Middletown holiday homes

We found 2,441 holiday rentals — enter your dates for availability
Discover a selection of 11 homes, 23 apartments and other holiday rentals in Middletown that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Middletown

Showing deals for:8 Jan - 15 Jan

Bedroom # 1 with sink and mirror
Living area with fabulous stone wood burning fireplace, Great vintage furniture
Combined Rustic Living room and Dining room, all Knotty Pine Interior
Kitchen, fully furnished with dishes, utensils, cookware and wine glasses.
Exceptional
(44 reviews)

Creekside Knotty Pine 1930s Lodge on 575 Acre Forest Preserve

Milford

8% off
NZ$4,332
for 7 nights, 1 room
NZ$619 per night
includes taxes & fees
Creekside Knotty Pine 1930s Lodge on 575 Acre Forest Preserve
High ceilings and lake views in this gorgeous living room
Dining
Dining
Interior
Exceptional
(5 reviews)

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Monticello

15% off
NZ$6,335
for 7 nights, 1 chalet
NZ$905 per night
includes taxes & fees
Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
Exterior
Beautiful back deck
Master Bedroom
Living Room
Exceptional
(227 reviews)

HUGE discount this wknd! Escape to a BEAUTIFUL Secluded, Streamfront HOT TUB

Bushkill

8% off
NZ$3,151
for 7 nights, 1 home
NZ$450 per night
includes taxes & fees
HUGE discount this wknd! Escape to a BEAUTIFUL Secluded, Streamfront HOT TUB
Interior
Property grounds
Room
Bar (on property)
Exceptional
(58 reviews)

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Monticello

7% off
NZ$8,772
for 7 nights, 1 home
NZ$1,253 per night
includes taxes & fees
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Room
Living area
Terrace/patio
Interior
Exceptional
(17 reviews)

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen

8% off
NZ$2,384
for 7 nights, 1 cottage
NZ$341 per night
includes taxes & fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Living area
Living area
Room
Terrace/patio
Exceptional
(64 reviews)

Knotty Pine Cottage on 575 Acre Forest Preserve

Milford

8% off
NZ$2,866
for 7 nights, 1 cottage
NZ$409 per night
includes taxes & fees
Knotty Pine Cottage on 575 Acre Forest Preserve
Dining
Interior
Living area
Pool
Exceptional
(43 reviews)

Hemlock Estate: Indoor Hot Tub, Pool, Game Room; Spacious, Ski & More!

Monticello

7% off
NZ$7,996
for 7 nights, 1 villa
NZ$1,142 per night
includes taxes & fees
Hemlock Estate: Indoor Hot Tub, Pool, Game Room; Spacious, Ski & More!
Living area
Exterior
Room
Private kitchen
Exceptional
(11 reviews)

Cozy 1-bedroom cabin in amazing Milford with WiFi, AC next to stream.

Milford

8% off
NZ$2,769
for 7 nights, 1 cabin
NZ$396 per night
includes taxes & fees
Cozy 1-bedroom cabin in amazing Milford with WiFi, AC next to stream.
5 star ensuite bathroom with tub, hand shower, and rain shower.
450sqft of living space: super comfy kingsize bed (+ 2 optional twin beds)
Enjoy your private deck, lawn, firepit, and grill!
You are welcome to fish, swim, or paddleboard in our 2 acre pond
Exceptional
(26 reviews)

Luxury retreat w/ private deck, garden, firepit on organic farm

Gardiner

8% off
NZ$3,067
for 7 nights, 1 cabin
NZ$438 per night
includes taxes & fees
Luxury retreat w/ private deck, garden, firepit on organic farm
Bethel Lake House is setback on a private acre.
Peaceful & Quiet Winter Retreat. Enjoy a warm fire and view the iced over lake.
Stunning Fall views from our deck and dock. Many guests plan ahead for the Fall
A color picture of shades of black and white over an iced over lake. Peaceful
Exceptional
(207 reviews)

Relaxing Lakefront, Very Clean. Great for Families.

Smallwood

9% off
NZ$5,372
for 7 nights, 1 home
NZ$767 per night
includes taxes & fees
Relaxing Lakefront, Very Clean. Great for Families.
Dining Room looking into living room
Family room
Family Room
Kitchen
Exceptional
(28 reviews)

Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

Big Indian

8% off
NZ$10,762
for 7 nights, 1 chalet
NZ$1,537 per night
includes taxes & fees
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
Exterior
Property grounds
Sun-room with french doors
Bedroom 1, double bed
Exceptional
(41 reviews)

Waterfront property, perfect winter getaway, directly on the Willowemoc!

Livingston Manor

11% off
NZ$2,892
for 7 nights, 1 cabin
NZ$413 per night
includes taxes & fees
Waterfront property, perfect winter getaway, directly on the Willowemoc!
Family room with wood stove
Hot tub on the deck and open year round
Kitchen
Dining area
Excellent
(13 reviews)

Casa Nera | Heated Pool • Hot Tub • Ski

Swan Lake

15% off
NZ$5,931
for 7 nights, 1 home
NZ$847 per night
includes taxes & fees
Casa Nera | Heated Pool • Hot Tub • Ski
Exterior
Living area
Large living room area with lots of seating to gather around and create memories
Cook up a great meal in this luxurious kitchen with tons of space to entertain
Exceptional
(9 reviews)

Lake Front Home w/Dock, Kayak, Canoe Right On Lake Hopatcong w/AC Wifi Huge Deck

Lake Hopatcong

8% off
NZ$3,927
for 7 nights, 1 home
NZ$561 per night
includes taxes & fees
Lake Front Home w/Dock, Kayak, Canoe Right On Lake Hopatcong w/AC Wifi Huge Deck
Exterior
Living area
Outdoor dining
Property grounds
Exceptional
(9 reviews)

6 Acre Private Hudson Valley Estate

Highland

8% off
NZ$17,976
for 7 nights, 1 home
NZ$2,568 per night
includes taxes & fees
6 Acre Private Hudson Valley Estate
Living area
Outdoor dining
Interior
Exterior
Exceptional
(9 reviews)

Immerse in your private woods in our modern cabin

Livingston Manor

11% off
NZ$5,071
for 7 nights, 1 cabin
NZ$724 per night
includes taxes & fees
Immerse in your private woods in our modern cabin
Walk way to back yard from side of the house
View of the dining room
Hallway with pocket doors on main floor
Original mahogany wood work and French Chandliers though out the house
Exceptional
(18 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

20% off
NZ$10,124
for 7 nights, 1 home
NZ$1,446 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
French Doors leading to a veranda offer a wonderful connection to the outdoors, making it the perfect spot to start your day with a cup of morning coffee or tea.
Dining
A Special Place for Your Special Times! 4 bedroom, 3.5 baths, Full Kitchen, Kitchenette, 2 Living Areas, 2 Dining Areas, Full access to backyard with dining area, fire pit with adirondack chairs, BBQ grill, hammock on 2 acres of land.
A cozy bedroom boasts a unique charm with its stone wall and wide plank flooring. Queen size bed with luxury linens you'll find it hard to leave. For your comfort we installed a MiniSplit system for heating and AC. Creating warm ambiance to enjoy.
Exceptional
(27 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
NZ$5,178
for 7 nights, 1 home
NZ$740 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Interior
Private kitchen
Exterior
Outdoor dining
Exceptional
(13 reviews)

Spacious Westtown Home, Firepit, Up to 10 Guest

Westtown

8% off
NZ$4,422
for 7 nights, 1 home
NZ$632 per night
includes taxes & fees
Spacious Westtown Home, Firepit, Up to 10 Guest
This sitting area is another great space to gather around the faux fireplace.
George Washington was president when these original hardwood floors were made!
Our home sits on 5 partially-wooded acres. Welcome to the country!
Here's the spacious farmhouse kitchen. A leaf expands the table to seat 6.
Exceptional
(20 reviews)

Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres

Milton

16% off
NZ$4,488
for 7 nights, 1 home
NZ$641 per night
includes taxes & fees
Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
Interior
Outdoor dining
Exterior
Firewood for the fire pit.
Exceptional
(36 reviews)

Lakefront family friendly peaceful Catskills retreat!

Wurtsboro

8% off
NZ$6,237
for 7 nights, 1 home
NZ$891 per night
includes taxes & fees
Lakefront family friendly peaceful Catskills retreat!
Exterior detail
Pool
Private kitchen
Dining
Exceptional
(89 reviews)

Private Hilltop Getaway with Hot Tub & Seasonal Saltwater Heated Pool

Damascus

8% off
NZ$7,088
for 7 nights, 1 home
NZ$1,013 per night
includes taxes & fees
Private Hilltop Getaway with Hot Tub & Seasonal Saltwater Heated Pool
Interior
Dining
Outdoor dining
Living area
Exceptional
(8 reviews)

Dancing Doe Estate with Wood Stove, Hot Tub & Firepit

Jeffersonville

12% off
NZ$5,678
for 7 nights, 1 home
NZ$811 per night
includes taxes & fees
Dancing Doe Estate with Wood Stove, Hot Tub & Firepit
View of valley and lush evergreens. Queen bed. Spacious closet
Whip up delicious meals in the spacious, bright kitchen with ample counter space
Comfortably seats 8 and also doubles as a large board game table.
Settle into the many comfy seats in the Family Room.
Exceptional
(41 reviews)

Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Highland

8% off
NZ$7,755
for 7 nights, 1 home
NZ$1,108 per night
includes taxes & fees
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

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    Enjoy full kitchens, laundry, pools, gardens and more

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Head to the friendly city of Middletown

Enjoy the area's churches, architecture and festivals with a rental holiday home in Middletown. This welcoming city attracts visitors thanks to its shopping and restaurants. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Middletown

Are you searching for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Middletown has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Goshen Historic Track (6.1 mi / 9.8 km)
  • LEGOLAND® New York (7.5 mi / 12 km)
  • Warwick Valley Winery and Distillery (10.7 mi / 17.2 km)
  • Brotherhood Winery (13.5 mi / 21.7 km)
  • Mount Peter Ski Area (15.3 mi / 24.6 km)
  • Ice Time Sports Complex (17.2 mi / 27.6 km)

Exploring the natural features in Middletown

Whether you're an adventurous traveller or just want to appreciate the scenery, Middletown is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • The Rock Sports Complex (10.3 mi / 16.5 km)
  • Neversink River (13.4 mi / 21.6 km)
  • Lake Louise Marie (14.2 mi / 22.9 km)
  • Sam's Point Preserve (15.7 mi / 25.3 km)
  • Arrow Park Lake and Lodge (16.9 mi / 27.2 km)
  • Sterling Lake (18.6 mi / 29.9 km)

Travelling to and around Middletown

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 17.8 mi (28.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Middletown when booking a holiday rental?
When considering a holiday rental in Middletown, New York, the downtown area is an excellent choice. This vibrant neighbourhood offers a variety of properties, from charming apartments to spacious houses, suiting different preferences and group sizes. Staying downtown puts you within walking distance of some delightful attractions, such as the Paramount Theatre, which hosts a range of performances and events, and the nearby Galleria at Crystal Run, a popular shopping destination with numerous dining options.Another appealing area is the scenic Wallkill Valley, known for its picturesque views and outdoor activities. This neighbourhood features a selection of holiday rentals, great for those seeking a more tranquil escape. The nearby Wallkill River offers opportunities for kayaking and fishing, while the beautiful hiking trails in the region invite nature lovers to explore the stunning surroundings.
Where are the best Middletown ski resort rentals?
For skiing near Middletown, New York, the nearest ski areas are located in the nearby Catskill Mountains, specifically around resorts such as Mountain Creek and Belleayre. For holiday rentals, travellers should consider the quaint towns of Warwick and Vernon, which provide convenient access to these ski resorts.In Warwick, visitors can find charming cabins and modern chalets that often include amenities like hot tubs, fireplaces, and expansive decks superb for après-ski relaxation. Many properties in this area also feature fully equipped kitchens, allowing guests to prepare their own meals after a day on the slopes.In Vernon, you can explore cozy lodges and family-friendly hotels that cater to various group sizes, with features like game rooms and proximity to local shops and dining options. Some rentals even offer stunning views of the surrounding mountains, enhancing the overall experience.The region around Middletown is not only great for skiing but also for outdoor enthusiasts, with opportunities for hiking and exploring in the warmer months. Properties in these towns often provide easy access to nature trails and scenic spots, making them ideal for year-round getaways.
What is the most popular type of holiday rental accomodation in Middletown?
In Middletown, holiday houses are the most popular type of holiday rental, with around 32 available across the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many also offer outdoor spaces for relaxation and gatherings. Additionally, there are approximately 24 campsites for those looking for a more adventurous stay, providing a great experience amidst nature. Cottages are another option, with about 12 available, typically offering a quaint and cosy atmosphere. While cabins and villas are less common, several can still be found, appealing to those seeking a rustic or luxurious retreat.
Are there any family house rentals in Middletown?
In Middletown, New York, there are some family-friendly house rentals available, with around 14 options to choose from. Visitors can find accommodations in various neighbourhoods, offering spacious living areas ideal for gatherings and comfortable family stays. Many properties come equipped with full kitchens, allowing for easy meal preparation, as well as amenities such as outdoor spaces where children can play.The town is conveniently located near attractions like the Wallkill River National Wildlife Refuge, which is superb for outdoor activities such as hiking and birdwatching. Families can also explore local parks and play areas that cater to children of all ages.
Can I rent a holiday home with a pool or hot tub in Middletown?
In Middletown, New York, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located in the scenic Hudson Valley, provides a variety of options for travellers seeking a relaxing getaway. Many properties in the area come equipped with private pools and hot tubs, superb for unwinding after a day of exploring.Visitors can expect amenities such as spacious outdoor areas, fully equipped kitchens for home-cooked meals, and comfortable living spaces designed for families or groups.
Are there pet-friendly house rentals in Middletown?
In Middletown, New York, there are ten pet-friendly house rentals available, providing a variety of options for travellers with furry companions. Many of these properties feature comfortable amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces where pets can roam. The rentals often come with essentials like Wi-Fi, air conditioning, and laundry facilities, ensuring a convenient stay for families or groups.The surrounding area offers several parks that are superb for enjoying time outdoors with pets. For example, the nearby Fancher-Davidge Park features walking trails and open spaces, allowing for leisurely strolls and playtime. Additionally, the scenic Wallkill River provides opportunities for walking along the riverbanks, making it a delightful spot for pet owners.
Are there any remote work holiday rentals in Middletown?
In Middletown, New York, there are around 60 holiday rentals available that are suitable for remote work. This charming city offers a range of accommodations equipped with essential amenities for a productive stay. Many properties feature free Wi-Fi, ensuring that guests can stay connected, and are designed with comfortable workspaces or desks in the rooms.The area also boasts numerous points of interest, such as the scenic parks and outdoor spaces ideal for taking breaks or enjoying fresh air during work hours. Additionally, the proximity to local cafes and restaurants adds convenience for meals or a change of scenery from the home office. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Middletown?
In Middletown, popular holiday rental amenities include kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoying the fresh air. Additionally, pet-friendly options are available, permitting guests to bring their furry companions along, while some rentals accommodate service animals. Onsite parking is another amenity commonly found, ensuring guests have convenient access to their vehicles.
When is the best time to visit Middletown for a holiday rental?
The best time to visit Middletown for a holiday rental is during the peak season from June to August. This vibrant period attracts families and outdoor enthusiasts looking to enjoy the warm summer weather. With temperatures ranging from 20 to 30 degrees Celsius, it's ideal for exploring the scenic beauty of the Hudson Valley, participating in outdoor activities, and enjoying local events.July is particularly popular, offering a lively option filled with festivals, farmers' markets, and opportunities for hiking in the nearby Catskill Mountains. Visitors can experience firsthand the rich cultural scene, dine at local eateries, and relish the charm of Middletown's historic downtown.For those seeking a more budget-friendly experience, consider visiting in December. While this falls outside the main tourist season, it offers a unique opportunity to enjoy the festive atmosphere, including holiday decorations and events that create a warm and welcoming environment.Ultimately, the best time to book your holiday rental in Middletown hinges on whether you prefer the bustling summer activities or the quieter, cosy charm of winter festivities.
What are the top attractions in Middletown?
Middletown, New York, offers a variety of attractions that highlight its charm and natural beauty. One of the main draws is the Hudson Valley, which surrounds the area and provides stunning landscapes, great for outdoor activities such as hiking and biking. Nearby, the scenic Wawayanda State Park features numerous trails and a lovely lake for swimming and picnicking.In the heart of Middletown, visitors can explore the vibrant downtown area, which boasts a mix of shops, restaurants, and the historic Paramount Theatre, known for hosting a range of performances and events. The nearby Galleria at Crystal Run is a popular shopping destination with various retail outlets and dining options.For those interested in history, the Orange County Fairgrounds often hosts events and fairs throughout the year, while the nearby city of Newburgh, just a short drive away, offers historic sites and beautiful riverfront parks along the Hudson River.
Are all fees included in the Middletown holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Middletown holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Middletown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Middletown holiday homes?
You can find great discounts on holiday homes in Middletown on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Middletown holiday home booking on Bookabach?
To find Middletown holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Middletown?
A long-stay holiday home in Middletown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Middletown holiday home?
Book your Middletown holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Middletown?
Prices for holiday homes in Middletown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Middletown to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.