Holiday houses 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 The Galena Territory
4.93 out of 5 average rating, 216 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
An open living area is featured, showcasing a cozy sofa adorned with decorative pillows. A patterned chair with the word 'home' is positioned next to a small wooden table, which holds a few items. The area is brightened by natural light from sliding glass doors.
Home in The Galena Territory
4.98 out of 5 average rating, 158 reviews

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

Top Guest favourite
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.
Home in The Galena Territory
4.98 out of 5 average rating, 175 reviews

*Winter Getaway! Fireplace, Hot Tub, Fire Tables*

Step into Rolling Hills Retreat, a sanctuary from the everyday bustle! Our dog-friendly rental offers breathtaking views and numerous amenities for your pleasure and relaxation. Enjoy a swim in the indoor or outdoor pool, and discover a variety of amenities that promise an unforgettable stay. *Pickle Ball *Basketball *Pool Tables *Hiking Trails *Workout Room *Tennis Courts *Brand new (June 2024) Marina with boat rental (additional charge) *Ping Pong tables *Arcade *Scenic Waterfall *Kayaking

Top Guest favourite
An open-plan living and dining area features a glass dining table surrounded by black chairs. A gray sofa is positioned against the wall, and a modern kitchen with white cabinets and appliances is visible. Natural light enters through windows, illuminating the space.
Apartment in Downtown Dubuque
4.94 out of 5 average rating, 246 reviews

1157#5 / Walkable Downtown Retreat near Millwork

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.

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 The Galena Territory
4.98 out of 5 average rating, 195 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

Top Guest favourite
An open living space showcases exposed brick walls and dark wood flooring. A round wooden dining table with four chairs is positioned adjacent to a cozy black armchair and ottoman. The kitchen area includes a refrigerator and cabinets, with a warm light illuminating the room.
Loft in Galena
4.88 out of 5 average rating, 834 reviews

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)

Guest favourite
Home in The Galena Territory
4.95 out of 5 average rating, 260 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.

Superhost
A cozy seating area is highlighted by a mounted television displaying a serene landscape. A stone fireplace, with glowing flames, adds warmth to the space. A green sofa is complemented by soft faux fur throws. Small side tables and potted plants enhance the inviting decor.
Tiny home in The Galena Territory
4.93 out of 5 average rating, 170 reviews

Cozy Romantic Getaway*Electric Fireplace*King bed

Enjoy the cozy setting of this romantic nature retreat at The Hygge Haus. Hygge ("hooga") is about taking time away from the daily rush to be together with people you care about - or even yourself - to relax and enjoy life's quieter pleasures. Come hygge in our cozy house meant for two, wrap in a fuzzy blanket by a fire. Feel contentment in sharing a cozy meal at the table, talking on the chaise built for two. Relax, unwind, & explore the Galena Territory and nature. Cozy up!

Top Guest favourite
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.
Home in Galena
4.96 out of 5 average rating, 577 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!

Top Guest favourite
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 The Galena Territory
4.95 out of 5 average rating, 118 reviews

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

Relax with the whole family at this peaceful getaway. A beautifully renovated, 3 bedroom / 3 bathroom townhome located within The Galena Territory in Galena, Illinois. This home is a perfect, peaceful getaway that sleeps up to eight (8) people comfortably. Whole home Golf Lake Self Check in WiFi Coffee Oven Dishwasher Grill BBQ accessories Washer/Dryer Free parking Board games Exercise equipment Pool table Deck Outdoor dining Child friendly Pack 'n play Pickleball set

Guest favourite
A modern soaking tub is centered against a natural wood accent wall. A wooden bath tray rests across the tub, holding a glass of red wine and a book. Soft blue water adds a serene touch to the inviting space.
Townhouse in The Galena Territory
4.92 out of 5 average rating, 128 reviews

2 Bedroom Townhouse w/Soaking Tub + Rain Shower

Welcome to Dear Galena, a modern Zen retreat on a corner-unit townhouse golf villa with a wooded view. It's the perfect getaway for couples, friends, family or just you! Situated within The Galena Territory and near Eagle Ridge South Golf Course, this townhouse has two bedrooms - each with a king size bed and two bathroom. A pull out sofa bed for additional guest and high-speed Wi-Fi for streaming and all of your work from home needs.

Top Guest favourite
The exterior of a revitalized 1950s car wash is showcased, featuring a curved awning and a large glass door. The building has a bright white facade with a red accent roof, and signage reading 'The Car Wash Inn' and '$1.25 WASH' is displayed.
Home in Shullsburg
4.99 out of 5 average rating, 201 reviews

The Car Wash Inn A Unique Stay

Enjoy a unique stay inside a beautifully revitalized single bay 1950s car wash. Only minutes away from historic downtown Shullsburg. This space has been thoughtfully designed to retain it's industrial charm with a nostalgic ambiance, while offering modern amenities for a comfortable stay. ~20 miles to Galena, IL ~25 miles to Mineral Point, WI ~25 miles to Dubuque, IA ~ATV Trail Access with large parking area

Popular amenities for Guilford holiday rentals

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