Montgomery Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Montgomery vacation rentals

Exterior

Cabin in Montgomery

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
10.0 out of 10, Exceptional, (3 reviews)
"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.
$262 nightly
The price is $296
Jan 29 - Jan 30
Total with taxes and fees
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
1 bedroom, desk, iron/ironing board, free WiFi

Apartment in Montgomery

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful stay. Responded quickly to any issues even if it was a tiny one. Would absolutely stay here again. "
United States
Richard D.
$235 nightly
The price is $268
Jan 26 - Jan 27
Total with taxes and fees
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Fridge, microwave, oven, stovetop

Vacation Home in Montgomery

New Farmhouse-Hot Tub, King Beds, Game Room & View
10.0 out of 10, Exceptional, (15 reviews)
"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.
$1,040 nightly
The price is $1,186
Jan 22 - Jan 23
Total with taxes and fees
New Farmhouse-Hot Tub, King Beds, Game Room & View
Fridge, microwave, oven, stovetop

Vacation Home in Montgomery

Luxury 3BR with King Beds in Montgomery Village
2.0 star property
$465 nightly
The price is $472
Jan 25 - Jan 26
Total with taxes and fees
Luxury 3BR with King Beds in Montgomery Village
Microwave, oven, stovetop, dishwasher

Apartment in Montgomery

Modern Hudson Valley Apt 202 - King/Queen/Twin
9.8 out of 10, Exceptional, (16 reviews)
"We had a great stay!! I booked for a “get ready” spot for my wedding and it was everything I could have dreamed of. Everything was perfect and very clean! Can’t wait to book again Very centrally located near some amazing small boutiques, a couple restaurants. The town seemed like a popular spot on the weekend! "
United States
Tiffani H.
$236 nightly
The price is $269
Jan 25 - Jan 26
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
Property grounds

Mobile Home in Pine Bush

TRANQUIL MOUNTAIN SOLITUDE
10.0 out of 10, Exceptional, (4 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
$246 nightly
The price is $276
Feb 14 - Feb 15
Total with taxes and fees
TRANQUIL MOUNTAIN SOLITUDE
TV

Apartment in Highland Falls

Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$175 nightly
The price is $191
Feb 4 - Feb 5
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
Terrace/patio

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 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$216 nightly
The price is $219
Feb 1 - Feb 2
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Terrace/patio

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
$303 nightly
The price is $317
Jan 22 - Jan 23
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Fridge, oven, stovetop, coffee/tea maker

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
$254 nightly
The price is $258
Jan 25 - Jan 26
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Interior

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12 reviews)
"The breakfast was lovely!"
United States
Tara
$256 nightly
The price is $290
Jan 22 - Jan 23
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
Dining

Apartment in Beacon

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
$213 nightly
The price is $245
Jan 22 - Jan 23
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Exterior detail

Cottage in Putnam Valley

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$434 nightly
The price is $478
Jan 22 - Jan 23
Total with taxes and fees
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
3 bedrooms, desk, iron/ironing board, travel crib

Apartment in Highland Falls

Local Artist Inspired | Walk to WestPoint + King Bed
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
$370 nightly
The price is $376
Jan 22 - Jan 23
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
Interior

Vacation Home in Warwick

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.4 out of 10, Exceptional, (8 reviews)
"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.
$134 nightly
The price is $151
Feb 9 - Feb 10
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior

Vacation Home in Kerhonkson

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
10.0 out of 10, Exceptional, (32 reviews)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
$169 nightly
The price is $172
Jan 26 - Jan 27
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

Apartment in Wallkill

Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (24 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
$159 nightly
The price is $162
Jan 22 - Jan 23
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Smart TV

Cottage in Goshen

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
$283 nightly
The price is $295
Jan 22 - Jan 23
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
1 bedroom, free WiFi, bed sheets

Vacation Home in High Falls

The Studio at the Inn at High Falls
8.0 out of 10, Very Good, (34 reviews)
"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
Jan 22 - Jan 23
Total with taxes and fees
The Studio at the Inn at High Falls
Smart TV

Cabin in Rock Hill

Trails Head Cabin
9.8 out of 10, Exceptional, (99 reviews)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
$152 nightly
The price is $171
Jan 22 - Jan 23
Total with taxes and fees
Trails Head Cabin
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montgomery Hotel Reviews

Borland House Inn

Borland House Inn

10/10 Excellent
"Breakfast was hot and tasty. Staff were all pleasant and accommodating. "
wendy 2-night trip
Posted 2 days ago
Borland House Inn

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 $125 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 an electric kettle, 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 12 Expedia vacation rentals in Montgomery for a memorable vacation.

What can I see and do in Montgomery?

Thomas Bull Memorial Park and Orange County Arboretum 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.