Montgomery Vacation Rentals

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Vacation Rentals in Montgomery

Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill
9.6 out of 10, Exceptional, (48)
"Nice place"
United States
mary B.
$310 nightly
The price is $351
Dec 3 - Dec 4
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
$585 nightly
The price is $691
Dec 3 - Dec 4
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.
Exterior
Trails Head Cabin

Trails Head Cabin

Rock Hill
9.8 out of 10, Exceptional, (96)
"Great location that's super close to the trailhead, very convenient for those that want to hike in the area! Very easy check-in and reasonably priced. My partner and I had a wonderful time staying here."
United States
Qiuwei Z.
$174 nightly
The price is $195
Dec 4 - Dec 5
Total with taxes and fees
Trails Head Cabin
Interior
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Monticello
9.6 out of 10, Exceptional, (50)
"Amazing spot in the Catskills! Plenty of beds and rooms."
United States
Taurance R.
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
$398 nightly
The price is $452
Dec 3 - Dec 4
Total with taxes and fees
Rustic Cabin in Fishkill!
Exterior
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

Pine Bush
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.
$198 nightly
The price is $222
Dec 4 - Dec 5
Total with taxes and fees
TRANQUIL MOUNTAIN SOLITUDE
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
$272 nightly
The price is $308
Dec 3 - Dec 4
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!

Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!

New Paltz
10.0 out of 10, Exceptional, (136)
"Great location, comfortable cabin, responsive host!"
United States
Theresa M.
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Terrace/patio
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland
9.4 out of 10, Exceptional, (10)
"Enjoyed the stay. Nice place to relax for a weekend."
United States
Marie J.
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2

Newburgh
9.4 out of 10, Exceptional, (30)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
$169 nightly
The price is $200
Dec 3 - Dec 4
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

new paltz
9.6 out of 10, Exceptional, (5)
"5 stars!!! 100% recommended and I will be coming back! Host is prompt, attentive, and is great with communication!! No complaints at all!!! "
United States
Fantasia
$634 nightly
The price is $710
Dec 3 - Dec 4
Total with taxes and fees
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Interior
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

Kerhonkson
9.8 out of 10, Exceptional, (23)
"Comfortable accommodations. Everything you need for a relaxing holiday "
United States
Susan W.
$261 nightly
The price is $292
Dec 5 - Dec 6
Total with taxes and fees
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Exterior
Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B

Ellenville
10.0 out of 10, Exceptional, (2)
"The cabin was clean, and full of all necessities, cookware, etc. we needed. Hot tub was amazing and overall home was very comfortable and cozy. We wish we could have stayed longer! "
United States
Cristina
Tiny Home, King Bed & Hot Tub, Unit B
Outdoor dining
The House In Highland- Secluded Retreat

The House In Highland- Secluded Retreat

Highland
10.0 out of 10, Exceptional, (18)
"Very nice location and private."
United States
Patrick P.
The House In Highland- Secluded Retreat
Children's area
Hickory on Willow Lake

Hickory on Willow Lake

Fishkill
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
$485 nightly
The price is $552
Dec 29 - Dec 30
Total with taxes and fees
Hickory on Willow Lake
Exterior
The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

High Falls
8.0 out of 10, Very Good, (33)
"We loved our studio — it was cozy, charming, and fit our needs perfectly. Frank went above and beyond to make us feel comfortable, and his hospitality really stood out. Everything was spotless and well-kept, and we had everything we needed for a relaxing stay. The location was convenient, the space felt welcoming, and little touches made it even more enjoyable. We would definitely stay here again and highly recommend it to anyone looking for a comfortable and stress-free getaway!"
United States
Ya-elle G.
$240 nightly
The price is $268
Dec 3 - Dec 4
Total with taxes and fees
The Studio at the Inn at High Falls
Interior
Luxury 9BR Retreat w/Pool & Hot Tub

Luxury 9BR Retreat w/Pool & Hot Tub

Chester
7.0 out of 10, Good, (2)
"Pool was not open or usable but we were not interested in doing that "
United States
John D.
Luxury 9BR Retreat w/Pool & Hot Tub
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh
9.8 out of 10, Exceptional, (20)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Property grounds
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Wallkill
10.0 out of 10, Exceptional, (70)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
$211 nightly
The price is $237
Dec 3 - Dec 4
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
4 bedrooms, iron/ironing board, WiFi
Mountain Peak Retreat - Pool - Hot Tub

Mountain Peak Retreat - Pool - Hot Tub

Ellenville
10.0 out of 10, Exceptional, (6)
"This place is amazing, silence that’s what I need it, clean, pool, jacuzzi, view impressive "
United States
Jorge L.
$886 nightly
The price is $992
Dec 3 - Dec 4
Total with taxes and fees
Mountain Peak Retreat - Pool - Hot Tub
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

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"The room was very nice especially the shower. I stayed at a huge variety of hotels and I never had a shower as good was what they had. By far a very relaxing experience. Smooth check in and check out process and front desk staff was very accommodating! "
Crystal 1-night trip
Posted 1 day ago
Holiday Inn Express Poughkeepsie by IHG

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 $195 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 a coffee maker, 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.