Search Holiday Rentals in Montgomeryville

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Top Holiday Rentals in Montgomeryville

Our top choices for Montgomeryville holiday rentals

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

10.0 out of 10, Exceptional, (40)
"Super nice cabin that was in an excellent location! So clean and had everything we needed for a nice relaxing weekend away! Would highly recommend and we plan to visit again! "
Romantic Cabin: Secluded Woods, Hot Tub, and Privacy in the Driftless Region.

Blakley Hobbit Large Cabin

8.4 out of 10, Very good, (37)
"We loved this spot and will definitely be booking it again. The cabin has everythinf you need for a quick easy vacation. "
The price is £128
includes taxes & fees
24 Aug - 25 Aug
Blakley Hobbit Large Cabin

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

9.2 out of 10, Wonderful, (5)
"Nice place across from a campground. "
The price is £237
includes taxes & fees
25 Aug - 26 Aug
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

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

9.8 out of 10, Exceptional, (55)
"Beautiful get away. Private and Peaceful."
The price is £137
includes taxes & fees
28 Aug - 29 Aug
Hygge Hideaway. Pet friendly, cozy retreat & 3 minute walk to the river!

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

10.0 out of 10, Exceptional, (43)
"Was a wonderful Valentine’s Day weekend very quiet cozy stay will definitely be staying there again "
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

Blakley Hobbit Small Cabin

7.8 out of 10, Good, (45)
"Very nice place. 10/10 would stay again"
The price is £93
includes taxes & fees
24 Aug - 25 Aug
Blakley Hobbit Small Cabin

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

10.0 out of 10, Exceptional, (148)
"Great cabin and solitude. Cabin is very nice and has everything. Really enjoyed the property."
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

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

10.0 out of 10, Exceptional, (31)
"Great location, great cabin."
Maplewood Cabin: Secluded Romance with Private Hot Tub while Star Gazing.

Upper Place Vacation Cottage

9.6 out of 10, Exceptional, (35)
"Great host and communication. Everything went as planned and the Driftless area never disappoints. "
Upper Place Vacation Cottage

Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.

9.8 out of 10, Exceptional, (6)
"secluded yet very close to town, beautiful, very private, very clean, everything is new,we have been welcomed with vine, snack, water in the fridge, little forest around the cabin is amazing, we were lucky it was snowing little bit but enough to have winter idyll, very warm and cosy, will be back for fishing season. Loved it "
Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.

Private location 2 bedroom mobile home great view of the Mississippi River

9.8 out of 10, Exceptional, (10)
"Nice place along the Mississippi River. "
The price is £116
includes taxes & fees
25 Aug - 26 Aug
Private location 2 bedroom mobile home great view of the Mississippi River

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

10.0 out of 10, Exceptional, (163)
"Great stay"
Cozy quaint cabin tucked back in the woods- Secluded, private - couples getaway

Secluded cabin on 75 acres 360 views cedar hot tub infrared sauna outdoor Shower

10.0 out of 10, Exceptional, (77)
"Always enjoy my time here."
Secluded cabin on 75 acres 360 views cedar hot tub infrared sauna outdoor Shower

Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View

9.8 out of 10, Exceptional, (141)
"Great spot for trout fishing and a great place to stay and relax on the porch after a full day exploring the many trout streams."
Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View

Wagonwheel Ranch

2.0 star property
9.6 out of 10, Exceptional, (10)
"Beautiful place in a beautiful area"
Wagonwheel Ranch

River Road Getaway

9.6 out of 10, Exceptional, (25)
"The set up of the property was very nice, multiple deck seating areas, very nice concrete fire pit right off the back deck. Park across the street, beautiful views of the scenic drive of the Wisconsin River, would really be beautiful to see in the fall with the leaves changing l."
The price is £180
includes taxes & fees
26 Aug - 27 Aug
River Road Getaway

Serenity cabin at Crooked Creek

10.0 out of 10, Exceptional, (8)
"Came up to see mom. Me and my siblings wanted something other that the typical 3 motel rooms. Cabin was clean and quiet. Nice to be able to share a weekend together without the spouses. Cannot wait to rebook for family reunion or another getaway. "
The price is £124
includes taxes & fees
1 Sept - 2 Sept
Serenity cabin at Crooked Creek

SereniTree Cabin - Modern Rustic Getaway tucked in the trees

10.0 out of 10, Exceptional, (97)
"Amazing property with great amenities, and super peaceful! Easy to get lost in nature, though not too far from nearby towns."
SereniTree Cabin - Modern Rustic Getaway tucked in the trees

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

10.0 out of 10, Exceptional, (255)
"We had a wonderful stay. Great hosts and a perfect cabin."
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location

Charming 2-bedroom house in Viroqua with AC

10.0 out of 10, Exceptional, (1)
"We stayed in this cozy home in Virocqua and really enjoyed it. Amy has done a great job of decorating and has added so many interesting pieces of art. It’s furnished with everything you need and the beds are very comfortable. I absolutely loved the claw foot soaking tub! What a luxury. We spent many hours on the deck enjoying such a peaceful setting. We came to enjoy the Saturday farm market just a few blocks away. We will definitely return to enjoy everything about this great little town...
Charming 2-bedroom house in Viroqua with AC
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Montgomeryville Hotel Reviews

Frequently asked questions

Are there holiday rentals in Montgomeryville?

Yes, there are holiday rentals close to the most popular sights in Montgomeryville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Montgomeryville has to offer?

River Road Getaway: This holiday home rental outside of Montgomeryville has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 Kickapoo River. In the wider area, you’ll find Eagle Cave and Viroqua Country Club.

What are holiday rentals like in Montgomeryville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montgomeryville. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip.