Places to stay in Middletown, NY

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Middletown, NY place to stay
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35 Best places to stay in Middletown, NY

Best family friendly Middletown, NY lodging

Among the 35 accommodations in Middletown, NY, here are the 4 best for families

Great Goshen Get-away Close To Legoland! - Middletown, NY
9.8 98 reviews
Middletown, NY
28/08 – 05/09
SG$337/nighttotal: SG$2696 (8 )

Great Goshen Get-away Close To Legoland!

2 3
apartment , Goshen
This apartment is conveniently located in Goshen, just a short drive from Legoland New York, Woodbury Commons Shopping Outlets, and Bear Mountain State Park. It has consistently received excellent ratings for its cleanliness, location, and overall user experience.
The property features two separate units, providing flexibility and privacy for guests. Each unit is equipped with modern amenities, including a fully equipped kitchen, air conditioning, and parking, as well as a dedicated game room for entertainment.
Pinnacle Pointe By Relaxtay | 600-acre Private Luxury Estate With Spa, Pool, Theater & Lake - Middletown, NY
10 1 review
Middletown, NY
28/08 – 05/09
SG$8421/nighttotal: SG$67368 (8 )

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

7 3
house , Bloomingburg
This family-friendly villa is located in downtown Middletown, waterfront, 24 kilometres from Highland Lake and 19 kilometres from Paramount Theatre.
This expansive property offers accommodation for up to 24 guests across 7 bedrooms and 8 bathrooms, featuring a private swimming pool, hot tub, and on-site activities such as kayaking and table tennis.
12 Person Glamping Tent- Rte 66 - Middletown, NY
9.5 22 reviews
Middletown, NY
12/08 – 19/08
SG$203/nighttotal: SG$1421 (7 )

12 Person Glamping Tent- Rte 66

1 3
glamping , Scotchtown
This glamping shelter is situated just a short distance from Middletown, offering easy access to shopping, dining, and attractions like Legoland and local wineries. It has received excellent ratings for location, cleanliness, and user experience.
The tent features a full-size bed, twin bunk beds, and a folding chair/bed, comfortably accommodating up to 15 guests. The property also includes a shared pool, a private outdoor area with seating, hammocks, a grill, and a picnic table, as well as discounted access to adventure activities such as a ropes course, paintball, and a camo run tube ride.
Parkway House Goshen Bed And Breakfast Suite 2 - Middletown, NY
Middletown, NY
12/08 – 19/08
SG$819/nighttotal: SG$5733 (7 )

Parkway House Goshen Bed And Breakfast Suite 2

2 3
house , Goshen
Parkway House Goshen Bed And Breakfast Suite 2 is located in Goshen, 22.5 kilometres from Stewart International Airport, 24.1 kilometres from Metro-North Harriman Station, and 37 kilometres from Bear Mountain State Park.
This recently renovated holiday home offers 800 square meters of living space with 2 bedrooms, accommodating up to 11 guests, and features air conditioning, free WiFi, a garden, terrace, and an outdoor fireplace.

Best Middletown, NY lodgings with a pool

Among the 35 accommodations in Middletown, NY, here are the 4 best ones with a pool

Industrial Modern Home - 360 Views! - Middletown, NY
10 14 reviews
Middletown, NY
12/08 – 19/08
SG$1639/nighttotal: SG$11473 (7 )

Industrial Modern Home - 360 Views!

1 3
apartment , Middletown
This secluded five-bedroom house sits on a hilltop in Middletown, just 1.5 hours from New York City, offering a tranquil escape from the hustle and bustle. The property is surrounded by centuries-old stone walls and trees, creating a peaceful ambiance.
The spacious property comfortably accommodates up to 14 guests, with a variety of sleeping arrangements to suit different needs. The house features modern amenities, a large garden, a swimming pool, and a jacuzzi, ensuring a comfortable and enjoyable stay.
Glamping Tent- 11 Person Max Cap. - Middletown, NY
8.7 3 reviews
Middletown, NY
12/08 – 19/08
SG$171/nighttotal: SG$1197 (7 )

Glamping Tent- 11 Person Max Cap.

1 3
glamping , Scotchtown
This glamping shelter is situated just minutes from Middletown, offering easy access to shopping, dining, and attractions like Legoland and local wineries. The surrounding area is quiet and private, perfect for a relaxing getaway.
The Fionna - Amazing Glamping tent can accommodate up to nine guests and features a bedroom and bathroom. Guests can enjoy a range of amenities, including a private outdoor area with a grill, fire pit, and hammock, as well as access to a shared pool and discounted rates at a nearby paintball shop.
9 Person Glamping Tent- White Owl - Middletown, NY
10 3 reviews
Middletown, NY
28/08 – 05/09
SG$134/nighttotal: SG$1072 (8 )

9 Person Glamping Tent- White Owl

1 3
glamping , Scotchtown
This glamping shelter is located just a few kilometres from Middletown, providing easy access to shopping, restaurants, and attractions like Legoland and local wineries. The surrounding area is quiet and peaceful, offering a tranquil escape from the hustle and bustle of everyday life.
The White Owl-soar With The Birds offers a comfortable stay for up to nine guests. The tent is equipped with a bed, linens, a picnic table, a hammock, a grill, a fire pit, a swimming pool, and solar electricity.
Glamping Tent (7 Guests Max)-  Guests. - Middletown, NY
Middletown, NY
28/08 – 05/09
SG$263/nighttotal: SG$2104 (8 )

Glamping Tent (7 Guests Max)- Guests.

1 3
glamping , Scotchtown
This rustic glamping shelter is located just a short drive from Middletown, providing easy access to shopping, dining, and attractions like Legoland and local wineries. The surrounding area is peaceful and secluded, perfect for a relaxing getaway.
The Dream offers a unique glamping experience with a focus on a relaxed, nature-inspired setting. It can accommodate up to seven guests and features a comfortable living space with a bedroom and bathroom. Guests can enjoy modern amenities like solar-powered electricity, a grill, fire pit, picnic table, and hammock, as well as on-site activities and amenities available for purchase.

Frequently asked questions about accommodations in Middletown, NY

Destinations nearby

Best Middletown, NY accommodations with a garden

Beautiful Log Cabin Style House - Middletown, NY
9.5 150 reviews
Middletown, NY
21/08 – 23/08
SG$516/nighttotal: SG$1032 (2 )

Beautiful Log Cabin Style House

1 5
apartment , Scotchtown
This log cabin-style house is located in a quiet, private setting just minutes from Middletown, offering easy access to major shopping areas and restaurants. The property has received excellent ratings for location, cleanliness, and user experience.
The cabin offers three bedrooms and one bathroom, accommodating up to twelve guests. Guests can enjoy amenities such as a sauna, swimming pool, and a private garden, along with a range of entertainment options including a flat-screen TV, video games, and a fire pit.
Serene Rustic Retreat With Lake - Middletown, NY
Middletown, NY
28/08 – 05/09
SG$486/nighttotal: SG$3888 (8 )

Serene Rustic Retreat With Lake

3 3
house , Otisville
This Serene Rustic Retreat near Otisville, New York, offers a peaceful escape approximately 45km from the DM Weil Gallery and 47km from Stewart International Airport.
The 149 square metre property boasts three bedrooms, three bathrooms, and can comfortably accommodate up to eleven guests, featuring a fully equipped kitchen, Jacuzzi, private parking, and complimentary Wi-Fi.
Cozy Delight - Middletown, NY
9.3 25 reviews
Middletown, NY
28/08 – 05/09
SG$330/nighttotal: SG$2640 (8 )

Cozy Delight

1 3
apartment , Scotchtown
This Scotchtown holiday home is situated near Middletown, New York, approximately 10-15 km from Middletown's shopping mall and major hospital.
The three-bedroom property, sleeping four, boasts a kitchen with fridge, freezer, and microwave, air conditioning, a garden, parking, and internet access; enjoying gorgeous sunset views.
Pinnacle Pointe | Year-round Pool Spa Lake Theater - Middletown, NY
9.7 7 reviews
Middletown, NY
28/08 – 05/09
SG$7768/nighttotal: SG$62144 (8 )

Pinnacle Pointe | Year-round Pool Spa Lake Theater

1 3
house , Bloomingburg
This Relaxtay mountain estate is located in Bloomingburg, approximately 161 kilometres from New York City, set on 971,245 square metres of private land with panoramic mountain views.
This expansive 9,500 sq ft lodge offers accommodation for 16 guests, featuring a year-round heated pool, a private lake with kayaks and a boat, a home cinema, arcade, pool table, bar, full gym, and spa facilities including a sauna and massage chairs, alongside a chef’s kitchen, outdoor dining areas, a firepit, mini golf, and a playground.

Best Middletown, NY accommodations with a kitchen

Private Glamping Tent For 2 - Middletown, NY
9.5 11 reviews
Middletown, NY
22/07 – 26/07
SG$150/nighttotal: SG$600 (4 )

Private Glamping Tent For 2

1 2
glamping , Scotchtown
This glamping tent is located near Scotchtown, within easy reach of Legoland and local wineries. It has received excellent ratings for user experience, location, and cleanliness.
The tent sleeps up to three guests and features a full-size bed, twin-over-twin bunk beds, and a folding chair/bed. Enjoy a private outdoor area with seating, hammocks, a grill, and a picnic table, as well as access to a shared pool and discounted activities like a ropes course, paintball, and a camo run tube ride.
House Near Legoland, Farms, And Airport/ Train - Middletown, NY
Middletown, NY
22/07 – 26/07
SG$556/nighttotal: SG$2224 (4 )

House Near Legoland, Farms, And Airport/ Train

3 2
apartment , Scotchtown
This family-friendly flat in Scotchtown is ideally positioned for exploring the Hudson Valley, located just 8 kilometres from Legoland New York and offering convenient access to the Metro-North train station and Stewart International Airport for straightforward travel.
This three-bedroom flat accommodates up to four guests and features essential amenities including a kitchen, air conditioning, and parking, with nearby opportunities for fruit picking and exploring riverfront towns.
Elegant Town Home Middletown Suburb Close To City - Middletown, NY
Middletown, NY
25/06 – 04/07
SG$622/nighttotal: SG$5598 (9 )

Elegant Town Home Middletown Suburb Close To City

3 2
apartment , Washington Heights
This modern house is situated in Middletown, New York, just a short drive from Washington Heights and its attractions. The surrounding area offers a peaceful change of pace, with vineyards, breweries, and historical sites close by.
This three-bedroom, three-bathroom property provides spacious and comfortable accommodation for your stay. The house is fully equipped with modern amenities, including air conditioning, a Jacuzzi, and parking, as well as travel brochures to help you explore the local area.
Heritage Hideaway - Middletown, NY
9.2 18 reviews
Middletown, NY
12/08 – 19/08
SG$188/nighttotal: SG$1316 (7 )

Heritage Hideaway

1 3
apartment , Middletown
This Middletown apartment, ideally located in the downtown area, is within easy walking distance of the Heritage Trail, local breweries, restaurants, the Paramount Theatre, and Garnet Health Medical Centre.
The one-bedroom flat offers a queen-size bed and a sofa bed, accommodating up to four guests, and includes a private porch, parking, and all necessary amenities such as a fridge, freezer, microwave, and air conditioning.
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