described as Galena's hidden gems. Look for tucked-away walking trails and historic sites outside the main business area.
What are the best foods to try in Galena?
Galena has Midwestern classics like hearty breakfasts, local meats, and fresh-baked pies, along with craft chocolates and regional wines. Dishes featuring farm-fresh produce are often available at independently owned restaurants.
What should I bring for a trip to Galena?
Pack comfortable walking shoes and layers, as weather can change quickly, especially in spring and fall. An umbrella and sun protection are helpful, and a camera is useful for capturing historic streets and scenic overlooks.
What is the nightlife in Galena like?
Galena has a relaxed nightlife scene centered on local pubs, wine bars, and occasional live music around Main Street. Evening strolls and outdoor patios are popular ways to enjoy the town after dark.
What are the most popular events or festivals in Galena?
Galena hosts annual events such as a vibrant Halloween parade, holiday festivals, and art fairs throughout the year. Seasonal celebrations in late spring and autumn often feature music, food, and local traditions.
Are there family friendly vacation rentals in Galena?
Travelers will find many family-friendly vacation rentals in Galena, especially near parks or Main Street. Features like multiple bedrooms, full kitchens, and outdoor space are frequently available.
When is the best time to visit Galena?
Late spring through early fall is often recommended for comfortable temperatures and regular local events. Autumn is especially popular due to changing leaf colors and seasonal celebrations.
Quick stats about holiday rentals in Galena

Total holiday rentals
Explore 170 holiday rentals in Galena

Nightly prices starting at
Galena holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 17,990 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
170 of Galena holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Galena rentals

4.9 Average rating
Galena stays are highly rated by guests – averaging 4.9 out of 5!
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