Montgomery Holiday Rentals

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Holiday Rentals in Montgomery

Holiday Home in Fishkill

9.6 out of 10, Exceptional, (47)
"Great place for a quiet stay"
United States
Shawn M.
The price is AU$516
includes taxes & fees
30 Nov - 1 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Holiday Home in Newburgh

9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is AU$1,066
includes taxes & fees
1 Dec - 2 Dec
Large,Cozy,Bright Apartment, Business Themed.

Cabin in Rock Hill

9.8 out of 10, Exceptional, (95)
"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.
The price is AU$335
includes taxes & fees
2 Dec - 3 Dec
Trails Head Cabin

Holiday Home in 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!

Cabin in Fishkill

10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is AU$697
includes taxes & fees
1 Dec - 2 Dec
Rustic Cabin in Fishkill!

Cottage in Fort Montgomery

9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is AU$475
includes taxes & fees
30 Nov - 1 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Mobile Home in 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.
The price is AU$343
includes taxes & fees
2 Dec - 3 Dec
TRANQUIL MOUNTAIN SOLITUDE

Villa in Monroe

6.8 out of 10, (5)
"It was a great home with lots of space indoor and outside. "
United States
Yogita R.
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Cabin in Newburgh

9.4 out of 10, Exceptional, (29)
"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.
The price is AU$308
includes taxes & fees
1 Dec - 2 Dec
Cabin in the heart of the Hudson Valley, Cabin 2

Holiday Home in 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

Holiday Home in 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.
The price is AU$862
includes taxes & fees
29 Dec - 30 Dec
Hickory on Willow Lake

Cabin in Ellenville

10.0 out of 10, Exceptional, (1)
Tiny Home, King Bed & Hot Tub, Unit B

Holiday Home in High Falls

8.0 out of 10, Very good, (32)
"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.
The price is AU$417
includes taxes & fees
6 Dec - 7 Dec
The Studio at the Inn at High Falls

Holiday Home in Highland

10.0 out of 10, Exceptional, (18)
"Very nice location and private."
United States
Patrick P.
The House In Highland- Secluded Retreat

Villa in 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

Holiday Home in Kerhonkson

8.8 out of 10, Excellent, (3)
"We had a great time. The tent and toilet were clean. We appreciated the water provided and the cookware. The only thing to note is that there is a bit of walking on a rocky trail before reaching the campsite (not next to the parking spot). The river was fun to explore but can be difficult for younger kids to get to. The campsite is close to Minnewaska State Park, very convenient. "
United States
Angie W.
The price is AU$235
includes taxes & fees
2 Dec - 3 Dec
Glamping Tent & Campsite by Minnewaska State Park

Holiday Home in 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
The price is AU$1,096
includes taxes & fees
8 Dec - 9 Dec
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Holiday Home in Ellenville

10.0 out of 10, Exceptional, (6)
"beautiful home. felt so comfortable. tje pool n hot tub are awesome. thought it would be great fir family reunion "
United States
Peter D.
The price is AU$1,532
includes taxes & fees
10 Dec - 11 Dec
Mountain Peak Retreat - Pool - Hot Tub

Holiday Home in 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

Apartment in Wallkill

10.0 out of 10, Exceptional, (70)
"Lovely, immaculately clean place, the river was so serene as we drank coffee on the back porch each morning. The first day I saw a blue heron perched on a river rock!The place offered thoughtful amenities, like a Keurig with a filter and coffee. The bed and pillows were very comfortable, we slept well. We so enjoyed our stay and given that we have family nearby and it's affordable, we hope to book it again!"
United States
Aggie P.
The price is AU$362
includes taxes & fees
1 Dec - 2 Dec
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
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

Find out more about Montgomery

Everything you need to know about Montgomery holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montgomery holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montgomery holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery holiday rentals we have selected for you start as low as AU$235 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Montgomery rentals

At Expedia, we put the best Montgomery holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Montgomery?

Yes, there are holiday rentals in Montgomery close to Orange County Arboretum, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Montgomery has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Montgomery?

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

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 holiday rental in Montgomery like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montgomery. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for small groups.