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35 Lodgings in Middletown, NY
10 14 reviews
Middletown, NY
06/20 – 06/27
$1622/nighttotal: $11354 (7 )
Industrial Modern Home - 360 Views!
1 2
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.
Middletown, NY
08/10 – 09/07
$379/nighttotal: $10612 (28 )
Luxury Home With Private Golf Course And Tennis Course Is More Then Home
3 1
apartment , Middletown
This 3-bedroom house is located in Middletown, just a short drive from the Paramount Theatre, Orange County Fair Speedway, and Soons Orchards. It's a great spot for families or groups of friends wanting to explore the area's attractions and enjoy a comfortable stay. This vacation rental offers a fully equipped kitchen, a private balcony, a fitness center, and a tennis court. Guests can also enjoy a barbecue grill, free Wi-Fi, and parking.
9.8 6 reviews
Middletown, NY
08/28 – 09/05
$215/nighttotal: $1720 (8 )
Abomb! Adorable 2-bdrm Chalet With Lots Of Room!
2 3
chalet , Wurtsboro
This Wurtsboro, New York chalet is located within 3 miles of Mamakating Library, Veteran's Memorial Park, Sullivan County Parks & Recreation, Masten Lake, and the Mamakating Farmers Market, offering easy access to local attractions and amenities. This two-bedroom, one-bathroom cabin sleeps six and features a kitchen with a fridge and microwave, air conditioning, a terrace, a garden, a spa, parking, and internet access; barbecue grills are available for guest use.
Middletown, NY
08/10 – 09/07
$213/nighttotal: $5964 (28 )
Nature Escape - Studio In The Forest
1 1
studio , Scotchtown
This secluded Nature Escape studio is located in Middletown, offering a forest setting with convenient access to cultural attractions like the Paramount Theatre and shopping at Galleria at Crystal Run. This studio accommodates up to 5 guests and includes heating, towels, bed linens, soap, and toilet paper, with check-out at 10:00 AM.
9.4 6 reviews
Middletown, NY
06/29 – 07/03
$1109/nighttotal: $4436 (4 )
Spacious 6br Villa - Serene Scenic Mountain Escape\n\n
6 4
apartment , Bloomingburg
This Bloomingburg mountainside home is located within three miles of Bloomingburg Village Hall and Wurtsboro Ridge State Forest, and six miles from Mamakating Farmers Market and Veteran's Memorial Park. This spacious six-bedroom residence boasts 3200 square feet of living space, accommodating up to 18 guests, and features a fully equipped kitchen, free Wi-Fi, a terrace, and a garden.
8.6 4 reviews
Middletown, NY
06/29 – 07/03
$661/nighttotal: $2644 (4 )
The Perfect Up To Date Private Getaway To Call Home For A While
6 4
apartment , Bloomingburg
This house is located within a 5km radius of Bloomingburg Village Hall, Wurtsboro Ridge State Forest, and Veteran's Memorial Park, offering easy access to local attractions. The house has received a "very good" user rating, indicating its quality and appeal to travelers. This 6-bedroom vacation rental comfortably sleeps up to 20 guests, providing ample space for families or groups. You'll enjoy a fully equipped kitchen, a terrace, a garden, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
9.3 3 reviews
Middletown, NY
06/20 – 06/27
$3448/nighttotal: $24136 (7 )
Welcome To The Farmhouse At The Barn!
1 2
gîte , Scotchtown
This charming farmhouse, located in the beautiful Hudson Valley, is a short drive from attractions like Legoland and the Renaissance Faire. Guests consistently rate this home excellent for its location, cleanliness, and overall experience. This spacious vacation rental, ideal for large groups, comfortably accommodates up to 16 guests in 8 bedrooms and 4 bathrooms. The home features modern amenities, a large garden, and parking, making it the perfect place to relax and enjoy the Hudson Valley.
9.8 95 reviews
Middletown, NY
08/28 – 09/05
$262/nighttotal: $2096 (8 )
2 Unit Condo Minutes From Lego Land
2 3
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.
10 3 reviews
Middletown, NY
08/28 – 09/05
$165/nighttotal: $1320 (8 )
9 Person- Glamping Tent Site- Aphrodite
1 3
glamping , Scotchtown
This glamping site, a private family campground and outdoor adventure park, is located just minutes from Middletown, NY, offering convenient access to dining, shopping, and entertainment. This accommodation offers a private outdoor area with seating and a grill, a shared pool, and on-site stores, with capacity for 9 guests and featuring 1 bathroom, fans, lighting, a fridge, potable water, and a fire pit.
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.
Middletown, NY
08/28 – 09/05
$252/nighttotal: $2016 (8 )
Close To Trails: Studio W/ Water Views
1 3
apartment , Otisville
This apartment in Westbrookville offers proximity to nature and local attractions, being a 5-minute walk from Gobbler's Knob State Forest and Sheriff H. Frank Bigger Memorial Park, and within 3 miles of Bashakill Vineyards and Otisville Veterans Memorial Park. Enjoy a private balcony, complimentary WiFi in public areas, on-site barbecue grills, and free self-parking at this Otisville rental.
9.1 15 reviews
Middletown, NY
08/10 – 09/07
$120/nighttotal: $3360 (28 )
Studio Chic In The City
1 1
apartment , Middletown
This Middletown studio apartment offers a convenient downtown location, close to Middletown's restaurants and shops. The unit features a queen-size bed, a full kitchen with a fridge, freezer, and microwave, one bathroom, free Wi-Fi, and on-site parking for guests.
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.
9.4 29 reviews
Middletown, NY
06/29 – 07/03
$202/nighttotal: $808 (4 )
Cozy Loft Cabin High Above Bashakill Wildlife Refuge
1 4
cabin , Otisville
This Otisville mountain cabin, near the Mamakating Environmental Education Center, Sheriff H. Frank Bigger Memorial Park, and Gobbler's Knob State Forest, offers easy access to outdoor recreation and local attractions like the Mamakating Farmers Market and Bashakill Vineyards. This 400-square-foot getaway boasts two bedrooms, one bathroom, sleeps four, and includes amenities such as a kitchenette with a refrigerator and microwave, a terrace, free Wi-Fi, and a Smart TV.
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.
9.4 13 reviews
Middletown, NY
08/10 – 09/07
$162/nighttotal: $4536 (28 )
Blooming Tranquil Getaway
1 1
apartment , Bloomingburg
This Bloomingburg apartment rental is conveniently located a ten-minute drive from NY State Route 20, offering easy access to attractions like Woodbury Common Premium Outlets, Bethel Woods Center for the Arts, Legoland New York, and various casinos within a 20-mile radius. The spacious bi-level unit features three bedrooms sleeping up to six guests, two bathrooms, a fully equipped kitchen with dishwasher, a private garden with a deck, fire pit, and propane grill, plus keyless entry and free parking.
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.
Best Middletown, NY lodging with a pool
Among the 35 accommodations in Middletown, NY, here are the 4 best ones with a pool
9.7 63 reviews
Middletown, NY
08/28 – 09/05
$84/nighttotal: $672 (8 )
Victor-amazing Glamping Experience-middletown Ny
1 3
glamping , Scotchtown
This Scotchtown glamping experience offers a private, quiet setting just minutes from Middletown's shopping and dining, and is a short drive to Legoland and local wineries. This accommodation accommodates up to 8 guests and features a private outdoor area with seating, a grill, and hammocks, along with access to a shared swimming pool with a slide, discounted adventure activities like a ropes course, and portable bathrooms with nearby flushing toilets and showers.
9.6 15 reviews
Middletown, NY
08/10 – 09/07
$72/nighttotal: $2016 (28 )
Waterlily-best Glamping Experience, Middletown Ny
1 1
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.
9.7 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.
8.7 3 reviews
Middletown, NY
08/28 – 09/05
$155/nighttotal: $1240 (8 )
Glamping Tent- 11 Person Max Cap.
1 3
glamping , Scotchtown
This glamping site in Scotchtown is located minutes from Middletown's shopping and dining, and is close to attractions like Legoland and local wineries. This family-friendly, pet-friendly glamping accommodation accommodates up to 11 guests and features a private outdoor area with a propane grill, a shared swimming pool with a slide, and on-site activities like paintball and a ropes course.
Frequently Asked Questions about accommodations in Middletown, NY
What are the most convenient modes of transportation within Middletown, NY?
Middletown is pretty walkable, especially in the downtown area. If you're looking to get around further, the Middletown Transit bus system is a good option. And of course, you can always rent a car if you want to explore the surrounding areas.
What are the best accommodations in Middletown, NY?
What outdoor activities and adventures are popular in and around Middletown, NY?
You can enjoy hiking and biking at the Minisink Preserve or Harriman State Park, both just a short drive from Middletown. For a day of fun on the water, head to Lake Minnewaska State Park Preserve, where you can go swimming, kayaking, or boating.
What are the best accommodations with a pool in Middletown, NY?
What types of accommodations are available in Middletown, NY?
Middletown has a good selection of hotels, motels, and bed and breakfasts to choose from. You can find everything from budget-friendly options to more luxurious stays, depending on your preferences.
What are the best accommodations with a jacuzzi in Middletown, NY?
Spring and fall are great times to visit Middletown, with pleasant temperatures and beautiful foliage. Summer can get hot and humid, but it's a good time to enjoy outdoor activities. Winter can be cold, but it's a nice time to see the area covered in snow.
What are the best accommodations for families and kids in Middletown, NY?
What local dishes and culinary experiences are a must-try in Middletown, NY?
You have to try the pizza at Joe's Pizza, a local favorite. And for a sweet treat, head to The Chocolate Moose for their famous ice cream. Don't forget to check out the farmers' market on Saturdays for fresh, local produce.
What are the best pet friendly accommodations in Middletown, NY?
In which part of Middletown, NY should you consider renting accommodation?
The downtown area is a good choice for being close to shops, restaurants, and attractions. If you're looking for something quieter, you might consider staying in the north end of town, which is a little more residential.
What are the best accommodations with parking in Middletown, NY?
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.
10 1 review
Middletown, NY
06/20 – 06/27
$978/nighttotal: $6846 (7 )
A Hudson Valley Barn Celebration
1 2
farm , Middletown
This Middletown, New York farm offers a family-friendly escape with six bedrooms and four bathrooms, comfortably accommodating up to sixteen guests. The property includes a full kitchen with modern appliances, air conditioning, a jacuzzi, a fitness center, and ample parking; additional details regarding specific acreage or proximity to Middletown attractions are unavailable.
Middletown, NY
06/29 – 07/03
$635/nighttotal: $2540 (4 )
Lovely House With Ac In The Heart Of Goshen There Is A Spectacular Pool
5 4
apartment , Florida
This 5-bedroom, 3-bathroom estate in Goshen, New York, offers 10-guest capacity and is located approximately 9 minutes from LEGOLAND New York Resort, near the historic Goshen Historic Track, and about 1 hour from Downtown Manhattan. This spacious 2.3-acre property features a swimming pool, terrace/balcony, garden, and parking, with air conditioning and internet provided, and is conveniently situated near Woodbury Common Premium Outlets and other local attractions.
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.
Best Middletown, NY accommodation with a kitchen
10 4 reviews
Middletown, NY
08/28 – 09/05
$312/nighttotal: $2496 (8 )
Nature Escape Studio - Sleeps 5
1 3
cabin , Scotchtown
This pet-friendly cabin rental, part of the Ring Homestead Adventure Camp near Middletown, NY, offers easy access to Scotchtown attractions. The one-bedroom, one-bathroom cottage features an open-plan design with a queen bed and bunk bed, sleeping up to five guests, and includes a kitchen, propane grill, fire pit, and summer pool access; hot tub and sauna rentals are available.
9.5 148 reviews
Middletown, NY
08/10 – 09/07
$238/nighttotal: $6664 (28 )
Beautiful Log Cabin Style House
1 1
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.
9.3 25 reviews
Middletown, NY
08/28 – 09/05
$257/nighttotal: $2056 (8 )
Cozy Delight
1 3
apartment , Scotchtown
This Scotchtown house rental near Middletown, NY, offers convenient proximity to Middletown's shopping mall and a major hospital. The three-bedroom, one-bathroom home sleeps four guests and includes a kitchen with a fridge, freezer, and microwave, air conditioning, a garden, parking, and internet access.
9.3 3 reviews
Middletown, NY
08/10 – 09/07
$120/nighttotal: $3360 (28 )
The Columbus Hotel | The Canopy Studio | 52-301
1 1
apartment , Middletown
This apartment is located in a central Middletown district, offering easy access to local shops and dining establishments. This accommodation offers a kitchen, air conditioning, and internet for up to 2 guests, serving as a convenient base for exploring Middletown.