Vacation rentals in Guilford

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Top-rated vacation rentals in Guilford

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Top guest favorite

A cozy cabin is nestled on a grassy hillside, surrounded by trees. A wooden deck wraps around the cabin, providing outdoor space. Stone steps, lined with potted flowers, lead up to the cabin entrance, enhancing the natural setting.

Cabin in Benton

4.95 out of 5 average rating, 125 reviews

Our cabin's a win-win

In 1834, it was a chicken coop nestled between the house and barn. Today, it's a cozy cabin just a stone's throw away from the villa and venue. From the private, rural setting to the rustic decor, you'll feel as though you've traveled back to simpler times. It's unique, refreshing and oh-so tranquil. If you're looking for a little hush and a lot less rush, you're going to fall in love with this little home away from home. While you're visiting, get the scoop on how we transformed this coop.

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, 209 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

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

4.97 out of 5 average rating, 159 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

Guest favorite

A modern, two-story house is set against a lush green landscape, featuring dark exterior siding and a pitched roof. A welcoming entrance is framed by two white chairs on a front porch, with trees and a bright blue sky in the background.

Home in The Galena Territory

5 out of 5 average rating, 7 reviews

Modern Home in Galena Territory

Goodbye dated vacation rental vibes! Kick back and relax in this calm, stylish space that's been completely renovated with a fresh, Scandinavian modern aesthetic. You'll love the peaceful serenity this home delivers, just minutes from fun Galena Territory amenities, including indoor/outdoor pools, tennis/pickleball courts, game room, fitness center, marina, and restaurants. Plus, a relaxing 15 minute drive through the countryside gets you to popular downtown Galena shopping and restaurants.

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

4.95 out of 5 average rating, 108 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

Villa in The Galena Territory

4.98 out of 5 average rating, 146 reviews

King bed, Wood Fireplace, Near Spa, Golf, Trails

✓ Peaceful, nature views ✓ Serene, wooded backdrop ✓ Lovely Fall colors ✓ Well equipped kitchen w/modern appliances ✓ Gas grill on deck ✓ Smart TV on each level ✓ Computer desk ✓ Fireplace w/supply of firewood ✓ King sized bed ✓ 2 Full baths ✓ Near hiking trails & paved walking trails ✓ Stonedrift Spa, 3 min drive ✓ North Course & Driving Range, 2 min drive ✓ Downtown Galena, 15 min drive ✓ Owner's Club access ✓ Indoor pool ✓ Lake access ✓ Chestnut Mountain (Ski & Zipline), 25 min drive

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, 120 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, 175 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 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 The Galena Territory

4.99 out of 5 average rating, 134 reviews

*Fall Fun* *Hot tub-Fire-3 king beds-Game room*

Relax, unwind, & explore at this fall retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful fall 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 pit 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 fall adventure!

Guest favorite

A gravel fire pit area is positioned in the foreground, surrounded by a circular stone border. The spacious yard is framed by trees, providing a natural setting. In the background, a cozy wooden house with a deck is partially visible, blending harmoniously into the landscape.

Home in The Galena Territory

4.95 out of 5 average rating, 252 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

A warm living space features a brown leather sofa and an ottoman, positioned on a vivid area rug. Above the cozy bed, a gallery wall showcases a variety of framed photographs. Natural light floods the room through several windows, adding to the inviting ambiance.

Tiny home in Darlington

4.99 out of 5 average rating, 399 reviews

The Bower, Farm Stay

Thank you for checking out The Bower at Arbor Crest Acres! We would be happy to host you! We are headed into our 6th year hosting and have enjoyed it so much! The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The Bower is just inside the property on the edge of the woods. We invite you to explore the property and enjoy the animals. The west end of the land over looks town and is a great place to watch the sunset and the goats graze.

Top guest favorite

A blue A-frame house is showcased, surrounded by greenery. The brick walkway leads to a cedar deck, framed by landscaping. Windows are visible on the sides, allowing natural light to fill the interior.

Chalet in Elizabeth

4.92 out of 5 average rating, 357 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