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Montgomery Vacation Rentals

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Dec 25 - Dec 26
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Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Montgomery vacation rentals

1 bedroom, desk, iron/ironing board, free WiFi
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Apartment in Montgomery

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
10.0 out of 10, Exceptional, (2)
"Spacey, clean, best location"
United States
Assaf B.
$236 nightly
The price is $270
Jan 19 - Jan 20, 2026
Total with taxes and fees
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Exterior
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Cabin in Montgomery

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
10.0 out of 10, Exceptional, (2)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
$173 nightly
The price is $196
Jan 11 - Jan 12, 2026
Total with taxes and fees
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Fridge, microwave, oven, stovetop
New Farmhouse-Hot Tub, King Beds, Game Room & View

Vacation Home in Montgomery

New Farmhouse-Hot Tub, King Beds, Game Room & View
10.0 out of 10, Exceptional, (15)
"We loved our stay here! The property is gorgeous and the hosts were helpful and communicative. The house was clean and had everything we needed."
United States
Emily B.
$1,080 nightly
The price is $1,232
Jan 15 - Jan 16, 2026
Total with taxes and fees
New Farmhouse-Hot Tub, King Beds, Game Room & View
Microwave, oven, stovetop, dishwasher
Modern Hudson Valley Apt 202 - King/Queen/Twin

Apartment in Montgomery

Modern Hudson Valley Apt 202 - King/Queen/Twin
9.8 out of 10, Exceptional, (15)
"So clean and spacious! Everything was great "
United States
Dorene W.
$237 nightly
The price is $270
Dec 29 - Dec 30
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
Exterior
TRANQUIL MOUNTAIN SOLITUDE

Mobile Home in Pine Bush

TRANQUIL MOUNTAIN SOLITUDE
10.0 out of 10, Exceptional, (4)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
$212 nightly
The price is $237
Dec 31 - Jan 1, 2026
Total with taxes and fees
TRANQUIL MOUNTAIN SOLITUDE
Apartment, 2 Bedrooms, Balcony, Garden View | Exterior
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

Apartment in Poughkeepsie

2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
2.0 star property
10.0 out of 10, Exceptional, (5)
"My friends and I rented this property for a long girls weekend to attend an event in the area. We liked the historical aspect of the property and Gary was an excellent host. His banana bread was amazing! We would definitely stay again. "
United States
Sara
$232 nightly
The price is $272
Dec 28 - Dec 29
Total with taxes and fees
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
Interior
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Vacation Home in Kerhonkson

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
10.0 out of 10, Exceptional, (32)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
$198 nightly
The price is $201
Jan 8 - Jan 9, 2026
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Terrace/patio
Dream getaway apartment in the foot of Gunks Ridge

Apartment in Wallkill

Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
$164 nightly
The price is $166
Jan 8 - Jan 9, 2026
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Terrace/patio
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Chalet in Gardiner

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
2.0 star property
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$220 nightly
The price is $223
Jan 8 - Jan 9, 2026
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Vacation Home in Warwick

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
$137 nightly
The price is $155
Jan 5 - Jan 6, 2026
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Fridge, microwave, oven, stovetop
The Meyer: spacious family home with hot tub minutes to downtown New Paltz

Vacation Home in New Paltz

The Meyer: spacious family home with hot tub minutes to downtown New Paltz
10.0 out of 10, Exceptional, (12)
"Clean environment, quiet, family friendly and was well equipped. Our family enjoyed staying and the host was available for any questions. "
United States
Awa Malicka B.
$312 nightly
The price is $349
Jan 8 - Jan 9, 2026
Total with taxes and fees
The Meyer: spacious family home with hot tub minutes to downtown New Paltz
Fridge, microwave, oven, stovetop
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Apartment in Beacon

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
10.0 out of 10, Exceptional, (49)
"Great room and location. A nice home base for exploring the area. "
United States
Bob G.
$216 nightly
The price is $249
Jan 8 - Jan 9, 2026
Total with taxes and fees
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Exterior
The Studio at the Inn at High Falls

Vacation Home in High Falls

The Studio at the Inn at High Falls
8.0 out of 10, Very Good, (34)
"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "
United States
William K.
$240 nightly
The price is $268
Dec 26 - Dec 27
Total with taxes and fees
The Studio at the Inn at High Falls
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Vacation Home in Highland Falls

Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$431 nightly
The price is $437
Jan 14 - Jan 15, 2026
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Dining
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Apartment in Warwick

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
10.0 out of 10, Exceptional, (33)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
$230 nightly
The price is $260
Jan 11 - Jan 12, 2026
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Apartment in Beacon

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
$202 nightly
The price is $233
Jan 6 - Jan 7, 2026
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Exterior
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.

Apartment in Wurtsboro

Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
9.0 out of 10, Wonderful, (2)
"The host was very welcoming and very responsive. The apartment was very cute and super clean. I came up for a Halloween event put on by a friend the location was very convenient in the downtown area and I could walk to most of the places I needed to get to I very much enjoyed my stay here and would stay again if I’m in the area. "
United States
Sheena C.
$240 nightly
The price is $270
Jan 21 - Jan 22, 2026
Total with taxes and fees
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
Exterior
Trails Head Tiny House

Vacation Home in Rock Hill

Trails Head Tiny House
9.0 out of 10, Wonderful, (19)
"Host was very friendly and helpful. "
United States
Michael R.
$111 nightly
The price is $125
Dec 29 - Dec 30
Total with taxes and fees
Trails Head Tiny House
Exterior
Trails Head Cabin

Cabin in Rock Hill

Trails Head Cabin
9.8 out of 10, Exceptional, (98)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
$194 nightly
The price is $218
Jan 4 - Jan 5, 2026
Total with taxes and fees
Trails Head Cabin
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
$348 nightly
The price is $367
Jan 12 - Jan 13, 2026
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
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

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Great"
Raju 1-night trip
Posted 19 hours ago
Hampton Inn & Suites Poughkeepsie

Find out more about Montgomery

Everything you need to know about Montgomery vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montgomery vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montgomery vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montgomery. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montgomery in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $218 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montgomery rentals

At Expedia, we put the best Montgomery vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montgomery rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montgomery vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montgomery. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Montgomery?

Yes, you can find vacation rentals in Montgomery near Orange County Arboretum, or you can choose a more secluded option if you're looking for extra privacy while you relax. Our travelers say Montgomery has a good selection of restaurants. Make sure you have time to check out the gardens and shopping during your trip.

What are some of the best vacation rentals that Montgomery has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Montgomery offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Montgomery?

Choose from 11 Expedia vacation rentals in Montgomery for a memorable vacation.

What can I see and do in Montgomery?

Orange County Arboretum and Thomas Bull Memorial Park are a couple of lovely local spots to get outside and enjoy nature. While here, City Winery Hudson Valley and Highland Lakes State Park are other places worth a visit.

What’s a vacation rental in Montgomery like?

Vacation rentals are privately owned properties where you can stay for short or long periods in Montgomery. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.