Cromwell Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Cromwell

Terrace/patio
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

Cromwell
10.0 out of 10, Exceptional, (25)
"Our family had a fantastic stay. The home was very clean. Enough room for everyone to stretch out. The two kitchens were very helpful. We really enjoyed the game room and pickleball court. We look forward to returning. "
United States
Lisa W.
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL
Dining
Newly Remodeled Cabin Steps from Sylvan Lake

Newly Remodeled Cabin Steps from Sylvan Lake

Rome City
10.0 out of 10, Exceptional, (48)
"We have a great stay. House was clean and comfortable. "
United States
kf
Newly Remodeled Cabin Steps from Sylvan Lake
View from property
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!

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

2.0 star property
Leesburg
10.0 out of 10, Exceptional, (6)
"Generous space for our group of 12. We practically lived in the game room for meals and fun time with the kids. Mornings having coffee in the Great Room, watching the sun come up over the lake, was such a great quiet time. Pleanty of parking. It was a good weekend."
United States
Terry M.
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!
Outdoor spa tub
HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Middlebury
10.0 out of 10, Exceptional, (62)
"Nice, quiet place for a ladies weekend. Would recommend and stay here again."
United States
Stephanie K.
The price is ￥19,446
￥40,271 total
includes taxes & fees
Dec 9 - Dec 10
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Property grounds
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

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

Shipshewana
9.8 out of 10, Exceptional, (32)
"We had a lovely time in Shipshewana. The rental was very nice, and very comfortable. "
United States
Julie M.
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.
Property grounds
Book your Fall Getaway now ! Our Season ends November 22!

Book your Fall Getaway now ! Our Season ends November 22!

Goshen
9.0 out of 10, Wonderful, (6)
"Private and peaceful."
United States
Tina c.
Book your Fall Getaway now ! Our Season ends November 22!
Living area
Lakefront Home on Lake Webster

Lakefront Home on Lake Webster

North Webster
9.4 out of 10, Exceptional, (34)
"Very cute place. Great views, everything you need for a stay. Parking is the only downfall but not enough for us to return. "
United States
Lisette M.
Lakefront Home on Lake Webster
Outdoor dining
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks

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

Wawaka
10.0 out of 10, Exceptional, (9)
"The home is beautiful. Everything we needed was on site. We thoroughly enjoyed the house and our stay. The decks are wonderful and it was so nice having a dock on site. "
United States
Alan C.
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks
Exterior
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

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

Warsaw
10.0 out of 10, Exceptional, (17)
"Wonderful home, lovely views on the lake, great communication with owner and host. We very much enjoyed our stay!"
United States
Carol B.
The price is ￥27,139
￥51,586 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Fridge, microwave, oven, stovetop
Freedom Farm

Freedom Farm

Middlebury
9.8 out of 10, Exceptional, (43)
"Such a beautiful place and amazing hospitality!"
United States
Terry R.
Freedom Farm
Dining
The Heron House @Waldron Lake

The Heron House @Waldron Lake

Wawaka
9.8 out of 10, Exceptional, (31)
"The owner was always very helpful and quick to answer any questions! The house was clean and very nice! Having the kayaks and paddle boat was so wonderful and the small sand beach worked well for our family!"
United States
cathy s.
The price is ￥35,882
￥89,706 total
includes taxes & fees
Dec 8 - Dec 9
The Heron House @Waldron Lake
Smart TV, video games
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!

Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!

Goshen
9.6 out of 10, Exceptional, (16)
"Location was convenient for biking the the Pumpkin Vine Trail."
United States
Jon C.
The price is ￥24,433
￥44,237 total
includes taxes & fees
Dec 7 - Dec 8
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!
Fridge, microwave, oven, stovetop
Emma's Place

Emma's Place

LaGrange
10.0 out of 10, Exceptional, (56)
"Enjoyed our stay! Would definitely stay here again."
United States
James S.
The price is ￥23,270
￥52,807 total
includes taxes & fees
Dec 7 - Dec 8
Emma's Place
Fridge, microwave, stovetop, dishwasher
Lake Wawasee Retreat: private pool, hot tub & pier

Lake Wawasee Retreat: private pool, hot tub & pier

2.0 star property
Syracuse
Lake Wawasee Retreat: private pool, hot tub & pier
Exterior
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,

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

Syracuse
9.6 out of 10, Exceptional, (30)
"This was a good spot for our family lake getaway. We were able to put the boat at the dock for easy lake access. The host was very accommodating and friendly. "
United States
Lindsay K.
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,
Property grounds
Water front cottage on beautiful Upper Long Lake

Water front cottage on beautiful Upper Long Lake

Albion
9.4 out of 10, Exceptional, (83)
"All was great at the property"
United States
David C.
Water front cottage on beautiful Upper Long Lake
Living area
Log Cabin Haus in Amish Country Shipshewana, Indiana

Log Cabin Haus in Amish Country Shipshewana, Indiana

Shipshewana
9.8 out of 10, Exceptional, (31)
"Excellent property. Great location. "
United States
Julie W.
Log Cabin Haus in Amish Country Shipshewana, Indiana
Property grounds
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Leesburg
10.0 out of 10, Exceptional, (1)
"Fantastic place to get away right on the water. Enjoyed our 3 day stay with my husband and our puppy. There is a fenced in yard and a dock. Wonderful place to relax. Our host was very helpful and easy to get in touch with.Recommend highly "
United States
Lenora F.
The price is ￥38,783
￥79,402 total
includes taxes & fees
Dec 24 - Dec 25
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Interior
`Burning Pine Inn' Farm House in Amish country.

`Burning Pine Inn' Farm House in Amish country.

Middlebury
10.0 out of 10, Exceptional, (26)
"Awesome property, wonderful host, our kids loved visiting the horses every day! Looking forwarding to a future stay! Absolutely recommend!"
United States
Jonathan M.
`Burning Pine Inn' Farm House in Amish country.
Fridge, microwave, oven, dishwasher
Cozy Lake House On The Channel With Access To 5 Lakes!

Cozy Lake House On The Channel With Access To 5 Lakes!

Wolcottville
9.6 out of 10, Exceptional, (41)
"My 3 nieces and I book a trip every year and found this place. It was very cozy and relaxing. The host was communicative and nice. It was so great to be able to use the paddle boat and kayaks! The neighbors were also friendly. Overall Nice stay"
United States
Vallerie M.
The price is ￥23,735
￥42,816 total
includes taxes & fees
Dec 7 - Dec 8
Cozy Lake House On The Channel With Access To 5 Lakes!
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

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

10/10 Excellent
"Great staff Great room Clean pool/spa Great food Great service"
Nathan 1-night trip
Posted 3 days ago
Essenhaus Inn & Conference Center

Find out more about Cromwell

Search for holiday rentals in Cromwell on Expedia! You can easily find your home rentals, villas, holiday apartments in Cromwell using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cromwell!

Frequently asked questions

Can I find vacation rentals in Cromwell?

Yes, we give you a choice of vacation rentals close to popular sights in Cromwell, or you can select a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Cromwell has to offer?

Newly Remodeled Cabin Steps from Sylvan Lake: This vacation home rental outside of Cromwell is located on a lake and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Cromwell?

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

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 larger area.

What’s a vacation rental in Cromwell like?

A vacation rental is a private property you can book for short or long periods in Cromwell. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.