Vacation rentals in Middletown, NY

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Middletown, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Middletown, NY

Browse Vacation Rentals in the Historic District of Middletown, NY

These vacation rentals in the downtown area of Middletown, NY offer unbeatable walking access to vibrant local life, dining, and culture.

The Columbus Hotel | The Balcony Suite | 52-201 - Middletown, NY
9.2 27 reviews

The Columbus Hotel | The Balcony Suite | 52-201

apartment, Middletown
This downtown Middletown apartment is conveniently located within walking distance of the Heritage Trail, local breweries, restaurants, the Paramount Theatre, and Garnet Health Medical Center, with easy access to Routes 17 and 84.
This one-bedroom, one-bathroom unit sleeps four guests comfortably with a queen-size bed, pull-out couch, private porch, parking, and includes a kitchen equipped with a refrigerator, freezer, and microwave.
The Columbus Hotel | The Upper Studio | 52-402 - Middletown, NY
8.5 4 reviews

The Columbus Hotel | The Upper Studio | 52-402

apartment, Middletown
This one-bedroom, one-bathroom apartment in Middletown offers a convenient base with easy access to public transportation and local attractions.
This unit accommodates up to two guests and features air conditioning, internet, and a full kitchen for a comfortable stay.
The Columbus Hotel | The Gold Suite | 89-207 - Middletown, NY
10 1 review

The Columbus Hotel | The Gold Suite | 89-207

apartment, Middletown
This private studio apartment is located in a residential area of Middletown, offering convenient access to the Hudson Valley.
This studio features a kitchenette, a private bathroom, and a dedicated workspace, ideal for solo travelers, professionals, or students needing accommodation for short or extended stays.
The Columbus Hotel | The Weekender Suite | 52-204 - Middletown, NY
9.3 27 reviews

The Columbus Hotel | The Weekender Suite | 52-204

apartment, Middletown
This studio apartment is located in downtown Middletown, a 1-minute walk from Clemson Bros Brewery and surrounded by dining and shopping options, with easy access to NY-17 and Route 84.
This studio offers a full kitchen, air conditioning, parking, and an on-site washer and dryer, accommodating up to two guests.

Best Middletown, NY vacation rentals with air conditioning

Hudson Valley Horse Farm Stay | 10 Min To Legoland - Middletown, NY
10 12 reviews

Hudson Valley Horse Farm Stay | 10 Min To Legoland

gîte, Scotchtown
This Scotchtown lakefront apartment offers a unique farmstay experience on a 7-acre property near Goshen's Heritage Trail and Harness Racing Museum, approximately two hours from Manhattan.
The one-bedroom, one-bathroom unit sleeps two guests and includes a fully equipped kitchen with a dishwasher, air conditioning, parking, canoe and paddleboat access, and on-site amenities such as a grill, firepit, and picnic tables.
Secluded Farmhouse, 30 Acres Private Estate. - Middletown, NY
9.4 117 reviews

Secluded Farmhouse, 30 Acres Private Estate.

apartment, Bloomingburg
This 1800s house is located in Bloomingburg, on 30 acres of woods and fields, close to the Shawangunk Wine Trail, Minnewaska State Park, and the Storm King Art Center. The property has excellent ratings for location, cleanliness, and user experience.
This spacious home has 6 bedrooms and 2 bathrooms, making it ideal for families or groups of up to 16 guests. Amenities include a private pool, tennis court, stream with swimming hole, pond, barn, and a variety of outdoor spaces to explore.
The Reservoir Home Near Winery’s And Legoland - Middletown, NY
9.8 89 reviews

The Reservoir Home Near Winery’s And Legoland

apartment, Goshen
The Reservoir Retreat is located in a peaceful Goshen neighborhood, just five minutes from the village center and Legoland. The property has earned excellent ratings for its location, cleanliness, and overall experience.
This four-bedroom, two-bathroom house can comfortably accommodate up to 10 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and internet access. Enjoy the serene pond and fountain in the backyard, explore the surrounding woods for wildlife viewing, and take advantage of the proximity to local attractions like Chester, breweries, wineries, and apple orchards.
The Wooden Igloo Near Legoland Ny - Middletown, NY
10 22 reviews

The Wooden Igloo Near Legoland Ny

apartment, Middletown
The Wooden Igloo, a unique one-bedroom apartment rental near Middletown, New York, offers a secluded yet convenient location, just 9 miles from LEGOLAND New York and within a short drive of Soons Orchards and other attractions.
This luxurious 1-bedroom rental boasts 3 bathrooms, sleeps 12 guests, includes a fully equipped kitchen, air conditioning, a swimming pool, parking, and internet access, promising a memorable getaway.

Frequently Asked Questions about vacation rentals in Middletown, NY

  • What are the top family-friendly attractions in Middletown, NY?

    The Middletown Thrall Park is a great place for families, with its playground, walking trails, and even a carousel. The Orange County Arboretum is also a great option, with its beautiful gardens and walking trails.
  • What are the best Airbnb and vacation rentals in Middletown, NY?

  • When is the best time to book a vacation rental in Middletown, NY?

    The best time to book a vacation rental in Middletown is during the shoulder seasons, like spring or fall. The weather is still nice, but the crowds are smaller and the prices are lower.
  • What are the most popular Airbnbs in Middletown, NY?

  • What are the best budget-friendly activities in Middletown, NY?

    The Wallkill Valley Rail Trail is a great way to get some exercise and enjoy the scenery, and it's free! The Middletown Thrall Park is also a great place to spend a day, with its playground, walking trails, and picnic areas.
  • What are the best vacation rentals with a pool in Middletown, NY?

    Want Peace Of Mind and Palace Near Woodbury Mall are the best vacation rentals with a pool in Middletown, NY.

  • What are the best restaurants with local dishes in Middletown, NY?

    The 'The Brick House' is a great spot for local dishes, they have a fantastic menu with a focus on fresh, seasonal ingredients. 'The Gusto Restaurant' is also a great option, they offer a variety of Italian dishes.
  • What are the best rentals for families and kids in Middletown, NY?

  • What are the best walking or cycling routes in Middletown, NY?

    The Wallkill Valley Rail Trail is a great option for both walking and cycling, it's a paved trail that runs for miles along the Wallkill River. The Orange County Arboretum also has a number of walking trails.
  • What are the best rentals or Airbnbs with a jacuzzi in Middletown, NY?

    Beautiful Spacious House and Elegant Town Home Middletown Suburb Close To City are the best vacation rentals or Airbnb with a jacuzzi in Middletown, NY.

  • Are there pet-friendly attractions in Middletown, NY?

    The Wallkill Valley Rail Trail is pet-friendly, so you can bring your furry friend along for a walk or bike ride. The Thrall Park also has a dog park.
  • What are the benefits of choosing a vacation rental in Middletown, NY?

    Vacation rentals offer more space and privacy than a hotel. They can also be a more affordable option, especially if you're traveling with a group.
  • What are the top sports attractions and facilities in Middletown, NY?

    Middletown has a few sports facilities, including the Middletown High School Athletic Complex, which has a football field, track, and baseball field. There's also the Middletown YMCA, which offers a variety of fitness classes and activities.

Popular destinations

Choose the Right Vacation Rentals with a Terrace in Middletown, NY

Enjoy your own private terrace with city skyline views at these vacation rentals in Middletown, NY.

Lakefront Cottage 10 Min To Legoland Farmstay - Middletown, NY
No reviews

Lakefront Cottage 10 Min To Legoland Farmstay

cottage, Mechanicstown
This Hudson Valley lakefront cottage near Middletown, New York, is seven minutes from Goshen Village and an hour and fifteen minutes from New York City, offering easy access to LEGOLAND New York and local wineries.
The one-bedroom, one-bathroom guesthouse sleeps two, features a private dock, canoe, and paddleboat, a fenced courtyard, firepit, grill, and includes a pack 'n play and toddler bed upon request.
Hike & Fish: Outdoor Retreat Near Trails - Middletown, NY
9.6 10 reviews

Hike & Fish: Outdoor Retreat Near Trails

house, Otisville
This Wurtsboro vacation home, near Otisville, offers convenient access to hiking trails and is approximately 31 miles from Bethel Woods Center for the Arts and 29 miles from Stewart International Airport.
This 840-square-foot house features one bedroom, one bathroom, and can comfortably accommodate seven guests, boasting amenities such as a fully equipped kitchen, air conditioning, a private balcony, free Wi-Fi, and parking.
Country House W/hot Tub, Deck, Grill & Fire Pit - Middletown, NY
9.8 64 reviews

Country House W/hot Tub, Deck, Grill & Fire Pit

apartment, Chester
This family-friendly vacation home is located in a rural area of Goshen, just 2.2 miles from Castle Fun Center and within 6 miles of both LEGOLAND® New York and the Harness Racing Museum and Hall of Fame. The home has earned excellent user ratings, ensuring a comfortable and enjoyable stay.
This three-bedroom house can accommodate up to six guests, making it perfect for families or groups. The property offers a range of amenities, including a private yard, a swimming pool, a terrace, and a fully equipped kitchen.
Close To Trails: Studio W/ Water Views - Middletown, NY
10 11 reviews

Close To Trails: Studio W/ Water Views

studio, Otisville
This Westbrookville studio, near the Basher Kill and a short drive from Bashakill Vineyards & Winery and Resorts World Catskills, offers easy access to hiking trails in the Bashakill Wildlife Management Area and several state parks.
This 240-square-foot apartment features two bedrooms, one bathroom, sleeps four, and includes a kitchenette with a mini-fridge, hot plate, air fryer, and Keurig, plus a furnished porch, on-site charcoal grill, and access to a spa.

Compare Vacation Rentals for Families in Middletown, NY

These kid-friendly vacation rentals in Middletown, NY keep you close to top city attractions for a stress-free family vacation.

Creekside Farmhouse: Restored Farmhouse With Private Pond & Hot Tub - Middletown, NY
10 1 review

Creekside Farmhouse: Restored Farmhouse With Private Pond & Hot Tub

apartment, Unionville
This 3600 sq ft, 1800s waterfront farmhouse rental in Westtown, near Unionville, is located 13 miles from LEGOLAND® New York and 11 miles from Mountain Creek Ski Resort.
This pet-friendly estate offers 4 bedrooms, 4 bathrooms, a private pond, waterfall, hot tub, in-ground pool, and a dedicated workout room, accommodating up to 10 guests with outdoor amenities including a fire pit and proximity to the Appalachian Trail for hiking.
5bdrm Estate/tennis Near Legoland - Middletown, NY
9.9 66 reviews

5bdrm Estate/tennis Near Legoland

apartment, Scotchtown
This renovated 1917 farmhouse is located just outside Scotchtown, a short drive from attractions like Legoland, Stewart Airport, and Woodbury Commons. It boasts excellent user, location, and cleanliness ratings, making it a great choice for travelers seeking a comfortable and convenient stay. This 5-bedroom, 2-bathroom house has multiple living areas, including a fireplace-equipped living room, dining room, and den, offering ample space for families and friends. Enjoy amenities like a heated pool, a tennis court, a fire pit, and two patios, perfect for relaxing and enjoying the beautiful Hudson Valley scenery.
Glamping Tent- 10 Person Max Capacity - Middletown, NY
9.7 28 reviews

Glamping Tent- 10 Person Max Capacity

glamping, Scotchtown
This glamping site is located within a private family campground and outdoor activity park in Scotchtown, a short drive from Middletown, NY, and approximately 10 miles from Legoland.
This family-friendly glamping tent accommodates up to 10 guests and offers a private outdoor area with seating, hammocks, a grill, and a fire pit, along with access to a shared swimming pool, with hot tub and sauna available for an additional fee.
Spectacular Historic Mansion W/pool&tennis - Middletown, NY
No reviews

Spectacular Historic Mansion W/pool&tennis

apartment, Chester
This Goshen vacation home, near Legoland New York and Castle Fun Center, provides luxurious mountainside lodging with scenic views, only 3 miles from family attractions.
This 10-bedroom, 6-bathroom property sleeps 26 guests and boasts a private pool, hot tub, game room, tennis court, and fully equipped kitchen; enjoy free Wi-Fi and on-site entertainment.

Best Middletown, NY vacation rentals with parking

Pool, Fire Pit Bedroom & Alaska King Sleeps 16 - Middletown, NY
No reviews

Pool, Fire Pit Bedroom & Alaska King Sleeps 16

house, Chester
2 Unit Condo Minutes From Lego Land - Middletown, NY
9.8 109 reviews

2 Unit Condo Minutes From Lego Land

apartment, Goshen
Glenmere Mansion - Middletown, NY
No reviews

Glenmere Mansion

manor house, Florida
9 Person Glamping Tent- The Plaza - Middletown, NY
9.8 10 reviews

9 Person Glamping Tent- The Plaza

glamping, Scotchtown

Find the Best Luxury Vacation Rentals in Middletown, NY

Stay in a luxury city-center vacation rental in Middletown, NY for a sophisticated urban escape with premium 5-star amenities.

Glamping Tent- 11 Person Max Cap. - Middletown, NY
8.7 3 reviews

Glamping Tent- 11 Person Max Cap.

glamping, Scotchtown

Discover Pet-Friendly Vacation Rentals in Middletown, NY

Travel with ease to Middletown, NY with pet-friendly rentals located near local dog parks and scenic city walks.

Beautiful Log Cabin Style House - Middletown, NY
9.5 153 reviews

Beautiful Log Cabin Style House

apartment, Scotchtown
9 Person Glamping Tent- Chipmunk - Middletown, NY
9.6 15 reviews

9 Person Glamping Tent- Chipmunk

glamping, Scotchtown
The Four Seasons Glamping - Middletown, NY
8.4 5 reviews

The Four Seasons Glamping

glamping, Scotchtown
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space - Middletown, NY
10 32 reviews

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

apartment, Chester

Top-Rated Vacation Rentals with a Pool in Middletown, NY

Choose a vacation rental in Middletown, NY with a swimming pool for a proper workout or a leisurely dip right in the heart of the city.

12 Person Glamping Tent- Rte 66 - Middletown, NY
9.5 22 reviews

12 Person Glamping Tent- Rte 66

glamping, Scotchtown
Sunshine- -Best Glamping Experience, Middletown Ny - Middletown, NY
9.7 12 reviews

Sunshine- -Best Glamping Experience, Middletown Ny

glamping, Scotchtown
9 Person Glamping Tent- Athena - Middletown, NY
No reviews

9 Person Glamping Tent- Athena

glamping, Scotchtown
9 Person Glamping Tent- Aurora - Middletown, NY
10 2 reviews

9 Person Glamping Tent- Aurora

glamping, Scotchtown

Top Vacation Rentals with a Hot Tub in Middletown, NY

Unwind after exploring the city with a private hot tub in your own Middletown, NY vacation rental.

Pinnacle Pointe | Year-round Pool Spa Lake Theater - Middletown, NY
9.8 10 reviews

Pinnacle Pointe | Year-round Pool Spa Lake Theater

house, Bloomingburg
Creekside Farmhouse: Private Pond & Hot Tub - Middletown, NY
9.6 37 reviews

Creekside Farmhouse: Private Pond & Hot Tub

apartment, Unionville
Pinnacle Pointe By Relaxtay | 600-acre Private Luxury Estate With Spa, Pool, Theater & Lake - Middletown, NY
10 3 reviews

Pinnacle Pointe By Relaxtay | 600-acre Private Luxury Estate With Spa, Pool, Theater & Lake

house, Bloomingburg
9 Person- Glamping Tent Site- Aphrodite - Middletown, NY
10 3 reviews

9 Person- Glamping Tent Site- Aphrodite

glamping, Scotchtown
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