Photo by ViajandoconAna Rustrian

Montgomery Holiday Rentals

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Holiday Rentals in Montgomery

Quaint village, walk to restaurants and shops.
9.8 out of 10, Exceptional, (7)
"Wonderfully quaint place within walking distance of downtown restaurants/pubs. Cant wait to come back"
Quaint village, walk to restaurants and shops.
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (99)
"Wonderful hilltop location. Beautiful view. Nice apartment. Great hosts. Wish we could have stayed longer! "
The price is AU$376
includes taxes & fees
1 Oct - 2 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Trails Head Tiny House
9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is AU$183
includes taxes & fees
9 Oct - 10 Oct
Trails Head Tiny House
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (47)
"This property was very comfortable, clean and had everything we needed. I was able to visit with my West Point Cadet for a weekend and cook a meal for her and we had a lovely time. "
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
6.6 out of 10, (8)
"My family was in the area for an event. We had a very pleasant time and the house is spacious and perfect for a weekend getaway!"
The price is AU$1,247
includes taxes & fees
28 Sept - 29 Sept
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Cabin in the heart of the Hudson Valley, Cabin 4
8.8 out of 10, Excellent, (15)
"A bright and surprisingly well furnished space considering its "tiny house" appearance (refrigerator, microwave, coffeemaker, snacks). The bathroom looks newly renovated, is stylish and spacious. The location is quiet and private, as well as very convenient to Rte 9W. When there were communication glitches, Julie was very responsive. One note of caution: if you don't care for lilac/purple paint on the walls, you might want to choose one of her other cabins; I wouldn't paint my own walls that...
The price is AU$240
includes taxes & fees
29 Sept - 30 Sept
Cabin in the heart of the Hudson Valley, Cabin 4
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
9.6 out of 10, Exceptional, (38)
"The whole family had a great time! We would love to come back!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley
Trails Head Cabin
9.8 out of 10, Exceptional, (68)
"Enjoyed a ride for a bachelor's trip in the Catskill Mountains. The cabin was a perfect overnight stop. "
The price is AU$306
includes taxes & fees
1 Oct - 2 Oct
Trails Head Cabin
The Studio at the Inn at High Falls
8.0 out of 10, Very good, (21)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The price is AU$381
includes taxes & fees
30 Sept - 1 Oct
The Studio at the Inn at High Falls
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
9.0 out of 10, Wonderful, (4)
"The home was in a perfect spot with lake views and is nicely close to town. We picked the home for its closeness to the rein fair and I’m so glad we did, It was wonderfully quiet and relaxing after a long day of hanging out at the rein fair !"
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
Mountain View escape
10.0 out of 10, Exceptional, (38)
"Everything about the property was perfect! I would highly recommend"
Mountain View escape
Huge house with amazing kitchen, near great hiking; great for groups!
9.8 out of 10, Exceptional, (40)
"The house is genuinely spacious. It easily accommodated our group of 15 people. There are nine real, full-sized bedrooms, and the common spaces are supersized, including the dining room & kitchen, and the glorious, endless wrap-around porch. It is an old house, a little frayed around the edges, and probably not the right choice for those who prefer new, sleek and immaculate. But we loved its quirks and charm. Its former lives as a boarding house, and later as the home of an artist, are very...
Huge house with amazing kitchen, near great hiking; great for groups!
Kick back & relax in this peaceful, stylish place to stay with the whole family.
10.0 out of 10, Exceptional, (17)
"After having great difficulty with a different host and property, We were thrilled with Malka and the house. She rescued us from a nightmare and was responsive to all of our needs. The house is lovely and very clean. I would highly recommend this property."
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Cottage Suites
3.0 star property
8.0 out of 10, Very good, (3)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
Cottage Suites
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
9.2 out of 10, Wonderful, (22)
"This property was clean and exactly as described. We were in the area for a family gathering and it allowed us a quiet place to regroup with our dog at night. Highly recommend and are hoping to visit again. "
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Catskills cabin over waterfall with views & hot tub
9.8 out of 10, Exceptional, (62)
"The cabin and property were lovely. It’s a little piece of heaven overlooking beautiful mountains and picturesque skies! You can’t get more peaceful than sitting there watching the glider planes in this beautiful space while listening to the waterfall beneath you and enjoying a drink. Couple of issues we had - the hot tub was not operational and we were really looking forward to it. I was even more disappointed when I saw how nice it looked! Inside there is no shower - you have to stand in...
Catskills cabin over waterfall with views & hot tub
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (43)
"The house was neat, clean and exactly as advertised. Two outdoor firepits and right on the water. Was great!"
The price is AU$370
includes taxes & fees
27 Oct - 28 Oct
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
5 Acre Modern Mountain Farm
9.6 out of 10, Exceptional, (21)
"Property was spacious and clean. We truly felt like we were the only ones around. We had access to a grill and fire pit both were ready to go for us. We had A very hot week which it was a relief to come back to the property and get cooled off with the air conditioning. Our only complaint was the lower shower the water pressure was terrible so we all basically ended up using the shower on the main floor. Also we had access to air mattresses but was unable to locate an air pump. Overall was a...
The price is AU$832
includes taxes & fees
30 Sept - 1 Oct
5 Acre Modern Mountain Farm
Gardiner Modern Farm House.
8.4 out of 10, Very good, (7)
"Great place, loved the location—easy to get into town (New Paltz) or out to the trail heads to hike."
The price is AU$688
includes taxes & fees
21 Oct - 22 Oct
Gardiner Modern Farm House.
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Other types of properties in Montgomery you may be interested in

Holiday Inn Express & Suites Montgomery, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (599)
"No sound insulation. I was hearing the conversation next door through the wall. "
The price is AU$156
includes taxes & fees
29 Sept - 30 Sept
Holiday Inn Express & Suites Montgomery, an IHG Hotel
Super 8 by Wyndham Montgomery Maybrook
2.5 star property
6.4 out of 10, (1000)
"Staff was extremely friendly, Room was ok beds are hard."
The price is AU$121
includes taxes & fees
9 Oct - 10 Oct
Super 8 by Wyndham Montgomery Maybrook
The Kartrite Resort & Indoor Waterpark
4.0 star property
7.8 out of 10, Good, (1030)
"What an awesome family little getaway at kartrite amazing patio for the kiddos to play right outside the place was so much fun so much to do the movie for the kids was great after water parks closed. Special shout out to Gloria front desk staff who checked me in when the room was ready I had an issue because I had cash not cards but she helped me and waited patiently for me to get the total funds available for payment she also granted me a small discount wow she really made it happen thank you "
The price is AU$272
includes taxes & fees
27 Oct - 28 Oct
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.

Frequently asked questions

Are there holiday rentals in Montgomery?

Yes, you can find holiday rentals where you'll be only 11.2 mi (18 km) from LEGOLAND® New York, providing a more remote option to escape the hustle and bustle. 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?

Trails Head Tiny House: This holiday home rental outside of Montgomery is situated on a river, and has a BBQ and free WiFi to help you feel content during your stay. Kitchen amenities include a stovetop, kitchenware and an electric kettle.

How many holiday rentals are there in Montgomery?

Choose from 6 Expedia holiday rentals in Montgomery for a memorable holiday.

What can I see and do in Montgomery?

Orange County Arboretum and Highland Lakes State Park are a couple of lovely local spots to get outside and enjoy nature. You’ll find favourite places to visit such as LEGOLAND® New York and Woodbury Common Premium Outlets in the wider area.

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.