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Vacation rentals in Middletown

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Quick stats about vacation rentals in Middletown

  • Total vacation rentals

    Explore 30 vacation rentals in Middletown

  • Nightly prices starting at

    Middletown vacation rentals start at G$10,459 GYD 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 vacation rentals include wi-fi access

  • Popular amenities for guests

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

Top-rated vacation rentals in Middletown

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

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Top guest favorite
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, 581 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 4 people.

ValueLocationHiking

Top guest favorite
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, 140 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.

FamilyValueNearby

Superhost
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh
4.81 out of 5 average rating, 134 reviews

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

FamilyValueQuiet

Guest favorite
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, 108 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!"

FamilyLocationAccuracy

Guest favorite
Home in Godeffroy
5.0 out of 5 average rating, 20 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!

FamilyLocationQuiet

Guest favorite
Home in Slate Hill
5.0 out of 5 average rating, 23 reviews

The Wooden Igloo Near Legoland NY

Unwind in tranquility at The Wooden Igloo, a unique and spacious home that is fully equipped with a touch of luxury. It's situated in a quiet, secluded area just minutes away from some of the major attractions like LEGOLAND NY Theme Park (9 miles), Soons Orchards (2.4 miles), and Orange County Arboretum (14.6 miles) for memorable outings. Indulge in shopping and dining adventures at The Galleria at Crystal Run (7.6 miles), Chester Mall (10.5 miles), Orange Plaza (6.9 miles) and much more!

FamilyLocationCleanliness

Top guest favorite
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
4.92 out of 5 average rating, 341 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.

ValueFamilyHospitality

Top guest favorite
Home in Montgomery
5.0 out of 5 average rating, 21 reviews

The B House

The “B” house, constructed in the 19th century, underwent renovations and modernizations to accommodate contemporary living standards while preserving its original architectural charm. The house boasts magnificent beams that span the entire interior, creating a sense of grandeur. Additionally, newly renovated appliances and updated bathrooms have been installed throughout the property. The kitchen features an expansive open space, elegant countertops, cooking essentials are top-notch.

LocationFamilyKitchen

Guest favorite
A charming two-story villa is set amidst lush greenery, showcasing light blue siding and large windows. A circular driveway leads to a spacious garage, while outdoor seating is arranged with four chairs near a small table, inviting gatherings in the serene surroundings.
Villa in Bloomingburg
4.87 out of 5 average rating, 112 reviews

Spacious 6BR Villa | Serene Scenic Mountain Escape

Escape to this spacious 6-bedroom mountain villa, a peaceful retreat perfect for families and groups. Just about 1 hour from New York City, enjoy beautiful scenic views, comfortable living spaces, a well-equipped home, and plenty of outdoor space. Explore nearby hiking trails and local attractions, or simply relax and enjoy the quiet surroundings. Whether you're planning a family getaway or a weekend with friends, it's the perfect place to unwind, reconnect, and make lasting memories.

FamilyValueCondition

Guest favorite
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
4.9 out of 5 average rating, 90 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.

ValueFamilyComfort

Top guest favorite
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, 218 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.

LocationFamilyGetting around

Superhost
Home in Middletown
4.93 out of 5 average rating, 29 reviews

Tiny Camp, Hot Tub Haven + fire pit.

Tiny Camp – Your Perfect Getaway Under the Stars Perfect for unforgettable evenings beneath open skies, this private and cozy two-bedroom retreat is designed for rest, connection, and recharge. Relax in the spacious backyard with a hot tub, elegant fire pit, and BBQ—ideal for a romantic escape, peaceful reset, or quality time with friends and family. Just 200 yards away, enjoy access to the Neversink River, known for world-class trout fishing.

FamilyLocationQuiet

Popular amenities for Middletown vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Stay near Middletown's top sights

Orange County Fair Speedway

20 locals recommend

Paramount Theatre

14 locals recommend

Fancer Davidge Park

3 locals recommend

Other great vacation rentals in Middletown

Guest favorite
Home in Wurtsboro
5.0 out of 5 average rating, 21 reviews

Bashakill Hillside Cottage East

LocationFamilyHiking

Top guest favorite
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, 74 reviews

The Alexandria - Wurtsboro, NY

FamilyValueAccess

The exterior of a custom-designed home is presented, surrounded by lush green lawns and tall trees. A neatly paved driveway leads to the entrance, which is softly illuminated by path lights. The welcoming facade features multiple windows, allowing natural light to fill the interior.
Home in Middletown
4.78 out of 5 average rating, 68 reviews

Country Modern Home w/5-Acre land Relax Retreat

FamilyValueBackyard

Apartment in Middletown
4.69 out of 5 average rating, 13 reviews

The Columbus Hotel | The Courtyard Suite | 89-303

LocationValueNearby

The exterior of the house features a combination of natural stone and siding, providing a unique texture. Large windows allow ample natural light. The entrance includes double wooden doors, flanked by decorative stone columns, set against manicured grass and a paved driveway.
Home in Middletown
4.78 out of 5 average rating, 27 reviews

Lake trail retreat

LocationFamilyAccuracy

Guest favorite
Home in Middletown
4.75 out of 5 average rating, 8 reviews

Cozy Delight Home

FamilyValueDecor

Top guest favorite
Home in Montgomery
5.0 out of 5 average rating, 26 reviews

Luxe 3BR 2.5 bath King Beds in Montgomery Village

LocationFamilyCheckout

Home in Otisville
4.75 out of 5 average rating, 44 reviews

Movies & Meadows | Pool, Arcade & Game Room

ValueLocationAccuracy

When is the best time to visit Middletown?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$18,199 GYDG$19,663 GYDG$19,454 GYDG$19,872 GYDG$20,500 GYDG$23,219 GYDG$21,127 GYDG$21,127 GYDG$21,127 GYDG$20,290 GYDG$19,663 GYDG$21,545 GYD
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.

Destinations to explore