Cromwell Holiday Rentals
Apartment
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $77/Night
7 Nights - US $540
House
- Warsaw
- ·
- Enchanted Hills
- 0.73 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
9 Guests
602.78 ft²
Oceanfront- Parking
Ocean View
View
US $439/Night
7 Nights - US $3,073
House
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
Internet
US $270/Night
7 Nights - US $1,888
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $103/Night
7 Nights - US $721
House
3 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Parking
- Internet
Pet Friendly
Security/Safety
US $682/Night
7 Nights - US $4,774
New
House
10.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
1050 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $389/Night
7 Nights - US $2,724
New
House
- Warsaw
- ·
- Enchanted Hills
- 0.11 mi to center
4 Bedrooms
3 Baths
14 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $711/Night
7 Nights - US $4,975
House
10.0Exceptional
(29 Reviews)
4 Bedrooms
2 Baths
8 Guests
2300 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $544/Night
7 Nights - US $3,806
House
- Indiana
- ·
- North Webster
- 0.72 mi to center
10.0Exceptional
(26 Reviews)
2 Bedrooms
2 Baths
10 Guests
1000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $388/Night
7 Nights - US $2,717
Luxury Holiday Rentals in Cromwell
Over 108+ Luxury Holiday Rentals in or Near Cromwell
House
- Warsaw
- ·
- Enchanted Hills
- 0.80 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $940/Night
7 Nights - US $6,582
New
House
- Warsaw
- ·
- Enchanted Hills
- 1.03 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
2 Baths
12 Guests
2000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $927/Night
7 Nights - US $6,492
New
House
- Indiana
- ·
- North Webster
- 0.69 mi to center
5 Bedrooms
3 Baths
38 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $761/Night
7 Nights - US $5,327
House
9.8Exceptional
(18 Reviews)
3 Bedrooms
2 Baths
12 Guests
1900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $719/Night
7 Nights - US $5,031
House
- Warsaw
- ·
- Enchanted Hills
- 1.34 mi to center
7 Bedrooms
3 Baths
20 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $714/Night
7 Nights - US $5,001
Cottage
9.8Exceptional
(45 Reviews)
5 Bedrooms
2 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $713/Night
7 Nights - US $4,994
House
- Indiana
- ·
- North Webster
- 1.57 mi to center
10.0Exceptional
(12 Reviews)
5 Bedrooms
2 Baths
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $694/Night
7 Nights - US $4,855
New
Cottage
- Indiana
- ·
- North Webster
- 0.77 mi to center
4 Bedrooms
2 Baths
10 Guests
1452 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $675/Night
7 Nights - US $4,723
House
- Warsaw
- ·
- Enchanted Hills
- 1.18 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $668/Night
7 Nights - US $4,673
Top-Rated Holiday Rentals with a Pool in Cromwell
Over 3+ The Best Private Villas and Holiday Rentals in Cromwell with a Pool
House
- Warsaw
- ·
- Enchanted Hills
- 0.43 mi to center
10.0Exceptional
(7 Reviews)
4 Bedrooms
3 Baths
16 Guests
Private Pool
Hot Tub- Parking
Pool
US $594/Night
7 Nights - US $4,155
House
10.0Exceptional
(8 Reviews)
5 Bedrooms
3 Baths
12 Guests
4600 ft²
- Private Pool
- Parking
- Pool
- Kitchen
US $1,072/Night
7 Nights - US $7,503
House
- Warsaw
- ·
- Enchanted Hills
- 0.49 mi to center
9.6Exceptional
(20 Reviews)
4 Bedrooms
3 Baths
11 Guests
3200 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $484/Night
7 Nights - US $3,390
Pet-Friendly Holiday Rentals in Cromwell
Over 32+ Pet-Friendly Holiday Rentals in or Near Cromwell
House
10.0Exceptional
(20 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $312/Night
7 Nights - US $2,187
House
- Indiana
- ·
- North Webster
- 1.53 mi to center
4 Bedrooms
1 Bath
8 Guests
1603.82 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $273/Night
7 Nights - US $1,913
House
10.0Exceptional
(18 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $316/Night
7 Nights - US $2,211
House
- Indiana
- ·
- North Webster
- 1.54 mi to center
3 Bedrooms
2 Baths
8 Guests
1829.86 ft²
- Parking
- Internet
- Pet Friendly
- Security/Safety
US $246/Night
7 Nights - US $1,720
Cottage
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
2600 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $394/Night
7 Nights - US $2,760
New
House
- Warsaw
- ·
- Enchanted Hills
- 0.34 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
10 Guests
832 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $621/Night
7 Nights - US $4,350
New
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
9 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $411/Night
7 Nights - US $2,876
House
9.8Exceptional
(37 Reviews)
4 Bedrooms
3 Baths
16 Guests
3000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $442/Night
7 Nights - US $3,094
House
9.6Exceptional
(24 Reviews)
5 Bedrooms
2 Baths
10 Guests
1600 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $303/Night
7 Nights - US $2,121
Large Holiday Rentals and Private Villas in Cromwell
Over 31+ Large Holiday Rentals and Private Villas in or Near Cromwell
House
- Indiana
- ·
- North Webster
- 0.63 mi to center
10.0Exceptional
(20 Reviews)
3 Bedrooms
2 Baths
10 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $373/Night
7 Nights - US $2,613
House
10.0Exceptional
(10 Reviews)
4 Bedrooms
3 Baths
14 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $621/Night
7 Nights - US $4,349
House
- Warsaw
- ·
- Enchanted Hills
- 1.02 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $462/Night
7 Nights - US $3,233
House
9.8Exceptional
(31 Reviews)
3 Bedrooms
3 Baths
100 Guests
2500 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $570/Night
7 Nights - US $3,988
New
House
- Warsaw
- ·
- Enchanted Hills
- 0.42 mi to center
9.8Exceptional
(28 Reviews)
4 Bedrooms
3 Baths
15 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $430/Night
7 Nights - US $3,009
House
- Warsaw
- ·
- Enchanted Hills
- 0.95 mi to center
9.6Exceptional
(9 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $596/Night
7 Nights - US $4,171
House
- Warsaw
- ·
- Enchanted Hills
- 0.23 mi to center
9.2Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $601/Night
7 Nights - US $4,210
Cottage
- Indiana
- ·
- North Webster
- 0.64 mi to center
8.0Excellent
(2 Reviews)
5 Bedrooms
3 Baths
20 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $428/Night
7 Nights - US $2,997
House
- Warsaw
- ·
- Enchanted Hills
- 1.67 mi to center
5 Bedrooms
5 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $640/Night
7 Nights - US $4,477
Wheelchair Accessible Holiday Homes in Cromwell
Over 2+ Wheelchair Accessible Holiday Homes in or Near Cromwell
House
- Warsaw
- ·
- Enchanted Hills
- 1.15 mi to center
9.4Exceptional
(6 Reviews)
5 Bedrooms
5 Baths
20 Guests
3772 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $1,002/Night
7 Nights - US $7,017
Cottage
4.8Average
(18 Reviews)
2 Bedrooms
1 Bath
6 Guests
995 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $175/Night
7 Nights - US $1,225
Cromwell Private Villas and Holiday Homes Under $200
Over 18+ Cromwell Private Villas and Holiday Homes Under $200
Cottage
- Indiana
- ·
- North Webster
- 0.73 mi to center
10.0Exceptional
(26 Reviews)
3 Bedrooms
1 Bath
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $189/Night
7 Nights - US $1,325
House
2 Bedrooms
1 Bath
6 Guests
904.17 ft²
Private Beach- Parking
Skiing- Ocean View
US $190/Night
7 Nights - US $1,327
Cottage
- Indiana
- ·
- North Webster
- 0.73 mi to center
1 Bedroom
1 Bath
- Kitchen
- Air Conditioner
- Security/Safety
US $167/Night
7 Nights - US $1,168
House
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
10 Guests
2000 ft²
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $159/Night
7 Nights - US $1,111
House
- Indiana
- ·
- North Webster
- 0.70 mi to center
7.0Very Good
(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $173/Night
7 Nights - US $1,212
Cottage
10.0Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $65/Night
7 Nights - US $452
Cottage
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
660 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $172/Night
7 Nights - US $1,205
Cottage
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $170/Night
7 Nights - US $1,190
Cottage
9.8Exceptional
(10 Reviews)
1 Bedroom
1 Bath
7 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $168/Night
7 Nights - US $1,176
Instantly Bookable Holiday Homes in Cromwell
Over 38+ Instantly Bookable Holiday Homes in or Near Cromwell
Cabin
- Indiana
- ·
- North Webster
- 1.69 mi to center
10.0Exceptional
(22 Reviews)
1 Bedroom
1 Bath
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $298/Night
7 Nights - US $2,085
House
- Indiana
- ·
- North Webster
- 1.38 mi to center
9.8Exceptional
(66 Reviews)
2 Bedrooms
1 Bath
5 Guests
600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $236/Night
7 Nights - US $1,650
New
Cottage
- Indiana
- ·
- North Webster
- 1.17 mi to center
9.4Exceptional
(40 Reviews)
2 Bedrooms
1 Bath
5 Guests
500 ft²
- Balcony/Terrace
- Air Conditioner
- Internet
- Pet Friendly
US $279/Night
7 Nights - US $1,952
House
- Indiana
- ·
- North Webster
- 1.54 mi to center
8.6Fabulous
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1828 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $276/Night
7 Nights - US $1,931
House
- Indiana
- ·
- North Webster
- 1.53 mi to center
8.0Excellent
(8 Reviews)
4 Bedrooms
1 Bath
8 Guests
1600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $239/Night
7 Nights - US $1,670
New
House
- Indiana
- ·
- North Webster
- 0.88 mi to center
1 Bedroom
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $371/Night
7 Nights - US $2,599
New
House
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Parking
- Skiing
- Balcony/Terrace
- Kitchen
US $218/Night
7 Nights - US $1,523
New
House
- Warsaw
- ·
- Enchanted Hills
- 1.44 mi to center
3 Bedrooms
1 Bath
10 Guests
953 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $230/Night
7 Nights - US $1,607
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
4 Guests
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
US $241/Night
7 Nights - US $1,686
Book a Last Minute Place to Stay in Cromwell
About Casai's Private Villas and Holiday Rentals in Cromwell
Discover more than 117 vacation rentals available in Cromwell. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Cromwell.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Cromwell, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Cromwell. On average, places to stay near Cromwell offer 709.59 ft², with nightly prices averaging US $411.
With Casai, finding and comparing holiday rentals in Cromwell is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Cromwell
| Type | Count |
|---|---|
| Vacation Homes | 76 |
| Cottages | 27 |
| Holiday Apartments | 3 |
Use these Quick Filters to Find a Holiday Rental in Cromwell
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Cromwell.
Weather in Cromwell, IN
View the weather forecast for Cromwell before booking your Cromwell Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Cromwell, IN
Casai offers a large selection of top attractions around Cromwell . Research things to do on your vacation before you visit Cromwell.
Frequently Asked Questions About Cromwell?
What are the top holiday rentals in Cromwell?
With numerous options available in Cromwell, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Cromwell:
- Lake Wawasee Channel front Home away from Home!
- Nicely Appointed, Comfy Cottage ON THE LAKE with Awesome Views - Sleeps 10
- Cozy three-bedroom cottage perfect for a lakeside get-away
- Webster Lake home
- Year Round, Updated, Lake Front Home on Beautiful All-Sport Webster Lake.
- Channel Property on Lake Wawasee - bring your boat/dog!
- Tranqulity and relaxtion destination
- Lake Front Boondoggle - Dog Friendly
- 4-bedroom house on Lake Wawasee with a stunning, screened in porch!
- The Boat House w/Dock: Enjoy Lake Life!
Which holiday homes in Cromwell are best for families?
If you're searching for a family-friendly holiday home in Cromwell, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Cromwell:
- Cozy cottage—lake Wawasee channel— easy access to lake
- The Boat House w/Dock: Enjoy Lake Life!
- "Sycamore Alley" on Webster Lake
How many Casai.com holiday rentals are available in Cromwell?
As of 2026, Casai boasts over 117 properties listed in the Cromwell area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Cromwell.
Map
