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Holiday rentals in Guilford

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Top-rated holiday rentals in Guilford

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Top guest favourite
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.
Home in Galena
4.93 out of 5 average rating, 218 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. )

Top guest favourite
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
4.96 out of 5 average rating, 127 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.

Top guest favourite
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.
Townhouse in Galena
4.98 out of 5 average rating, 131 reviews

Farmhouse Chic|Fireplace|View|Peloton|Near Town

Are you searching for a serene and idyllic countryside escape in a winter wonderland? Look no further. Our elegantly appointed farmhouse-inspired townhome is located in the picturesque Galena Territory, boasting an array of amenities such as indoor/outdoor swimming pools, a fitness center, game room, tennis courts, 20+ miles of hiking trails, a private lake and more. Surrounded by verdant hills, the home offers a peaceful retreat while being only 20 min from Chestnut Mountain Ski Resort.

Guest favourite
A comfortable living area is featured with two spacious sofas and a round coffee table. A wall-mounted television is positioned above a stylish fireplace, with large windows showcasing views of grassy landscapes. Soft textiles and decorative art add a welcoming touch.
Home in Galena
4.95 out of 5 average rating, 103 reviews

*King Bed*, *Fire Pit Table* & *Stunning Views*

Welcome to The Golf View, where relaxation and fun collide! This 1-bedroom, 2-bath abode is perfect for a romantic getaway or a golfing adventure with pals. Whip up a culinary masterpiece in the fully-equipped kitchen, chill out with some vintage tunes on the mezzanine loft, or binge-watch your favorite shows on the 50" Smart TV. Outside, unwind on the deck or get cozy around the fire pit table for some unforgettable nights. Book your stay now and get ready for a hole-in-one experience!

Top guest favourite
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
4.99 out of 5 average rating, 205 reviews

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

Guest favourite
Home in Galena
4.94 out of 5 average rating, 264 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.

Top guest favourite
The living area features a cozy sofa arranged around a fireplace, complemented by a wooden dining table. A modern kitchen area with green cabinetry is visible, alongside bar stools. Large windows allow natural light to illuminate the space, highlighting the warm wood flooring.
Flat in Galena
5 out of 5 average rating, 144 reviews

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.

Top guest favourite
A comfortable seating area features two black reclining chairs with plush pillows, set against a backdrop of exposed brick walls and modern lighting. A glimpse of the outdoor street is seen from nearby windows, enhancing the vibrant urban atmosphere.
Flat in Galena
4.97 out of 5 average rating, 147 reviews

Suite Victory #4 On Main St w/Reserved Parking

Suite Victory #4- 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.

Top guest favourite
A spacious dining area features a large wooden table surrounded by black chairs. A living space is visible in the background with comfortable seating, large windows, and a sleek gas fireplace. Natural light fills the room, highlighting the open and airy layout.
Holiday home in Galena
4.97 out of 5 average rating, 145 reviews

Hot Tub & Fire Pit | Galena Spring Escape

Welcome to Shenandoah Ridge—our thoughtfully designed 4-bedroom, 4.5-bath vacation rental tucked into the woods of The Galena Territory. Spacious, peaceful, and full of cozy touches to help you unwind. Whether you’re here for a family getaway, group trip, remote work retreat, or just time in nature, you’ll find everything you need to feel at home. Just 7 minutes to the Owners Club and 15 minutes to downtown Galena—close to the action, but still calm and quiet.

Guest favourite
Cabin in Galena
4.89 out of 5 average rating, 101 reviews

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.

Guest favourite
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.
Home in Galena
4.91 out of 5 average rating, 113 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!

Top guest favourite
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.
Flat in Galena
4.99 out of 5 average rating, 392 reviews

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 Guilford holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Guilford's top sights

Galena Cellars Vineyard

48 locals recommend

Shenandoah Riding Center

55 locals recommend

Galena On the Fly

25 locals recommend

Other great holiday rentals in Guilford

Guest favourite
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
4.93 out of 5 average rating, 94 reviews

The Ho Hum East on Apple Canyon Lake

Guest favourite
A spacious living area features a dark couch adorned with yellow pillows. A wooden coffee table sits in front, showcasing vases with dried flowers. A textured rug covers the floor, while large windows invite natural light, illuminating the handmade wall art above the couch.
Home in Galena
4.84 out of 5 average rating, 51 reviews

Bluffwood Bungalow - Secluded, Forested Getaway!

Top guest favourite
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.
Home in Galena
4.93 out of 5 average rating, 72 reviews

Cozy retreat in Galena Territory

Guest favourite
The exterior of a modern building is shown, featuring large windows and an intricately designed entrance. Potted plants adorn the entrance, complemented by stylish outdoor lighting fixtures. The sign for Roux & Lucia is displayed prominently, indicating the bakery located on the main floor.
Flat in Dubuque
4.96 out of 5 average rating, 23 reviews

Studio at Roux & Lucia

Superhost
A well-lit living area features a cozy orange sofa adorned with decorative pillows, positioned on a textured area rug. A stylish light fixture hangs above, and a compact electric fireplace sits nearby. The contemporary kitchen with green accents is visible in the background, adding a vibrant touch.
Cabin in Elizabeth
4.91 out of 5 average rating, 57 reviews

The Little Dipper A-Frame in Galena Country

Top guest favourite
Home in Platteville
4.95 out of 5 average rating, 85 reviews

Pale Blue Dot

Top guest favourite
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.
Home in Galena
4.99 out of 5 average rating, 97 reviews

Jackson Ready Properties

Top guest favourite
Home in Galena
5 out of 5 average rating, 14 reviews

Pleasant View School

Frequently Asked Questions

  • What are the best places to stay in Guilford Township?

    Guilford Township has a range of stays, including countryside homes, cabins, and guesthouses surrounded by rolling hills. Many visitors choose accommodations with scenic views and proximity to outdoor activities for a peaceful retreat.

  • What are the best things to do in Guilford Township with kids?

    Families often explore local parks, picnic areas, and nature trails around Guilford Township. Visiting nearby farms for hands-on animal experiences or seasonal activities is also frequently suggested for children.

  • What are some of the best things to do in Guilford Township?

    Explore rural landscapes, hike or bike local trails, and enjoy birdwatching throughout Guilford Township. Visiting historic barns or browsing antique shops around the area are also frequently suggested activities.

  • How is the weather in Guilford Township?

    Guilford Township has cold winters with temperatures from 11–32°F (-12–0°C), and warm summers reaching 78–82°F (26–28°C). Spring and fall bring milder days with chances for rain, so layers and a light rain jacket are useful.

  • When is the best time to visit Guilford Township?

    Late spring and early fall are often recommended in Guilford Township for mild temperatures and scenic countryside foliage. Summer attracts visitors interested in outdoor activities and local fairs.

  • What are the best places to visit in Guilford Township?

    Guilford Township has scenic lookouts, local parks, and farms where visitors can experience rural charm. Small museums or historic sites in the area provide insight into the township’s agricultural heritage.

  • What are some hiking trails in Guilford Township?

    Nature reserves and township parks around Guilford Township have trails suited for gentle walks and wildlife spotting. Paths often wind through rolling hills and woodlands, giving a sense of the region’s natural beauty.

  • What are some family activities we can do in Guilford Township?

    Families in Guilford Township can spend time at picnic areas, visit playgrounds, or explore walking trails together. Nearby farms sometimes feature seasonal activities, such as pumpkin picking or wagon rides.

  • What are some of the best day trip ideas from Guilford Township?

    Day trips from Guilford Township often include exploring historic downtowns nearby, venturing to riverside parks, or visiting local art galleries and markets in surrounding communities. State parks around the region are also popular for outdoor escapes.

  • Are there any pet friendly accommodations available in Guilford Township?

    Many accommodations in Guilford Township welcome pets, especially in countryside homes and cabins. Several local parks make it easy for guests and their pets to enjoy the outdoors together.

  • What are some local tips for visiting Guilford Township?

    Pack layers for changing weather and comfortable shoes for exploring rural paths. Locals suggest stopping by farm stands for fresh produce and checking community boards for seasonal events or markets.

  • What is Guilford Township known for?

    Guilford Township is known for its rolling farmland, historical sites, and strong sense of local community. The area is appreciated for outdoor activities and seasonal rural traditions.

  • What are the best hidden gems to explore in Guilford Township?

    Travelers often mention rustic barns, quiet woodland trails, and small antique shops as hidden gems in Guilford Township. Local farm stands sometimes surprise visitors with homemade treats or unique crafts.

  • What are the best foods to try in Guilford Township?

    Guilford Township has locally grown produce, farmhouse cheeses, and baked goods that reflect the area’s agricultural roots. Seasonal specialties like fresh sweet corn or homemade fruit pies are frequently suggested.

  • What should I bring for a trip to Guilford Township?

    Bring comfortable walking shoes, layered clothing for variable weather, and a water bottle for outdoor activities. A lightweight rain jacket is useful, as is a camera for capturing rural scenery.

  • What is the nightlife in Guilford Township like?

    Nightlife in Guilford Township focuses on casual local bars, family-friendly diners, and community events. Evenings are often low-key, with some live music at venues or outdoor gatherings during warm months.

  • What are the most popular events or festivals in Guilford Township?

    Guilford Township hosts country fairs, farmers’ markets, and seasonal festivals, especially during summer and fall harvest periods. Community gatherings often feature local food, music, and crafts in a relaxed, welcoming atmosphere.

  • Are there family friendly vacation rentals in Guilford Township?

    Guilford Township has several family friendly rentals, including spacious homes and cabins with amenities like outdoor space and kitchens. Many are close to parks or walking trails for easy access to nature.

  1. Airbnb
  2. United States
  3. Illinois
  4. Jo Daviess County
  5. Guilford