Find Hotels with Connecting Rooms in Montgomery, NY

Start date: Check-in selected.
To Date
End date: Check-out

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Montgomery Hotels with Connecting Rooms

Tonight
Nov 24 - Nov 25
Tomorrow
Nov 25 - Nov 26
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Top Montgomery Hotels with Connecting Rooms

Exterior
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 star property
Montgomery
8.8 out of 10, Excellent, (788)
"We really like the hotel and area very safe"
United States
Fiordaliza
$91 nightly
The price is $107
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express & Suites Montgomery by IHG
Room, 2 Queen Beds, Accessible, Non Smoking | Premium bedding, pillowtop beds, in-room safe, desk
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 star property
Crown Heights
8.8 out of 10, Excellent, (1006)
"Everything about this hotel was great would absolutely stay again "
United States
Amanda
$99 nightly
The price is $115
Dec 5 - Dec 6
Total with taxes and fees
Hampton Inn & Suites Poughkeepsie
Exterior
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
Chester
8.6 out of 10, Excellent, (1005)
"Great for a quick stay 👍"
United States
Jerry
$78 nightly
The price is $93
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG
Terrace/patio
Homewood Suites by Hilton Poughkeepsie

Homewood Suites by Hilton Poughkeepsie

3.0 star property
Poughkeepsie
9.6 out of 10, Exceptional, (1002)
"Rooms were clean, comfortable and spacious."
United States
MARIA
$103 nightly
The price is $120
Dec 7 - Dec 8
Total with taxes and fees
Homewood Suites by Hilton Poughkeepsie
Exterior
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3.0 star property
Poughkeepsie
8.8 out of 10, Excellent, (1007)
"Comfortable room."
United States
Samantha
$93 nightly
The price is $105
Dec 21 - Dec 22
Total with taxes and fees
Courtyard by Marriott Poughkeepsie
View from property
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
Goshen
8.8 out of 10, Excellent, (1002)
"This place is fantastic from the staff to the rooms. Very clean. Will definitely stay here again."
United States
Linda
$93 nightly
The price is $115
Dec 16 - Dec 17
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1015)
"Parking was very easy, beautiful area, very nice staff"
United States
Elizabeth
$101 nightly
The price is $115
Dec 1 - Dec 2
Total with taxes and fees
Overlook Lodge at Bear Mountain
Terrace/patio
Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

3.0 star property
Poughkeepsie
9.4 out of 10, Exceptional, (381)
"pleasant, quick check in, lovely room, excellent breakfast"
United States
Peter
$108 nightly
The price is $126
Dec 3 - Dec 4
Total with taxes and fees
Home2 Suites By Hilton Poughkeepsie
Fireplace
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3.0 star property
Middletown
8.6 out of 10, Excellent, (1003)
"The hotel was very clean, enjoyed my stay would recommend "
United States
Jessica
$93 nightly
The price is $109
Dec 14 - Dec 15
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
Waterslide
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4.0 star property
Monticello
8.2 out of 10, Very Good, (1822)
"Amazing stayed at the resort, second time here and still planning to come in the future!"
United States
Yeshua
$175 nightly
The price is $198
Dec 11 - Dec 12
Total with taxes and fees
The Kartrite Resort & Indoor Waterpark
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

Find out more about Montgomery

Discover top Montgomery attractions

Montgomery, New York, offers a delightful array of attractions perfect for quality-seeking travelers and their families. Begin your adventure at the historic Montgomery Village, where charming boutiques and local eateries line the streets, inviting you to stroll and shop. The nearby Stewart State Forest is a haven for outdoor enthusiasts, featuring miles of trails perfect for hiking and biking amidst breathtaking natural beauty. For a dose of history, visit the National Purple Heart Hall of Honor, which pays tribute to the sacrifices of veterans, offering a poignant experience for families to reflect upon together. The Hudson Valley Wine Trail is just a short drive away, where you can indulge in tastings at award-winning vineyards—an excellent way to unwind after a day of exploration. For accommodations, consider staying at one of the inviting hotels near the village center, where attentive staff cater to your every need, ensuring a relaxing and pampered stay. With easy access to both scenic spots and local attractions, Montgomery provides a perfect base to create lasting family memories.

Find the best hotels with connecting rooms in Montgomery

Travelers seeking accommodations with connecting rooms in Montgomery, New York, will find these top hotel options ideal for their needs, ensuring comfort and convenience for families or groups.

Holiday Inn Express & Suites Montgomery by IHG

  • Why it's great for extra space: For travelers in search of connecting rooms, the Holiday Inn Express & Suites Montgomery by IHG is an excellent choice with a high guest review rating of 8.8. The hotel offers spacious rooms with connecting room options, ideal for families or groups who wish to stay close while enjoying their own space. Guests can start their day off right with a complimentary breakfast, providing a variety of options to fuel up before exploring the area.
  • Other amenities: In addition to its family-friendly amenities, the hotel boasts a range of amenities to enhance the guest experience. Enjoy 24-hour fitness facilities and a health club for those who want to maintain their workout routine. Other conveniences include free self-parking, daily housekeeping, and the option for rollaway extra beds. Guests will appreciate the child-friendly window design, complimentary toiletries, and the availability of a microwave for in-room dining. With nearby winery tours and release events, there’s something for everyone to enjoy.
  • Nearby attractions: Orange County Farmers Museum - 2.12 miles, City Winery Hudson Valley - 2.55 miles, Thomas Bull Memorial Park - 4.72 miles

Top Montgomery Hotel Reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Spotless room "
Yaakov 1-night trip
Posted 9 hours ago
Hampton Inn & Suites Poughkeepsie

Frequently asked questions

How much do hotels with connecting rooms in Montgomery cost?
Hotels with connecting rooms in Montgomery range from $93 to $198 per night. These stays provide plenty of room for your whole family at a price that won't stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with connecting rooms in Montgomery?
There are multiple hotels with connecting rooms in Montgomery with a total average guest review rating of 8.7. Hampton Inn & Suites Newburgh Stewart Airport comes highly recommended if you're traveling with the kids or just want some extra space. This 2.5-star hotel also features a swimming pool and WiFi. Homewood Suites Stewart Airport is another top pick with connecting rooms. It has a 3-star rating and conveniences such as a barbecue grill and a swimming pool.
How many hotels with adjoining rooms are there in Montgomery?
You'll find 2 hotels with adjoining rooms in Montgomery. Whether you're taking a trip with the little ones or planning a getaway with some friends, Expedia can help you find the best space for your squad.
What are the best cheap hotels with connecting rooms in Montgomery?
Hampton Inn & Suites Newburgh Stewart Airport is one of the best cheap hotels with connecting rooms in Montgomery and includes premium bedding and a swimming pool. Another favorite that's easy on the wallet is Holiday Inn Express & Suites Montgomery, an IHG Hotel. Conveniences here include a swimming pool and a cafe. Rates for hotels with connecting rooms start from just $93 per night. If you're chasing something free and fun to do in Montgomery, Orange County Arboretum deserves a spot on your itinerary. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the top motels with connecting rooms in Montgomery?
Super 8 by Wyndham Montgomery Maybrook is a top choice, located around 2 mi southeast of downtown Montgomery. Offering free WiFi and complimentary breakfast, this motel with connecting rooms is a great budget-friendly place to kick back and relax between adventures.When it's time to lace up some comfy sneakers and go sightseeing, make a beeline for Thomas Bull Memorial Park. Orange County Arboretum is another leading attraction in Montgomery.
Are there any family-friendly hotels with connecting rooms in Montgomery?
A trip with your group in Montgomery is a cinch at Homewood Suites Stewart Airport. With connecting rooms and amenities including complimentary breakfast and laundry facilities, your crew will feel right at home at this 3-star stay. Home2 Suites by Hilton Middletown is another family-friendly hotel with connecting rooms. It has a 3-star rating and conveniences including a nearby theme park and complimentary breakfast. Montgomery has plenty of family-friendly attractions to explore that'll keep the kids entertained. Orange County Farmers Museum and Orange County Arboretum promise a fun-fueled day for all ages.
Why book your hotel with connecting rooms in Montgomery with Expedia?
Reserving a hotel with connecting rooms in Montgomery is as simple as clicking on your travel dates and picking the option that suits your style. On the lookout for something budget friendly or upmarket, or a stay that also features a kitchen? Use Expedia's search filters to narrow your results even further and find your dream fit.
How can I find cheap hotels with connecting rooms in Montgomery?
A great way to find cheap hotels with connecting rooms in Montgomery is with Expedia's user-friendly filter tool. Refine your search results by budget, star rating and amenities to take advantage of unbeatable deals with only a few clicks.
What is there to do in Montgomery near my hotel with connecting rooms?
The ideal travel accessory is a well-planned to-do list. Thomas Bull Memorial Park is a top place to begin your adventures in Montgomery.

Explore a world of travel with Expedia