Hotels with a Pool in Middletown

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Hotels with a Pool in Middletown

An indoor swimming pool with lounge chairs and a stone wall.

A modern lobby with a brown sofa, yellow armchairs, a patterned carpet, and a decorative plant centerpiece.

A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

1. Sleep Inn & Suites Middletown - Goshen

Middletown

Indoor pool

$102

$120 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with clear water, surrounded by walls with a blue and white color scheme, and equipped with safety railings and seating areas.

A modern bathroom with a large mirror, a sink, and a shower.

A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

A hotel room with two beds, a desk, a TV, and a chair.

2. La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

Indoor pool

$113

$134 total

includes taxes & fees

Nov 3 - Nov 4

A swimming pool with chairs and sun loungers, large windows, and a tiled wall with a wavy pattern.

A modern hotel lobby with a fireplace, comfortable seating, and a television.

A modern bar area with a curved counter, bar stools, and a television screen.

A modern hotel lobby with a seating area, large windows, and a television screen.

3. Courtyard by Marriott Middletown Goshen

Middletown

Indoor pool

$101

$119 total

includes taxes & fees

Oct 28 - Oct 29

An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.

A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.

A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.

A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.

4. Holiday Inn Express & Suites Middletown - Goshen by IHG

Middletown

Indoor pool
Pool loungers

$115

$136 total

includes taxes & fees

Nov 4 - Nov 5

A poolside area with red umbrellas, a pool, and a fenced patio with chairs and tables.

A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.

5. Hampton Inn by Hilton Middletown

Middletown

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Connecting rooms available

$93

$109 total

includes taxes & fees

Nov 2 - Nov 3

A swimming pool with four lounge chairs and a metal ladder.

A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.

A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

A modern living room with a large TV, comfortable seating, and a patterned rug.

6. Candlewood Suites Middletown Goshen by IHG

Middletown

Indoor pool

$118

$139 total

includes taxes & fees

Oct 19 - Oct 20

An indoor swimming pool with a tiled edge, surrounded by orange and teal chairs, and large windows allowing natural light.

An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.

A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.

A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.

7. Home2 Suites by Hilton Middletown

Middletown

Indoor pool

$161

$193 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.

A spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.

An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.

A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.

8. Residence Inn by Marriott Middletown Goshen

Middletown

Indoor pool

$188

$222 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with a 9-foot depth warning.

A modern hotel lobby with a large map mural, seating areas, and a reception desk.

A hotel with a central entrance pavilion, a flag, and a landscaped garden.

A Simon Premium Outlet sign at Woodbury Commons.

9. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Indoor pool
Pool loungers

$127

$156 total

includes taxes & fees

Nov 4 - Nov 5

A swimming pool with colorful umbrellas and lounge chairs.

A restaurant with multiple dining tables and chairs, a central counter with a chef figure, and colorful hanging lights.

A family inside an elevator with a blue patterned floor and a wall with cartoon characters.

A hotel room with a large bed, a bookshelf, a mural, and a window with curtains.

10. LEGOLAND Hotel NEW York

Goshen

Poolside bar
Pool loungers

$108

$259 total

includes taxes & fees

Oct 12 - Oct 13

A rectangular swimming pool with a metal ladder, surrounded by a low fence and trees.

A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

A spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee table.

11. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Pool
Free breakfast
Free parking
Free WiFi
Connecting rooms available
Air conditioning

$129

$159 total

includes taxes & fees

Nov 1 - Nov 2

A rectangular swimming pool with a wooden deck and a fence.

A lobby with a reception desk, a Coca-Cola refrigerator, a Day's Inn sign, and a seating area with a chair and table.

A bathroom with a sink, mirror, towel rack, and toilet.

A hotel room with a desk, television, two beds, a chair, and a window with curtains.

12. Days Inn by Wyndham Middletown

New Hampton

Pool
Free breakfast
Free parking
Free WiFi
Connecting rooms available
Air conditioning

$77

$90 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled wall.

A gym with treadmills, elliptical machines, and a bench press.

A lobby with a stone fireplace, two armchairs, a coffee table, and a dining area with tables and chairs.

A hotel lobby with a reception desk, a patterned carpet, a stone wall, and a seating area with a checkered sofa and ottoman.

13. Hampton Inn Matamoras/Milford

Matamoras

Indoor pool

$109

$119 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with clear reflections, lounge chairs, and large windows offering views of the outdoors.

A bar area with a long counter, multiple stools, and a variety of bottles and glasses.

A hallway with a wooden floor, glass doors, and a sign for Annie's Lounge.

A spacious dining area with multiple tables and chairs, a high ceiling with grid patterns, and large abstract paintings on the walls.

14. Best Western Hunt's Landing Hotel Matamoras/Milford

Matamoras

Indoor pool
Pool loungers

$121

$132 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with a tiled floor, surrounded by lounge chairs and a high, sloped ceiling.

A hotel room with a desk, two chairs, a printer, and a sign indicating free Wi-Fi in all rooms.

A hotel room with two beds, a desk, a chair, a television, and a door.

A hotel room with a sofa, a small table, a TV, a desk with a chair, and a bed.

15. Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

New Windsor

Indoor pool

$99

$117 total

includes taxes & fees

Oct 18 - Oct 19

An indoor swimming pool with clear water, tiled floor, and a few lounge chairs.

An outdoor seating area with red chairs and tables, a fire pit, and a bar visible through the window.

A modern bar area with a central island, bar stools, and overhead lighting.

16. Resorts World Catskills Casino

Monticello

Indoor pool
Pool loungers
Full-service spa

$156

$202 total

includes taxes & fees

Oct 13 - Oct 14

A hotel lobby with a reception desk, bar area, and a television displaying news.

A hotel room with a kitchenette, a living area with a sofa and a TV, and a large window with curtains.

A hotel room with a bed, desk, TV, and a sofa.

A hotel reception desk with a large 'happy.' poster on the wall, a counter with a computer, and a display of brochures.

17. Hampton Inn & Suites Newburgh Stewart Airport

Newburgh

Indoor pool

$139

$164 total

includes taxes & fees

Oct 28 - Oct 29

A swimming pool with a deck, surrounded by potted plants and outdoor furniture.

A large, two-story white house with a wrap-around porch and a small front garden.

A garden with a stone fountain, a wooden gazebo, and various shrubs and flowers.

A dining table set outdoors with white chairs, a floral tablecloth, and a vase of flowers.

18. The Dominion House Bed & Breakfast

Chester

Outdoor pool
Pool loungers

$215

$243 total

includes taxes & fees

Oct 8 - Oct 9

A large outdoor swimming pool surrounded by trees and a covered pavilion.

A wooden reception desk with a man standing behind it, a staircase, and a wooden interior.

A table set for a formal event with candles, flowers, and glassware.

A long dining table set with multiple place settings, including plates, glasses, and candles.

19. Overlook Lodge at Bear Mountain

Bear Mountain

Full-service spa

$88

$108 total

includes taxes & fees

Nov 2 - Nov 3

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

A multi-story hotel with a prominent entrance, stone pillars, and a well-maintained lawn.

A spacious living area with a curved sofa, a fireplace, and a modern chandelier.

A spacious hotel lobby with a large dining table, comfortable seating, and ceiling fans.

20. Homewood Suites Stewart Airport

New Windsor

Indoor pool
Hot tub

$147

$174 total

includes taxes & fees

Nov 1 - Nov 2

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Discover your perfect hotel with a pool in Middletown

Breakfast included

Hot tub

4 stars

Spa

5 stars

Hotels with pools and free breakfast in Middletown

A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.

A gym with treadmills, a weight bench, and various exercise equipment.

A vending machine area with two beverage dispensers and a snack shelf stocked with various products.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

$113

$134 total

includes taxes & fees

Nov 3 - Nov 4

A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.

Holiday Inn Express & Suites Middletown - Goshen by IHG

Middletown

$115

$136 total

includes taxes & fees

Nov 4 - Nov 5

A Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.

Sleep Inn & Suites Middletown - Goshen

Middletown

$102

$120 total

includes taxes & fees

Nov 1 - Nov 2

A gym with exercise equipment, treadmills, and weight machines.

Hampton Inn by Hilton Middletown

Middletown

$93

$109 total

includes taxes & fees

Nov 2 - Nov 3

Residence Inn by Marriott Middletown Goshen

Middletown

$188

$222 total

includes taxes & fees

Nov 1 - Nov 2

A modern restaurant with a central island, multiple tables, and chairs.

Home2 Suites by Hilton Middletown

Middletown

$161

$193 total

includes taxes & fees

Nov 1 - Nov 2

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top landmarks in Middletown

A large Ferris wheel against a sunset sky.

Orange County Fairgrounds

8.0/10 (87 reviews)

Orange County Fairgrounds is 0.3 mi (0.6 km) from central Mechanicstown, why not stop by during your stay. If you'd also like to explore some of the parks in Mechanicstown, head to The Rock Sports Complex and Orange County Arboretum.

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A lake surrounded by dense vegetation and a hill with a house in the background.

Highland Lakes State Park

8.0/10 (43 reviews)

Highland Lakes State Park is 5.8 mi (9.3 km) from central Middletown, why not stop by during your stay.

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Highland Lake

10.0/10 (3 reviews)

Highland Lake is 3 mi (4.9 km) from central Middletown, why not stop by during your stay.

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Orange County Fair Speedway

8.4/10 (119 reviews)

You can catch an event at Orange County Fair Speedway, located 1.4 mi (2.2 km) from central Mechanicstown.

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Galleria at Crystal Run

8.6/10 (200 reviews)

If you like shopping, take time out to go to Galleria at Crystal Run when in Middletown.

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Paramount Theatre

7.8/10 (96 reviews)

If you’re after a show while in the center of Middletown, you might want to get tickets at Paramount Theatre. If you want to experience more of the culture Middletown has to offer, head to Touro College of Osteopathic Medicine, Orange County Fair Speedway, and Orange County Fairgrounds.

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Orange County Community College

If you'd like to get a taste of Middletown student life, check out Orange County Community College, located 0.6 mi (0.9 km) from central Middletown.

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