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

Close To Trails: Studio W/ Water Views - Middletown, NY
9.8 8 reviews
Middletown, NY
29/06 – 03/07
SG$338/nighttotal: SG$1352 (4 )

Close To Trails: Studio W/ Water Views

2 4
studio , Otisville
This Westbrookville studio apartment is located near the Basher Kill, a short drive (approximately 3-5 km) from Bashakill Vineyards & Winery, and within 32-48 km of attractions including Resorts World Catskills and LEGOLAND New York.
The 22-square-metre self-catering apartment sleeps four guests, boasts two bedrooms, one bathroom, a kitchenette with an air fryer and Keurig, a terrace, and access to on-site parking, a spa, and a charcoal grill; fishing and hiking trails are also nearby.
Villa Paraiso - Middletown, NY
Middletown, NY
29/06 – 03/07
SG$654/nighttotal: SG$2616 (4 )

Villa Paraiso

2 4
house , Florida
Villa Paraiso is situated in Goshen, 21 kilometres from Metro-North Harriman Station and 35 kilometres from Bear Mountain State Park.
This spacious villa offers 902 square metres of living space, accommodating up to 19 guests with 2 bedrooms, 4 bathrooms, a fully equipped kitchen, a swimming pool, a hot tub, a terrace, a garden, a bar, and on-site parking.
Hudson Valley Horse Farm Stay | 10 Min To Legoland - Middletown, NY
10 6 reviews
Middletown, NY
28/08 – 05/09
SG$769/nighttotal: SG$6152 (8 )

Hudson Valley Horse Farm Stay | 10 Min To Legoland

1 3
gîte , Scotchtown
This Scotchtown lakefront apartment, situated approximately 320 kilometres from Manhattan and near Goshen's Heritage Trail and Harness Racing Museum, offers a unique Hudson Valley escape.
The self-contained flat boasts one bedroom, one bathroom, sleeping two guests, and includes a fully equipped kitchen with dishwasher, air conditioning, parking, on-site amenities such as a barbecue, fire pit, and access to canoes and paddleboats, plus three friendly horses on the 7-acre farm.
Spacious 6br Villa - Serene Scenic Mountain Escape\n\n - Middletown, NY
9.4 6 reviews
Middletown, NY
29/06 – 03/07
SG$1425/nighttotal: SG$5700 (4 )

Spacious 6br Villa - Serene Scenic Mountain Escape\n\n

6 4
apartment , Bloomingburg
This six-bedroom Bloomingburg house, situated on a mountainside, is approximately 5km from Bloomingburg Village Hall and Wurtsboro Ridge State Forest, and 10km from Mamakating Farmers Market and Veteran's Memorial Park.
The 297 square metre property offers spacious family accommodation for up to 18 guests, boasting a fully equipped kitchen, terrace, garden, and parking, alongside nearby hiking trails and local amenities.

Best Middletown, NY lodgings with a pool

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

Pinnacle Pointe By Relaxtay | 600-acre Private Luxury Estate With Spa, Pool, Theater & Lake - Middletown, NY
10 1 review
Middletown, NY
29/06 – 03/07
SG$11306/nighttotal: SG$45224 (4 )

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

7 4
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.
The Four Seasons Glamping - Middletown, NY
8.4 5 reviews
Middletown, NY
28/08 – 05/09
SG$129/nighttotal: SG$1032 (8 )

The Four Seasons Glamping

1 3
glamping , Scotchtown
The glamping tent is located just a few kilometres from Middletown, offering easy access to shopping, dining, and attractions like Legoland and local wineries. The tent has received excellent ratings for user experience, location, and cleanliness.
The accommodation has a private outdoor area with seating, a hammock, a propane grill, and a picnic table. Guests can enjoy access to a shared pool, discounted rates for activities at the Ring Homestead Adventure Camp, and a comfortable stay with amenities like solar electricity, a grill, fire pit, picnic table, hammock, and a pool.
9 Person Glamping Tent- Chipmunk - Middletown, NY
9.7 13 reviews
Middletown, NY
28/08 – 05/09
SG$134/nighttotal: SG$1072 (8 )

9 Person Glamping Tent- Chipmunk

1 3
glamping , Scotchtown
Chipmunk Cove#26 is situated in Scotchtown, just a short distance from Legoland and other attractions. This accommodation receives excellent ratings for location, cleanliness, and user experience.
The tent offers a spacious layout, accommodating up to 45 guests, making it perfect for large groups. Amenities include picnic tables, BBQ grills, a fridge, and a bonfire pit, alongside access to Adventureland for additional entertainment.
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.

Frequently asked questions about accommodations in Middletown, NY

Destinations nearby

Best Middletown, NY accommodations with a garden

Cozy Loft Cabin High Above Bashakill Wildlife Refuge - Middletown, NY
9.4 29 reviews
Middletown, NY
29/06 – 03/07
SG$260/nighttotal: SG$1040 (4 )

Cozy Loft Cabin High Above Bashakill Wildlife Refuge

1 4
cabin , Otisville
This Otisville mountain lodge is situated near the Mamakating Environmental Education Centre, Sheriff H. Frank Bigger Memorial Park, and Gobbler's Knob State Forest (all within 5km), and 10km from the Mamakating Farmers Market and Bashakill Vineyards.
The 37-square-metre property boasts two bedrooms, one bathroom, sleeps four, and includes a kitchenette with a fridge and microwave, a patio, free Wi-Fi, and a Smart TV.
Serene And Modern Woodland Retreat, Hudson Valley & Catskills - Middletown, NY
10 5 reviews
Middletown, NY
28/08 – 05/09
SG$498/nighttotal: SG$3984 (8 )

Serene And Modern Woodland Retreat, Hudson Valley & Catskills

3 3
apartment , Montgomery
This three-bedroom, two-bathroom Montgomery holiday home is conveniently located approximately 13km from LEGOLAND® New York and 7km from Angry Orchard.
The self-catering property sleeps six guests and boasts a fully equipped kitchen with appliances including a coffee maker and ice maker, in-unit laundry, Wi-Fi, a private terrace, on-site parking, and access to a spa and garden.
Abomb! Adorable 2-bdrm Chalet With Lots Of Room! - Middletown, NY
9.8 6 reviews
Middletown, NY
28/08 – 05/09
SG$276/nighttotal: SG$2208 (8 )

Abomb! Adorable 2-bdrm Chalet With Lots Of Room!

2 3
chalet , Wurtsboro
This Wurtsboro holiday home is ideally situated within 5km of Mamakating Library, Veteran's Memorial Park, Sullivan County Parks & Recreation, Masten Lake, and the Mamakating Farmers Market.
Sleeping six guests in two bedrooms and one bathroom, this pet-friendly chalet boasts a fully equipped kitchen, air conditioning, a terrace, garden, spa, parking, and Wi-Fi, with barbecue facilities available on-site.
Pinnacle Pointe By Relaxtay 600 Acre Private Luxury Estate With Spa, Pool, Theater And Lake - Middletown, NY
Middletown, NY
29/06 – 03/07
SG$17031/nighttotal: SG$68124 (4 )

Pinnacle Pointe By Relaxtay 600 Acre Private Luxury Estate With Spa, Pool, Theater And Lake

7 4
house , Bloomingburg
This luxury private estate, offering 965 hectares of seclusion, is located 37 kilometres from Stewart International Airport and 37 kilometres from DM Weil Gallery in High View.
This 7-bedroom villa boasts 863 square meters of floor area, accommodates up to 47 guests, and features a swimming pool, jacuzzi, sauna, fitness centre, billiards, and table tennis, with golf, fishing, canoeing, and hiking available nearby.

Best Middletown, NY accommodations with a kitchen

The Perfect Up To Date Private Getaway To Call Home For A While - Middletown, NY
8.6 4 reviews
Middletown, NY
29/06 – 03/07
SG$850/nighttotal: SG$3400 (4 )

The Perfect Up To Date Private Getaway To Call Home For A While

6 4
apartment , Bloomingburg
This house is located just 3 kilometres from Bloomingburg Village Hall, Wurtsboro Ridge State Forest, and Veteran's Memorial Park, offering easy access to local attractions and a peaceful mountain setting. The property has received very good user ratings, suggesting a comfortable and enjoyable stay.
This 6-bedroom house, spanning 334 square metres, comfortably accommodates up to 20 guests. The house has a fully equipped kitchen, a terrace, a garden, and a parking space, making it ideal for families and groups looking for a relaxing getaway.
Pond + Gazebo: Expansive Hudson Valley Escape! - Middletown, NY
Middletown, NY
28/08 – 05/09
SG$1550/nighttotal: SG$12400 (8 )

Pond + Gazebo: Expansive Hudson Valley Escape!

5 3
house , Goshen
This spacious 5-bedroom holiday home is located in Goshen, offering convenient access to local attractions in the Hudson Valley.
This 408 square meter holiday home features a fully equipped kitchen, four bathrooms, an outdoor dining area, a private patio, on-site parking, complimentary WiFi, and air conditioning, with a guest capacity of 27.
House Near Legoland, Farms, And Airport/ Train - Middletown, NY
Middletown, NY
10/08 – 07/09
SG$421/nighttotal: SG$11788 (28 )

House Near Legoland, Farms, And Airport/ Train

1 1
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
10/08 – 07/09
SG$584/nighttotal: SG$16352 (28 )

Elegant Town Home Middletown Suburb Close To City

3 1
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.
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