Vacation rentals in Guilford Township

Townhouse in The Galena Territory

A living area features a stone fireplace with an elegant wood mantel, flanked by shelves adorned with plants and decorative items. Comfortable seating includes a sofa and armchair, with soft lighting creating a welcoming ambiance. A staircase leads to a loft space above.

4.9 out of 5 average rating, 167 reviews

The Airy Aerie: Owners' Club access, golf nearby!

Welcome to the Airy Aerie: an avian themed townhome in the heart of the Galena Territory. Our space has been carefully curated to reflect the diversity of birds you will find in the natural surroundings of the area. There are two ensuite bedrooms and a full kitchen featuring granite countertops and stainless steel appliances. There is a loft space upstairs where a rollout twin bed can be set up. Our home can accommodate a maximum of 6 overnight guests (assuming 1 person on the twin rollout bed).

4.93 out of 5 average rating, 199 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. )

4.97 out of 5 average rating, 143 reviews

Pools, Hot Tub, Fire tables, dog friendly

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

Villa in The Galena Territory

4.98 out of 5 average rating, 134 reviews

Semi-private Pool, King Bd, Near Spa, Golf, Trails

✓Near hiking trails & paved walking trails ✓Stonedrift Spa, 3 min drive ✓North Course & Driving Range, 2 min drive ✓Downtown Galena, 15 min drive ✓Semi-private outdoor pool, steps away ✓Well equipped kitchen w/modern appliances ✓Gas grill ✓Smart TV on each level w/Roku & YouTube TV ✓Computer desk ✓Fireplace w/supply of firewood ✓Queen sofa bed ✓2 Full baths ✓Owner's Club access ✓Indoor pool ✓Lake access ✓Chestnut Mountain (Ski & Zipline), 25 min drive ✓Guest favorites: "cleanliness & comfort"

4.98 out of 5 average rating, 754 reviews

A small cottage is illuminated by warm outdoor lighting, creating a welcoming ambiance. A gravel path leads up to the door, surrounded by trees. Two white chairs are positioned nearby, inviting relaxation amid the tranquil woodland setting.

Tiny home in Darlington

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

Treehouse in The Galena Territory

A stone firepit surrounded by wooden benches is situated amid lush greenery. The octagon-shaped house is visible in the background, featuring floor-to-ceiling windows that reflect the surrounding woods. The private hot tub is positioned on the deck, enhancing the outdoor experience.

4.98 out of 5 average rating, 159 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

4.95 out of 5 average rating, 242 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.

4.92 out of 5 average rating, 345 reviews

An A-frame structure is surrounded by lush greenery, showcasing a large wooden deck that wraps around the house. Windows display a cozy interior, while the sloped roofline contributes to the house's unique design. Sunlight filters through the trees, creating a serene atmosphere.

Chalet in Elizabeth

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

Cabin in The Galena Territory

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.

4.98 out of 5 average rating, 116 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. Stay cozy by the wood fireplace or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball (8 amenity cards). Adventure awaits—book your perfect getaway today!

Townhouse in The Galena Territory

A modern living room features a stone fireplace as the focal point, with expansive windows that invite natural light. A wooden coffee table is centered on a cozy area rug, complemented by comfortable seating and a view of the outdoor deck.

4.9 out of 5 average rating, 115 reviews

Spring Creek Sanctuary

Come enjoy nature's splendor at the "Spring Creek Sanctuary", a modern condo located in the Galena Territories. Our two spacious bedrooms & two bathrooms allow for groups or families to stay in comfort and style. All can congregate in the shared spaces to enjoy a well stocked kitchen, cozy living room with a wood burning fireplace and the deck area with it's beautiful views. Be sure to check out the amenities included with your stay!

Vacation home in The Galena Territory

A spacious living area is framed by large windows allowing natural light to fill the room. A stone fireplace serves as a focal point, surrounded by comfortable sofas adorned with cushions. The high ceiling and wooden beams contribute to an open, inviting atmosphere.

4.96 out of 5 average rating, 109 reviews

Aspen House - A Private Quiet 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!

5 out of 5 average rating, 163 reviews

A retro kitchenette is showcased, featuring vintage-style red appliances, including a refrigerator and a stove. Above, two bicycles are displayed on the wall. The stainless steel counters are complemented by a stylish backsplash, creating a nostalgic ambiance.

Home in Shullsburg

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

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Popular amenities for Guilford Township vacation rentals

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Other great vacation rentals in Guilford Township

4.98 out of 5 average rating, 84 reviews

Cozy Galena Townhome

ColleenRating, 5 stars4 days ago

Nice place! Loved the pool as well. Beautiful area.

Superhost

A secluded screened porch offers a tranquil retreat surrounded by lush greenery. Large windows provide an unobstructed view of the forest, while a comfortable chair and a flat surface enhance the inviting atmosphere.

4.83 out of 5 average rating, 42 reviews

Bluffwood Bungalow - Secluded, Forested Getaway!

MadalynRating, 5 stars2 weeks ago

We ended up having the perfect family reunion here! There was more space than expected for us - we loved the open floor plan around the kitchen which looked out into the forest. We even saw some wildlife pass through down there while drinking our coffee in the morning. There was lots to do - the adults enjoyed playing pool at the house and the kids had fun using the pool at the owners club. We all loved being out in nature and hiking the local trails! The host had good recommendations and was responsive and accommodating. Would recommend for a getaway!

The exterior of the home is displayed, featuring a large two-story structure with a combination of stone and siding. Expansive green lawn surrounds the property, with a mature tree nearby. Rolling hills are visible in the distance under an overcast sky.

5 out of 5 average rating, 21 reviews

Galena Retreat-Cogan View!

BonnieRating, 5 stars6 days ago

Michelle’s home was wonderful. The location is very serene and the house was exceptionally clean and well equipped for a relaxing stay. The house has bedrooms and bathrooms on all three levels, along with a screened in porch, multiple decks, and two fireplaces, with easy access (no stairs) to the main entry. Seating throughout the home is invitingly cozy and comfortable. There was a welcome basket of treats in the kitchen, such a nice touch. We really enjoyed our time at this lovely home.

Superhost

A spacious game area is featured with a large ping pong table and several paddles visible. Natural light filters through numerous large windows, providing a scenic view of the surrounding landscape. The warm wooden walls and ceiling create a cozy atmosphere.

4.93 out of 5 average rating, 15 reviews

Available July 4th-Luxury 6BD,Theater, Pool Access

VanessaRating, 5 stars1 week ago

I visited Linda's place with a big group of friends including three kiddos and it was absolutely perfect! Plenty of space for everyone and a ton of things to do on the property. The location was easy to get to and close to the downtown Galena area. The pictures really don't do the house justice. It's beautiful with a lot of space. Leading up the trip and during I had several questions. Responses always came super quickly (usually under 5 minutes). She was a delight to talk to worked to make sure our trip went perfectly. I'd highly recommend this property to anyone looking to visit the Galena area. Everyone in my group would 100% return.

5 out of 5 average rating, 17 reviews

The Galena Chalet- 3bdrm-3 bath

LaurenRating, 5 stars4 months ago

We had a great experience at this cozy home! Perfect chalet vibe for our ski trip. The downstairs room with two beds was a little chilly compared to the rest of the house, but it was negative temps when we visited and didn’t affect our overall feelings for the home, just something to consider if you have littler ones in that room.

The exterior of a spacious house is highlighted, featuring a sloped roof and large glass windows. A wooden deck surrounds the upper level, offering seating and shaded areas. A view of the green lawn and surrounding trees creates a serene environment. A hot tub is visible on the lower level.

4.97 out of 5 average rating, 31 reviews

*Golf*Hot Tub* Firepit*Owners Club*Dogs OK

MariaRating, 5 stars1 week ago

Cynthia was incredibly responsive and helped make our weekend stay truly memorable! We loved the open layout and warm, welcoming ambiance from the moment we walked in. I would highly recommend this place to anyone and would love to return for my next Galena visit!

4.98 out of 5 average rating, 40 reviews

A wooden deck is presented with a picnic table and a decorative rug, surrounded by greenery. Trees provide shade, while a spacious field extends beyond, offering an unobstructed view of the countryside. The sky is clear, contributing to a serene outdoor setting.

Cabin in Elizabeth

Galena Countryside Cabin

BethanyRating, 5 stars3 days ago

We had a great weekend at the Owl A-frame. It was absolutely beautiful. It was clean and had everything we needed (and more) to enjoy our visit. It was the perfect size for us (two adults and two teen kids). We will definitely be going back!

An outdoor deck is shown featuring comfortable furniture and a fire pit table. The expansive, grassy area extends toward a picturesque golf course, framed by trees and distant buildings under a blue sky with scattered clouds.