Cromwell Holiday Rentals

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Holiday Rentals in Cromwell

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

10.0 out of 10, Exceptional, (24)
"House and property had more than enough activities to keep up completely entertained for our entire stay. Loved the game room, pickleball court, hot tub and kayaks!!"
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

Charming 3-bedroom house located on Main Street in Downtown Middlebury

10.0 out of 10, Exceptional, (3)
"We enjoyed and appreciated our stay at The Cozy Cottage. Griffon was very nice and allowed us an early check in and welcomed us to stay as long as we wanted on the day of check out. Would definitely recommend and stay again! "
The price is AU$492
includes taxes & fees
4 Sept - 5 Sept
Charming 3-bedroom house located on Main Street in Downtown Middlebury

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

10.0 out of 10, Exceptional, (7)
The price is AU$547
includes taxes & fees
10 Sept - 11 Sept
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

10.0 out of 10, Exceptional, (1)
"Very nice property clean nicely decorated very nice for the couple nights that we stayed there. I would recommend it highly"
The price is AU$510
includes taxes & fees
4 Sept - 5 Sept
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Newly Remodeled Cabin Steps from Sylvan Lake

10.0 out of 10, Exceptional, (43)
"Nice little place for my wife and I prior to a state conference. Good access to lake and kayaks were provided. Good proximity to Amish country. "
Newly Remodeled Cabin Steps from Sylvan Lake

Lakefront Home on Lake Webster

9.6 out of 10, Exceptional, (32)
"It was amazing spot! Very cozy and peaceful the view of the water was amazing will be recommend others to this location! "
Lakefront Home on Lake Webster

Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

9.8 out of 10, Exceptional, (28)
"House was very clean, well stocked and a beautiful location. Easy access to town as well. Loved our stay!!!"
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

Year Round Lake Front Cottage on Quiet Cove on Webster Lake

9.0 out of 10, Wonderful, (37)
"We had a great time getting away from Fort Wayne for the weekend."
Year Round Lake Front Cottage on Quiet Cove on Webster Lake

Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks

10.0 out of 10, Exceptional, (8)
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks

Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

10.0 out of 10, Exceptional, (48)
"We loved our weekend getaway. It was charming and relaxing and everything we were looking for. "
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (156)
"It was a nice spot, near to the events we took in, over the weekend."
Charming farmhouse in peaceful countryside

Emma's Place

10.0 out of 10, Exceptional, (53)
"This is a beautiful house. Very clean nice fenced in back yard. Real quiet location. Host is very friendly. We will stay here again if it is available our next trip back."
The price is AU$491
includes taxes & fees
7 Sept - 8 Sept
Emma's Place

Woodside Retreat in the Heart of Amish Country

10.0 out of 10, Exceptional, (6)
"We had a wonderful time here. We stayed here to "unplug" and refresh and it was the perfect place to do so! Comfortable, very clean, with personal touches down to the snacks provided- all made for a stay we will be back for!"
The price is AU$309
includes taxes & fees
4 Sept - 5 Sept
Woodside Retreat in the Heart of Amish Country

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

10.0 out of 10, Exceptional, (26)
"We love this place we were hear last October for sweetest day and came back on memorial day wknd we love the pool ,hot tub and the river in the back it's beautiful and also the game room with the massage chair ."
The price is AU$734
includes taxes & fees
4 Sept - 5 Sept
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (59)
"Very clean, nicely appointed. Ping pong table and hot tub were a real bonus! "
The price is AU$360
includes taxes & fees
14 Sept - 15 Sept
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Our family group of 14 really enjoyed this lake house. It had everything we needed. The outside areas were really nice & the game room was a real hit with kids & adults. Communication with host Joe was great. We hope to stay there again!!"
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!

beautiful cottage by the lake. Relax and enjoy your stay.

9.8 out of 10, Exceptional, (23)
"Very nice, wish there was bars or restaurants on the lake"
beautiful cottage by the lake. Relax and enjoy your stay.

Beautiful Skinner Cottage overlooking the lake

9.8 out of 10, Exceptional, (108)
"We were just in for a weekend getaway, this spot was perfect. Great view and access to the lake. My boys enjoyed going out fishing and just being outside. Everything was good!"
Beautiful Skinner Cottage overlooking the lake

New Kid in Town, Lake Wawasee , 2 Bedroom Condo Channel Front with Boat Pier

9.4 out of 10, Exceptional, (28)
"The place was very nice and the manager helped me enjoy my stay every day."
New Kid in Town, Lake Wawasee , 2 Bedroom Condo Channel Front with Boat Pier

⚓️Direct lake view with available Tritoon boat rental

9.8 out of 10, Exceptional, (12)
"The house and location are phenomenal. The pictures on the website don’t do it justice. You are on the lake and the view is amazing! The owners are super nice and very accommodating. Book now! You won’t be disappointed. "
⚓️Direct lake view with available Tritoon boat rental
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 Cromwell Hotel Reviews

Find out more about Cromwell

Find out more about Cromwell

Everything you need to know about Cromwell holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cromwell holiday rental for you. At Expedia, you can take your pick from private holiday 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 Cromwell holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cromwell holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cromwell. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cromwell holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cromwell holiday rentals we have selected for you start as low as AU$309 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cromwell rentals

At Expedia, we put the best Cromwell holiday 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 Cromwell 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 Cromwell holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cromwell. 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 holiday rentals in Cromwell?

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

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL : This highly rated holiday home rental in Cromwell is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Cromwell?

Choose from 3 Expedia holiday rentals in Cromwell for a memorable holiday.

What’s there to see and do in Cromwell?

While you're exploring the area, Lake Wawasee and Webster Lake are a couple of picturesque spots to get outside and enjoy nature. Wawasee Golf Club and South Shore Golf Club are a couple of places you'll find in the wider area.

What’s a holiday rental in Cromwell like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cromwell. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.