Montgomeryville Vacation Rentals

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Vacation Rentals in Montgomeryville

The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

10.0 out of 10, Exceptional, (135)
"We had a great time staying here. It was just what we needed, get away to the country for a few days. Everything is first class, from communicating with Dan to sitting on the surround porch, even though it was a bit brisk. Would go back in a second, perfect location, beautiful house and quiet."
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

Cozy quaint cabin tucked back in the woods- Secluded, private - couples getaway

10.0 out of 10, Exceptional, (155)
"What a way to escape and relax perfect couple get away. "
Cozy quaint cabin tucked back in the woods- Secluded, private - couples getaway

SereniTree Cabin - Modern Rustic Getaway tucked in the trees

10.0 out of 10, Exceptional, (86)
"The place was cooler than the pictures. Tucked way back in a private community was very cool. Great view of the timber and the animals. Our only complaint is that the remotes need labels, I know first world problems right!! You will not be disappointed with this cabin or the views."
SereniTree Cabin - Modern Rustic Getaway tucked in the trees

Romantic Cabin: Secluded Woods, Hot Tub, and Privacy in the Driftless Region.

10.0 out of 10, Exceptional, (32)
"We had an excellent time! A peaceful property that's well maintained. Easy check in/out process and communicative hosts. Would recommend this property to any friends or family."
Romantic Cabin: Secluded Woods, Hot Tub, and Privacy in the Driftless Region.

Cozy first floor at the heart of downtown Viroqua

10.0 out of 10, Exceptional, (34)
"Second time staying and it was even better than the first time. This is the place to stay if you enjoy cooking your own meals. But the town of Viroqua also offers plenty of options for food when you want to eat out. The apartment has plenty of room, yet has a cozy feel."
The price is CA $133
CA $249 total
includes taxes & fees
Apr 18 - Apr 19
Cozy first floor at the heart of downtown Viroqua

Arcadian Cabin at Bishop Branch, creek-front, public land access, great location

10.0 out of 10, Exceptional, (239)
"We had a wonderful stay. Great hosts and a perfect cabin."
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location

The Honey Haven

10.0 out of 10, Exceptional, (33)
"We sadly didn’t make our trip. Nonetheless, kindness and hospitality Jennifer offered in her actions ensured we will make it there on our next adventure to the area."
The price is CA $222
CA $350 total
includes taxes & fees
Apr 20 - Apr 21
The Honey Haven

Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

10.0 out of 10, Exceptional, (38)
"A few hours after checking into the VRBO on Friday, there was a mechanical issue in the house related to the extreme cold weather which could have ruined our entire weekend; however, the property owner promptly got someone on sight first thing Saturday morning, determined the issue couldn't be fixed immediately, found a property within 1 mile where we could stay for no additional fee, AND gave us a refund. Kelsey went above and beyond to make things right and I so very much appreciate it! She...
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

Wagonwheel Ranch

2.0 star property
10.0 out of 10, Exceptional, (3)
"Ideal spot for a family gathering of three couples -- plenty of space; plenty of those small food items you put in refrigerator door (but don't want to buy for just a two night stay). Chris is a very responsive host. And if you come with two EV's, there are two external outlets (both 110v) for slow charging. A bonus. Nearest charger is in the Food Coop parking lot in Viroqua - no charge. "
Wagonwheel Ranch

Cozy and charming. Your home away from home in the heart of Viroqua.

9.8 out of 10, Exceptional, (10)
"The house was lovely and very clean, cozy, and welcoming. The high ceilings, woodwork and thoughtful design of the space made us feel inspired just by taking them in. We especially appreciated that the space was very clean but without the smell of artificial fragrances. Viroqua is a friendly community and a nice place to visit."
Cozy and charming. Your home away from home in the heart of Viroqua.

Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route

9.0 out of 10, Wonderful, (24)
"Tub/shower could be cleaned better. Outdoor rubber sidewalk was lumpy. Could improve for disabled persons. Overall nice stay"
Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route

Larsen Hunters Rustic Cabin

8.8 out of 10, Excellent, (3)
"Very nice place. I enjoyed the stay."
Larsen Hunters Rustic Cabin

Nice Cape Cod home near the Mississippi River (Scenic River Inn)

9.8 out of 10, Exceptional, (125)
"Probably the 10-15th time staying here with a group of friends. Deb is a great host and definitely will be back here again and again. Great place on the Great River Road!"
Nice Cape Cod home near the Mississippi River (Scenic River Inn)

Charming 2-bedroom country house with AC, WiFi in soothing Viola

10.0 out of 10, Exceptional, (1)
"Property just as described. Well maintained. Had an excellent stay."
The price is CA $250
CA $435 total
includes taxes & fees
Apr 19 - Apr 20
Charming 2-bedroom country house with AC, WiFi in soothing Viola

Blakley Hobbit Large Cabin

8.2 out of 10, Very good, (32)
"If you're looking for a place just to sleep and be one with nature this is it! Kinda like glamping. There was mice poop everywhere, it's that time of year, didn't scare us. But their was no forks, towels, napkins, they only provided 1 trash bag we went through in a hurry and had to use grocery bags for garbage. Ran to gas station for forks and paper towels. The oven dorsnt wirk, so took 4 hours tobake a 20min bitter braid. Other than thst a good place to rough it and relax"
The price is CA $125
CA $235 total
includes taxes & fees
Apr 21 - Apr 22
Blakley Hobbit Large Cabin

Hygge Hideaway. Pet friendly, cozy retreat & 3 minute walk to the river!

10.0 out of 10, Exceptional, (39)
"Honestly, was very nice place. "
Hygge Hideaway. Pet friendly, cozy retreat & 3 minute walk to the river!

Maplewood Cabin: Secluded Romance with Private Hot Tub while Star Gazing.

10.0 out of 10, Exceptional, (30)
"My spouse and I needed a secluded get away from the city and this place was perfect. We cooked and relaxed in the private woods and hot tub all week. Will def be back. "
Maplewood Cabin: Secluded Romance with Private Hot Tub while Star Gazing.

Upper Place Vacation Cottage

9.6 out of 10, Exceptional, (31)
"We had an absolutely wonderful weekend at the cabin and enjoyed hiking the property. Luke's hill is a butt buster! We loved the fact that we could bring our dog and that there was no cell service or internet. Just family time and quietness. "
Upper Place Vacation Cottage

Two Bedroom airy modern apartment - Green Door

10.0 out of 10, Exceptional, (53)
"do it"
Two Bedroom airy modern apartment - Green Door

Country Living at its Finest

9.8 out of 10, Exceptional, (201)
"The cabin was perfect for our stay. It’s was so clean, had everything we needed for four relaxing days. The porch was perfect for coffee in the morning and reading - even though it was pretty chilly. Nuthin’ a parka couldn’t handle. My husband trout fished in the morning and evening, and we had great meals in Viroqua, which is such a cool city!"
Country Living at its Finest
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Montgomeryville you may be interested in

AmericInn by Wyndham Viroqua

2.5 star property
8.2 out of 10, Very good, (278)
"Very good!"
The price is CA $170
CA $190 total
includes taxes & fees
Apr 23 - Apr 24
AmericInn by Wyndham Viroqua

Ramada by Wyndham Richland Center

3.0 star property
8.4 out of 10, Very good, (563)
"Nice room. Very clean. Staff were very friendly and helpful. Only problem was with the tv. The volume didn’t work. "
The price is CA $126
CA $141 total
includes taxes & fees
May 4 - May 5
Ramada by Wyndham Richland Center

AmericInn by Wyndham Boscobel

2.5 star property
8.8 out of 10, Excellent, (408)
"Friendly employees"
The price is CA $117
CA $129 total
includes taxes & fees
Apr 28 - Apr 29
AmericInn by Wyndham Boscobel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Are there vacation rentals in Montgomeryville?

Yes, we offer vacation rentals near the most popular points of interest in Montgomeryville, or you can select a more secluded option if you're looking for relaxation.

What's the top vacation rental in Montgomeryville?

The Honey Haven: Visitors like this Montgomeryville vacation home rental. It offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Montgomeryville?

While exploring the area, visit family-friendly sights like WI River Outings, or get outside and enjoy nature at Eagle Cave. In the larger area, you’ll find Fortney Underground Theater and Kickapoo River.

What are vacation rentals like in Montgomeryville?

Vacation rentals are private properties you can stay in for a short or long stay in Montgomeryville. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.