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Vacation rentals in Guilford

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Top-rated vacation rentals in Guilford

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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 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. )

Guest favorite
A spacious game room features a traditional billiard table set against a warm wood-paneled wall. Decorative elements include a dartboard and a wooden rack for cues. Natural light filters in from a nearby door, enhancing the inviting atmosphere of the space.
Home in Galena
4.88 out of 5 average rating, 111 reviews

Tranquil Home Away From Home

This home has a relaxing atmosphere, surrounded by woods and wildlife. Though, still easily accessible in the Galena Territory. You'll be sure to have a relaxing and wonderful time, in it's superbly decorated interior. Featuring farmhouse and country styles all it's own. The rolling hills of the area are beautiful in every season and the Galena area has lots to offer it visitors, golf, historical buildings, antiquing, fishing and boating on Lake Galena, canoeing and biking along the Galena River

Top guest favorite
A well-maintained cabin is set amid lush greenery, featuring a stone accent facade. The exterior includes a two-car garage with a vibrant teal door, and a welcoming porch with blue chairs inviting relaxation. Spacious lawns surround the cabin, enhancing the natural setting.
Cabin in Galena
4.98 out of 5 average rating, 109 reviews

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Unwind in our comfortable Galena Territory cabin with 3 bedrooms, 3 full baths and sofa sleeper. EV Charging outlet in garage. Strong Eero boosted Wi-Fi; Roku streaming on every floor. Stone wood burning fireplace. Three-season room with scenic sunrise and wooded views. Lower-level walkout to patio with hot tub, fire pit and beautiful stargazing. Minutes away from the Lake Galena Marina, golf, tennis, pool, and fitness center. 15 mins from Chestnut Mountain and historic downtown Galena.

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 Galena
4.96 out of 5 average rating, 130 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
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, 102 reviews

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

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

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 Galena
4.99 out of 5 average rating, 212 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
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
4.81 out of 5 average rating, 108 reviews

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.

Superhost
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
4.89 out of 5 average rating, 133 reviews

Serenity Cabins - A rustic, yet upscale cabin!

Welcome to Serenity Cabins. Whether your stay here is for a vacation, anniversary, family get together, romantic get away, or spiritual retreat, you'll find your stay to be welcoming, relaxing, memorable, full of charm and you'll love the luxurious modern amenities while feeling the rustic atmosphere. You can fall asleep with the sounds of nature and the whispers of the winds. Go for quiet walks as you surround yourself by nature's natural beauty or unwind in front of the fireplace.

Guest favorite
Home in Galena
4.94 out of 5 average rating, 266 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 favorite
An outdoor fire pit is surrounded by several black Adirondack chairs, set among fallen leaves. The cabin is visible in the background, illuminated by warm lights, creating a cozy ambiance. Tall trees frame the scene, providing a sense of seclusion.
Cabin in Galena
4.98 out of 5 average rating, 173 reviews

Family Fun! Hot Tub•Fire Pit•Game Room•3 Kings!

Ultimate Family Escape in Galena Territory! Unwind, explore, and make memories at this chic, spacious cabin! Sip coffee on the deck as deer wander by, soak in the hot tub, and gather around the fire pit for s’mores. Relax on the screen porch or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball. Adventure awaits—book your perfect getaway today! Family fun!-Hot tub-Fire pit-3 king beds-Game room

Top guest favorite
A modern living area features a cozy seating arrangement with two armchairs and a plush sofa. A decorative rug lies beneath a coffee table, while a television is mounted above a fireplace. Large windows provide natural light, complemented by artwork on the walls.
Apartment in Galena
5 out of 5 average rating, 152 reviews

Ulysses Suites, Suite 303

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. The Presidential Suite 303 is located on the 3rd floor.

Guest favorite
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.
Vacation home in Galena
4.94 out of 5 average rating, 137 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!

Popular amenities for Guilford vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Guilford's top sights

Galena Cellars Vineyard

48 locals recommend

Shenandoah Riding Center

56 locals recommend

Galena On the Fly

25 locals recommend

Other great vacation rentals in Guilford

Guest favorite
The open-concept living area features a spacious sectional sofa positioned in front of a modern fireplace. Large windows allow natural light to fill the space, while a dining area with a wooden table and chairs is visible in the background. Tasteful decor enhances the minimalist aesthetic.
Home in Galena
4.91 out of 5 average rating, 22 reviews

Early check-in/Late check-out (JAN-MARCH)

Guest favorite
A well-appointed home is nestled among trees, featuring a spacious front porch illuminated by soft lighting. The evening sky casts a warm glow, enhancing the serene setting. A paved driveway leads to the entrance, surrounded by manicured landscaping.
Cabin in Galena
4.85 out of 5 average rating, 94 reviews

Hot Tub, Fire Pit, Screen Porch | 4BR, 4BA Ensuite

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 Jo Daviess County
4.98 out of 5 average rating, 55 reviews

Long Bay Point Getaway

Guest favorite
A welcoming cabin exterior is framed by lush greenery, featuring a central entrance with a covered porch. The gentle slope of the pathway guides visitors toward the door. Large windows allow for natural light, while surrounding landscaping adds a touch of nature.
Cabin in Galena
4.93 out of 5 average rating, 81 reviews

The MacRae Cabin

Top guest favorite
A spacious bedroom is highlighted by a large bed, dressed in neutral bedding and decorative pillows. Natural light filters through a window draped with light curtains. A small bedside table and a decorative plant add subtle accents to the warm atmosphere.
Home in Benton
5 out of 5 average rating, 56 reviews

Family-Friendly Home Near Galena

Top guest favorite
A spacious living area features a stone fireplace surrounded by large windows that provide natural light. Comfortable seating arrangements include leather couches and a wooden coffee table. A large television mounted on the wall displays a serene landscape. Soft lighting enhances the inviting ambiance.
Cabin in Galena
4.96 out of 5 average rating, 52 reviews

Hot Tub and Firepit at Beautiful Fall Retreat

Guest favorite
A spacious outdoor porch features log pillars and stone accents, offering seating with a wooden rocking chair and a small table. The view showcases the tranquil lake, surrounded by lush greenery and distant hills under a clear blue sky.
Cottage in Galena
4.91 out of 5 average rating, 33 reviews

The Cottage on Lake Galena

Top guest favorite
A two-story vacation home is set amidst lush greenery, featuring a sloped roof and large windows. A welcoming pink front door creates a vibrant focal point. A path leads to the entrance, complemented by a driveway and surrounding trees that enhance the serene environment.
Home in Galena
5 out of 5 average rating, 22 reviews

The Galena Chalet- 3bdrm-3 bath

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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