Cromwell Vacation Rentals

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

Nature's Nest | Tiny Home #4 in Amish Country! : This vacation home rental outside of Cromwell has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

Dates

November 2026

December 2026

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Our top choices for Cromwell vacation rentals

A stone fireplace with a fire, surrounded by various board games and a plant.

1. Wawasee Retreat w/ Golf Cart & 1- min Lake Access

Cromwell

AED 898 total

includes taxes & fees

10 Nov - 11 Nov

A wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

2. Lakefront Fun on Papakeechie - Kayaks & More!

Syracuse

Jennie S.

AED 1,534 total

includes taxes & fees

7 Nov - 8 Nov

A modern building with large windows, a fire pit, outdoor seating, and a staircase leading to a deck.

3. Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana

Albion

Joan P.

AED 552 total

includes taxes & fees

30 Nov - 1 Dec

A two-story house with a covered porch, a front door, and a small front yard with shrubs.

4. Waterfront Family Gem w/ Private Dock in Syracuse

Syracuse

AED 1,683 total

includes taxes & fees

8 Nov - 9 Nov

5. Waterfront Family Gem w/ Private Dock in Syracuse

Syracuse

AED 1,747 total

includes taxes & fees

8 Nov - 9 Nov

A wooden deck with picnic tables and a view of a lake.

6. Fishing · Kayaks · Firepit · Paddleboat

Pierceton

Kim S.

AED 998 total

includes taxes & fees

8 Nov - 9 Nov

A lakeside property with a dock, boats, and a grassy area with outdoor seating.

7. Heart Jacuzzi · Kayaks · Firepit · Pier

Warsaw

Lisa S.

AED 1,140 total

includes taxes & fees

11 Nov - 12 Nov

A wooden deck with a white railing, a black chair, and a view of a lake with boats and a dock.

8. Backwater Lake Cottage | Tiki Bar & Paddleboat

North Webster

AED 1,482 total

includes taxes & fees

8 Nov - 9 Nov

A modern building with a large entrance, outdoor seating, and a well-maintained lawn.

9. Hearthstone Hideaway #5 | Shewana Tiny Home Village

Shipshewana

Rita S.

AED 776 total

includes taxes & fees

9 Nov - 10 Nov

A hot tub with wooden benches, a TV screen displaying streaming services, and a covered patio area.

10. Winter Extravaganza!! Hot tub, huge game room + MORE!!

Milford

Rachel A.

AED 1,264 total

includes taxes & fees

9 Nov - 10 Nov

A black house with a patio area featuring outdoor furniture and a grill.

11. Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!

Syracuse

Panacea G.

AED 1,214 total

includes taxes & fees

8 Nov - 9 Nov

A cabin with a wooden deck, a front door, and a garage.

12. Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain

Pierceton

John K.

AED 1,246 total

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with a central island, bar stools, a dining table with chairs, and a view of the outdoors.

13. Turtle Alley on Wawasee

Syracuse

AED 1,915 total

includes taxes & fees

7 Nov - 8 Nov

14. Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

North Webster

AED 2,055 total

includes taxes & fees

23 Nov - 24 Nov

A house with a dock extending into a pond, surrounded by trees and other houses.

15. Cozy lakefront home on Big Barbee Lake

Pierceton

Allison M.

AED 1,040 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Wolcottville

Robert W.

AED 1,140 total

includes taxes & fees

8 Nov - 9 Nov

A hot tub with a view of a grassy field and a cloudy sky.

17. | Hot Tub | Amish Farm Country | Pergola | Deck |

Middlebury

Tim B.

A brown front door with a glass panel and a welcome sign. A 'HOME' sign is mounted on the wall to the left.

18. Amish Alley Guesthouse,no cleaning fee,near TLA

Topeka

Mario

AED 912 total

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a dining area, large windows, and a surfboard mounted on the wall.

19. Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom

Syracuse

Bob T.

AED 2,184 total

includes taxes & fees

6 Dec - 7 Dec

A covered porch with two chairs and a table, a brick wall, and string lights.

20. Superb 5-bedroom farmhouse in Goshen with WiFi, AC

Goshen

Sally F.

AED 1,376 total

includes taxes & fees

8 Nov - 9 Nov

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Find vacation rentals that suit your style

Top Cromwell Hotel Reviews

A spacious lobby with a wooden herringbone floor, a central seating area with sofas and chairs, a staircase connecting two levels, and a large plant in the center.

Oakwood Resort

Syracuse

10/10 Excellent

Pat

A swimming pool with four lounge chairs and large windows with a forest view.

Holiday Inn Express & Suites Warsaw - E Center by IHG

Warsaw

10/10 Excellent

Lucia

A modern reception area with a curved desk, seating area, and a view of the outside.

Tru by Hilton Warsaw

Warsaw

10/10 Excellent

Che

A multi-level hotel interior with a central staircase, a dining area, and a balcony with a white picket fence.

Essenhaus Inn & Conference Center

Middlebury

10/10 Excellent

Jennie

A sunlit room with white Adirondack chairs, a potted plant, and a view of the outdoors.

Blue Gate Garden Inn

Shipshewana

10/10 Excellent

Marna

A modern living room with a stone wall, a flat-screen TV, a wooden ceiling, a blue and white rug, a beige sofa, and a dining area with a wooden partition.

Fairfield Inn & Suites by Marriott Goshen

Goshen

10/10 Excellent

Steve J

A modern hotel room with a large bed, a desk, a chair, and a TV.

Gallops Motel

Kendallville

10/10 Excellent

The room was huge with a huge bathroom as well! It had a walk-in shower with a rainfall shower head and regular shower head for personal choice. The rainfall shower head was so relaxing and unique to anywhere else I have stayed! The room was clean, neat and organized! All of this is extremely surprising given that it is behind a gas station and above a party store. Only recommendations I would have are to put non-slip strips or something on the shower floor as it is very slippery, and to put a...

Tina

An indoor swimming pool with clear water, surrounded by windows and chairs.

Hampton Inn Warsaw

Warsaw

10/10 Excellent

Lena

A rooster statue, a silo, and a red barn with a white house in the background.

Farmstead Inn & Conference Center

Shipshewana

10/10 Excellent

Check-in was very easy. The desk clerk was polite and offered us a booklet about local shops and tourist sites. The room was larger than we expected with two nicely padded recliner chairs and very clean. Housekeeping had left a note welcoming us. Their towels were very thick and soft. the breakfast buffet had the usual selections of hot and cold items. It was a nice large dining area with tablecloths and windows all around with a view of a small playground for kids that we thought was a...

Delisa

A motel with a white exterior, a covered front porch, and a horse-drawn carriage decoration.

Der Ruhe Blatz Motel

Shipshewana

10/10 Excellent

Dorothy

A hotel room with two beds, each with a patterned bedspread, a nightstand with a lamp, and a framed cityscape picture on the wall.

Super 8 by Wyndham Shipshewana

Shipshewana

10/10 Excellent

Overall it was a great stay, we had tickets to a show and the hotel was right next to the venue didn't have to move the car which was great. The room was clean and the bed was comfortable, bathroom could be a little bigger and the breakfast hours could be extended, the current time us 6am-9am could extend to 10am as there is nothing open on Sunday and after being at a show the night before some people like to sleep a little kater

Roger

A hotel room with a large bed, a desk, a flat-screen TV, and a wall-mounted TV.

Comfort Inn Kendallville East

Kendallville

10/10 Excellent

Elizabeth

A spacious hotel lobby with a central seating area, multiple dining tables, and a large sofa.

Hampton Inn & Suites Middlebury

Middlebury

10/10 Excellent

Nikki

A hotel room with a large bed, a flat-screen TV, a wooden dresser, a bathroom with a bathtub, and a desk with a chair.

Holiday Inn Express Hotel & Suites Goshen by IHG

Goshen

10/10 Excellent

NJtoIND

A hotel lobby with a reception desk, a patterned armchair, a staircase, and framed artwork on the walls.

Best Western Kendallville Inn

Kendallville

10/10 Excellent

Mr.

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?

Nature's Nest | Tiny Home #4 in Amish Country!: This vacation home rental outside of Cromwell has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Cromwell?

Choose from 4 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 Diamond 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.

Cromwell Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cromwell vacation rentals

1. Wawasee Retreat w/ Golf Cart & 1- min Lake Access

2. Lakefront Fun on Papakeechie - Kayaks & More!

3. Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana

4. Waterfront Family Gem w/ Private Dock in Syracuse

5. Waterfront Family Gem w/ Private Dock in Syracuse

6. Fishing · Kayaks · Firepit · Paddleboat

7. Heart Jacuzzi · Kayaks · Firepit · Pier

8. Backwater Lake Cottage | Tiki Bar & Paddleboat

9. Hearthstone Hideaway #5 | Shewana Tiny Home Village

10. Winter Extravaganza!! Hot tub, huge game room + MORE!!

11. Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!

12. Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain

13. Turtle Alley on Wawasee

14. Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

15. Cozy lakefront home on Big Barbee Lake

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

17. | Hot Tub | Amish Farm Country | Pergola | Deck |

18. Amish Alley Guesthouse,no cleaning fee,near TLA

19. Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom

20. Superb 5-bedroom farmhouse in Goshen with WiFi, AC

Find vacation rentals that suit your style

Top Cromwell Hotel Reviews

Oakwood Resort

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Cromwell?

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

How many vacation rentals are there in Cromwell?

What’s there to see and do in Cromwell?

What’s a vacation rental in Cromwell like?