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, (9)
"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, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AU$386
includes taxes & fees
30 Nov - 1 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (11)
"So nice we keep coming back. Can't recommend highly enough and will be back in the spring. "
The Scenic Mansion With Breathtaking View

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$194
includes taxes & fees
1 Dec - 2 Dec
Trails Head Tiny House

Trails Head Cabin

9.8 out of 10, Exceptional, (73)
"Great property right next to the State trails. Very dog friendly. "
The price is AU$322
includes taxes & fees
1 Dec - 2 Dec
Trails Head Cabin

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

The Studio at the Inn at High Falls

7.8 out of 10, Good, (22)
"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 Studio at the Inn at High Falls

Cozy Loft Cabin high above Bashakill Wildlife Refuge

9.2 out of 10, Wonderful, (15)
"Hikers’ Haven was a beautiful getaway. Vin was a great host and the cabin was cozy and well located"
The price is AU$244
includes taxes & fees
1 Dec - 2 Dec
Cozy Loft Cabin high above Bashakill Wildlife Refuge

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is AU$546
includes taxes & fees
2 Dec - 3 Dec
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Mountain View escape

10.0 out of 10, Exceptional, (43)
"Charming. Peaceful. Beautiful. Well-designed. Well-stocked. I cannot recommend this place enough. It is the ideal getaway for an individual or couple. Hope to have a reason to return soon! "
Mountain View escape

Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

9.8 out of 10, Exceptional, (90)
"Very close to hiking and biking trails! Beds were comfortable "
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

Huge house with amazing kitchen, near great hiking; great for groups!

10.0 out of 10, Exceptional, (44)
"Northeastern's annual Alternative Weekend trips had an amazing stay over Veteran's Day weekend! The group volunteered with the local Woodstock Animal Sanctuary. Students and staff raved about the house!"
Huge house with amazing kitchen, near great hiking; great for groups!

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.2 out of 10, Good, (11)
"Great space and very comfortable for a group "
The price is AU$1,304
includes taxes & fees
26 Nov - 27 Nov
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

Cabin in the heart of the Hudson Valley, Cabin 4

8.8 out of 10, Excellent, (18)
"The description of the property was accurate; however, a few things surprised me that would have affected my decision to book or not. First, the house is located beside a busy road where traffic is moving all hours of the day and night at 35-55 mph. For some, this isn't a big deal. For others, it's not as quiet as described. Thankfully, I was delighted to see the room provided a noise machine. Secondly, there is no fan. Only the A/C and heater provided any air movement if you didn't want the...
The price is AU$254
includes taxes & fees
2 Dec - 3 Dec
Cabin in the heart of the Hudson Valley, Cabin 4

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, (64)
"We looked forward to a get away to enjoy the Catskills foliage in October and this cabin checked all the boxes. The owners, Adam and Chrissy, were more than helpful in answering our questions (especially the last minute TV questions before a big game, and how to operate the shower). They welcomed our larger old dog, which was priceless. The inside of the cabin is cozy and nostalgic, but you cannot beat the view! We loved listening to the waterfall below, the layers of colors in the foliage were...
Catskills cabin over waterfall with views & hot tub

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

Renovated 1850's Cottage on Storm King Mountain

9.8 out of 10, Exceptional, (14)
"Great place!"
Renovated 1850's Cottage on Storm King Mountain

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

10.0 out of 10, Exceptional, (117)
"The home is nestled in the woods and surrounded by amazing boulders . The mid century home is comfortable and stunning . We stayed at the house for a quiet weekend visiting friends in the area. The home is well equipped and a joy to stay and relax in . The area is a hikers dream and there are many amazing places to explore . The working fireplace adds a magical atmosphere. We hope to visit this property again . "
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
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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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, (632)
"Clean and friendly staff. Convenient location to shopping and food"
The price is AU$148
includes taxes & fees
9 Dec - 10 Dec
Holiday Inn Express & Suites Montgomery, an IHG Hotel

Super 8 by Wyndham Montgomery Maybrook

2.5 star property
6.4 out of 10, (1054)
"Bb"
The price is AU$118
includes taxes & fees
2 Dec - 3 Dec
Super 8 by Wyndham Montgomery Maybrook

The Kartrite Resort & Indoor Waterpark

4.0 star property
7.8 out of 10, Good, (1093)
"Great service, super clean"
The price is AU$389
includes taxes & fees
1 Dec - 2 Dec
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Montgomery?

Yes, there are holiday rentals close to the most popular sights in Montgomery, 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?

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, a coffee maker and kitchenware.

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. While here, City Winery Hudson Valley and Thomas Bull Memorial 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.