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Vacation rentals in Middletown

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Top-rated vacation 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, 362 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, 120 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, 125 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.

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, 551 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

Guest favourite
Cabin in Wurtsboro
4.94 out of 5 average rating, 417 reviews

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.

Top guest favourite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg
4.99 out of 5 average rating, 126 reviews

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.

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
4.95 out of 5 average rating, 376 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
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, 316 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 modern dining area features a wooden table surrounded by stylish chairs. Five pendant lights hang above the table, providing soft illumination. A plant stands nearby, contributing to the fresh ambiance, while a sliding door offers access to outdoor space.
Cottage in Pine Bush
4.95 out of 5 average rating, 119 reviews

Modern BoHo 3BR Cottage Near by Hiking, Winery

Our newly modern bohemian cottage (aka Green House!) is perfect for your next weekend getaway or a new WFH locale. Decompress from city stress in this calm, serenely appointed private home. Close to attractions but far enough away to escape, you'll never want to leave. NYC: 79 mi. Hunter Mountain Ski Resort: 60 mi. Pine Bush - groceries/supplies: 7 mi. Middletown - shopping (Walmart, Target, Best Buy, Home Depot): 16 mi. Hiking trails: 7 mi. Horseback riding: 7 mi. Sky diving: 15 mi.

Guest favourite
A serene pond is surrounded by lush green grass and natural landscaping. Smooth stones are placed along the edge of the water, reflecting the blue sky and distant hills. The area offers a peaceful atmosphere with hints of nature visible in the scenery.
Apartment in Middletown
4.93 out of 5 average rating, 174 reviews

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.

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, 212 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.

Guest favourite
Barn in Wurtsboro
4.93 out of 5 average rating, 118 reviews

Catskills Barn Retreat w/Fireplace & 9 Acres

Escape to this architecturally striking Catskills barn set on 9 private acres. Designed for gathering, the soaring living room features a massive stone fireplace, dramatic spiral staircase, and cozy seating for long nights in. Perfect for birthdays, friend weekends, and family getaways, with private hiking trails, fire pit evenings, and playful nooks like the bright silo lounge and hanging chair comfortably sleeping 12 people across 4 bedrooms — all just 90 minutes from NYC.

Popular amenities for Middletown vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Middletown

A charming log cabin is nestled in a lush green landscape, surrounded by trees and well-maintained lawns. The cabin features a welcoming porch and multiple windows, allowing natural light to fill the interior. A tranquil country setting is evident within the serene environment.
Home in Middletown
4.87 out of 5 average rating, 102 reviews

Hudson Valley Log Cabin with Lake Access & View

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, 123 reviews

Modern Woodland Retreat, Hudson Valley & Catskills

Top guest favourite
A vibrant display of purple flowers stands prominently in the foreground, with a charming blue house partially visible in the background. Lush green grass surrounds the property, and tall trees can be seen in the distance, creating a serene natural setting.
Home in Wurtsboro
4.97 out of 5 average rating, 61 reviews

The Alexandria - Wurstboro, NY

Guest favourite
A cozy living room features a navy blue sofa adorned with decorative pillows. A wooden coffee table sits on a patterned area rug. Light floods in from large windows, revealing views of the lake outside, while a flat-screen TV is mounted above a wooden shelf.
Cottage in Port Jervis
4.89 out of 5 average rating, 88 reviews

Lake front house

Apartment in Middletown
4.6 out of 5 average rating, 15 reviews

Heritage Hideaway

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, 9 reviews

Casa Bashakill

Top guest favourite
Barn in Montgomery
4.97 out of 5 average rating, 34 reviews

16taft

Top guest favourite
A single-story cottage is presented with a light-colored exterior and a welcoming front porch. A carport is included on one side, while a neatly maintained lawn features shrubs and trees in the background. The sky displays a mix of clouds and blue hints.
Cottage in Montgomery
5 out of 5 average rating, 76 reviews

The Pullman Cottage NYC Escape • Dogs Stay Free

When is the best time to visit Middletown?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$118 CAD$128 CAD$126 CAD$84 CAD$102 CAD$137 CAD$137 CAD$137 CAD$137 CAD$132 CAD$128 CAD$140 CAD
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.

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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