Holiday rentals in Middletown
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Middletown
Guests agree: these stays are highly rated for location, cleanliness and more.
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.
Mindful Escape: Theater, Trails, Wood Stove
Exhale and recharge in this luxurious space at the foot of the Shawangunk Mountains. This gem features an open-concept kitchen and living room, perfect for connecting with nature. Enjoy the high-end Foster Leather Sofa, cozy movie nights on a 120" projector screen, and a wood-burning stove for chilly evenings. Every detail, from fresh linens to a meaningful library, is thoughtfully curated. Discover hidden messages throughout the house, inviting you to explore and unwind in this serene retreat.
Historic Stunner w/WasherDryer, Balcony, 2 bedroom
Our cozy historical 2 bedroom apartment with river views, two porches, and modern upgrades is just what you need for a delightful getaway or focused work-cation. We've preserved historical charms (hardwood floors, historical trim, retro fixtures) while adding in modern amenities (washer/dryer, dishwasher, stylish bathroom, new kitchen, electric car charger, etc!). Less than a mile from the Newburgh-Beacon Ferry launch, which connects you to Metro North Train. Note: Located on the second floor!
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
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
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.
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.
Forest Spa Retreat on Cascading Brook • 90 Min NYC
Tucked into an evergreen forest, The Water House is a private spa retreat set above a cascading brook—where flowing water shapes your stay. Spend slow mornings on the deck, unwind in the hot tub, and gather by the fire pit under the stars. Find a quiet moment beside the Japanese-inspired pond. Inside, soft textures and vintage style create a warm, calming atmosphere designed to reconnect you with nature while offering the restful comfort of a boutique retreat.
The Pullman Cottage NYC Escape • Dogs Stay Free
Discover a warm and charming two-bedroom retreat in the heart of the Village of Montgomery. Guests love the home’s cozy, lived-in comfort and unbeatable walkability to shops, restaurants, and bars. Perfectly situated near top wedding venues—The Venue at Winding Hills and City Winery—and centrally located between the JW World Headquarters and Bethels. Just 90 minutes from NYC, it’s an ideal Hudson Valley escape for relaxation, celebration, or a peaceful getaway.
The Treecastle at the Roundhouse Homestead
The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill
Popular amenities for Middletown holiday rentals
Other great holiday rentals in Middletown
Hudson Valley Modern Apartment. King Bed/Queen
The Alexandria - Wurstboro, NY
Cabin96-Shawangunk Mountain View
Sauna - Pool table - Foosball - Arcade - Grill
Blooming Bnb (close to Lego land &much more)
16taft
Casa Bashakill
The Columbus Hotel | The City Suite | 89-201
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €75 | €81 | €80 | €53 | €65 | €87 | €87 | €87 | €87 | €84 | €81 | €89 |
| 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 holiday rentals in Middletown
Total holiday rentals
Explore 40 holiday rentals in Middletown
Nightly prices starting at
Middletown holiday rentals start at €34 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 holiday 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
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Boston Holiday rentals
- Pittsburgh Holiday rentals
- Ocean City Holiday rentals
- Niagara Falls Holiday rentals
- Newark Holiday rentals
- Jersey City Holiday rentals
- Baltimore Holiday rentals
- Portland Holiday rentals
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- American Dream
- Bethel Woods Center for the Arts
- Bushkill Falls
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Delaware Water Gap National Recreation Area
- Resorts World Catskills
- Promised Land State Park
- Nickelodeon Universe
- Brotherhood, America's Oldest Winery
- Mohonk Preserve
- Mount Peter Ski Area
- Walkway Over the Hudson State Historic Park
- Storm King Art Center
- Wawayanda State Park
- Shawnee Mountain Ski Area
- SoJo Spa Club
- Woodloch Resort
- Paterson Great Falls National Historical Park