Vacation rentals in Middletown
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Top-rated vacation rentals in Middletown
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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.
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.
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.
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
The Water House - Spring Spa on a Cascading Brook
The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and gas fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.
Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.
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.
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
Just Around The Corner
This roomy, modern and immaculate apartment is situated conveniently near town, but far enough away that you can enjoy the countryside. Enjoy the view of the pond and sounds of nature. A one bedroom that sleeps six with three queen beds in separate rooms divided by doors. (Please note the listing price is for 4 guests. Each additional guest is $25 per night). We are 6 min to Middletown, 18 min to Legoland, 21 min to Wallkill, 49 min to Warwick and just under one hour to Patterson, NY.
Special Nest w Private Entrance River View Porches
Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!
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.
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.
Popular amenities for Middletown vacation rentals
Other great vacation rentals in Middletown
Hudson Valley Log Cabin with Lake Access & View
Hudson Valley Modern Apartment. Village Center.
Modern Woodland Retreat, Hudson Valley & Catskills
The Alexandria - Wurstboro, NY
Great Small Barn
Lake trail retreat
Hike & Fish: Outdoor Retreat Near Trails
Near Legoland | Woodbury Commons | Hot Tub & Pool
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $120 CAD | $108 CAD | $98 CAD | $84 CAD | $102 CAD | $138 CAD | $138 CAD | $138 CAD | $138 CAD | $132 CAD | $128 CAD | $140 CAD |
| Avg. temp | -4 °C | -2 °C | 2 °C | 9 °C | 14 °C | 19 °C | 22 °C | 21 °C | 17 °C | 10 °C | 5 °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.
Quick stats about vacation rentals in Middletown
Total vacation rentals
Explore 40 vacation rentals in Middletown
Nightly prices starting at
Middletown vacation rentals start at $54 CAD per night before taxes and fees
Verified guest reviews
Over 600 verified reviews to help you choose
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
40 of Middletown vacation rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Middletown rentals
4.6 Average rating
Middletown stays receive an average rating of 4.6 out of 5 from guests
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