Sullivan Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Sullivan vacation rentals

A Staybridge Suites hotel with a brick facade, a central entrance with a covered porch, and a flagpole with an American flag.

1. Spacious Accessible Studio w/ Walk-In Shower

Spacious Accessible Studio w/ Walk-In Shower
Oconomowoc
The price is CA $176
CA $217 total
includes taxes & fees
Nov 30 - Dec 1
Spacious Accessible Studio w/ Walk-In Shower
A two-story building with a balcony and outdoor seating area.

2. Historic Downtown Luxury-Lake-Coffee-Spa like BA

Historic Downtown Luxury-Lake-Coffee-Spa like BA
Delafield
9.6 out of 10, Exceptional, (10 reviews)
"Loved the location and it was just the perfect size for the two of us. Will definitely stay here again when we are in Delafield. "
United States
Becky M.
The price is CA $214
CA $350 total
includes taxes & fees
Nov 12 - Nov 13
Historic Downtown Luxury-Lake-Coffee-Spa like BA
A residential backyard with a fire pit, outdoor seating, and string lights.

3. Sytlish Retreat Near Wedding Venues & Downtown

Sytlish Retreat Near Wedding Venues & Downtown
Oconomowoc
10.0 out of 10, Exceptional, (31 reviews)
"Nicely remodeled home that was perfect for our trip to Oconomowoc"
United States
Carl G.
The price is CA $345
CA $770 total
includes taxes & fees
Nov 7 - Nov 8
Sytlish Retreat Near Wedding Venues & Downtown
A hot tub under a covered area with a wooden roof, surrounded by a white fence, trees, and a clear sky.

4. Private Hot Tub • Bright Home Near Downtown

Private Hot Tub • Bright Home Near Downtown
Oconomowoc
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was wonderful. Our host was very responsive to questions, and the home was welcoming and had all needed amenities. "
United States
Heather F.
The price is CA $262
CA $468 total
includes taxes & fees
Nov 15 - Nov 16
Private Hot Tub • Bright Home Near Downtown
A Staybridge Suites hotel with a brick facade, a central entrance with a covered porch, and a flagpole with an American flag.

5. Queen Studio Suite w/ Kitchenette in Oconomowoc

Queen Studio Suite w/ Kitchenette in Oconomowoc
Oconomowoc
The price is CA $176
CA $217 total
includes taxes & fees
Nov 30 - Dec 1
Queen Studio Suite w/ Kitchenette in Oconomowoc
A cozy room with a wooden ceiling, a black sofa with colorful cushions, a round coffee table with flowers, and a black chair.

6. Historic Downtown- King Bed-St Johns Acad-Shopping

Historic Downtown- King Bed-St Johns Acad-Shopping
Delafield
9.8 out of 10, Exceptional, (14 reviews)
"This is an incredible hidden gem in Delafield. Loved every minute of our stay!"
United States
Holly L.
The price is CA $274
CA $439 total
includes taxes & fees
Nov 12 - Nov 13
Historic Downtown- King Bed-St Johns Acad-Shopping
A Staybridge Suites hotel with a brick facade, a central entrance with a covered porch, and a flagpole with an American flag.

7. Accessible 1-BR Queen Suite w/ Roll-In Shower

Accessible 1-BR Queen Suite w/ Roll-In Shower
Oconomowoc
The price is CA $208
CA $255 total
includes taxes & fees
Nov 30 - Dec 1
Accessible 1-BR Queen Suite w/ Roll-In Shower
A Staybridge Suites hotel with a brick facade, a central entrance with a covered porch, and a flagpole with an American flag.

8. Accessible 1-BR Suite w/ Two Double Beds

Accessible 1-BR Suite w/ Two Double Beds
Oconomowoc
The price is CA $208
CA $255 total
includes taxes & fees
Nov 30 - Dec 1
Accessible 1-BR Suite w/ Two Double Beds
A Staybridge Suites hotel with a brick facade, a central entrance with a covered porch, and a flagpole with an American flag.

9. Accessible 1BR Suite | Pool & Daily Breakfast

Accessible 1BR Suite | Pool & Daily Breakfast
Oconomowoc
The price is CA $208
CA $254 total
includes taxes & fees
Nov 30 - Dec 1
Accessible 1BR Suite | Pool & Daily Breakfast
Exterior

10. Relax & Reboot in this Charming 2-Bedroom Townhome

Relax & Reboot in this Charming 2-Bedroom Townhome
Ixonia
9.2 out of 10, Wonderful, (7 reviews)
"The house worked out just perfect for us! The surrounding grounds are beautiful also. A’Lisa was a very nice host and very easy to get into contact with. We will definitely be back!"
United States
Jon S.
The price is CA $433
CA $540 total
includes taxes & fees
Nov 6 - Nov 7
Relax & Reboot in this Charming 2-Bedroom Townhome
A Staybridge Suites hotel with a brick facade, a central entrance with a covered porch, and a flagpole with an American flag.

11. 2-BR Suite w/ King & Double Beds + Kitchen

2-BR Suite w/ King & Double Beds + Kitchen
Oconomowoc
10.0 out of 10, Exceptional, (1 review)
"The two bedroom suite was perfect! The room was spotless and the furnishings were comfortable. They had breakfast and a social hour in the evening. It was very nice. We didn’t use the pool and it was great. Would definitely stay here again."
United States
Sharon J.
The price is CA $340
CA $417 total
includes taxes & fees
Nov 30 - Dec 1
2-BR Suite w/ King & Double Beds + Kitchen
A modern kitchen with a stainless steel refrigerator, a black stove, and wooden flooring.

12. 3BR Home Near Hahns Lake – Newly Updated Kitchen

3BR Home Near Hahns Lake – Newly Updated Kitchen
Johnson Creek
10.0 out of 10, Exceptional, (1 review)
"House is great. Host was excellent when responding to any questions. FYI the bedrooms and bathroom were upstairs. Enjoy our time very much."
United States
D M.
The price is CA $228
CA $466 total
includes taxes & fees
Nov 9 - Nov 10
3BR Home Near Hahns Lake – Newly Updated Kitchen
A Staybridge Suites hotel with a brick facade, a central entrance with a covered porch, and a flagpole with an American flag.

13. Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast

Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast
Oconomowoc
10.0 out of 10, Exceptional, (1 review)
"."
United States
Rhonda M.
The price is CA $340
CA $417 total
includes taxes & fees
Nov 30 - Dec 1
Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast
A bedroom with a large bed, a desk, and a chair. There are windows with curtains, a hanging light fixture, and a framed picture on the wall.

14. Historic Downtown-Old World Charm-Dining-Coffee

Historic Downtown-Old World Charm-Dining-Coffee
Delafield
9.8 out of 10, Exceptional, (10 reviews)
"Great place to rest and relax on a fun weekend getaway. "
United States
Jeffrey C.
The price is CA $243
CA $400 total
includes taxes & fees
Nov 12 - Nov 13
Historic Downtown-Old World Charm-Dining-Coffee
A Staybridge Suites hotel with a brick facade, a central entrance with a covered porch, and a flagpole with an American flag.

15. Accessible 2-BR Suite w/ Tub & 2 Bathrooms

Accessible 2-BR Suite w/ Tub & 2 Bathrooms
Oconomowoc
The price is CA $339
CA $403 total
includes taxes & fees
Nov 30 - Dec 1
Accessible 2-BR Suite w/ Tub & 2 Bathrooms
A modern kitchen with a large island, stainless steel sink, and pendant lights.

16. Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Waukesha
9.8 out of 10, Exceptional, (43 reviews)
"Great place and very clean"
United States
Jason d.
The price is CA $233
CA $502 total
includes taxes & fees
Nov 8 - Nov 9
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
A log cabin with a stone foundation, a large garage, and a well-maintained lawn.

17. Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub

Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub
Pewaukee
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful place to stay nice and peaceful"
United States
Danny H.
The price is CA $1,507
CA $1,862 total
includes taxes & fees
Nov 16 - Nov 17
Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub
A two-story house with a front porch, a chimney, and a garage.

18. 4 bedroom house 7 min.to Erin Hills SAND VALLEY GOLF COURSE HOLY HILL WHISTLING

4 bedroom house 7 min.to Erin Hills SAND VALLEY GOLF COURSE HOLY HILL WHISTLING
Hartford
The price is CA $1,132
CA $1,697 total
includes taxes & fees
Nov 12 - Nov 13
4 bedroom house 7 min.to Erin Hills SAND VALLEY GOLF COURSE HOLY HILL WHISTLING
A spacious living area with a high ceiling, wooden beams, and large windows.

19. Dome House on Whitewater Lake

Dome House on Whitewater Lake
Whitewater
10.0 out of 10, Exceptional, (3 reviews)
"Very quiet, clean and lots of amenities! We had a hiccup with the water/shower, and our host not only communicated quickly but had a plumber over to fix it before the day was over!! She went above and beyond to make our stay comfortable!! A very enjoyable stay!"
United States
Rachel
The price is CA $280
CA $689 total
includes taxes & fees
Nov 12 - Nov 13
Dome House on Whitewater Lake
A wooden deck with a glass railing overlooking a snowy landscape with trees.

20. Eclectic Hubertus Home w/ Game Room & Fire Pit!

Eclectic Hubertus Home w/ Game Room & Fire Pit!
3.0 star property
Hubertus
The price is CA $467
CA $1,078 total
includes taxes & fees
Nov 16 - Nov 17
Eclectic Hubertus Home w/ Game Room & Fire Pit!
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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
apart-hotel image
Aparthotels
Aparthotels

Top Sullivan Hotel Reviews

A Staybridge Suites hotel with a prominent entrance, flagpoles, and a well-lit facade.
Staybridge Suites Milwaukee West-Oconomowoc by IHG

Staybridge Suites Milwaukee West-Oconomowoc by IHG

Staybridge Suites Milwaukee West-Oconomowoc by IHG
Oconomowoc

10/10 Excellent

Great stay
Canada
Craig
Reviewed June 9, 2025
Staybridge Suites Milwaukee West-Oconomowoc by IHG

Find out more about Sullivan

Everything you need to know about Sullivan 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 Sullivan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Sullivan vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sullivan vacation rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sullivan vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sullivan vacation rentals we have selected for you start as low as CA $175 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sullivan rentals

At Expedia, we put the best Sullivan 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 Sullivan 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 Sullivan 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 Sullivan. 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

Can I find vacation rentals in Sullivan?

Yes, we give you a choice of vacation rentals close to top points of interest in Sullivan, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Sullivan?

Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!: Visitors like this Sullivan vacation home rental. It is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Sullivan?

Explore the area and family-friendly sights such as Fowler Lake Park, or get out into nature at a spot like Lac La Belle. In the larger area, you’ll find Hawks Inn and Johnson Creek Premium Outlets.

What are vacation rentals like in Sullivan?

Vacation rentals are privately owned accommodations you can stay in for a short or long stay in Sullivan. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.