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Holiday houses in Middletown

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Quick stats about holiday rentals in Middletown

  • Total holiday rentals

    Explore 30 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at $72 AUD per night before taxes and fees

  • Verified guest reviews

    Over 290 verified reviews to help you choose

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Middletown holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Middletown rentals

Top-rated holiday rentals in Middletown

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

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Top Guest favourite
Place to stay in Warwick
4.96 out of 5 average rating, 374 reviews

Luxe Penthouse Studio MainSt Warwick, SteamShower!

Relax & Indulge in our Luxe Penthouse Studio with Elevator & Parking! Beautifully furnished on Main St. in Warwick- Walk to Everything! Panoramic windows with amazing views over Warwick. Spa steam shower with bluetooth speakers, luxury bath toiletries, Heavenly King bed with Egyptian cotton linens, 65 in. HD Smart TV, reclining leather theater seats, velvet loungers convert into sleepers, fully stocked designer kitchen with all appliances, Nespresso & Keurig, coffee, tea, bottled water included.

Top Guest favourite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick
4.99 out of 5 average rating, 128 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Top Guest favourite
A spacious living area features large glass doors that bring in natural light and provide views of the outdoors. Comfortable seating includes a modern sofa and armchair, accompanied by a coffee table and a dining area positioned nearby.
Chalet in Pine Bush
4.98 out of 5 average rating, 133 reviews

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

Top Guest favourite
A charming two-story cottage is surrounded by vibrant landscaping, featuring a mix of colorful flowers. The exterior is painted in green with maroon shutters adorning the windows. A wooden staircase leads to the upper entrance, while a welcoming front door is accented by a small planter.
Guest suite in Montgomery
4.94 out of 5 average rating, 567 reviews

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

Top Guest favourite
A serene outdoor seating area features two wooden chairs positioned beside a stone platform. A fire pit with a crackling flame is set in front of the chairs, overlooking a gently flowing creek and lush greenery, creating a tranquil nature retreat.
Cabin in Millrift
4.98 out of 5 average rating, 280 reviews

Remote Waterfall Cabin at Swiftwater Acres

Deep in a lush oak forest, on the bank of Bushkill Creek sits this hidden oasis. This is simply THEE most private abode in the entire area. Situated just feet from the water, the falls can be seen and heard from every room within the cabin’s charming, rustic interior. This spectacular 45 acre parcel is set within a vast reserve of state land: an oasis within an oasis. Just 90 minutes from NYC, this is a truly sublime atmosphere, perfect for those seeking a rejuvenating and inspiring getaway.

Guest favourite
A scenic pathway leads towards a charming log cabin, surrounded by a natural landscape of trees and grass. The cabin features a sloped roof and large windows, offering a welcoming appearance. A gravel area is visible in the background, enhancing the rustic setting.
Home in Bloomingburg
4.9 out of 5 average rating, 102 reviews

Quiet Homey Rustic Retreat

"Escape to the perfect blend of tranquility and excitement! This charming 3-bedroom log cabin, just 120 minutes from the hustle and bustle of New York City, offers the ideal retreat. Nestled 15 minutes from Resort Casino, 10 minutes from the vibrant Middletown shopping area, and a short drive to Woodbury Commons, Warwick, and Robberio Winery. Plus, family fun awaits just 20 minutes away at Lego Land. Your rustic haven awaits, where city convenience meets the serenity of a log cabin retreat!"

Top Guest favourite
Home in Godeffroy
5 out of 5 average rating, 11 reviews

1860 Schoolhouse: A luxury retreat (Hot Tub, BBQ)

Welcome to the 1860 Schoolhouse, a storied getaway set amidst the tranquility of nature. Built in 1860, it served as a place of education through the civil war era. It was remodeled in 2003 with all the modern comfort, while still preserving the historic rustic charm. A perfect countryside retreat awaits with amenities like hot tub, fire pit, outdoor movies, wood stove, high-end kitchen ware, L'Occitane toiletries, hotel-quality linens, and BBQ grill. Come ring the school bell in the house!

Guest favourite
A cozy living area is showcased with two accent chairs, one in a warm terracotta tone and another in vibrant red, featuring a playful design. The wooden floor complements the inviting atmosphere, while framed artwork adorns the walls, adding visual interest to the space.
Guest suite in Chester
4.94 out of 5 average rating, 386 reviews

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–6 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

Guest favourite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.98 out of 5 average rating, 385 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Guest favourite
The cottage is surrounded by lush green grass and mature trees, offering a serene outdoor setting. A well-maintained pathway leads to the inviting entrance, while the structure features light-colored siding and large windows, creating a seamless connection with nature.
Cottage in Goshen
4.91 out of 5 average rating, 326 reviews

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.

Guest favourite
A spacious living area highlights a brown leather sectional sofa, accompanied by two wooden coffee tables with decorative inlays. A dining area is visible in the background, featuring a wooden table and chairs. Natural light fills the room through large windows under a vaulted ceiling.
Home in Middletown
4.91 out of 5 average rating, 85 reviews

Historic Meets Modern 1900 Farmhouse Plus

Enjoy rest and relaxation in this historic 120 year old farm house. This house has all the character of a historic home lovingly renovated and updated. A modern living room addition features a cathedral ceiling and access to two separate decks. One is for sun and open air, another shaded with a mature wisteria over the pergola. The house is surrounded by lush gardens. Plenty of space to reconnect with family and friends or just enjoy a rest after a day of local activities.

Top Guest favourite
A red house is surrounded by vibrant autumn foliage, highlighting orange and yellow leaves on trees. A gravel path leads to the home, with two chairs visible in the outdoor seating area. Natural landscaping complements the serene wooded setting.
Home in Middletown
4.98 out of 5 average rating, 215 reviews

Peace and quiet. Comfy, private house to relax in

Quiet property,almost 8 acres, of beautiful wooded property . Set back from the road. Many trails, wineries and breweries nearby. Legoland is 20 minutes away and many antique shops within 30 minutes or so. We live in the other house on the property, so we are accessible. You can take a stroll on the path by the stream or sit on the spacious 35 x 10 foot deck and enjoy the natural setting of the property. Fire pit is now available. Enjoy the night air and gaze at the stars.

Popular amenities for Middletown holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Middletown

Top Guest favourite
Apartment in Montgomery
4.95 out of 5 average rating, 20 reviews

Cozy studio apartment with everything you need!

Guest favourite
A circular stone patio surrounds a central fire pit, featuring six red Adirondack chairs. The modern house with a welcoming entrance is partially obscured by lush green trees in the background, creating a natural and serene environment.
Home in Montgomery
4.95 out of 5 average rating, 128 reviews

Modern Woodland Retreat, Hudson Valley & Catskills

Superhost
Home in Montgomery

Treehouse-Inspired Cabin Escape w/ Theatre & Gym

Guest favourite
Apartment in Pine Bush
4.91 out of 5 average rating, 33 reviews

Explore and Relax On The Knoll

Superhost
A welcoming countryside retreat is showcased, featuring a two-car garage at the front. The surrounding area is filled with lush green trees and a well-maintained lawn that creates a serene atmosphere. A long driveway leads up to the entrance of the home.
Home in Bloomingburg
4.69 out of 5 average rating, 13 reviews

Blooming Bnb (close to Lego land &much more)

Guest favourite
A serene outdoor space features a private pool surrounded by a well-maintained garden. A koi pond with lily pads adds tranquility, while lounge chairs provide comfortable seating. Lush greenery and colorful shrubs create a peaceful atmosphere, perfect for relaxation and enjoying nature.
Home in Montgomery
4.91 out of 5 average rating, 46 reviews

Serene Hudson Valley Escape Hottub/Pool/King Suite

Guest favourite
A charming two-story house is surrounded by greenery, featuring a welcoming porch with railings and several columns. A brick path leads to the front steps, while large windows allow natural light to fill the rooms. The roof exhibits a distinct design detail at the peak.
Home in Wurtsboro
5 out of 5 average rating, 12 reviews

Casa Bashakill

Top Guest favourite
A striking red barn-style building is framed by lush greenery and a well-maintained stone wall. The entrance features double garage doors, complementing the rustic charm. Soft ornamental grasses and flowering plants add a touch of color to the exterior.
Barn in Montgomery
4.98 out of 5 average rating, 41 reviews

16taft

When is the best time to visit Middletown?

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Avg. price$125 AUD$135 AUD$134 AUD$89 AUD$108 AUD$145 AUD$145 AUD$145 AUD$145 AUD$140 AUD$135 AUD$148 AUD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Middletown?

    Stays around downtown Middletown and nearby residential neighborhoods are frequently suggested for easy access to restaurants, shops, and cultural sites. Many rentals have space for groups or families and often provide convenient amenities.

  • What are the best things to do in Middletown with kids?

    Families can explore local parks, discover hands-on activities at interactive museums, or enjoy playgrounds and seasonal sports facilities. Movie theaters and nearby nature centers are also frequently suggested for children.

  • What are some of the best things to do in Middletown?

    Wander downtown shops and galleries, catch a show at the Paramount Theatre, or enjoy outdoor recreation at local parks. Farmers markets and food festivals help visitors connect with regional flavors throughout the year.

  • How is the weather in Middletown?

    Middletown experiences cold winters near 16–35°F (−9–1°C) and warm, humid summers reaching 59–82°F (15–28°C). Expect rain throughout the year and bring layers, as temperatures can shift with the seasons.

  • When is the best time to visit Middletown?

    Late spring through early autumn is often recommended for milder weather, local fairs, and outdoor events. Winter has a festive atmosphere but colder temperatures, so pack accordingly if visiting then.

  • What are the best places to visit in Middletown?

    Middletown has arts centers, historic downtown streets, and family parks that are often recommended by visitors. The Paramount Theatre and nearby museums feature local culture and entertainment throughout the year.

  • What are some hiking trails in Middletown?

    Explore walking paths in Fancher-Davidge Park or the Heritage Trail, both known for nature views and gentle terrain. For broader experiences, nearby preserves often feature wooded trails and opportunities for birdwatching.

  • What are some family activities we can do in Middletown?

    You can enjoy picnics or open spaces at local parks, attend community events in town, or try bowling and mini golf venues. Throughout the year, Middletown hosts family-friendly performances and cultural programs.

  • What are some of the best day trip ideas from Middletown?

    Day trips from Middletown often include visits to local orchards, nearby wineries, or state parks known for hiking and scenic views. Exploring museums or cultural sites in surrounding towns is also frequently suggested.

  • Are there any pet friendly accommodations available in Middletown?

    Many accommodations in Middletown welcome pets, especially in residential neighborhoods and around green spaces. Park areas and walkable streets make it convenient to explore with dogs.

  • What are some local tips for visiting Middletown?

    Arrive early for local events or farmers markets, as parking can fill up quickly. Explore the arts scene and ask residents for favorite eateries, as many family-run spots are known for standout regional dishes.

  • What is Middletown known for?

    Middletown is known for its historic downtown, community events, and the Paramount Theatre, which highlights local arts and entertainment. It also has a tradition of welcoming farmers markets and seasonal festivals.

  • What are the best hidden gems to explore in Middletown?

    Middletown has independent art galleries, historic architecture along side streets, and local bakeries popular with residents. Tucked-away parks and seasonal events provide quieter ways to experience the community.

  • What are the best foods to try in Middletown?

    Middletown has pizzerias with New York-style pies, diners serving classic American fare, and delis known for hearty sandwiches. Many local spots also prepare bagels, Italian dishes, and baked treats that reflect the region's diverse influences.

  • What should I bring for a trip to Middletown?

    Pack layers for shifting temperatures, as Middletown has warm summers, cool evenings, and cold winters. Comfortable walking shoes and a rain jacket are handy year-round, and in winter, hats and gloves are often helpful.

  • What is the nightlife in Middletown like?

    Middletown has a relaxed nightlife scene with neighborhood taverns, live music at historic venues, and casual late-night eateries. Locals often gather for events at the Paramount Theatre or enjoy conversation at downtown lounges.

  • What are the most popular events or festivals in Middletown?

    Middletown hosts street fairs in the warmer months, annual parades, and cultural festivals that bring together local vendors and live music. The Paramount Theatre features touring shows and film screenings throughout the year.

  • Are there family friendly vacation rentals in Middletown?

    Middletown has a variety of family-friendly vacation rentals, especially near parks and central neighborhoods. Many offer kitchens, multiple bedrooms, and outdoor spaces suited for group gatherings.

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