Find Hotels with a Pool in Montgomery, NY

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Check availability on Montgomery Hotels with a Pool

Top Montgomery Hotels with a Pool

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Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Montgomery
  • Pool
  • Pet friendly
  • Air conditioning
  • Parking available
  • Barbecue grill
  • Fireplace
10.0 out of 10, Exceptional, (1)
$173 nightly
The price is $196
Nov 16 - Nov 17
Total with taxes and fees
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Indoor pool, sun loungers
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
Chester
  • Indoor pool
  • Pool loungers
8.4 out of 10, Very Good, (1001)
Splash into vacation mode at the pristine indoor pool, complete with inviting sun loungers for post-swim relaxation. Families appreciate the hotel's proximity to LEGOLAND New York while enjoying spotlessly clean rooms with premium bedding and thoughtful amenities.
$83 nightly
The price is $98
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG
BBQ/picnic area
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 star property
Middletown
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
8.6 out of 10, Excellent, (1002)
Dive into summer refreshment at the seasonal outdoor pool, open from May through September. Beyond swimming, this hotel entices with nearby adventures including hiking trails, kayaking, and mountain biking, plus a modern fitness center for year-round activity.
$80 nightly
The price is $95
Dec 3 - Dec 4
Total with taxes and fees
Hampton Inn by Hilton Middletown
Indoor pool
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
Middletown
  • Indoor pool
9.4 out of 10, Exceptional, (902)
Sparkling waters await in the tranquil indoor pool area, open daily from 9:00 AM to 9:00 PM for refreshing swims regardless of weather. Guests praise the spotless facilities, including a rejuvenating hot tub and well-equipped fitness center for complete vacation balance.
$110 nightly
The price is $130
Nov 16 - Nov 17
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
  • Full-service spa
8.4 out of 10, Very Good, (1010)
Seasonal outdoor swimming invites summer splashes amid breathtaking mountain scenery. After hiking local trails, guests rejuvenate with spa treatments, including deep-tissue massages and facials, before enjoying fresh cuisine at the onsite café.
$104 nightly
The price is $118
Nov 18 - Nov 19
Total with taxes and fees
Overlook Lodge at Bear Mountain
Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

3.0 star property
Goshen
  • Outdoor pool
8.6 out of 10, Excellent, (19)
Pool toys transform the outdoor pool into a delightful aquatic playground at this LEGOLAND hotel. After swimming, families can enjoy the on-site restaurant, arcade room, and garden, making this vibrant getaway perfect for creating lasting memories.
$242 nightly
The price is $285
Nov 14 - Nov 15
Total with taxes and fees
LEGOLAND Hotel NEW York
Indoor pool
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3.0 star property
Crown Heights
  • Indoor pool
9.0 out of 10, Wonderful, (1002)
Swimmers glide through crystal-clear waters in the immaculately maintained indoor pool, perfect for all-season enjoyment. Modern rooms with sound-insulated walls and thoughtful amenities complement the 24-hour fitness center and inviting firepit area.
$110 nightly
The price is $128
Nov 23 - Nov 24
Total with taxes and fees
Hyatt Place Poughkeepsie / Hudson Valley
Sports facility
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3.0 star property
Fishkill
  • Indoor pool
8.6 out of 10, Excellent, (1002)
Swimmers enjoy year-round aquatic bliss at the temperature-controlled indoor pool, a perfect complement to the comprehensive 24-hour fitness center. Adventure seekers appreciate nearby hiking trails, while business travelers value the laptop-friendly workspaces.
$92 nightly
The price is $104
Dec 1 - Dec 2
Total with taxes and fees
Hilton Garden Inn Fishkill
Seasonal outdoor pool
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
Goshen
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Gym
8.8 out of 10, Excellent, (1001)
Swimming sessions in the seasonal outdoor pool create perfect summer memories at this exceptionally clean hotel. Complementing aquatic enjoyment, guests appreciate the 24-hour fitness center, complimentary breakfast buffet, and consistently helpful staff.
$93 nightly
The price is $115
Dec 2 - Dec 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
Indoor pool
Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

3.0 star property
Poughkeepsie
  • Indoor pool
9.4 out of 10, Exceptional, (372)
Swimming sessions await at the inviting indoor pool, complemented by well-equipped kitchenettes in each spacious room. After a peaceful night's rest, guests savor a delicious breakfast buffet before exploring nearby Vassar College.
$111 nightly
The price is $129
Nov 30 - Dec 1
Total with taxes and fees
Home2 Suites By Hilton Poughkeepsie
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 Montgomery Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"clean rooms "
christine 1-night trip
Posted 2 days ago
Sleep Inn & Suites Middletown - Goshen

Frequently asked questions

What are some accommodations with pools in Montgomery?
Holiday Inn Express & Suites Montgomery by IHG: Hotel, 7-minute walk from Resorts World Catskills. Features a children's pool, an indoor pool, and a water park. Super 8 by Wyndham Montgomery Maybrook: Hotel, 1-minute walk from Bear Mountain State Park. Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Borland House Inn: Hotel, 4-minute walk from Resorts World Catskills. Provides 6 restaurants, a pool, and a full-service spa. The Kartrite Resort & Indoor Waterpark: Features continental, an indoor pool, and complimentary wired internet access. The Crossroads Hotel, Newburgh: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Offers daily, an indoor pool, and complimentary wired internet access.
What is there to see and do in Montgomery?
Explore places like LEGOLAND® New York and Woodbury Common Premium Outlets while you're in the area. The picturesque setting of Orange County Arboretum and Thomas Bull Memorial Park showcase the area's natural beauty. You'll also discover lots of options for restaurants in Montgomery.
When is the best time to book a hotel with a pool in Montgomery?
Taking into account the local weather in Montgomery is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Montgomery are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

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