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Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest suite in Montgomery
Garden View Guest Cottage
Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people
7–14 Dec, Individual Host
£110 per night
Guest favourite
Tiny home in Montgomery
The Trek by 127 Cabin Co.
Take a break from your day to day and enjoy this serene and unique escape. The Trek is a brand NEW custom built and designed cabin nestled in the heart of the Hudson Valley! It is a high class, off-the-grid experience. Come and snuggle up in a cozy cabin watching your favorite movie, reading a book or enjoy a night under the stars around the fire pit. The Trek is a great place to escape the busy. Minutes from cafes, shops and more. PLEASE NOTE this cabin does not have running water in Nov-Aprl.
11–18 Mar
£146 per night
Guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.
15–22 Oct, Individual Host
£123 per night

Popular amenities for Middletown holiday rentals

Stay near Middletown's top sights

Orange County Fair Speedway9 locals recommend
IHOP4 locals recommend
ShopRite of Middletown12 locals recommend
ALDI3 locals recommend
DeStefano's Olde Erie3 locals recommend
Saffron3 locals recommend

Other great holiday rentals in Middletown

Guest favourite
Cabin in Wurtsboro
Fall Spa Retreat on a Cascading Brook -WATER HOUSE
25 Sept – 2 Oct
£285 per night
Guest favourite
Guest house in Montgomery
Luxury mins from angry orchard and city winery
8–15 Nov
£137 per night
Guest favourite
Farm stay in Goshen
Bright Farm House- Tranquil setting
9–16 Mar, Individual Host
£188 per night
Guest favourite
Home in Rhinebeck
Architectural wonder in the woods
16–23 Jul, Individual Host
£461 per night
Guest favourite
Flat in Warwick
THE GEM: In The Heart Of It All!
25 Mar – 1 Apr, Individual Host
£107 per night
Guest favourite
Cottage in Greenwood Lake
Luxury Cottage with Spectacular Lake Views
7–14 Nov, Individual Host
£295 per night
Guest favourite
Cabin in Kerhonkson
Zink Cabin | Mountain Views w/ Hot Tub
30 Dec – 6 Jan, Professional Host
£413 per night
Guest favourite
Home in Pine Bush
Queen's Gate Est. 1820 Modern Farmhouse
27 Sept – 4 Oct, Individual Host
£139 per night
Apartment in Middletown
Chic Haven: Modern & Stylish and Cozy Ambiance
17–24 Nov
£90 per night
Guest favourite
Cottage in Middletown
⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes
8–15 Mar, Individual Host
£124 per night
Guest favourite
Home in Middletown
Adorable three bedroom Irish Cape Home.
29 Sept – 6 Oct
£170 per night
Guest favourite
Home in Middletown
Wawayanda Lodge - Port Jervis, Hudson River
5–12 Mar, Professional Host
£193 per night

Quick stats about holiday rentals in Middletown

Total rentals

50 properties

Wifi availability

50 properties include access to wifi

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.3K reviews

Nightly prices starting at

£24 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Orange County
  5. Middletown