121+ Private Villas and Holiday Rentals in Middletown |
Middletown Holiday Rentals
House
10.0Exceptional
(83 Reviews)
4 Bedrooms
2 Baths
8 Guests
1472 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $187/Night
7 Nights - US $1,309
House
9.8Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
6 Guests
Spa- Balcony/Terrace
- Parking
Child Friendly
US $326/Night
7 Nights - US $2,282
Apartment
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
Air Conditioner- Child Friendly
US $335/Night
7 Nights - US $2,348
House
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
2 Guests
360 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $111/Night
7 Nights - US $774
Apartment
9.3Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
96.88 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
Internet
US $90/Night
7 Nights - US $630
House
10.0Exceptional
(27 Reviews)
3 Bedrooms
2 Baths
8 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $347/Night
7 Nights - US $2,430
Condo
10.0Exceptional
(21 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $340/Night
7 Nights - US $2,378
House
- Indiana
- ·
- Delaware County
- 7.30 mi to center
10.0Exceptional
(9 Reviews)
4 Bedrooms
3 Baths
11 Guests
3099 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,091/Night
7 Nights - US $7,639
Cottage
10.0Exceptional
(8 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $108/Night
7 Nights - US $757
Luxury Holiday Rentals in Middletown
Over 112+ Luxury Holiday Rentals in or Near Middletown
House
- Muncie
- ·
- New Castle
- 5.12 mi to center
1 Bedroom
2 Baths
8 Guests
3003.13 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
US $579/Night
7 Nights - US $4,055
House
- Muncie
- ·
- New Castle
- 5.12 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
3000 ft²
- Fireplace/Heating
Ocean View
View- Kitchen
US $569/Night
7 Nights - US $3,986
House
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $552/Night
7 Nights - US $3,864
House
9.0Exceptional
(8 Reviews)
3 Bedrooms
1 Bath
8 Guests
Private Pool- Hot Tub
- Fireplace/Heating
Pool
US $372/Night
7 Nights - US $2,602
House
9.8Exceptional
(18 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $362/Night
7 Nights - US $2,535
New
House
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
- Air Conditioner
US $346/Night
7 Nights - US $2,422
Villa
8.0Excellent
(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
1700.7 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $344/Night
7 Nights - US $2,410
House
8.8Fabulous
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $343/Night
7 Nights - US $2,403
New
House
- Indiana
- ·
- Perkinsville
- 13.69 mi to center
1 Bedroom
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $289/Night
7 Nights - US $2,025
Top-Rated Holiday Rentals with a Pool in Middletown
Over 20+ The Best Private Villas and Holiday Rentals in Middletown with a Pool
Other
10.0Exceptional
(9 Reviews)
3 Bedrooms
1 Bath
6 Guests
2200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $196/Night
7 Nights - US $1,372
Hotel
8.8Fabulous
(1001 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
Breakfast
US $114/Night
7 Nights - US $800
Hotel
8.8Fabulous
(523 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $128/Night
7 Nights - US $894
Hotel
8.8Fabulous
(275 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $109/Night
7 Nights - US $760
Hotel
8.7Fabulous
(289 Reviews)
1 Bath
247.57 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $102/Night
7 Nights - US $714
Hotel
- Indiana
- ·
- Mount Pleasant
- 3.40 mi to center
8.6Fabulous
(90 Reviews)
1 Bath
- Pool
- Kitchen
- Parking
- Air Conditioner
US $123/Night
7 Nights - US $862
Hotel
8.5Fabulous
(203 Reviews)
1 Bath
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
US $187/Night
7 Nights - US $1,311
Hotel
8.4Excellent
(1000 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $75/Night
7 Nights - US $526
Hotel
8.4Excellent
(190 Reviews)
10 Baths
368.12 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $123/Night
7 Nights - US $862
Pet-Friendly Holiday Rentals in Middletown
Over 17+ Pet-Friendly Holiday Rentals in or Near Middletown
House
- Muncie
- ·
- New Castle
- 1.68 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $249/Night
7 Nights - US $1,741
Hotel
7.1Very Good
(405 Reviews)
4 Baths
204.51 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $59/Night
7 Nights - US $416
Hotel
6.0Good
(494 Reviews)
1 Bath
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $67/Night
7 Nights - US $471
House
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $143/Night
7 Nights - US $1,002
Hotel
6.0Good
(102 Reviews)
2 Baths
161.45 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $76/Night
7 Nights - US $531
House
9.6Exceptional
(41 Reviews)
3 Bedrooms
2 Baths
6 Guests
1700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $229/Night
7 Nights - US $1,602
House
- Indiana
- ·
- New Lisbon
- 20.76 mi to center
9.6Exceptional
(36 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $158/Night
7 Nights - US $1,104
House
- Indiana
- ·
- New Lisbon
- 19.66 mi to center
8.8Fabulous
(46 Reviews)
3 Bedrooms
2 Baths
6 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $166/Night
7 Nights - US $1,160
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $137/Night
7 Nights - US $958
Large Holiday Rentals and Private Villas in Middletown
Over 4+ Large Holiday Rentals and Private Villas in or Near Middletown
New
House
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $238/Night
7 Nights - US $1,667
House
9.8Exceptional
(14 Reviews)
5 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $314/Night
7 Nights - US $2,195
House
9.4Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
1700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $417/Night
7 Nights - US $2,918
House
- Indiana
- ·
- Delaware County
- 2.72 mi to center
6 Bedrooms
6 Baths
16 Guests
13000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Air Conditioner
US $2,500/Night
7 Nights - US $17,500
Wheelchair Accessible Holiday Homes in Middletown
Over 12+ Wheelchair Accessible Holiday Homes in or Near Middletown
House
5.0Average
(20 Reviews)
3 Bedrooms
2 Baths
6 Guests
1664 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $175/Night
7 Nights - US $1,225
Hotel
8.3Excellent
(88 Reviews)
12 Baths
176.71 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $136/Night
7 Nights - US $950
Hotel
9.0Exceptional
(888 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $123/Night
7 Nights - US $860
Hotel
- Indiana
- ·
- Mount Pleasant
- 3.34 mi to center
8.2Excellent
(49 Reviews)
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $161/Night
7 Nights - US $1,127
Hotel
8.2Excellent
(946 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $104/Night
7 Nights - US $729
Hotel
8.0Excellent
(192 Reviews)
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Breakfast
US $229/Night
7 Nights - US $1,601
Hotel
8.0Excellent
(1000 Reviews)
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $93/Night
7 Nights - US $653
Hotel
7.9Very Good
(331 Reviews)
1 Bath
204.51 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $75/Night
7 Nights - US $525
Hotel
7.7Very Good
(313 Reviews)
6 Baths
290.63 ft²
- Private Pool
- Pool
- Kitchen
- Parking
US $104/Night
7 Nights - US $728
Middletown Private Villas and Holiday Homes Under $200
Over 55+ Middletown Private Villas and Holiday Homes Under $200
House
- Indiana
- ·
- New Lisbon
- 14.04 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Bedding/Linens
US $177/Night
7 Nights - US $1,239
House
7.5Very Good
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1194.79 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $136/Night
7 Nights - US $950
Hotel
7.8Very Good
(732 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $81/Night
7 Nights - US $564
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $96/Night
7 Nights - US $673
House
- Muncie
- ·
- New Castle
- 0.15 mi to center
1 Bedroom
1 Bath
4 Guests
914.93 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $162/Night
7 Nights - US $1,134
House
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
4 Guests
1600 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $169/Night
7 Nights - US $1,186
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Laundry
US $74/Night
7 Nights - US $517
House
9.6Exceptional
(38 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $119/Night
7 Nights - US $836
House
- Muncie
- ·
- New Castle
- 0.15 mi to center
9.6Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $145/Night
7 Nights - US $1,015
Instantly Bookable Holiday Homes in Middletown
Over 39+ Instantly Bookable Holiday Homes in or Near Middletown
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
1400 ft²
- Ocean View
- View
- Kitchen
- Parking
US $241/Night
7 Nights - US $1,686
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $243/Night
7 Nights - US $1,704
Apartment
- Muncie
- ·
- New Castle
- 0.28 mi to center
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $161/Night
7 Nights - US $1,129
Apartment
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $85/Night
7 Nights - US $597
House
- Muncie
- ·
- New Castle
- 0.15 mi to center
9.2Exceptional
(7 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $116/Night
7 Nights - US $813
House
9.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $104/Night
7 Nights - US $729
House
- Muncie
- ·
- New Castle
- 0.15 mi to center
8.6Fabulous
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $121/Night
7 Nights - US $848
Apartment
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Laundry
US $104/Night
7 Nights - US $730
House
7.0Very Good
(11 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $91/Night
7 Nights - US $640
Book a Last Minute Place to Stay in Middletown
About Casai's Private Villas and Holiday Rentals in Middletown
Discover more than 121 vacation rentals available in Middletown. 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 Middletown.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Middletown, 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 Middletown. On average, places to stay near Middletown offer 531.62 ft², with nightly prices averaging US $205.
With Casai, finding and comparing holiday rentals in Middletown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Middletown
| Type | Count |
|---|---|
| Vacation Homes | 64 |
| Holiday Apartments | 20 |
| Cottages | 3 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Middletown
★ 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 Middletown.
Weather in Middletown, IN
View the weather forecast for Middletown before booking your Middletown 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 Middletown, IN
Casai offers a large selection of top attractions around Middletown . Research things to do on your vacation before you visit Middletown.
Frequently Asked Questions About Middletown?
What are the top holiday rentals in Middletown?
With numerous options available in Middletown, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Middletown:
- short walk to Ball State University Campus - Quiet Neighborhood
- Settle in at the Petite Retreat.
- Super Charming Modern Cottage
- 'Downtown Delight' w/Patio! 1 Mi to Ball State
- Hickory Hill Estates (Muncie)
- Quiet Rural Setting featuring a Spacious Beautiful 1800s Farmhouse ALL Updated
- The Cardinal. Newly built 1-bedroom cottage w/WiFi and AC in delightful Muncie
- Providence Hideaway: Trailer parking. near Henry Co Saddle Club, pet-friendly
- Stunning, unique, and secluded barndominium. Walking trails, wildlife, & quiet
- Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
How many holiday rentals have private pools in Middletown?
Discover a selection of holiday rentals with private pools near Middletown with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Middletown are best for families?
If you're searching for a family-friendly holiday home in Middletown, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Middletown:
- 3-bedroom house with nice yard in Muncie + patio + plenty of parking
- Stylish New Castle Escape with Garage and by Parks-Family Friendly
- Anderson Chesterfield Travel Inn
How many Casai.nz holiday rentals are available in Middletown?
As of 2026, Casai boasts over 121 properties listed in the Middletown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Middletown.
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