Dorchester Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Dorchester Vacation Homes

Our top choices for Dorchester vacation homes

Tiny House on Upper Iowa River w/ hot tub
Outdoor spa tub

Tiny House on Upper Iowa River w/ hot tub

8.6 out of 10, Excellent, (37)
"Great place, fully stocked and close proximity to river fun!! "
The price is CA $156
CA $315 total
includes taxes & fees
Aug 26 - Aug 27
Tiny House on Upper Iowa River w/ hot tub
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!
Property grounds

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

9.8 out of 10, Exceptional, (499)
"My best friend and I stayed in this cabin for a fun get together. We would highly recommend it! The hot tub was a plus and the area was very lush and well maintained. Our dogs also enjoyed their time getting to explore the area and having so much room in the yard. Thanks for a great stay! "
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!
The Hen House Retreat - A Comfortable Place to Roost
Exterior detail

The Hen House Retreat - A Comfortable Place to Roost

9.6 out of 10, Exceptional, (84)
"We enjoyed taking it easy watching some movies and crafting together for the weekend."
The price is CA $224
CA $275 total
includes taxes & fees
Aug 25 - Aug 26
The Hen House Retreat - A Comfortable Place to Roost
The Driftless Blue Villa | Hot Tub & Fireplace | Close to Downtown
Dining

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

10.0 out of 10, Exceptional, (11)
"We had a great time staying here, and the space was wonderful. The weather didn’t allow us to take full advantage of the hot tub, but it was great when we could get in there. We would definitely stay here again."
The price is CA $249
CA $344 total
includes taxes & fees
Sep 14 - Sep 15
The Driftless Blue Villa | Hot Tub & Fireplace | Close to Downtown
Secluded Home - Views of Mississippi River remote location 15 min from La Crosse
Beach towels

Secluded Home - Views of Mississippi River remote location 15 min from La Crosse

10.0 out of 10, Exceptional, (160)
"Truly enjoyed our time here- perfect gathering spot for family and friends. Clean, comfortable, and great location for day trips. Loved the upper level kitchen, pool, darts, game room! "
Secluded Home - Views of Mississippi River remote location 15 min from La Crosse
Cozy 4 bedroom relax atmosphere enjoy beauty of bluff country driftless region
Smart TV, DVD player, books

Cozy 4 bedroom relax atmosphere enjoy beauty of bluff country driftless region

9.6 out of 10, Exceptional, (27)
"This was the perfect place for a relaxing weekend away from the daily stresses of life."
Cozy 4 bedroom relax atmosphere enjoy beauty of bluff country driftless region
Farmhouse Within City Limits & Close to Luther College
Fridge, microwave, oven, stovetop

Farmhouse Within City Limits & Close to Luther College

10.0 out of 10, Exceptional, (60)
"Everything was very nice. The house is well maintained and very clean. The kitchen has everything we could want. The beds were comfortable. The location is very quiet. The yard is quite pleasant."
The price is CA $308
CA $528 total
includes taxes & fees
Aug 25 - Aug 26
Farmhouse Within City Limits & Close to Luther College
Country in the City | Massage Chair and Fireplace | Close to Downtown
Property grounds

Country in the City | Massage Chair and Fireplace | Close to Downtown

10.0 out of 10, Exceptional, (50)
"We really enjoyed our stay, especially the back yard and deck. Very quiet and comfortable. Loved the chickens!"
Country in the City | Massage Chair and Fireplace | Close to Downtown
Renovated charmer in the heart of Decorah’s Park District
Smart TV, fireplace

Renovated charmer in the heart of Decorah’s Park District

10.0 out of 10, Exceptional, (83)
"Great girls weekends!!!"
Renovated charmer in the heart of Decorah’s Park District
Nice Cape Cod home near the Mississippi River (Scenic River Inn)
Dining

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

9.8 out of 10, Exceptional, (129)
"I will stay there again"
Nice Cape Cod home near the Mississippi River (Scenic River Inn)
Scenic View Lodge- w/ hot tub & POOL
Outdoor spa tub

Scenic View Lodge- w/ hot tub & POOL

9.6 out of 10, Exceptional, (15)
"Perfect location right by the river, described exactly as it was, nice bedrooms plenty of space, the sectional was so comfy! The dining room table was nice and big for all of us. Enjoyed the hot tub! Would stay again!!!"
The price is CA $187
CA $460 total
includes taxes & fees
Sep 1 - Sep 2
Scenic View Lodge- w/ hot tub & POOL
Auggie's home in Mississippi
Interior

Auggie's home in Mississippi

10.0 out of 10, Exceptional, (62)
"Clean quiet place to stay with great view of Mississippi. Close to La Crosse for any needs. Will definitely stay again!"
Auggie's home in Mississippi
Room on the Ridge / HOT TUB / Sleeps 2
Outdoor spa tub

Room on the Ridge / HOT TUB / Sleeps 2

10.0 out of 10, Exceptional, (2)
"We had a relaxing time sitting by the fire pit and hot tub that overlooked the river and landscape. "
The price is CA $115
CA $215 total
includes taxes & fees
Sep 7 - Sep 8
Room on the Ridge / HOT TUB / Sleeps 2
Cozy Oak Street Cottage
Exterior

Cozy Oak Street Cottage

9.8 out of 10, Exceptional, (6)
"Great property and great hosts. Spotlessly clean and every amenity i could think of. Will definitely book again."
The price is CA $121
CA $234 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Oak Street Cottage
Large property close to the Mississippi River. Sleeps up to 12. Pet Friendly.
Smart TV, fireplace, books

Large property close to the Mississippi River. Sleeps up to 12. Pet Friendly.

9.8 out of 10, Exceptional, (25)
"Great location and spacious house. Really enjoyed our stay. Easy access in and out. Highly recommend! "
Large property close to the Mississippi River. Sleeps up to 12. Pet Friendly.
Indoor Fish Cleaning - Darts - Poker - Newly Remodeled
Smart TV, video games, stereo

Indoor Fish Cleaning - Darts - Poker - Newly Remodeled

9.8 out of 10, Exceptional, (10)
"Very good property with amazing location and amenities "
Indoor Fish Cleaning - Darts - Poker - Newly Remodeled
Charming House with Amazing Views! Next to Marina and Tiki Bar
Interior

Charming House with Amazing Views! Next to Marina and Tiki Bar

9.8 out of 10, Exceptional, (23)
"Great place to stay!"
Charming House with Amazing Views! Next to Marina and Tiki Bar
Eagles Landing Sleeps 10 HOT TUB
Outdoor spa tub

Eagles Landing Sleeps 10 HOT TUB

10.0 out of 10, Exceptional, (14)
"This house was exactly what we wanted again as all 10 of our family were able to attend with three adult couples and four adult grandsons. It made a great place for another memorable family celebration!"
Eagles Landing Sleeps 10 HOT TUB
House near Trout Run Trail w/EV charger
Fridge, microwave, oven, stovetop

House near Trout Run Trail w/EV charger

10.0 out of 10, Exceptional, (30)
"As described, close to downtown and a lot of other attractions. Would recommend staying here "
The price is CA $249
CA $475 total
includes taxes & fees
Sep 7 - Sep 8
House near Trout Run Trail w/EV charger
Majestic View Sleeps 8-HOT TUB
Fridge, microwave, oven, stovetop

Majestic View Sleeps 8-HOT TUB

10.0 out of 10, Exceptional, (42)
"We greatly enjoyed our stay. The view is simply amazing! We saw eagles, cardinals, blue jays, buzzards, robins, squirrels, rabbits and more. Everything you need is included inside this four bedroom home. Enjoy!! "
Majestic View Sleeps 8-HOT TUB
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
Sign in
Sign up, it's free

Top Dorchester Hotel Reviews

Sportsmen Motel

Sportsmen Motel

10/10 Excellent
"This is, indeed, a motel for sportsmen. Our room had a backwoods theme, but was also prepped for folks coming in from a day in the backwoods. I think it’s being upgraded room by room (lots of building supplies blocking a couple of rooms), and kudos to whoever is taking in what seems to be a labor of love. The motel is not actually in Dorchester- don’t let Google misdirect you- and is quite isolated, so bring your own breakfast. But it’s also in the heart of the Driftless, which is a wonderful place to visit. "
Karen 2-night trip
Posted 18 hours ago
Sportsmen Motel