Book Holiday Homes in Cromwell

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Featured Holiday Homes in Cromwell

Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake

Pierceton IN
The price is AU$386 per night from 17 May to 18 May
AU$386
17 May - 18 May
includes taxes & fees
Located in Warsaw, this vacation home is a 1-minute drive from Big Barbee Lake and 6 minutes from Tippecanoe Lake.
Opens in a new windowCozy lakefront home on Big Barbee Lake
Emma's Place

Emma's Place

LaGrange IN
The price is AU$478 per night from 17 May to 18 May
AU$478
17 May - 18 May
includes taxes & fees
With a stay at this vacation home in LaGrange, you'll be within a 15-minute drive of Parkview LaGrange Hospital and Maple Wood Nature Center.
Opens in a new windowEmma's Place
Natural Nook | Tiny Home #2 in Amish Country!

Natural Nook | Tiny Home #2 in Amish Country!

Shipshewana IN
The price is AU$340 per night from 25 May to 26 May
AU$340
25 May - 26 May
includes taxes & fees
With a stay at this vacation home in Shipshewana, you'll be within a 5-minute walk of North Park and Davis Mercantile.
Opens in a new windowNatural Nook | Tiny Home #2 in Amish Country!
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Charming farmhouse in peaceful countryside

Charming farmhouse in peaceful countryside

Nappanee IN
Located in Nappanee, this vacation home is in a rural location, within a 15-minute drive of Derksen Farm & Wetlands and Nappanee Dog Park.
Opens in a new windowCharming farmhouse in peaceful countryside
Waters Edge Cottage on Big Barbee Lake!

Waters Edge Cottage on Big Barbee Lake!

Pierceton IN
Located in Pierceton, this vacation home is on the waterfront, a 1-minute drive from Big Barbee Lake and 6 minutes from Tippecanoe Lake.
Opens in a new windowWaters Edge Cottage on Big Barbee Lake!
Nature's Nest | Tiny Home #4 in Amish Country!

Nature's Nest | Tiny Home #4 in Amish Country!

Shipshewana IN
The price is AU$295 per night from 25 May to 26 May
AU$295
25 May - 26 May
includes taxes & fees
With a stay at this vacation home in Shipshewana, you'll be within a 5-minute walk of North Park and Davis Mercantile.
Opens in a new windowNature's Nest | Tiny Home #4 in Amish Country!
Charming 3-bedroom house located on Main Street in Downtown Middlebury

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

Middlebury IN
With a stay at this vacation home in Middlebury, you'll be within a 10-minute walk of East Park and Memorial Park.
Opens in a new windowCharming 3-bedroom house located on Main Street in Downtown Middlebury
Lake House | Kayaks | Patio/Deck | Private Pier

Lake House | Kayaks | Patio/Deck | Private Pier

Rome City IN
Located in Rome City, this vacation home is on the waterfront, a 4-minute drive from Eagle Island and 5 minutes from Sylvan Lake.
Opens in a new windowLake House | Kayaks | Patio/Deck | Private Pier
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

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

Leesburg IN
The price is AU$751 per night from 17 May to 18 May
AU$751
17 May - 18 May
includes taxes & fees
Located in Warsaw, this vacation home is a 3-minute drive from Tippecanoe Lake and 5 minutes from Big Barbee Lake.
Opens in a new windowBeautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
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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.

Cromwell Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cromwell vacation homes are the perfect way for you to wing it.

Holiday houses in Cromwell let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cromwell in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cromwell adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cromwell with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cromwell vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cromwell Holiday Homes essential information

Accommodation
156 Holiday Homes
Lowest Price
AU$171
Highest Price
AU$751
Popular accommodation
Cozy lakefront home on Big Barbee Lake, Emma's Place, Natural Nook | Tiny Home #2 in Amish Country!, Charming farmhouse in peaceful countryside, Waters Edge Cottage on Big Barbee Lake!, Nature's Nest | Tiny Home #4 in Amish Country!, Charming 3-bedroom house located on Main Street in Downtown Middlebury, Lake House | Kayaks | Patio/Deck | Private Pier, Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Top trending hotels in Cromwell

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL

Cromwell IN
Located in Enchanted Hills, this vacation home is on the waterfront, a 1-minute drive from Lake Wawasee and 6 minutes from Wawasee Golf Club.
Opens in a new windowLake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL
Farmstead Inn & Conference Center

Farmstead Inn & Conference Center

2.5 out of 5
370 S Van Buren St Shipshewana IN
Fully refundableReserve now, pay when you stay
The price is AU$195 per night from 31 May to 1 June
AU$195
31 May - 1 June
includes taxes & fees
With a stay at Farmstead Inn & Conference Center in Shipshewana, you'll be in a shopping district, just a 4-minute walk from Shipshewana Auction and Flea Market ...
Opens in a new windowFarmstead Inn & Conference Center
Van Buren Hotel

Van Buren Hotel

4 out of 5
1175 Van Buren Street Shipshewana IN
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 17 May to 18 May
AU$184
17 May - 18 May
includes taxes & fees
Located in Shipshewana, Van Buren Hotel is in a shopping district, within a 10-minute drive of Blue Gate Theater and Shipshewana Flea Market.
Opens in a new windowVan Buren Hotel
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Blue Gate Garden Inn

Blue Gate Garden Inn

2.5 out of 5
800 South Van Buren Street Shipshewana IN
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 17 May to 18 May
AU$171
17 May - 18 May
includes taxes & fees
Located in Shipshewana, Blue Gate Garden Inn is connected to the convention center, a 3-minute walk from Blue Gate Performing Arts Center and 6 minutes by foot ...
Opens in a new windowBlue Gate Garden Inn
Don't see what you're looking for?
See all available properties in Cromwell
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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.

Top Picks

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.