Cromwell Holiday 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

Tonight
17 Jul - 18 Jul
Tomorrow
18 Jul - 19 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Cromwell

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL
Relax in a serene outdoor setting with a fire pit, Adirondack chairs, and a dock.

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

10.0 out of 10, Exceptional, (22)
"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
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks
Relax with a view of the water from this outdoor seating area featuring a sofa, chairs, and table.

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

10.0 out of 10, Exceptional, (5)
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks
Cozy Amish Country Cabin on Shipshewana Lake!
Enjoy meals or meetings in this serene room with a round table and four chairs, overlooking lush greenery through a large window.

Cozy Amish Country Cabin on Shipshewana Lake!

9.8 out of 10, Exceptional, (123)
"Beautiful spot to just relax or to run into town and visit the stores. "
Cozy Amish Country Cabin on Shipshewana Lake!
Charming farmhouse in peaceful countryside
Sit on the porch and enjoy the view from the window, surrounded by a cozy atmosphere.

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (150)
"it was a nice place to stay "
Charming farmhouse in peaceful countryside
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,
Stylish home with a central gable roof and attached garage, set amidst a well-manicured lawn and an entrance.

Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,

9.6 out of 10, Exceptional, (26)
"Easy to access, great owner and an amazing location!"
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,
New Kid in Town, Lake Wawasee , 2 Bedroom Condo Channel Front with Boat Pier
Enjoy outdoor dining and socializing on the spacious balcony with comfortable seating and tables.

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

9.6 out of 10, Exceptional, (23)
"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
Cozy lakefront home on Big Barbee Lake
Enjoy a comfortable stay in this well-appointed living space with a dining table, sofa, and fully equipped kitchen.

Cozy lakefront home on Big Barbee Lake

10.0 out of 10, Exceptional, (5)
The price is HK$1,342
HK$2,470 total
includes taxes & fees
20 Jul - 21 Jul
Cozy lakefront home on Big Barbee Lake
Webster Lake Home w/ Patio ~ 3 Mi to Town!
Situated on a grassy lawn, this charming home offers a serene view of a nearby lake.

Webster Lake Home w/ Patio ~ 3 Mi to Town!

6.0 out of 10, (1)
"We enjoyed being so close to the water. There was a great view of the lake and sunsets. The kitchen and living room were updated and pleasant to be in. There were new TVs in the rooms with good viewing selections. The air conditioners in each room were newer worked well. But the kitchen sink was dirty and stained and there was no dish soap. Cookware was provided but the skillets were olds and nonstick services were scratched up and the plates and utensils were like the cheapest ones from the...
Webster Lake Home w/ Patio ~ 3 Mi to Town!
Beautiful Skinner Cottage overlooking the lake
Relax in a serene outdoor seating area with wicker furniture and a large window offering a view of the surrounding landscape.

Beautiful Skinner Cottage overlooking the lake

9.8 out of 10, Exceptional, (103)
"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
Newly Remodeled Cabin Steps from Sylvan Lake
Enjoy a serene lake view from this room, featuring a table and chairs, a green door, and a window with multiple panes.

Newly Remodeled Cabin Steps from Sylvan Lake

10.0 out of 10, Exceptional, (42)
"We would love to stay here again."
Newly Remodeled Cabin Steps from Sylvan Lake
Couples getaway TINY Log Cabin by the pine trees
Situated in a serene, natural setting, this cabin offers a peaceful retreat with a porch for relaxation and dining.

Couples getaway TINY Log Cabin by the pine trees

10.0 out of 10, Exceptional, (29)
"we really enjoyed our stay, will keep this one on our list of repeats"
Couples getaway TINY Log Cabin by the pine trees
Lakefront Home on Lake Webster
Enjoy a scenic lake view from the large window in this cabin's cozy living area, featuring a comfortable sofa and TV.

Lakefront Home on Lake Webster

9.6 out of 10, Exceptional, (29)
"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
Views, Swimming & Family Fun: Chapman Lake Retreat
Enjoy dining or socializing on the deck with a view of the water.

Views, Swimming & Family Fun: Chapman Lake Retreat

10.0 out of 10, Exceptional, (5)
"We came this gorgeous massive house with our kids and in laws. Everything was absolutely amazing! Not only is this house spacious and beautiful, but it has everything you need to keep kids entertained: pool table, ping pong, darts, golden 2025 live big buck hunger games! We enjoyed family dinners and moving nights with large screen and huge comfy couch. The best part was watching the kids catch fish off the pier. Can't wait to come back this summer and swim! The hosts were very kind and...
Views, Swimming & Family Fun: Chapman Lake Retreat
Lakeside Indiana Vacation Rental Near Fort Wayne!
Enjoy cooking in this well-equipped kitchen with a central island, microwave, oven, toaster, and refrigerator.

Lakeside Indiana Vacation Rental Near Fort Wayne!

10.0 out of 10, Exceptional, (17)
"Very clean and they location was wonderful!!"
Lakeside Indiana Vacation Rental Near Fort Wayne!
Spacious & Newly Renovated 3-bedroom house in Warsaw/Winona Lake
Relax in a serene outdoor space surrounded by lush greenery and a small garden.

Spacious & Newly Renovated 3-bedroom house in Warsaw/Winona Lake

9.6 out of 10, Exceptional, (7)
"The house was comfortable. We came to town for a wedding and had little time for more. The home served our needs and we felt safe and comfortable "
The price is HK$1,020
HK$1,811 total
includes taxes & fees
22 Jul - 23 Jul
Spacious & Newly Renovated 3-bedroom house in Warsaw/Winona Lake
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain
Cozy cabin with a large garage door and a charming front porch.

3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain

9.4 out of 10, Exceptional, (10)
"This isn't our first time staying here and we love it. It's easy to find, simple living and quiet. Also, there is food delivery available so we don't have to cook after a long hunt."
The price is HK$1,177
HK$2,514 total
includes taxes & fees
31 Jul - 1 Aug
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain
Woodside Retreat in the Heart of Amish Country
Cozy retreat with a small table, heart-shaped chairs, and a potted plant, surrounded by string lights and a decorative plant.

Woodside Retreat in the Heart of Amish Country

10.0 out of 10, Exceptional, (5)
"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 HK$903
HK$1,587 total
includes taxes & fees
18 Jul - 19 Jul
Woodside Retreat in the Heart of Amish Country
Indian Lakes Cabin with private beach and dock lake side
Relax in a cozy seating area with a cushioned bench and enjoy the view of the lakeside deck with outdoor furniture and a grill.

Indian Lakes Cabin with private beach and dock lake side

9.6 out of 10, Exceptional, (79)
"Awesome time. My son had a blast and definitely coming back."
Indian Lakes Cabin with private beach and dock lake side
Emma's Place
Enjoy cooking in this well-equipped kitchen with an island, microwave, and refrigerator.

Emma's Place

9.8 out of 10, Exceptional, (45)
"Very accommodating "
The price is HK$1,177
HK$2,462 total
includes taxes & fees
19 Jul - 20 Jul
Emma's Place
Park model located at Yogi Jellystone Park. Not far from the beach.
Enjoy cooking in this well-equipped kitchen with a stove, microwave, and sink.

Park model located at Yogi Jellystone Park. Not far from the beach.

10.0 out of 10, Exceptional, (5)
"The camper was very nice and spacious. My family loved staying here. Definitely recommend to anyone who would want to stay here . "
Park model located at Yogi Jellystone Park. Not far from the beach.
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

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.