Ashippun Holiday Rentals
House
10.0Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
6 Guests
760 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $315/Night
7 Nights - US $2,207
House
10.0Exceptional
(1 Review)
3 Bedrooms
4 Baths
12 Guests
3831.95 ft²
- Fireplace/Heating
Pet Friendly
Parking
Internet
US $383/Night
7 Nights - US $2,681
Bed & Breakfast
- Fort Atkinson
- ·
- Watertown
- 0.45 mi to center
9.8Exceptional
(83 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Air Conditioner- Internet
US $117/Night
7 Nights - US $822
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Air Conditioner
US $396/Night
7 Nights - US $2,775
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
8 Guests
796.53 ft²
- Fireplace/Heating
- Parking
- Internet
Child Friendly
US $267/Night
7 Nights - US $1,871
Apartment
9.8Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
8 Guests
800 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $284/Night
7 Nights - US $1,991
Apartment
9.8Exceptional
(6 Reviews)
1 Bedroom
1 Bath
6 Guests
750 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
View
US $190/Night
7 Nights - US $1,331
House
- Milwaukee
- ·
- Peninsular Park
- 0.07 mi to center
9.6Exceptional
(30 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $634/Night
7 Nights - US $4,438
Apartment
9.6Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $362/Night
7 Nights - US $2,537
Luxury Holiday Rentals in Ashippun
Over 157+ Luxury Holiday Rentals in or Near Ashippun
House
- Milwaukee
- ·
- Oconomowoc
- 2.78 mi to center
10.0Exceptional
(3 Reviews)
8 Bedrooms
5 Baths
15 Guests
10700 ft²
Private Pool- Oceanfront
Hot Tub- Fireplace/Heating
US $3,736/Night
7 Nights - US $26,154
House
- Milwaukee
- ·
- Oconomowoc Lake
- 0.84 mi to center
10.0Exceptional
(8 Reviews)
5 Bedrooms
5 Baths
13 Guests
8100 ft²
- Hot Tub
Spa- Fireplace/Heating
- Balcony/Terrace
US $3,203/Night
7 Nights - US $22,418
House
- Milwaukee
- ·
- Oconomowoc
- 3.12 mi to center
9.6Exceptional
(36 Reviews)
8 Bedrooms
8 Baths
20 Guests
10500 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $2,579/Night
7 Nights - US $18,051
House
- Milwaukee
- ·
- Oconomowoc
- 2.69 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
3200 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $2,554/Night
7 Nights - US $17,876
New
House
- Milwaukee
- ·
- Oconomowoc
- 3.84 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $2,279/Night
7 Nights - US $15,950
House
- Milwaukee
- ·
- Oconomowoc
- 1.91 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
4800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,937/Night
7 Nights - US $13,559
House
10.0Exceptional
(29 Reviews)
5 Bedrooms
4 Baths
12 Guests
3800 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Ocean View
US $1,815/Night
7 Nights - US $12,702
House
10.0Exceptional
(9 Reviews)
4 Bedrooms
3 Baths
8 Guests
3600 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,298/Night
7 Nights - US $9,083
House
10.0Exceptional
(18 Reviews)
4 Bedrooms
2 Baths
8 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,240/Night
7 Nights - US $8,680
Top-Rated Holiday Rentals with a Pool in Ashippun
Over 35+ The Best Private Villas and Holiday Rentals in Ashippun with a Pool
Other
10.0Exceptional
(45 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
US $304/Night
7 Nights - US $2,125
Apartment
- Milwaukee
- ·
- Oconomowoc
- 2.47 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Pool
- Breakfast
- Parking
US $205/Night
7 Nights - US $1,432
Apartment
- Milwaukee
- ·
- Oconomowoc
- 2.42 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
- Hot Tub
- Pool
- Breakfast
- Parking
US $201/Night
7 Nights - US $1,408
House
- Milwaukee
- ·
- Oconomowoc
- 1.29 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $146/Night
7 Nights - US $1,020
Hotel
- Milwaukee
- ·
- Oconomowoc
- 2.64 mi to center
9.2Exceptional
(863 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $125/Night
7 Nights - US $878
Hotel
- Milwaukee
- ·
- Summit Corners
- 0.19 mi to center
9.2Exceptional
(171 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Parking
US $131/Night
7 Nights - US $918
Hotel
- Milwaukee
- ·
- Summit Corners
- 0.26 mi to center
9.0Exceptional
(675 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
US $120/Night
7 Nights - US $837
Hotel
- Fort Atkinson
- ·
- Watertown
- 2.03 mi to center
9.0Exceptional
(576 Reviews)
1 Bath
- Hot Tub
- Pool
- Breakfast
- Kitchen
US $109/Night
7 Nights - US $762
Hotel
8.8Fabulous
(431 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $191/Night
7 Nights - US $1,339
Pet-Friendly Holiday Rentals in Ashippun
Over 44+ Pet-Friendly Holiday Rentals in or Near Ashippun
House
10.0Exceptional
(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $220/Night
7 Nights - US $1,539
House
9.8Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1905.21 ft²
- Spa
- Fireplace/Heating
- Pet Friendly
- Parking
US $287/Night
7 Nights - US $2,009
House
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $353/Night
7 Nights - US $2,472
Apartment
9.3Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
8 Guests
1194.79 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $150/Night
7 Nights - US $1,050
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $248/Night
7 Nights - US $1,733
Cabin
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $239/Night
7 Nights - US $1,670
House
- Milwaukee
- ·
- Oconomowoc
- 2.49 mi to center
10.0Exceptional
(25 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $692/Night
7 Nights - US $4,844
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
1 Bath
8 Guests
1250 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $275/Night
7 Nights - US $1,926
House
- Milwaukee
- ·
- Oconomowoc
- 3.61 mi to center
9.6Exceptional
(102 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $381/Night
7 Nights - US $2,664
Large Holiday Rentals and Private Villas in Ashippun
Over 34+ Large Holiday Rentals and Private Villas in or Near Ashippun
House
- Milwaukee
- ·
- Oconomowoc
- 2.25 mi to center
10.0Exceptional
(127 Reviews)
4 Bedrooms
3 Baths
13 Guests
2500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $578/Night
7 Nights - US $4,043
House
9.8Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
10 Guests
2002.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $360/Night
7 Nights - US $2,520
House
10.0Exceptional
(101 Reviews)
5 Bedrooms
3 Baths
13 Guests
4140 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $939/Night
7 Nights - US $6,572
House
8.6Fabulous
(5 Reviews)
8 Bedrooms
7 Baths
25 Guests
788.45 ft²
- Fireplace/Heating
- View
- Breakfast
- Parking
US $98/Night
7 Nights - US $686
House
- Milwaukee
- ·
- Oconomowoc
- 2.04 mi to center
10.0Exceptional
(41 Reviews)
4 Bedrooms
3 Baths
10 Guests
3500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $836/Night
7 Nights - US $5,853
House
10.0Exceptional
(9 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $669/Night
7 Nights - US $4,683
House
9.8Exceptional
(45 Reviews)
3 Bedrooms
2 Baths
100 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $352/Night
7 Nights - US $2,461
House
9.6Exceptional
(15 Reviews)
5 Bedrooms
2 Baths
16 Guests
3300 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,089/Night
7 Nights - US $7,626
House
- Milwaukee
- ·
- Okauchee Lake
- 1.01 mi to center
9.4Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
10 Guests
2500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,137/Night
7 Nights - US $7,956
Wheelchair Accessible Holiday Homes in Ashippun
Over 13+ Wheelchair Accessible Holiday Homes in or Near Ashippun
Condo
4.0Average
(1 Review)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $150/Night
7 Nights - US $1,049
Hotel
- Milwaukee
- ·
- Oconomowoc
- 2.67 mi to center
8.8Fabulous
(151 Reviews)
10 Baths
544.65 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $172/Night
7 Nights - US $1,206
Hotel
9.6Exceptional
(465 Reviews)
1 Bath
- Kitchen
- Parking
- Air Conditioner
- Internet
US $293/Night
7 Nights - US $2,049
Condo
- Milwaukee
- ·
- Oconomowoc
- 2.72 mi to center
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $261/Night
7 Nights - US $1,826
Hotel
- Milwaukee
- ·
- Summit Corners
- 0.23 mi to center
8.8Fabulous
(98 Reviews)
1 Bath
340.86 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $219/Night
7 Nights - US $1,531
Condo
- Milwaukee
- ·
- Oconomowoc
- 2.61 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $208/Night
7 Nights - US $1,456
Hotel
- Milwaukee
- ·
- Summit Corners
- 0.19 mi to center
8.8Fabulous
(42 Reviews)
1 Bath
520.25 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $251/Night
7 Nights - US $1,759
Hotel
8.7Fabulous
(16 Reviews)
5 Baths
738.4 ft²
- Fireplace/Heating
- Breakfast
- Pet Friendly
- Parking
US $179/Night
7 Nights - US $1,253
Hotel
- Fort Atkinson
- ·
- Watertown
- 2.08 mi to center
8.6Fabulous
(115 Reviews)
1 Bath
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $96/Night
7 Nights - US $671
Ashippun Private Villas and Holiday Homes Under $200
Over 20+ Ashippun Private Villas and Holiday Homes Under $200
Apartment
- Milwaukee
- ·
- Oconomowoc
- 2.80 mi to center
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Pool
- Breakfast
- Kitchen
US $199/Night
7 Nights - US $1,395
Bed & Breakfast
- Fort Atkinson
- ·
- Watertown
- 0.63 mi to center
8.0Excellent
(45 Reviews)
2 Bedrooms
2 Baths
4 Guests
345.03 ft²
- Parking
- Air Conditioner
- Internet
US $95/Night
7 Nights - US $665
Hotel
8.2Excellent
(552 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $100/Night
7 Nights - US $702
Apartment
- Milwaukee
- ·
- Oconomowoc
- 2.83 mi to center
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Pool
- Breakfast
- Kitchen
US $140/Night
7 Nights - US $980
Hotel
7.6Very Good
(133 Reviews)
9 Baths
382.72 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $134/Night
7 Nights - US $939
Condo
- Fort Atkinson
- ·
- Watertown
- 2.03 mi to center
10.0Exceptional
(37 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $187/Night
7 Nights - US $1,311
House
- Fort Atkinson
- ·
- Watertown
- 0.47 mi to center
9.8Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $188/Night
7 Nights - US $1,319
House
- Fort Atkinson
- ·
- Watertown
- 3.08 mi to center
9.8Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $197/Night
7 Nights - US $1,381
Condo
- Milwaukee
- ·
- Oconomowoc
- 1.08 mi to center
9.4Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
6 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $166/Night
7 Nights - US $1,162
Instantly Bookable Holiday Homes in Ashippun
Over 66+ Instantly Bookable Holiday Homes in or Near Ashippun
Apartment
9.6Exceptional
(7 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $423/Night
7 Nights - US $2,964
Cabin
7.8Very Good
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $371/Night
7 Nights - US $2,595
House
1 Bedroom
1 Bath
4 Guests
620 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $270/Night
7 Nights - US $1,887
Apartment
- Milwaukee
- ·
- Oconomowoc
- 2.37 mi to center
2 Bedrooms
1 Bath
8 Guests
- Hot Tub
- Pool
- Breakfast
- Parking
US $354/Night
7 Nights - US $2,481
Apartment
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Pool
- Breakfast
- Parking
US $252/Night
7 Nights - US $1,764
Apartment
- Milwaukee
- ·
- Oconomowoc
- 2.87 mi to center
1 Bedroom
1 Bath
6 Guests
- Hot Tub
- Pool
- Breakfast
- Parking
US $204/Night
7 Nights - US $1,429
Apartment
- Milwaukee
- ·
- Oconomowoc
- 2.71 mi to center
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Pool
- Breakfast
- Kitchen
US $202/Night
7 Nights - US $1,417
Apartment
- Milwaukee
- ·
- Oconomowoc
- 2.67 mi to center
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Pool
- Breakfast
- Kitchen
US $202/Night
7 Nights - US $1,417
House
10.0Exceptional
(88 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $232/Night
7 Nights - US $1,622
Book a Last Minute Place to Stay in Ashippun
About Casai's Private Villas and Holiday Rentals in Ashippun
Discover more than 166 vacation rentals available in Ashippun. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Ashippun.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Ashippun, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Ashippun. On average, places to stay near Ashippun offer 1078.38 ft², with nightly prices averaging US $633.
With Casai, finding and comparing holiday rentals in Ashippun is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Ashippun
| Type | Count |
|---|---|
| Vacation Homes | 95 |
| Holiday Apartments | 29 |
| Cottages | 2 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Ashippun
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Ashippun.
Weather in Ashippun, WI
View the weather forecast for Ashippun before booking your Ashippun Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Ashippun, WI
Casai offers a large selection of top attractions around Ashippun . Research things to do on your vacation before you visit Ashippun.
Frequently Asked Questions About Ashippun?
What are the top holiday rentals in Ashippun?
With numerous options available in Ashippun, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Ashippun:
- Sunsets on the lake at Mill Pond Cottage-Pickleball, Water Sports, Hiking &more
- Victorian Lake Home
- Spacious Lake House with Beautiful Views and 123 Feet of Swimming Frontage
- Nagawicka Woods-Beautiful Lake Country Ranch Home
- Pet-friendly, Kid-friendly Farmhouse near Holy Hill, Ice Age Trail, State Forest
- Piper's Retreat: 4 bed, 2.5 bath by Erin Hills Golf, Glacier Hills, Holy Hill
- Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
- Charming Historic Upper Walk to Downtown, Festivals & Beach
- Rock River Haven - charming, spacious, peaceful
- One-of-a-kind Blue Tree House Retreat Holy Hill Getaway Hiking Trails
How many holiday rentals have private pools in Ashippun?
Discover a selection of holiday rentals with private pools near Ashippun with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Lakefront/Pool home - Grown-up Summer Camp, 30 minutes from RNC
- Cobblestone Hotel & Suites Hartford
- Super 8 by Wyndham Watertown WI
Which holiday homes in Ashippun are best for families?
If you're searching for a family-friendly holiday home in Ashippun, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Ashippun:
- Charming Historic Upper Walk to Downtown, Festivals & Beach
- Lakefront Wisconsin Escape w/Boat Dock & Kayaks!
- Mon Bijou
How many Casai.com holiday rentals are available in Ashippun?
As of 2026, Casai boasts over 166 properties listed in the Ashippun area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Ashippun.
People Also Ask
Finding the best prices in Ashippun
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