Holiday houses in Montgomery

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Top-rated holiday rentals in Montgomery

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Top Guest favourite
A charming treehouse is nestled among the lush branches of a large, mature oak tree. The wooden structure features multiple levels with a spacious deck that connects to the main entrance, surrounded by greenery, creating a serene and natural environment.
Home in Cottage Grove
4.98 out of 5 average rating, 718 reviews

Tree House Luxury Stay

Perched high in the majestic arms of a 150 year old Burr White Oak tree. This cozy 1200 square foot, seven-room house not only has breathtaking views it also has enchanting and delightful surprises befitting of a fairytale. Climb 40 feet up onto the Observation Tower, where a telescope waits for you, ready to scan the night sky, and reveal the panorama of the heavens -- overlooking 500 acres of natural splendor right next door. Step into the hot, bubbling jets of the jacuzzi, or warm caress of the rain shower, and restore your spirits by soothing your muscles, melting away any residual tensions of the day. Get a restful sleep in one of our soft beds. In the morning, pad around on in-floor radiant heated floors (so cozy during winter-time.) Or enjoy your morning coffee on one of four outside decks. And don’t forget to solve the mystery of the Treehouse, that awaits your discovery within its wood beamed walls. This treehouse was custom designed by its architect with three dimensional chess in mind. Artisan architectural details are found throughout. Crystal chandeliers bedeck its high ceilings, and marble countertops grace the elegant, fully appointed kitchen. (A surround sound system helps set the mood for those special dinners in the dining nook.) One of two fireplaces adds luxurious touches to the primary bedroom with a queen bed, and hideaway bed in the secret room, along with a jacuzzi and rain shower in the primary bath, as well as a second bathroom in the secret room. Perfect for honeymooners, couples, business/corporate overnights, solo travelers and families with children over twelve years old. These are only a few of the many luxury details in this spectacular vacation spot must-see. Spend your days snuggled up beside the fireplace of your choice, while enjoying the panoramic views. You can stream your favorite movies and shows with Broadband Wi-Fi throughout the house. Come down for a leisurely walk around the grounds, and stop by to visit and feed the goats and chickens that call Hope Glen Farm their home in the corral of this historic farmstead. Bring your stress levels down and your heart rate up by walking over to Washington County Cottage Grove Park Reserve, just steps away, and answer its call to explore over 550 acres of fields and forests. Go hiking and biking down its trails, geocaching the hills and ravines for hidden treasures, or spend the afternoon fishing and kayaking in the lakes. And don’t let cooler temperatures keep you from discovering the pristine natural beauty of winter! Winter activities include cross country skiing and snowshoeing on the blankets of snow. Breathe deeply of the crisp Minnesota winter air -- truly one of life’s great pleasures. Plus, only a ten minute drive brings you to nearby Afton Alps in Afton State Park offering downhill skiing and snowboarding. For clarity, the Treehouse has 2 private bedrooms: Bedroom 1 is has a queen bed. Bedroom 2 has a bedroom with standard sofa bed with attached half bathroom, which is the secret room a must find. Give yourself the gift of this luxurious enchanting TreeHouse Suite in the treetops, for a enchanting vacation experience you'll never forget. Something to write home about!

Top Guest favourite
The farmhouse is seen under a vibrant sunset, with warm hues illuminating the exterior. The wrap-around porch is framed by trees displaying autumn foliage. A rustic red barn is visible in the background, completing the serene countryside setting.
Farm stay in Webster
4.97 out of 5 average rating, 148 reviews

Farmhouse Retreat on 20 acre hobby farm.

Enjoy the rolling hills as you drive to your retreat at Anchor Farmhouse. Unplug as you hear the birds and the wind rustle through the leaves. A rustic red barn and animal life will greet your days. Relax as you watch the stunning sunsets or sunrises from your wrap-around porch. Settle into your cozy bed, wake up refreshed, and possibly join us for chicken chores. This is a place for the generations to connect and for friends and family to make memories. Note! We currently have Bernese puppies!

Top Guest favourite
The exterior of a spacious home is shown, surrounded by well-maintained green lawns and shrubs. A paved driveway leads to the front of the house, with trees providing natural shade. The structure features a traditional design with appealing landscaping in a quiet setting.
Guest suite in Faribault
4.96 out of 5 average rating, 398 reviews

Sherry's Suite

Our beautiful suite of private rooms will accommodate up to 4 people. You can expect a very private, peaceful and comfortable atmosphere. A place that you can call 'Home' while being away from yours. During this time, with the Coronavirus and the need for social distancing, Lisa & I would like to assure you that the Suite is completely yours and there is no shared space within the home. We take extra care in making sure you are in a safe, clean environment. Have safe travel's and stay healthy.

Top Guest favourite
A charming two-story farmhouse is set on a lush green landscape, surrounded by tall trees. The lawn is well-kept, providing a peaceful atmosphere. The clear sky above enhances the tranquility of the scene, while power lines add a subtle connection to the nearby road.
Guest suite in Prior Lake
4.93 out of 5 average rating, 298 reviews

Little Farm Getaway

Welcome to my little 8 acre oasis! Being the first farm I’ve ever lived on, I understand the peace and tranquility it can offer those who have never experienced it. Enjoy meeting my horses and mini donkeys, take a walk through my woods, or have a fire! Aside from being just far enough, but just close enough to all the happenings in the city, my newly remodeled private entry, ground level basement apartment offers an escape from the noise and a place to unwind and relax. NO CHORES REQUIRED! 😊

Guest favourite
The exterior of a charming historical home is displayed, featuring a blue facade and light-colored trim. Stairs lead to the front door, which is framed by large windows allowing abundant natural light. Lush greenery surrounds the entrance, enhancing the inviting curb appeal.
Home in New Prague
4.93 out of 5 average rating, 30 reviews

The Mill House

This historical home was built in 1901, and just 2 blocks off Main St it has a view of the old Mill. Perfect for walking Main St and enjoying all New Prague has to offer. Decorated with pieces from the owner’s collections of art and trains, it’s perfect for couples or a family with one main bedroom downstairs and two bedrooms upstairs. And to make your stay extra relaxing, there’s an electric fireplace in the main bedroom and a 4 person hot tub outside. You will feel right at home!

Superhost
A spacious room features a queen bed draped with light bedding, complemented by a cozy couch and soft pillows. Decorated with Turkish globes, the room is illuminated by natural light from surrounding windows. A small writing desk is positioned near the entrance.
Treehouse in Glencoe
4.95 out of 5 average rating, 151 reviews

Cozy Cedar Treehouse

Our space is a 30 x 12 cedar 4 season porch enhanced in boho decor with Earth's natural elements and warmth of a treehouse. Relaxing authentic Turkish globes surround you. Private sitting areas in the trees, perfect for grilling, entertaining or hanging low and watching the stars. Private courtyard for a more tranquil, intimate setting with a gas glass lit firepit. Come alone, bring your spouse, friend or child. It's a perfect spiritual retreat located 45 min west of MSP Airport.

Guest favourite
A bright bedroom area features a spacious bed with decorative pillows and bedside tables with lamps. A seating area includes a light-colored sofa and a coffee table, all set against a backdrop of large windows offering natural light and views of the surroundings.
Guest suite in New Prague
4.98 out of 5 average rating, 136 reviews

Cozy and Comfortable New Prague Suite

Welcome to the Ballinger Suite, a spacious two room unit in New Prague, MN. You will enjoy a private bedroom with a queen bed, tv and sitting area plus a separate living room with, sofa, tv, tech table, kitchenette and murphy bed creating a 2nd private sleeping option to accommodate 4 quests. A 3/4 bath and tile shower is conveniently accessible to both rooms. The property offers stunning views of St. Wenceslaus church and is convenient to main street, restaurants and golf.

Guest favourite
Apartment in Montgomery
5 out of 5 average rating, 6 reviews

Brewer Family Loft in Historic Brewery Building

Welcome to the Brewer Family Loft—a spacious 3BR, 2BA retreat inside the 130-year-old Montgomery Brewing Building. Designed for families and friends, it features a full kitchen, dining table for 6, cozy living room, 65" TV, and games for all ages. Located steps from restaurants, shops, and the local brewery, this historic space blends rich heritage with modern comfort—perfect for relaxing and reconnecting. Bring the whole family to this great place with lots of room for fun.

Top Guest favourite
The exterior of a two-story home is showcased, featuring a brick facade and large windows. Colorful perennial flower beds frame a winding pathway leading to the entrance. Lush green grass and tall trees surround the property, enhancing the outdoor appeal.
Home in Shakopee
4.95 out of 5 average rating, 134 reviews

Maple trails farm house

Fully furnished 4 Bedrooms with extra sofa beds for children, home with Bedding and Linens, Kitchen is equipped with Microwave, Refrigerator, Oven, Toaster, Coffee Maker, Dishwasher, Stove, Dishes and Silverware too. Large floor plan and over 4,500 sq.ft and has a terrific backyard oasis that includes a swimming pool ( open depending on weather permitting ) outdoor fireplace, a 3-season porch, perennial gardens and pond.Enjoy a calm stay with horses on property .

Top Guest favourite
A tiny house features natural wood siding with decorative flower boxes under the windows. The deck is furnished with a round table and four chairs, shaded by a large umbrella. Lush green trees and a tranquil lake are visible in the background.
Tiny home in Faribault
4.97 out of 5 average rating, 452 reviews

*Bless This Tiny House* on MN lake!

Bless This Tiny House is a 267 sqft Tiny House parked alongside a huge, beautiful deck overlooking the lake! Take the kayaks out on the lake! Chill in the hammock with a good book. Grill burgers and relax by the campfire while the sun sets! The Tiny is especially cozy in the winter! Unplug and play cards in the leisure loft! The perfect setting for a couple's retreat! Minimalism and contentment! Be inspired by the beauty of God's creation!

Guest favourite
A spacious living area features a comfortable sectional sofa and a recliner, arranged on a patterned area rug. Natural light fills the space through large windows, illuminating the cozy ambiance. A dining area is visible in the background, accompanied by a quilted wall hanging.
Home in Faribault
4.98 out of 5 average rating, 137 reviews

Furball Farm Inn

CAT LOVERS ONLY 😻 This beautiful old freshly updated farm house is on the same property as Furball Farm Cat Sanctuary! Renting our Airbnb will allow you to see behind the scenes! Visit the cats anytime between the hours of 9am-9pm on the days you are booked! Marley and Teddy are the resident cats there and they will keep you company! (They can go in and out) (Marley has had past history of being a naughty potty, see more info in details)

Guest favourite
An aerial view captures the expansive retreat surrounded by lush greenery. The property features a charming landscape with a vibrant garden, winding pathways, and a spacious deck, all inviting tranquility amid the natural scenery.
Home in Jordan
5 out of 5 average rating, 10 reviews

Private Home Retreat - Spacious Getaway

Escape to our serene retreat blending luxury with nature. Nestled amid open landscapes, this destination invites relaxation and adventure. Enjoy a gourmet kitchen, cozy master suite, and entertainment-ready basement with a game area and bar. Outdoor spaces include a deck overlooking a pond, a scenic bridge, and two miles of private trails with access to Jordan city paths. Wildlife, peaceful views, and modern comforts await. Book today!

Popular amenities for Montgomery holiday rentals

  1. Airbnb
  2. United States
  3. Minnesota
  4. Le Sueur County
  5. Montgomery