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Middletown Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
48 rentals in Middletown.
DJ Cozy 1bedroom, holiday rental in Middletown
DJ Cozy 1bedroom, holiday rental in Middletown
DJ Cozy 1bedroom, holiday rental in Middletown

DJ Cozy 1bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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This tiny house w/ in door and outdoor Fire Place is 15 min. from Lego Land, holiday rental in Middletown
This tiny house w/ in door and outdoor Fire Place is 15 min. from Lego Land, holiday rental in Middletown
This tiny house w/ in door and outdoor Fire Place is 15 min. from Lego Land, holiday rental in Middletown

This tiny house w/ in door and outdoor Fire Place is 15 min. from Lego Land

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sunshine Retreat: Cozy and Warm Studio, holiday rental in Middletown
Sunshine Retreat: Cozy and Warm Studio, holiday rental in Middletown
Sunshine Retreat: Cozy and Warm Studio, holiday rental in Middletown

Sunshine Retreat: Cozy and Warm Studio

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Chic Haven: Modern and Stylish and Cozy Ambiance, holiday rental in Middletown
Chic Haven: Modern and Stylish and Cozy Ambiance, holiday rental in Middletown
Chic Haven: Modern and Stylish and Cozy Ambiance, holiday rental in Middletown

Chic Haven: Modern and Stylish and Cozy Ambiance

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Haven: A Romantic Retreat in our Tiny House!, holiday rental in Middletown
Cozy Haven: A Romantic Retreat in our Tiny House!, holiday rental in Middletown
Cozy Haven: A Romantic Retreat in our Tiny House!, holiday rental in Middletown

Cozy Haven: A Romantic Retreat in our Tiny House!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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�Quiet country escape feet from easy Lake hike!, holiday rental in Middletown
�Quiet country escape feet from easy Lake hike!, holiday rental in Middletown
�Quiet country escape feet from easy Lake hike!, holiday rental in Middletown

�Quiet country escape feet from easy Lake hike!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury home with  private golf course and Tennis course is more then home, holiday rental in Middletown
Luxury home with  private golf course and Tennis course is more then home, holiday rental in Middletown
Luxury home with  private golf course and Tennis course is more then home, holiday rental in Middletown

Luxury home with private golf course and Tennis course is more then home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Elegant Town Home Middletown suburb close to city, holiday rental in Middletown
Elegant Town Home Middletown suburb close to city, holiday rental in Middletown
Elegant Town Home Middletown suburb close to city, holiday rental in Middletown

Elegant Town Home Middletown suburb close to city

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Madison Lodge - Port Jervis, Hudson River, holiday rental in Middletown
Madison Lodge - Port Jervis, Hudson River, holiday rental in Middletown
Madison Lodge - Port Jervis, Hudson River, holiday rental in Middletown

Madison Lodge - Port Jervis, Hudson River

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wawayanda Lodge - Port Jervis, Hudson River, holiday rental in Middletown
Wawayanda Lodge - Port Jervis, Hudson River, holiday rental in Middletown
Wawayanda Lodge - Port Jervis, Hudson River, holiday rental in Middletown

Wawayanda Lodge - Port Jervis, Hudson River

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Huge 6Br Suits, 8.55Bth & Indoor Pool at Goshen Vicinity NY, holiday rental in Middletown
Luxury Huge 6Br Suits, 8.55Bth & Indoor Pool at Goshen Vicinity NY, holiday rental in Middletown
Luxury Huge 6Br Suits, 8.55Bth & Indoor Pool at Goshen Vicinity NY, holiday rental in Middletown

Luxury Huge 6Br Suits, 8.55Bth & Indoor Pool at Goshen Vicinity NY

Holiday Rental House
6 bedrooms
9 bathrooms
Sleeps 10
Match: Sleeps
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The following properties within 20 miles of Middletown match all your filters:
Cozy Loft Cabin high above Bashakill Wildlife Refuge, holiday rental in Middletown
Cozy Loft Cabin high above Bashakill Wildlife Refuge, holiday rental in Middletown
Cozy Loft Cabin high above Bashakill Wildlife Refuge, holiday rental in Middletown

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Apartment in 120 year-old home with lots to offer, holiday rental in Middletown
Apartment in 120 year-old home with lots to offer, holiday rental in Middletown
Apartment in 120 year-old home with lots to offer, holiday rental in Middletown

Apartment in 120 year-old home with lots to offer

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Renovated Gorgeous Home in Goshen, holiday rental in Middletown
Newly Renovated Gorgeous Home in Goshen, holiday rental in Middletown
Newly Renovated Gorgeous Home in Goshen, holiday rental in Middletown

Newly Renovated Gorgeous Home in Goshen

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New! Updated Hudson Valley Farmhouse near Legoland and more, holiday rental in Middletown
New! Updated Hudson Valley Farmhouse near Legoland and more, holiday rental in Middletown
New! Updated Hudson Valley Farmhouse near Legoland and more, holiday rental in Middletown

New! Updated Hudson Valley Farmhouse near Legoland and more

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic Hudson Valley Farm House, holiday rental in Middletown
Historic Hudson Valley Farm House, holiday rental in Middletown
Historic Hudson Valley Farm House, holiday rental in Middletown

Historic Hudson Valley Farm House

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Hay Loft in Historic Barn - 4 Minutes to Legoland / Racetrack Views, holiday rental in Middletown
Hay Loft in Historic Barn - 4 Minutes to Legoland / Racetrack Views, holiday rental in Middletown
Hay Loft in Historic Barn - 4 Minutes to Legoland / Racetrack Views, holiday rental in Middletown

Hay Loft in Historic Barn - 4 Minutes to Legoland / Racetrack Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic Barn 2 Bedroom Apartment - 4 Minutes from Legoland NY / Racetrack View, holiday rental in Middletown
Historic Barn 2 Bedroom Apartment - 4 Minutes from Legoland NY / Racetrack View, holiday rental in Middletown
Historic Barn 2 Bedroom Apartment - 4 Minutes from Legoland NY / Racetrack View, holiday rental in Middletown

Historic Barn 2 Bedroom Apartment - 4 Minutes from Legoland NY / Racetrack View

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Route 66 - Glamping experience in Middletown NY, holiday rental in Middletown
Route 66 - Glamping experience in Middletown NY, holiday rental in Middletown
Route 66 - Glamping experience in Middletown NY, holiday rental in Middletown

Route 66 - Glamping experience in Middletown NY

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
More info
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Woodsie - best glamping experience Middletown ny, holiday rental in Middletown
Woodsie - best glamping experience Middletown ny, holiday rental in Middletown
Woodsie - best glamping experience Middletown ny, holiday rental in Middletown

Woodsie - best glamping experience Middletown ny

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Chelsea - Beautiful Middletown Glamping experience, holiday rental in Middletown
Chelsea - Beautiful Middletown Glamping experience, holiday rental in Middletown
Chelsea - Beautiful Middletown Glamping experience, holiday rental in Middletown

Chelsea - Beautiful Middletown Glamping experience

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
More info
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the Tent at Dunhill Pond, holiday rental in Middletown
the Tent at Dunhill Pond, holiday rental in Middletown
the Tent at Dunhill Pond, holiday rental in Middletown

the Tent at Dunhill Pond

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Sunshine- -Best glamping experience, Middletown ny, holiday rental in Middletown
Sunshine- -Best glamping experience, Middletown ny, holiday rental in Middletown
Sunshine- -Best glamping experience, Middletown ny, holiday rental in Middletown

Sunshine- -Best glamping experience, Middletown ny

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Victor-amazing glamping experience-Middletown NY, holiday rental in Middletown
Victor-amazing glamping experience-Middletown NY, holiday rental in Middletown
Victor-amazing glamping experience-Middletown NY, holiday rental in Middletown

Victor-amazing glamping experience-Middletown NY

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Studio apartment close to Catskill hiking trails and NYC, holiday rental in Middletown
Studio apartment close to Catskill hiking trails and NYC, holiday rental in Middletown
Studio apartment close to Catskill hiking trails and NYC, holiday rental in Middletown

Studio apartment close to Catskill hiking trails and NYC

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Bliss - beautiful Glamping experience in Middletown, NY, holiday rental in Middletown
Bliss - beautiful Glamping experience in Middletown, NY, holiday rental in Middletown
Bliss - beautiful Glamping experience in Middletown, NY, holiday rental in Middletown

Bliss - beautiful Glamping experience in Middletown, NY

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes, holiday rental in Middletown
⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes, holiday rental in Middletown
⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes, holiday rental in Middletown

⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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the Guest Suite at Dunhill Pond, holiday rental in Middletown
the Guest Suite at Dunhill Pond, holiday rental in Middletown
the Guest Suite at Dunhill Pond, holiday rental in Middletown

the Guest Suite at Dunhill Pond

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Waterlily-Best glamping experience, Middletown ny, holiday rental in Middletown
Waterlily-Best glamping experience, Middletown ny, holiday rental in Middletown
Waterlily-Best glamping experience, Middletown ny, holiday rental in Middletown

Waterlily-Best glamping experience, Middletown ny

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Relaxing Farm Cottage Escape, 10 Min from LEGOLAND, holiday rental in Middletown
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND, holiday rental in Middletown
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND, holiday rental in Middletown

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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The Goshen Getaways, holiday rental in Middletown
The Goshen Getaways, holiday rental in Middletown
The Goshen Getaways, holiday rental in Middletown

The Goshen Getaways

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Affiliated with FlipKey
Beautiful Log Cabin Style House, holiday rental in Middletown
Beautiful Log Cabin Style House, holiday rental in Middletown
Beautiful Log Cabin Style House, holiday rental in Middletown

Beautiful Log Cabin Style House

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
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The Great Goshen Getaway, holiday rental in Middletown
The Great Goshen Getaway, holiday rental in Middletown
The Great Goshen Getaway, holiday rental in Middletown

The Great Goshen Getaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful, relaxing 3 bedrooms. Entire house in the Catskill NY area, holiday rental in Middletown
Peaceful, relaxing 3 bedrooms. Entire house in the Catskill NY area, holiday rental in Middletown
Peaceful, relaxing 3 bedrooms. Entire house in the Catskill NY area, holiday rental in Middletown

Peaceful, relaxing 3 bedrooms. Entire house in the Catskill NY area

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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CHARMING  BOHO-STYLE COTTAGE IN MIDDLETOWN NY, holiday rental in Middletown
CHARMING  BOHO-STYLE COTTAGE IN MIDDLETOWN NY, holiday rental in Middletown
CHARMING  BOHO-STYLE COTTAGE IN MIDDLETOWN NY, holiday rental in Middletown

CHARMING BOHO-STYLE COTTAGE IN MIDDLETOWN NY

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Quaint country house nestled in the woods, holiday rental in Middletown
Quaint country house nestled in the woods, holiday rental in Middletown
Quaint country house nestled in the woods, holiday rental in Middletown

Quaint country house nestled in the woods

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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TheGoshenGetawaysHeatedPoolHotTubPetFriendly, holiday rental in Middletown
TheGoshenGetawaysHeatedPoolHotTubPetFriendly, holiday rental in Middletown
TheGoshenGetawaysHeatedPoolHotTubPetFriendly, holiday rental in Middletown

TheGoshenGetawaysHeatedPoolHotTubPetFriendly

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Goshe Farmhouse Legoland NY, holiday rental in Middletown
Goshe Farmhouse Legoland NY, holiday rental in Middletown
Goshe Farmhouse Legoland NY, holiday rental in Middletown

Goshe Farmhouse Legoland NY

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard, holiday rental in Middletown
Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard, holiday rental in Middletown
Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard, holiday rental in Middletown

Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Wawayanda House on 62 Acres - Multiple Fireplaces!, holiday rental in Middletown
Wawayanda House on 62 Acres - Multiple Fireplaces!, holiday rental in Middletown
Wawayanda House on 62 Acres - Multiple Fireplaces!, holiday rental in Middletown

Wawayanda House on 62 Acres - Multiple Fireplaces!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Goshen Renovated 5 Bedroom Country Home, holiday rental in Middletown
Goshen Renovated 5 Bedroom Country Home, holiday rental in Middletown
Goshen Renovated 5 Bedroom Country Home, holiday rental in Middletown

Goshen Renovated 5 Bedroom Country Home

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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PRISCILLA'S HOMESTEAD: Private Estate with Pool/Tennis/FirePit, holiday rental in Middletown
PRISCILLA'S HOMESTEAD: Private Estate with Pool/Tennis/FirePit, holiday rental in Middletown
PRISCILLA'S HOMESTEAD: Private Estate with Pool/Tennis/FirePit, holiday rental in Middletown

PRISCILLA'S HOMESTEAD: Private Estate with Pool/Tennis/FirePit

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Unique Dutch Barn in the Hudson Valley, holiday rental in Middletown
Unique Dutch Barn in the Hudson Valley, holiday rental in Middletown
Unique Dutch Barn in the Hudson Valley, holiday rental in Middletown

Unique Dutch Barn in the Hudson Valley

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Historic School House W/ Heated Pool - 1HR from NYC, holiday rental in Middletown
Historic School House W/ Heated Pool - 1HR from NYC, holiday rental in Middletown
Historic School House W/ Heated Pool - 1HR from NYC, holiday rental in Middletown

Historic School House W/ Heated Pool - 1HR from NYC

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Perfect up to date Private Getaway to call home for a while, holiday rental in Middletown
The Perfect up to date Private Getaway to call home for a while, holiday rental in Middletown
The Perfect up to date Private Getaway to call home for a while, holiday rental in Middletown

The Perfect up to date Private Getaway to call home for a while

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
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Beautiful Farm House, 30 acres private estate with pool, holiday rental in Middletown
Beautiful Farm House, 30 acres private estate with pool, holiday rental in Middletown
Beautiful Farm House, 30 acres private estate with pool, holiday rental in Middletown

Beautiful Farm House, 30 acres private estate with pool

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Mountain Villa ▪︎ Serene Nature ▪︎ 6 BR, holiday rental in Middletown
Mountain Villa ▪︎ Serene Nature ▪︎ 6 BR, holiday rental in Middletown
Mountain Villa ▪︎ Serene Nature ▪︎ 6 BR, holiday rental in Middletown

Mountain Villa ▪︎ Serene Nature ▪︎ 6 BR

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Mesmerizing and Luxurious Home, holiday rental in Middletown
Mesmerizing and Luxurious Home, holiday rental in Middletown
Mesmerizing and Luxurious Home, holiday rental in Middletown

Mesmerizing and Luxurious Home

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Frequently Asked Questions about Middletown