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Vacation rentals in Guilford

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Top-rated vacation rentals in Guilford

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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 favorite
Home in The Galena Territory
4.98 out of 5 average rating, 162 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

Guest favorite
Home in The Galena Territory
4.86 out of 5 average rating, 118 reviews

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

Top guest favorite
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 The Galena Territory
4.96 out of 5 average rating, 124 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 favorite
A cozy living area features a stone fireplace as the focal point, surrounded by large windows that provide views of the woods. A comfortable armchair and modern lamp are positioned nearby, while a TV and a stack of firewood add to the inviting ambiance.
Cabin in The Galena Territory
4.98 out of 5 average rating, 162 reviews

*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!

Top guest favorite
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 The Galena Territory
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.

Top guest favorite
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, 198 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 favorite
Home in The Galena Territory
4.95 out of 5 average rating, 262 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.

Guest favorite
Vacation home in The Galena Territory
4.95 out of 5 average rating, 135 reviews

Aspen House - A Secluded Getaway In Nature

Relax with your loved ones at the peaceful Aspen House. A Miner's Cottage nestled in a beautiful stand of aspen trees = a quiet retreat just for you! The property is surrounded by protected wooded green space with the Taylor Run trail adjacent on the northwest side. The Owners Club, pools & lake are accessible by hiking/ 5 minute drive. Enjoy bird watching, fishing, hiking and picnicking without driving anywhere!

Top guest favorite
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, 202 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

Guest favorite
An aerial view of the living room is displayed, showcasing a dark leather sectional couch positioned around a textured area rug. A wooden coffee table is centered in the space, while a flat-screen television is positioned next to a large stone feature wall. Natural light fills the room through large windows.
Villa in The Galena Territory
4.88 out of 5 average rating, 144 reviews

Spring Creek Sanctuary-2BR-Owners’ Club Access

Welcome to Spring Creek Sanctuary! This 2BR/2BA condo in Galena Territory offers comfort and nature. Relax by the wood-burning fireplace, cook in the modern kitchen, or unwind on the private deck with wooded views. Enjoy Owners’ Club amenities—pools, fitness, game room, tennis—plus nearby golf, trails, and Lake Galena. Just 15 minutes to historic downtown Galena, shopping, dining, and wineries!

Top guest favorite
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, 179 reviews

Covered Hot Tub • 2 Fire Tables • Huge Deck •

Relax at Rolling Hills Retreat, featuring a covered private hot tub, two fire tables, a huge upper deck, and a screened-in porch—perfect for outdoor living year-round. Enjoy Owner’s Club access with indoor/outdoor pools, pickleball, fitness center, marina, hiking & more. Every bedroom has a private bath for comfort and privacy. Dog-friendly, peaceful wooded setting just minutes from Galena.

Popular amenities for Guilford vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Guilford's top sights

Galena Cellars Vineyard

46 locals recommend

Shenandoah Riding Center

53 locals recommend

Galena On the Fly

25 locals recommend

Other great vacation rentals in Guilford

Top guest favorite
A spacious living room features a cozy seating area with a light grey sofa and a wooden coffee table. Large windows provide wooded views, and a large clock adorns the wall above a stone fireplace, where a warm fire can be seen flickering.
Home in The Galena Territory
4.98 out of 5 average rating, 82 reviews

Private 3BR/2BA Home in the Trees | Stonecrest

Top guest favorite
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.
Home in The Galena Territory
4.98 out of 5 average rating, 54 reviews

Long Bay Point Getaway

Top guest favorite
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 The Galena Territory
4.93 out of 5 average rating, 70 reviews

Cozy retreat in Galena Territory

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.
Home in The Galena Territory
4.87 out of 5 average rating, 30 reviews

The Tree House

Top guest favorite
The A-frame cabin, framed by trees, features a striking black exterior with warm wood accents. A large front window provides natural light, while a festive wreath adorns the entrance. Surrounding greenery adds to the serene atmosphere of the countryside setting.
Cabin in Elizabeth
4.97 out of 5 average rating, 86 reviews

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Top guest favorite
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 The Galena Territory
4.99 out of 5 average rating, 95 reviews

Jackson Ready Properties

Superhost
The exterior of a lodge-style resort is depicted, featuring a mix of stone and timber elements. Large windows and balconies invite natural light, while an expansive green lawn and trees create a peaceful setting. A stone pathway leads towards the entrance.
Condo in The Galena Territory
4.91 out of 5 average rating, 11 reviews

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena

Top guest favorite
The modern kitchen features white cabinetry, granite countertops, and stainless steel appliances. A central island provides additional workspace and seating. Pendant lighting hangs above the island, while a window allows natural light to fill the room, enhancing the functional layout.
Cottage in Galena
5 out of 5 average rating, 40 reviews

Aiken 1083 in Galena

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.

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