Search Vacation Homes in Middletown

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Vacation Homes in Middletown

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!"
$248 nightly
The price is $250
Aug 19 - Aug 20
Total includes taxes and fees
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
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)
"Great place to stay ! The home was clean, cozy, and had everything you could need from the multiple charging cubes to bathroom and kitchen essentials. If you appreciate antique furnishings this home has it. The backyard was nice and had cute pathways between the many trees and garden. Our dog loved all the smells too ! The host is quick to respond and easy going. Highly recommend ! "
Whitt’s End -- a spacious private lodging in a historic Springfield neighborhood
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
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."
$233 nightly
The price is $247
Aug 13 - Aug 14
Total includes taxes and fees
Modern Bungalow Home with Mid-Century Flair
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
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. "
$310 nightly
The price is $329
Aug 13 - Aug 14
Total includes taxes and fees
Wednesday’s Lair - Lincoln, Il
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."
$999 nightly
The price is $1,006
Aug 17 - Aug 18
Total includes taxes and fees
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
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!"
$136 nightly
The price is $144
Aug 18 - Aug 19
Total includes taxes and fees
Very Cozy and Secluded. Completely remodeled beautiful back apartment
Western Barn
Property grounds

Western Barn

9.6 out of 10, Exceptional, (7)
"As advertised."
Western Barn
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
The Pasfield House - Historic Mansion: The Bitsy
Outdoor dining

The Pasfield House - Historic Mansion: The Bitsy

$187 nightly
The price is $210
Aug 24 - Aug 25
Total includes taxes and fees
The Pasfield House - Historic Mansion: The Bitsy
Pasfield House Historic Mansion: The George Suite
Interior

Pasfield House Historic Mansion: The George Suite

10.0 out of 10, Exceptional, (1)
"Pasfield house is beautiful and was centrally located to the sightseeing we wanted to do. We would stay here again if we visit Springfield in the future."
$184 nightly
The price is $207
Sep 8 - Sep 9
Total includes taxes and fees
Pasfield House Historic Mansion: The George Suite
Gold Room at the Feitshans House
Exterior

Gold Room at the Feitshans House

8.8 out of 10, Excellent, (3)
"The home was relaxing and very pleasant. Also accessible to so many Springfield sites. We would definitely stay again."
Gold Room at the Feitshans House
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
New remodel three bedroom house in pleasant Springfield
Private kitchen

New remodel three bedroom house in pleasant Springfield

7.4 out of 10, Good, (11)
"Clean placeLet us grill outsideSpacious and comfy for what we needed"
$234 nightly
The price is $265
Aug 14 - Aug 15
Total includes taxes and fees
New remodel three bedroom house in pleasant Springfield
Blue Room at the Feitshans House
Exterior

Blue Room at the Feitshans House

10.0 out of 10, Exceptional, (1)
"The Blue Room at the Feitshans House was beautiful, elegant and very accomodating for our weekend stay in Springfield. It is centrally located to all the downtown historic activities and eateries are just a short drive in all directions. The home is tastefully decorated and has all the amenities one needs for a short or long term stay. We enjoyed the historical books and antiques throughout the home. It was easy to get in and out and parking is more than adequate. We had a wonderful stay in the...
$164 nightly
The price is $170
Aug 19 - Aug 20
Total includes taxes and fees
Blue Room at the Feitshans House
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. "
$214 nightly
The price is $238
Aug 14 - Aug 15
Total includes taxes and fees
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!
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!"
$255 nightly
The price is $257
Aug 19 - Aug 20
Total includes taxes and fees
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Pet friendly remodeled bungalow home just two blocks from Washington Park.
Outdoor dining

Pet friendly remodeled bungalow home just two blocks from Washington Park.

10.0 out of 10, Exceptional, (12)
"Perfect spot for our stay"
Pet friendly remodeled bungalow home just two blocks from Washington Park.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Travelodge by Wyndham Atlanta, Illinois

Travelodge by Wyndham Atlanta, Illinois

10/10 Excellent
"Clean room, friendly and helpful front desk staff."
Kaushika 1-night trip
Posted 1 day ago
Travelodge by Wyndham Atlanta, Illinois