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Montgomeryville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Montgomeryville vacation rentals

A wooden deck with a barbecue grill, overlooking a river and autumn foliage.

1. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (58 reviews)
"fishing cabin."
United States
joe
Blakley Hobbit Small Cabin
A wooden cabin surrounded by snow-covered trees.

2. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (53 reviews)
"This is a beautiful place to spend a couple of relaxing days. "
United States
Sujhey B.
$285 nightly
The price is $310
Oct 27 - Oct 28
Total with taxes and fees
Cabin on the Kickapoo
A rustic wooden cabin with a front porch, a staircase, and a small deck area.

3. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.2 out of 10, Very good, (48 reviews)
"A quiet spot w excellent scenery along the Kickapoo River. Great communication w host & easy check-in/out process."
United States
Rebecca B.
$160 nightly
The price is $169
Oct 19 - Oct 20
Total with taxes and fees
Blakley Hobbit Large Cabin
A grey door with a window above it and a doorbell on the right side.

4. Cozy first floor at the heart of downtown Viroqua

Cozy first floor at the heart of downtown Viroqua
Viroqua
10.0 out of 10, Exceptional, (62 reviews)
"Nice place to stay right in town perfect for a couple "
United States
Pete G.
$165 nightly
The price is $184
Oct 20 - Oct 21
Total with taxes and fees
Cozy first floor at the heart of downtown Viroqua
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television.

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

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Viola
9.0 out of 10, Wonderful, (18 reviews)
"excellent out of the way retreat close to things we wanted to do and great place for us and our cats, the hot tub was a great treat"
United States
Joseph W.
$297 nightly
The price is $313
Oct 19 - Oct 20
Total with taxes and fees
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
A room with a large window, a television on a wooden stand, a radiator, and a patterned carpet.

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

Private location 2 bedroom mobile home great view of the Mississippi River
Lynxville
9.8 out of 10, Exceptional, (38 reviews)
"Nice cute place. Beautiful view and feels very welcoming."
United States
Sandra H.
$145 nightly
The price is $153
Oct 19 - Oct 20
Total with taxes and fees
Private location 2 bedroom mobile home great view of the Mississippi River
A hot tub on a wooden deck with a view of a lake and trees.

7. Sunset Studio, Amazing River Views, HOT TUB! New Listing!

Sunset Studio, Amazing River Views, HOT TUB! New Listing!
Eastman
9.4 out of 10, Exceptional, (21 reviews)
"Loved it will be back!"
United States
Nick C.
$285 nightly
The price is $301
Nov 16 - Nov 17
Total with taxes and fees
Sunset Studio, Amazing River Views, HOT TUB! New Listing!
Two dogs sitting on a grassy field with a pond and trees in the background.

8. #4 Blakley Hobbit Campground-Tent spot

#4 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (2 reviews)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
$40 nightly
The price is $42
Oct 19 - Oct 20
Total with taxes and fees
#4 Blakley Hobbit Campground-Tent spot
A rustic cabin with a stone facade, wooden deck, and a large porch.

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

Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route
Eastman
9.0 out of 10, Wonderful, (34 reviews)
"We had a good stay, we loved the animals and the hot tub"
United States
Brooke N.
$316 nightly
The price is $333
Oct 22 - Oct 23
Total with taxes and fees
Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route
A hot tub under a wooden deck with a view of a green landscape.

10. Private Spa Cabin | Hot Tub, Sauna + Cold Plunge, Shalom Cabin

Private Spa Cabin | Hot Tub, Sauna + Cold Plunge, Shalom Cabin
Gays Mills
10.0 out of 10, Exceptional, (3 reviews)
"Wow! We were so impressed with the cabin. You walk up and can smell the cedar porch. The inside was beautifully decorated. Everything was perfect - from the cozy interior to the porch swing and hot tub at night! Peaceful and relaxing. "
United States
Morgan B.
$529 nightly
The price is $558
Oct 27 - Oct 28
Total with taxes and fees
Private Spa Cabin | Hot Tub, Sauna + Cold Plunge, Shalom Cabin
A spacious living room with a large sofa, a coffee table, and a view of a snowy landscape through large windows.

11. Copper Creek Getaway Sleeps 6 Hot Tub

Copper Creek Getaway Sleeps 6 Hot Tub
Seneca
10.0 out of 10, Exceptional, (2 reviews)
"Great area to explore, lots of friendly people. Enjoyed the trip and where we stayed was a great relaxing place."
United States
Cindy B.
$373 nightly
The price is $393
Oct 19 - Oct 20
Total with taxes and fees
Copper Creek Getaway Sleeps 6 Hot Tub
A wooden cabin with a porch, two windows, and a star decoration on the wall.

12. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"We had a great stay"
United States
Robert S.
$206 nightly
The price is $217
Oct 22 - Oct 23
Total with taxes and fees
River Road Retreat
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

13. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (63 reviews)
"This was my second time staying at the Honey Haven and I would love to stay again. The host does a wonderful job keeping the property in great shape and the area that the property is in is so special."
United States
Eric R.
$240 nightly
The price is $253
Oct 20 - Oct 21
Total with taxes and fees
The Honey Haven
A playground with various play structures, including a slide, swings, and climbing frames, surrounded by grass and trees.

14. River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (40 reviews)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveler
$206 nightly
The price is $217
Oct 22 - Oct 23
Total with taxes and fees
River Road Getaway
Two dogs sitting on a grassy field with a pond and trees in the background.

15. Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-RV spot #4
Viola
10.0 out of 10, Exceptional, (1 review)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
$70 nightly
The price is $74
Oct 19 - Oct 20
Total with taxes and fees
Blakley Hobbit Campground-RV spot #4
Two dogs sitting on a grassy field with a pond and trees in the background.

16. Blakley Hobbit Campground-RV spot #2

Blakley Hobbit Campground-RV spot #2
Viola
$70 nightly
The price is $74
Oct 19 - Oct 20
Total with taxes and fees
Blakley Hobbit Campground-RV spot #2
Two dogs sitting on a grassy field with a pond and trees in the background.

17. #9 Blakley Hobbit Campground-Tent spot

#9 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (1 review)
$40 nightly
The price is $42
Oct 19 - Oct 20
Total with taxes and fees
#9 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

18. Blakley Hobbit Campground-RV spot #1

Blakley Hobbit Campground-RV spot #1
Viola
9.0 out of 10, Wonderful, (4 reviews)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
$70 nightly
The price is $74
Oct 19 - Oct 20
Total with taxes and fees
Blakley Hobbit Campground-RV spot #1
Two dogs sitting on a grassy field with a pond and trees in the background.

19. #6 Blakley Hobbit Campground-Tent spot

#6 Blakley Hobbit Campground-Tent spot
Viola
$40 nightly
The price is $42
Oct 19 - Oct 20
Total with taxes and fees
#6 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

20. #3 Blakley Hobbit Campground-Tent spot

#3 Blakley Hobbit Campground-Tent spot
Viola
$40 nightly
The price is $42
Oct 19 - Oct 20
Total with taxes and fees
#3 Blakley Hobbit Campground-Tent spot
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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Top Montgomeryville Hotel Reviews

Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!

Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!

8/10 Good
"Ed was very knowledgeable and interesting. He gave us several great suggestions for places to visit and eat. He also offered us a tour of his property on his 4 wheeler, which was a lot of fun. I was able to feed the animals from the corn that grew on his property, too. Be sure to visit with him if you get the chance. The accommodations are part of Ed's house in the country. It's laid back and rural-not spotless but homey. :)"
Patricia 2-night trip
Posted 17 hours ago
Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!

Find out more about Montgomeryville

Everything you need to know about Montgomeryville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomeryville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montgomeryville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montgomeryville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montgomeryville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montgomeryville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $169 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montgomeryville rentals

At Expedia, we put the best Montgomeryville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montgomeryville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montgomeryville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montgomeryville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Upper Place Vacation Cottage: Visitors like this Montgomeryville vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

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 Viroqua Country Club and Tunnelville Cliffs State Natural Area.

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.