Photo by ViajandoconAna Rustrian

Montgomery Holiday Rentals

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Holiday Rentals in Montgomery

Exterior
Trails Head Tiny House
10.0 out of 10, Exceptional, (5)
"It was great"
The price is NZ$206
per night
16 May - 17 May
Trails Head Tiny House
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (34)
"Very nice property, immaculately clean and very close to the Riverside Art Venue. Both quiet and convenient for my time in Newburgh. I would definitely stay here again."
The price is NZ$296
per night
27 May - 28 May
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Fridge, microwave, oven, stovetop
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
10.0 out of 10, Exceptional, (34)
"Thanks so much for a great stay. This is such a wonderful place for large groups! Nice hikes in the area too, which we took advantage of. Kitchen and bar area was especially good for cooking and eating for 30+ people!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
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Exterior
Mountain View escape
10.0 out of 10, Exceptional, (24)
"We've stayed in a number of VRBOs and none have been as well-appointed and welcoming as this Mountain View Escape home. Privacy and space, while close to wonderful towns and places to explore. Highly recommend!"
Mountain View escape
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (3)
"Older manufactured home has been updated. We appreciated that each area had its own mini split unit for individual climate control. Area felt safe and quiet. Good hot water and water pressure. Kitchen was stocked for stovetop cooking but not much for baking, and no water glasses. (We just drank everything from the coffee cups.) Split bedroom layout was good for two couples. "
Cozy family-friendly home!
Property grounds
Secluded Cross Rd Getaway
10.0 out of 10, Exceptional, (11)
"The house was very clean and well appointed. Internet was great, and the bed was so comfortable. We met Eric, our host, who gave us invaluable info about a hike/waterfall nearby. The baseboard heat worked well, and there were plenty of pillows and two warm comforters. The jugs of bottled water were appreciated. There was a big grassy area for the dogs to romp. We spent the day at Minnewaska Preserve, only about 12 minutes away."
Secluded Cross Rd Getaway
Fridge, microwave, oven, stovetop
Warwick valley wineries, breweries, Legoland, hiking/skiing - kid friendly
10.0 out of 10, Exceptional, (3)
"House was comfortable for 8 adults and Stefanie was very responsive to inquiries. Close to restaurants in Warwick which was nice."
Warwick valley wineries, breweries, Legoland, hiking/skiing - kid friendly
Exterior
Getaway w/ ALL- Pool, Hot Tub, Game Room, Dog Run, Playground, Near Mountains!
10.0 out of 10, Exceptional, (9)
"Had a great time at this house. It is perfect for large groups and had so many great amenities. Doug was extremely responsive and helpful. Highly recommend!"
Getaway w/ ALL- Pool, Hot Tub, Game Room, Dog Run, Playground, Near Mountains!
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"The place was amazing! It was a very beautiful place and was close to everything I was needing to do. It was extremely clean and cozy and I would stay again for sure!"
Spectacular Log Home Estate North Wing Apt
Outdoor dining
Black Walnut Tree Farm: Farmhouse on 50 Acres
10.0 out of 10, Exceptional, (13)
"Four friends had a wonderful time at Black Walnut Tree Farm. The space was amazing! There was plenty of spaces that we could hang out together, but also we each had areas that we could retreat to. The kitchen was well-stocked ands spacious, the large living room had many comfortable seats around the fire, and there was a great sunroom where we could sit and play games. The grounds were huge and one could easily get lost walking around the property. We all loved the place and are collectively...
Black Walnut Tree Farm: Farmhouse on 50 Acres
Beach
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (34)
"We enjoyed staying here a few days. The place has been updated and was clean. We didn't use the fire pit but we did sit outside on the deck a couple times. The sound of the river is very relaxing."
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Exterior
Trails Head Cabin
9.8 out of 10, Exceptional, (56)
"We had a wonderful time, in spite of rain. The cabin was very comfortable and well stocked. It was literally less than a quarter of a mile to the hiking trails. Our dogs were very comfortable as well. One caveat. If you are coming in via RT. 209, do not turn off of Pine Kill Rd onto David Rhodes rd. Apparently GPS thinks you can go through, but it puts you on a dead end road. If you stay on Pine Kill, it will eventually route you the right way."
The price is NZ$347
per night
15 May - 16 May
Trails Head Cabin
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is NZ$440
per night
20 May - 21 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (39)
"Quiet, clean and very comfortable. Beautiful property located just minutes from town. Will definitely stay here again."
The price is NZ$360
per night
4 Jun - 5 Jun
Cozy country efficiency in the Hudson Valley
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (30)
"Family trip with teens and grandma. Beautiful home but unprepared for the gnats outside. Quiet location. Peaceful to sit outside around the fire pit. Kelly quickly responded to all questions and concerns. Kids enjoyed the ping pong table and grandma enjoyed the sunsets. Thank you for a great getaway!"
The price is NZ$626
per night
15 May - 16 May
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Property grounds
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.6 out of 10, Exceptional, (18)
"Wow Ryan, the owner was really nice guy just a great place to relax and enjoy firepit,.mountain views, outdoor sitting with tv, very private!!! I'll give this one 10+ review!!!!!"
The price is NZ$475
per night
15 May - 16 May
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Interior
The Higashi- comfy mountain home in New Paltz
9.4 out of 10, Exceptional, (6)
"Great house and location in the Hudson Valley. Value Friendly. Loved having 3 bedrooms and 2 bathrooms to use. Would stay here again!"
The price is NZ$442
per night
20 May - 21 May
The Higashi- comfy mountain home in New Paltz
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See all available properties in Montgomery
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.

Other types of properties in Montgomery you may be interested in

Exterior
Holiday Inn Express & Suites Montgomery, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (535)
"Hhhhh"
The price is NZ$252
per night
26 May - 27 May
Holiday Inn Express & Suites Montgomery, an IHG Hotel
Waterslide
The Kartrite Resort & Indoor Waterpark
4.0 star property
8.0 out of 10, Very good, (1011)
"The staff was friendly and courteous. They responded quickly to requests. The only thing me and my family did not like was the breakfast at Eat Eat Eat. The staff were not attentive. We had to ask for the food to be refilled. It was around 10:45 am and breakfast ended at 11. However, the food should have been fully stocked since patrons were still coming in and they were accepting patrons until 11. "
The price is NZ$324
per night
30 May - 31 May
The Kartrite Resort & Indoor Waterpark
Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building
Quality Inn Poughkeepsie
2.5 star property
8.0 out of 10, Very good, (226)
"Very clean rooms and friendly staff, but I only have three complaints. First, the beds were not queen size beds. More like twin. Second, when I looked up the hotel and it stated it served breakfast it would have been better to put continental breakfast. And last, my aunt left her belongings on the bed due to her health issues. We came back from my cousin funeral and her belongings were touched. I’ve stayed at several hotels and motels. Usually when the occupants belongings are on the bed the...
The price is NZ$199
per night
15 May - 16 May
Quality Inn Poughkeepsie
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Montgomery holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Montgomery. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Montgomery. Seeing all the best attractions is bound to make you fall in love with Montgomery. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Montgomery short-term rentals, that won’t be hard to do.

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 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 8 Expedia holiday rentals in Montgomery for a memorable holiday.

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. 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.

Recent reviews of Montgomery properties
Expedia verified reviews