
Apartment vacation rentals in Middletown
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Quick stats about apartment rentals in Middletown

Total vacation rentals
Explore 20 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at ﺩ.ﺇ 367 per night before taxes and fees

Verified guest reviews
Over 240 verified reviews to help you choose

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Middletown vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middletown rentals
Top-rated apartment rentals in Middletown
Guests agree: these apartments are highly rated for location, cleanliness, and more.

Luxe Loft 4 on Main St- Views! Steam Shower! W/D
Welcome to Luxe Studio #4 right on Main Street in Beacon. This is your home base for exploring the beautiful Hudson Valley! Walk to Dia Museum, train, restaurants, shops, galleries, hiking-all at your doorstep! Relaxing, meticulously clean space designed for comfort and indulgence with everything you could need- unforgettable steam shower, full kitchen, washer & dryer. Queen bed with luxe hotel-quality linens. 50” Toshiba 4K Fire TV, hardwood flooring, spacious bathroom with window &toiletries

HOT Sauna/COLD Plunge- Mountains-Hiking-NYC Trains
Your SPA - Cedar Barrel HOT SAUNA - Outdoor Cozy updated 1814 Cold Spring Village Classic-NATIONAL Historic Register Close to West Point & Beacon Guest Jack's comments "This apartment gave me the feel that I had my own place in a beautiful river town" Mountain Views - Sunny (12+ Windows) 3 Bedroom Modern Garden Apartment (850+SF) Cozy for 1 to 6 #1 Coffees & Teas Walk to Waterfalls, Hiking Trails, River Beaches, NYC trains Restaurants & cafes Outdoor living space in Garden - birds

Chichito's Japanese Retreat
Inspired by our travels to Asia and our love for the zen aesthetic, we welcome you to our cozy 2nd floor apartment on a duplex. A great place to take some time to relax and recharge from the hustle and bustle of life. Nestled in 16 acres of nature. A 1.5 hr drive from New York City, on the intersection of New York, NJ and Pennsylvania and a five minute drive to our charming small town of Port Jervis. Every detail of this home was put together with love in hopes that you make of it your haven.

Great apartment- closest to Legoland
Large studio apartment in an historic luxury setting. Guests have a private entrance with parking to a first floor, fun studio. Our property boasts a private tennis/pickleball court for guest use and is situated directly on the Heritage Trail, which is perfect for biking and jogging. Our home borders several hundred acres of scenic rural property, yet we are conveniently located in the charming, historic Village of Goshen - within walking distance to restaurants and the Trotting Horse Museum

Carriage House Apartment Close to Legoland NY
Immerse yourself in history in our newly renovated Carriage House, originally a historic horse barn, ensconced with hand hewn, exposed beams. This unique accommodation boasts modern amenities such as central air conditioning, a cozy fireplace, private laundry, and a fully working kitchen. Situated just a 4-minute drive from the renowned Legoland and opposite the prestigious Goshen Historic Race Track, we are perfectly positioned for both convenience and entertainment. @parkwayhousegoshen

Modena Mad House
Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

Unwind in a Bespoke Downtown Studio W Laundry
A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Cliff Top at Turtle Rock
Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

Dream getaway apartment in the foot of Gunks Ridge
Beautifully decorated space full of original art located in the foot of Shawangunk Ridge on the side of a large farm field and a forest. Get together with friends at the handmade farm dining table, feel hygge next to a wood-fired place, enjoy nature tranquility, and recharge. We provide ALL you need: clean towels, cooking essentials, complimentary high-end loose tea /coffee, friendly atmosphere, and good local advice. Apartment is a half basement part of a house but has full privacy.

Newly Restored 2BR
Designer 2BR in historic 1870 brick building with shared backyard oasis (covered lounges, fire pit, creek views). Walk the scenic abandoned railway tracks alongside Fishkill Creek to Main Street and the Roundhouse waterfall in 10 min. Design by Hudson Valley fixture Simone Eisold and art by Guggenheim Fellowship winning photographer Amanda Means. Two dedicated parking spots. Ask about upgrading to the private patio with treetop hot tub & Mt. Beacon vistas! [Permit: 2024-0027-STR]

Warwick Village Apt w Off St Parking 2 GIG WIFI
2 minutes to Warwick Village Farmers Market Our lovely apartment has earned 5 star reviews from over 300 guests. You'll love this private suite w private entrance Large kitchen, bedroom & stunning sun room loaded with plants Loved by gardeners, bicyclists, runners, artists, writers, diners, & shoppers. Visit Brew Pubs & Wineries, Woodbury Common, West Point, Catskills, Mt Peter, Mountain Creek, Heated bathroom floor & large shower Beautiful gas stove 300 MBPS Washer & dryer

Riverview Rowhouse, a vintage modern home
Stylishly renovated 1890 Rowhouse in Newburgh's up-and-coming Washington Heights District. Enjoy your morning coffee with views of the Hudson River and Mountains. Just 75 minutes from NYC, this home is a short drive to the Newburgh Waterfront and Liberty Street's hip new shops and restaurants such as Ms. Fairfax, The Flour Shop, Liberty Street Bistro, Mama Roux, The Newburgh Brewery, and more. Close proximity to the Beacon Ferry and a short drive to the Beacon train station.
Popular amenities for Middletown apartment rentals
Weekly apartment rentals

Gorgeous Suite w/ Private Entrance & Farm Friends

Airy Artsy Loft

Historic one-bedroom apartment

Log Cabin Apartment Great for Outdoor Enthusiasts

A Suite Downtown- Lake access, hiking, and more!

Cozy studio apartment with everything you need!

Lander pied-à-terre with outdoor movie & dog park!

Hudson Valley Escape | Walk to Downtown & Hiking
Private apartment rentals

Riversong on Hudson - Private Full 2nd Floor

The Treehouse, lush Parisian inspired Studio

Private Apt 2 Blocks MainSt/Roundhouse/MT/Maribeau

Breathtaking view’s condo

The Firenze Suite

The Lakeside Suite- Hudson Valley Restful Retreat

Explore and Relax On The Knoll

“The Loaf” in Sugar Loaf NY
Apartment rentals with a hot tub

Countryside Couples Suite

Foxglove Farm

The Still Life Studio- Centrally located Oasis

Mtn. Creek Heated Pool HotTub Sauna Fire Place

Relaxing Spa Retreat~Gorgeous View~Walk to Village

Swiss Spot

Premium 3 Bed Top Floor Views

Large condo near Mountain Creek & Crystal Springs
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 323 | ﺩ.ﺇ 345 | ﺩ.ﺇ 338 | ﺩ.ﺇ 349 | ﺩ.ﺇ 360 | ﺩ.ﺇ 404 | ﺩ.ﺇ 371 | ﺩ.ﺇ 371 | ﺩ.ﺇ 371 | ﺩ.ﺇ 356 | ﺩ.ﺇ 345 | ﺩ.ﺇ 378 |
| 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 |
Destinations to explore
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- Mountain Creek Resort
- Yankee Stadium
- American Dream
- MetLife Stadium
- Bushkill Falls
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Bethel Woods Center for the Arts
- Delaware Water Gap National Recreation Area
- Nickelodeon Universe
- Resorts World Catskills
- Promised Land State Park
- Storm King Art Center
- Mohonk Preserve
- Mountain Creek Water Park
- Peekamoose Blue Hole
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mount Peter Ski Area
- Wawayanda State Park
- SoJo Spa Club
- Shawnee Mountain Ski Area





