Vacation rentals in Guilford Township

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Top-rated vacation rentals in Guilford Township

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Guest favorite

Home in Galena

4.92 out of 5 average rating, 185 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

Home in Galena

4.89 out of 5 average rating, 105 reviews

Sweet Escape~Galena Territory~Hot Tub~Pool Table

Beautiful 6 bedroom, 5.5 bath home with a screened-in hot tub, pool table & fire-pit table in the gorgeous Galena Territory - perfect for enjoying Galena! The home boasts 4 en suite bedrooms, 3 king beds, 3 queen beds, and 1 twin bed. Bedrooms have a 32" smart TV. The large kitchen has a table that seats 6 and 3 island bar stools. The dining room seats 8. There are 2 refrigerators. There is a deck and screened-in porch, a living room and family room with a 65" flat-screen TV & DVD player.

Guest favorite

Home in Galena

4.97 out of 5 average rating, 125 reviews

Galena Territory Sun-Drenched TreeHouse w/ Views

Enjoy your respite in this 4000 sq ft, 3 bed/3 bath, sun-filled home. Perched on a hill in the Territory, the home is nestled among Oak trees w/ expansive views. Perfect for families, couples, friends, bird watchers and nature lovers alike. The private location is mere minutes from the Owners Club, Eagle Ridge, Stonedrift Spa, Golf, Shenandoah Riding Ctr, Marina, walking trails and only 15 minutes to Downtown Galena and Chestnut Mountain Ski Slopes. 3 levels of living and room to spread out!

Guest favorite

Home in Galena

4.98 out of 5 average rating, 82 reviews

King Bed | Semi-private Pool | Wood Fireplace

◆ Owner's club access ◆ Woodburning fireplace w/supply of wood ◆ Well equipped kitchen ◆ TV on each level ◆ Computer desk ◆ Queen sofa bed ◆ 2 Full bathrooms ◆ Gas grill ◆ Communal indoor pool open year round ◆ Workout facility ◆ Paved walking trails near parking lot ◆ Eagle Ridge Driving Range walking distance ◆ North Course conveniently up the road ◆ Access to 2 outdoor pools ◆ Seasonal lake access ◆ Serene, nature views ◆ Stonedrift Spa, 3 min drive ◆ Downtown Galena, approx. 10 min drive

Guest favorite

Home in Galena

4.91 out of 5 average rating, 11 reviews

Townhome-King Beds and massage chair!

Kick back & relax in this quiet, stylish townhouse in the Galena Territory. Located 10 minutes outside the city of Galena & only 5 minutes from the owners club with indoor and seasonal outdoor pools! Both bedrooms have king sized beds & their own bathroom connected to it! The loft area also has a queen pull out sofa sleeper. There are so many things to do in the territory... like go hiking, fishing, horseback riding, swimming, or relax in your massage chair! Chestnut ski resort is also close by!

Guest favorite

Tiny home in Darlington

4.98 out of 5 average rating, 590 reviews

Arbor Crest Cottage- Peaceful farm stay getaway.

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. Our 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.

Guest favorite

Home in Galena

4.95 out of 5 average rating, 201 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

Home in Galena

5.0 out of 5 average rating, 12 reviews

Jackson Ready Properties

Bring the whole family to this great place with lots of room for fun. Enjoy the patio or deck and cozy up to the outdoor firepit. Socialize with family and friends inside with two large living areas featuring plenty of seating and pool, foosball or wet bar to keep guests entertained. Three large bedrooms that sleep 6 comfortably as well as a sofa sleeper for kids or tag-along adults! Located within walking distance to the Owner's Club or a short cruise down the hill to the Marina.

Guest favorite

Chalet in Elizabeth

4.91 out of 5 average rating, 289 reviews

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

Guest favorite

Treehouse in Galena

4.98 out of 5 average rating, 59 reviews

Octagon house in woods- Hot tub, fireplace, pool

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 new 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.

Guest favorite

Cabin in Darlington

5.0 out of 5 average rating, 13 reviews

Hilltop Hideaway. Relax, unwind, and getaway!

Truly your own peaceful get-a-way. Meander your way over the cattle guard, through the creek, up the winding driveway, alongside the grazing cattle, to your secluded Hilltop Hideaway. If you're wanting to take part in the ATV trails of Lafayette County or you are just looking to get away from the hustle and bustle of life, we have the perfect place for you. Hilltop Hideaway has been our retreat for years, and we look forward to sharing it with you.

Guest favorite

Home in Shullsburg

5.0 out of 5 average rating, 85 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