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Middletown, NY accommodations
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35 Lodgings in Middletown, NY

Top-Rated Family Lodgings in Middletown, NY

These family-friendly lodgings in Middletown, NY offer plenty of room and keep city attractions within easy reach; find the perfect fit for your group.

Pond + Gazebo: Expansive Hudson Valley Escape! - Middletown, NY
Middletown, NY
08/28 – 09/05
$1256/nighttotal: $10048 (8 )

Pond + Gazebo: Expansive Hudson Valley Escape!

1 3
cottage , Goshen
This family-friendly cottage in Goshen offers convenient access to key historical sites, including the Harness Racing Museum and Hall of Fame, the Orange County Genealogical Society, and the Goshen Historic Track, all within 2 miles, with Charles J. Everett Memorial located 1.7 miles away. This accommodation provides a cozy fireplace, a well-equipped kitchen with a microwave and dishwasher, air conditioning, a garden, private patio, and complimentary WiFi in public areas, with free on-site parking available.
Industrial Modern Home - 360 Views! - Middletown, NY
10 14 reviews
Middletown, NY
08/12 – 08/19
$1275/nighttotal: $8925 (7 )

Industrial Modern Home - 360 Views!

1 3
apartment , Middletown
This Middletown, New York, house is a secluded hilltop retreat on 14 acres, 1.5 hours from New York City, offering complete privacy with centuries-old stone walls.
This 5-bedroom, 3-bathroom home sleeps 14 guests and features a pool, jacuzzi, and full kitchen with modern amenities, plus a separate pool house and ample outdoor space for relaxation.
Pinnacle Pointe By Relaxtay | 600-acre Private Luxury Estate With Spa, Pool, Theater & Lake - Middletown, NY
10 1 review
Middletown, NY
08/28 – 09/05
$6551/nighttotal: $52408 (8 )

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

7 3
house , Bloomingburg
This waterfront villa in downtown Middletown offers a 15-mile drive to Highland Lake and a 12-mile drive to the Paramount Theatre.
This family-friendly estate accommodates 24 guests with 7 bedrooms and 8 bathrooms, featuring a private pool, hot tub, kayaking, golf, foosball, and table tennis.
Great Goshen Get-away Close To Legoland! - Middletown, NY
9.8 98 reviews
Middletown, NY
08/21 – 08/23
$370/nighttotal: $740 (2 )

Great Goshen Get-away Close To Legoland!

2 5
apartment , Goshen
This spacious apartment is ideally located in Goshen, just a short drive from Legoland New York, Woodbury Commons Shopping Outlets, and Bear Mountain State Park. It consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The apartment offers two separate units combined, providing four bedrooms, two kitchens, and two bathrooms, perfect for large families or groups. It includes a dedicated game room, modern amenities, and easy access to a variety of attractions, shopping, and outdoor activities.

Best Middletown, NY lodging with a pool

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

9 Person Glamping Tent- White Owl - Middletown, NY
10 3 reviews
Middletown, NY
08/28 – 09/05
$104/nighttotal: $832 (8 )

9 Person Glamping Tent- White Owl

1 3
glamping , Scotchtown
This Scotchtown glamping experience offers a peaceful retreat with solar electricity, featuring 1 bathroom and accommodating up to 9 guests.
Enjoy on-site amenities like a grill, fire pit, picnic table, hammock, and pool, with Legoland and local wineries just a short drive away, and Middletown's shopping and dining within minutes.
Beautiful Log Cabin Style House - Middletown, NY
9.5 150 reviews
Middletown, NY
08/12 – 08/19
$394/nighttotal: $2758 (7 )

Beautiful Log Cabin Style House

1 3
apartment , Scotchtown
This log cabin-style apartment is located just minutes from Middletown, offering easy access to major shopping areas and restaurants. The apartment has received excellent ratings for location, cleanliness, and user experience. The apartment features three bedrooms and one bathroom, comfortably accommodating up to 12 guests. Amenities include a private sauna, a swimming pool, a fire pit, a large deck, and a variety of entertainment options like a video game, popcorn and slush machines, and access to discounted activities at the nearby Ring Homestead Adventure Camp.
Waterlily-best Glamping Experience, Middletown Ny - Middletown, NY
9.6 15 reviews
Middletown, NY
08/28 – 09/05
$89/nighttotal: $712 (8 )

Waterlily-best Glamping Experience, Middletown Ny

1 3
glamping , Scotchtown
This glamping rental is located in the Scotchtown district, a short drive from Middletown's shopping and dining, and close to attractions such as Legoland and local wineries.
This pet-friendly glamping site accommodates up to 12 guests and features a private outdoor area with seating, hammocks, and a grill, plus discounted access to on-site ropes course and paintball activities.
9 Person Glamping Tent- Chipmunk - Middletown, NY
9.7 13 reviews
Middletown, NY
08/28 – 09/05
$104/nighttotal: $832 (8 )

9 Person Glamping Tent- Chipmunk

1 3
glamping , Scotchtown
This glamping site is situated near Scotchtown, New York, offering convenient access to attractions such as Legoland, which is approximately 10 miles away.
This spacious glamping experience accommodates up to 9 guests, featuring a private outdoor area with seating and hammocks, a shared swimming pool, a jacuzzi, and portable toilets and showers, with nearby access to flushing facilities.

Frequently Asked Questions about accommodations in Middletown, NY

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Best Middletown, NY accommodation with a garden

Cozy Downtown Studio W/ Kitchen & Workspace - Middletown, NY
10 5 reviews
Middletown, NY
07/22 – 07/26
$175/nighttotal: $700 (4 )

Cozy Downtown Studio W/ Kitchen & Workspace

1 2
apartment , Middletown
This studio suite is centrally located in Middletown's downtown district, offering convenient access to dining, cafes, breweries, and essential services, with proximity to Touro College and Garnet Health Medical Center.
This apartment features a fully equipped kitchen with modern appliances, air conditioning, free on-site parking, and accommodates up to 2 guests with self-check-in via a smart lock.
Heritage Hideaway - Middletown, NY
9.2 18 reviews
Middletown, NY
08/12 – 08/19
$146/nighttotal: $1022 (7 )

Heritage Hideaway

1 3
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.
Serene Rustic Retreat With Lake - Middletown, NY
Middletown, NY
08/28 – 09/05
$378/nighttotal: $3024 (8 )

Serene Rustic Retreat With Lake

3 3
house , Otisville
This Otisville house rental, near the DM Weil Gallery and Stewart International Airport (28 and 29 miles away respectively), offers a tranquil escape in a rustic setting.
The 1600-square-foot home features three bedrooms, three bathrooms, a fully equipped kitchen, a Jacuzzi, and can comfortably accommodate up to 11 guests, with amenities including Wi-Fi and parking.
Private Glamping Tent For 2 - Middletown, NY
9.5 11 reviews
Middletown, NY
07/22 – 07/26
$117/nighttotal: $468 (4 )

Private Glamping Tent For 2

1 2
glamping , Scotchtown
This glamping site in Scotchtown is conveniently located near Legoland and local wineries, offering excellent proximity to popular attractions.
This pet-friendly glamping experience accommodates up to two guests and features a private outdoor area with a grill, shared access to a pool, and discounted activities like ropes courses and paintball.

Best Middletown, NY accommodation with a kitchen

Elegant Town Home Middletown Suburb Close To City - Middletown, NY
Middletown, NY
06/25 – 07/04
$484/nighttotal: $4356 (9 )

Elegant Town Home Middletown Suburb Close To City

3 2
apartment , Washington Heights
This modern vacation rental is located in Middletown, New York, just a short drive from Washington Heights and its attractions like the Paramount Theatre and Museum Village. The house offers a comfortable and relaxing escape from the city, with easy access to local wineries, breweries, and historical sites.
The three-bedroom, three-bathroom home provides plenty of space for families or groups. Enjoy modern appliances, a Jacuzzi, and a private parking space.
Pinnacle Pointe | Year-round Pool Spa Lake Theater - Middletown, NY
9.7 7 reviews
Middletown, NY
08/28 – 09/05
$6042/nighttotal: $48336 (8 )

Pinnacle Pointe | Year-round Pool Spa Lake Theater

1 3
house , Bloomingburg
This secluded mountain estate is located in Bloomingburg, approximately 5,280 feet from New York City.
This luxury house offers 7 bedrooms, 8 bathrooms, and sleeps 16 guests, featuring a year-round heated pool, private lake with kayaks and a boat, home theater, arcade, pool table, full bar, spa room with massage chairs and a cedar sauna, and a chef’s kitchen with an espresso bar.
12 Person Glamping Tent- Rte 66 - Middletown, NY
9.5 22 reviews
Middletown, NY
08/28 – 09/05
$187/nighttotal: $1496 (8 )

12 Person Glamping Tent- Rte 66

1 3
glamping , Scotchtown
This 12-person glamping tent, offered as "12 Person Glamping Tent- Rte 66," is situated near Middletown, New York, minutes from Scotchtown.
The unit sleeps up to 12 guests in a combination of full and twin beds and includes a mini-fridge, access to a shared pool (weather permitting), a hot tub and sauna (extra fee, reservations required), and a private outdoor area with a hammock, picnic table, propane grill, and fire pit.
Hike, Ski & Explore: Otisville Retreat W/ Yard! - Middletown, NY
Middletown, NY
08/12 – 08/19
$396/nighttotal: $2772 (7 )

Hike, Ski & Explore: Otisville Retreat W/ Yard!

4 3
house , Otisville
This Otisville vacation home is situated approximately 27 miles from DM Weil Gallery and Stewart International Airport, and around 29 to 30 miles from Mohonk Preserve and Metro-North Harriman Station.
This 2080 square foot, 4-bedroom dwelling accommodates up to 13 guests with 3 bathrooms, a fully equipped kitchen, air conditioning, WiFi, and a garden, offering an ideal base for outdoor enthusiasts exploring the Otisville area.
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