Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select Middletown Vacation Homes

Modern Bungalow Home with Mid-Century Flair
Fridge, oven, stovetop, dishwasher

Modern Bungalow Home with Mid-Century Flair

9.0 out of 10, Wonderful, (34)
"Great location. Close to downtown, restaurants, and the state fair and pet friendly too."
The price is CA $146
CA $301 total
includes taxes & fees
Aug 26 - Aug 27
Modern Bungalow Home with Mid-Century Flair
COZY BUNGALO
Fridge, microwave, oven, stovetop

COZY BUNGALO

9.4 out of 10, Exceptional, (65)
"We had an overnight here and it was just what we needed!"
COZY BUNGALO
Whitt’s End -- a spacious private lodging in a historic Springfield neighborhood
Property grounds

Whitt’s End -- a spacious private lodging in a historic Springfield neighborhood

10.0 out of 10, Exceptional, (2)
"Nice property very happy with our stay"
Whitt’s End -- a spacious private lodging in a historic Springfield neighborhood
New remodel three bedroom house in pleasant Springfield
Private kitchen

New remodel three bedroom house in pleasant Springfield

7.4 out of 10, Good, (12)
"Nice little house, convenient to fairgrounds. Upstairs front bedroom was a little warm. Vent fully open but not a lot of cold air flowing through. Bed in that bedroom was low, no problem for me but I could see it might be difficult for some. It was comfortable. Other bedrooms nice."
The price is CA $149
CA $369 total
includes taxes & fees
Aug 31 - Sep 1
New remodel three bedroom house in pleasant Springfield
Wednesday’s Lair - Lincoln, Il
Exterior

Wednesday’s Lair - Lincoln, Il

10.0 out of 10, Exceptional, (9)
"Lincoln has some great local shops and cafes. This house is conveniently located and has wonderful decor. "
The price is CA $242
CA $447 total
includes taxes & fees
Sep 1 - Sep 2
Wednesday’s Lair - Lincoln, Il
Charming Downtown Stay | Victorian Beauty & Modern Comfort
Exterior

Charming Downtown Stay | Victorian Beauty & Modern Comfort

9.6 out of 10, Exceptional, (19)
"Clean charming place to stay. On a girls trip we felt safe and the girls loved the big bedroom in the house!"
The price is CA $310
CA $346 total
includes taxes & fees
Sep 2 - Sep 3
Charming Downtown Stay | Victorian Beauty & Modern Comfort
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Exterior

Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

10.0 out of 10, Exceptional, (49)
"Great hosts and accommodations!"
The price is CA $302
CA $337 total
includes taxes & fees
Sep 2 - Sep 3
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Very Cozy and Secluded. Completely remodeled beautiful back apartment
Smart TV, DVD player, books, video library

Very Cozy and Secluded. Completely remodeled beautiful back apartment

10.0 out of 10, Exceptional, (56)
"This would be a great place for an extended stay! Great people and the place was very comfortable!"
The price is CA $118
CA $199 total
includes taxes & fees
Sep 1 - Sep 2
Very Cozy and Secluded. Completely remodeled beautiful back apartment
Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg
Interior

Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

10.0 out of 10, Exceptional, (24)
"Tons of character, wonderfully taken care of, great hosts, Aubrey is super easy to work with and very accommodating. Loved the flexibility to host our wedding in a unique way that fit us!"
Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg
Charming 2-bedroom house in fabulous Springfield with AC, WiFi
WiFi, bed sheets

Charming 2-bedroom house in fabulous Springfield with AC, WiFi

The price is CA $123
CA $330 total
includes taxes & fees
Aug 24 - Aug 25
Charming 2-bedroom house in fabulous Springfield with AC, WiFi
Historic Bungalow: For Groups & Families Sleeps 11
Exterior

Historic Bungalow: For Groups & Families Sleeps 11

9.2 out of 10, Wonderful, (11)
"Lots of room for my multi-generational family of 7! Our host was super-responsive and helpful."
Historic Bungalow: For Groups & Families Sleeps 11
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
View from property

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

9.8 out of 10, Exceptional, (13)
"Beautiful place to stay!!! So cozy and perfect!"
The price is CA $310
CA $346 total
includes taxes & fees
Sep 2 - Sep 3
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Tranquil 2-bedroom house with a massage chair and a multi-purpose 3rd room
Fridge, microwave, oven, stovetop

Tranquil 2-bedroom house with a massage chair and a multi-purpose 3rd room

2.0 star property
10.0 out of 10, Exceptional, (17)
"Host was easy to work with and property was nice! "
The price is CA $140
CA $327 total
includes taxes & fees
Sep 9 - Sep 10
Tranquil 2-bedroom house with a massage chair and a multi-purpose 3rd room
The Conkling House in the Old Aristocracy Hill Neighborhood
Exterior

The Conkling House in the Old Aristocracy Hill Neighborhood

8.0 out of 10, Very good, (6)
"We enjoyed our stay. This is a beautiful house, and it is lovely to have seven bedrooms for 11. There is not a conventional stovetop or oven. people. Note th We would stay here again."
The Conkling House in the Old Aristocracy Hill Neighborhood
Spacious & Cozy ~ Mins to Downtown
Fridge, microwave, oven, stovetop

Spacious & Cozy ~ Mins to Downtown

8.2 out of 10, Very good, (14)
"Enjoyed our stay as part of a family road trip."
Spacious & Cozy ~ Mins to Downtown
2b1b fenced backyard with deck, outdoor space near hospitals
Fridge, microwave, oven, stovetop

2b1b fenced backyard with deck, outdoor space near hospitals

9.0 out of 10, Wonderful, (6)
"This lovely home was a peaceful get away as our home was getting a makeover. It's a very convenient location and had all the amenities we needed. We would definitely stay again. "
2b1b fenced backyard with deck, outdoor space near hospitals
Beautiful Country Setting with Heated Inground Pool and Stocked Pond
Fridge, microwave, oven, stovetop

Beautiful Country Setting with Heated Inground Pool and Stocked Pond

10.0 out of 10, Exceptional, (97)
"Great place, pond and fishing was great. Big pool, nice hot tub with many things to do. We will rent again. Thanks"
Beautiful Country Setting with Heated Inground Pool and Stocked Pond
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Dining

Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

10.0 out of 10, Exceptional, (2)
"Amazing property. Couldn’t have asked for anything better. Kitchen, living room, laundry and dining room on every floor. Luxurious bedrooms. A beautiful old mansion. In the heart of Springfield. Every amenity you could imagine. We had an amazingly wonderful weekend of sharing and church family time."
The price is CA $700
CA $1,363 total
includes taxes & fees
Sep 8 - Sep 9
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Charming Springfield Home: 2 Mi to Downtown
Property grounds

Charming Springfield Home: 2 Mi to Downtown

10.0 out of 10, Exceptional, (18)
"We were in town for a couple days and really enjoyed our stay there. The house was nice and clean and convenient for downtown visits. "
Charming Springfield Home: 2 Mi to Downtown
Historic skatepark w/ Hot Tub located near Abe Lincoln's home!
Game room

Historic skatepark w/ Hot Tub located near Abe Lincoln's home!

9.0 out of 10, Wonderful, (7)
"This was perfect for us! Plenty of beds and space. Kids enjoyed the indoor skate park, pool table and hot tub. Great memories. Our host, George was just awesome. We hope to return next year!"
Historic skatepark w/ Hot Tub located near Abe Lincoln's home!
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 Middletown Hotel Reviews

Northfield Inn, Suites & Conference Center

Northfield Inn, Suites & Conference Center

10/10 Excellent
"Everything was fine "
Tom 1-night trip
Posted 10 hours ago
Northfield Inn, Suites & Conference Center