Dorchester Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Dorchester

Outdoor spa tub
Lazy River Cabin

Lazy River Cabin

Dorchester
8.8 out of 10, Excellent, (52)
"10/10 recommend this house, great space. Very clean. Good parking. "
United States
Madison S.
The price is HK$739
HK$1,761 total
includes taxes & fees
4 Jan - 5 Jan 2026
Lazy River Cabin
Outdoor spa tub
Tiny House on Upper Iowa River w/ hot tub

Tiny House on Upper Iowa River w/ hot tub

dorchester
8.8 out of 10, Excellent, (45)
"Great place. Loved sitting in hot tub watching the river at sunset. "
United States
Jim C.
The price is HK$630
HK$1,456 total
includes taxes & fees
8 Dec - 9 Dec
Tiny House on Upper Iowa River w/ hot tub
Outdoor spa tub
Hunters Hollow Lodge W/ Outdoor Hot Tub & New Swimming Pool

Hunters Hollow Lodge W/ Outdoor Hot Tub & New Swimming Pool

Dorchester
10.0 out of 10, Exceptional, (5)
"Clean spacious and good vibes "
United States
Gunner
Hunters Hollow Lodge W/ Outdoor Hot Tub & New Swimming Pool
Property grounds
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!

Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!

Ferryville
9.8 out of 10, Exceptional, (514)
"Fun spot to stay - hot tub and screened porch is great. "
United States
Anthony S.
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!
Outdoor spa tub
Wexford Hollow... 6 Bedroom Cabin W/Pool & Hot Tub

Wexford Hollow... 6 Bedroom Cabin W/Pool & Hot Tub

Lansing
8.6 out of 10, Excellent, (8)
"We really enjoyed our stay and had a great time. We enjoyed the peace and quiet. And having a pool is always great. "
United States
Tammy W.
The price is HK$739
HK$2,397 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wexford Hollow... 6 Bedroom Cabin W/Pool & Hot Tub
Interior
Walnut Ridge Cabin 2 Bedrooms and Hot Tub Jacuzzi

Walnut Ridge Cabin 2 Bedrooms and Hot Tub Jacuzzi

Waterville
8.6 out of 10, Excellent, (4)
"Beautiful cabin! We had so much fun ! "
United States
Erika M.
The price is HK$739
HK$1,857 total
includes taxes & fees
4 Jan - 5 Jan 2026
Walnut Ridge Cabin 2 Bedrooms and Hot Tub Jacuzzi
Interior
Romantic Cabin: Secluded Woods, Hot Tub, and Privacy in the Driftless Region.

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

Ferryville
9.8 out of 10, Exceptional, (48)
"Check in was easy, host followed through on firewood order, plenty of amenities were present."
United States
Emily H.
Romantic Cabin: Secluded Woods, Hot Tub, and Privacy in the Driftless Region.
Exterior
Rustic Hideaway Sleeps 4 HOT TUB

Rustic Hideaway Sleeps 4 HOT TUB

De Soto
10.0 out of 10, Exceptional, (35)
"It was a wonderful escape for celebrating 2 anniversaries! "
United States
Ashley U.
The price is HK$1,829
HK$3,351 total
includes taxes & fees
8 Dec - 9 Dec
Rustic Hideaway Sleeps 4 HOT TUB
Fridge, microwave, oven, stovetop
Secluded Rustic + Modern Log Cabin with hot tub by Stream, luxury getaway

Secluded Rustic + Modern Log Cabin with hot tub by Stream, luxury getaway

Ferryville
10.0 out of 10, Exceptional, (133)
"Overall it’s a nice little cabin away from everybody, which is truly nice. The hot tub is a huge plus! And the WIFI was really nice too! We had a great time on our romantic getaway "
United States
Jesse K.
Secluded Rustic + Modern Log Cabin with hot tub by Stream, luxury getaway
Outdoor pool
Log Cabin/ w hot tub, outdoor pool & pool table

Log Cabin/ w hot tub, outdoor pool & pool table

Lansing
9.8 out of 10, Exceptional, (58)
"Super enjoyed our time away here. "
United States
Erik B.
The price is HK$665
HK$1,800 total
includes taxes & fees
10 Dec - 11 Dec
Log Cabin/ w hot tub, outdoor pool & pool table
Exterior
The Sun Set River View, Luxury, private, amazing views of River with Hot Tub

The Sun Set River View, Luxury, private, amazing views of River with Hot Tub

Ferryville
10.0 out of 10, Exceptional, (129)
"We had a great time and the place was awesome!!"
United States
Oswaldo P.
The Sun Set River View, Luxury, private, amazing views of River with Hot Tub
Terrace/patio
Relax Amidst Nature On Clear Creek

Relax Amidst Nature On Clear Creek

New Albin
9.6 out of 10, Exceptional, (164)
"The location is great for those that want seclusion. The cabin is very well kept and has plenty of space/beds for guests"
United States
Bridgette J.
Relax Amidst Nature On Clear Creek
Outdoor spa tub
Eagles Nest- River View Cabin

Eagles Nest- River View Cabin

2.0 star property
De Soto
8.0 out of 10, Very good, (13)
"Great Cabin with a view of the Mighty Mississippi. Quiet and secluded enough but within driving distance of Viroqua"
United States
Donna E.
The price is HK$876
HK$1,926 total
includes taxes & fees
7 Dec - 8 Dec
Eagles Nest- River View Cabin
Interior
Spacious 2-bedroom loft above the International Owl Center in Houston, MN

Spacious 2-bedroom loft above the International Owl Center in Houston, MN

2.0 star property
Houston
10.0 out of 10, Exceptional, (15)
"Beautiful property for a stay. This property was spacious, clean and so beautifully decorated. Our only regret is that we weren’t staying longer."
United States
Heidi
The price is HK$1,938
HK$2,371 total
includes taxes & fees
7 Dec - 8 Dec
Spacious 2-bedroom loft above the International Owl Center in Houston, MN
Interior
The Nest: Beautiful Apartment Style Lodging In The Heart Of Downtown Decorah.

The Nest: Beautiful Apartment Style Lodging In The Heart Of Downtown Decorah.

Decorah
9.6 out of 10, Exceptional, (167)
"This is a nice little apartment in downtown. Great location to enjoy a walk through town and Saturday morning Farmers Market. "
United States
SALLY S.
The price is HK$736
HK$1,443 total
includes taxes & fees
15 Dec - 16 Dec
The Nest: Beautiful Apartment Style Lodging In The Heart Of Downtown Decorah.
3 bedrooms, desk, free WiFi, bed sheets
Cozy Ridge Retreat

Cozy Ridge Retreat

De Soto
9.6 out of 10, Exceptional, (32)
"Great place to kick back and unwind. The cabin was clean, and Michael was a great host, he was quick to respond to any questions we had. The view was absolutely amazing, and we were able to enjoy some wild life, deer, grouse and even a wood chuck! Would definitely recommend the cabin for a great get away."
United States
leanne J.
Cozy Ridge Retreat
Outdoor spa tub
Beaver Cabin

Beaver Cabin

Lansing
9.0 out of 10, Wonderful, (29)
"Was a very nice place to stay for the night.The kids had fun"
United States
Joe G.
The price is HK$662
HK$1,587 total
includes taxes & fees
18 Dec - 19 Dec
Beaver Cabin
Marina
Cozy cabin in adorable Genoa with AC, WiFi pet friendly and close the river.

Cozy cabin in adorable Genoa with AC, WiFi pet friendly and close the river.

2.0 star property
Genoa
9.8 out of 10, Exceptional, (18)
"Great place to stay.Host's are great people."
United States
gary w.
Cozy cabin in adorable Genoa with AC, WiFi pet friendly and close the river.
Dining
The Driftless Blue Villa | Hot Tub & Fireplace | Close to Downtown

The Driftless Blue Villa | Hot Tub & Fireplace | Close to Downtown

Decorah
10.0 out of 10, Exceptional, (15)
"This little Villa was perfect and close to all the fun things to do in Decorah. I would absolutely stay here again. "
United States
Jenna C.
The price is HK$1,160
HK$1,807 total
includes taxes & fees
9 Dec - 10 Dec
The Driftless Blue Villa | Hot Tub & Fireplace | Close to Downtown
Outdoor spa tub
Scenic View Lodge- w/ hot tub & POOL

Scenic View Lodge- w/ hot tub & POOL

Lansing
9.6 out of 10, Exceptional, (17)
"There was plenty of room for all 14 of us. Everyone enjoyed the pool and hot tub. Enjoyed exploring the town and around the area. Would definitely stay again."
United States
L P.
The price is HK$694
HK$2,137 total
includes taxes & fees
17 Dec - 18 Dec
Scenic View Lodge- w/ hot tub & POOL
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 Dorchester Hotel Reviews

Hotel Winneshiek

Hotel Winneshiek

10/10 Excellent
"Cool property. Hotel is very clean and staff is helpful. Rooms are nice. Breakfast was good and had decent options. "
Shawn 3-night trip
Posted 17 hours ago
Hotel Winneshiek

Find out more about Dorchester

Search for holiday rentals in Dorchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Dorchester using one of the methods below:

  • View our selection of featured holiday rentals in Dorchester
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Look no further and take a look at our great range of rental properties in Dorchester!

Frequently asked questions

Can I find a holiday rental in Dorchester?

Yes, there are holiday rentals close to the most popular sights in Dorchester, 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 Dorchester has to offer?

Tiny House on Upper Iowa River w/ hot tub: This highly rated holiday home rental in Dorchester offers 1 hot tub, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What’s there to see and do in Dorchester?

While exploring the area, visit family-friendly sights like Agora, or get outside and enjoy nature at Mount Hosmer Park. Beaver Creek Valley State Park and Seed Savers Exchange Heritage Farm are a couple of places you'll find in the wider area.

What’s a holiday rental in Dorchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Dorchester. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family trips.