Photo by ViajandoconAna Rustrian

Montgomery Vacation Rentals

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Vacation Rentals in Montgomery

Property grounds
Quaint village, walk to restaurants and shops.
The price is CA $253
CA $413 total
includes taxes & fees
May 27 - May 28
Quaint village, walk to restaurants and shops.
Luxury Studio | Private kitchen
Cottage Suites
3.0 star property
The price is CA $180
CA $351 total
includes taxes & fees
May 27 - May 28
Cottage Suites
1 bedroom, desk, iron/ironing board, travel crib
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
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Exterior
Trails Head Tiny House
10.0 out of 10, Exceptional, (5)
"It was great"
The price is CA $108
CA $169 total
includes taxes & fees
May 29 - May 30
Trails Head Tiny House
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 CA $251
CA $361 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (36)
"This sweet little apartment was perfect for my solo stay. Comfortable, quiet, and very easy to get to. Lovely view from the deck. It had a feeling of security and privacy. Vicky was quick with answering my emails."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Exterior
Trails Head Cabin
9.8 out of 10, Exceptional, (57)
"This is a great property we have now stayed multiple times and the property owners make sure everything is perfect on arrival. Will be staying again!"
The price is CA $171
CA $285 total
includes taxes & fees
Jun 2 - Jun 3
Trails Head Cabin
Property grounds
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, (21)
"place was great, exactly as described...ryan was great, no issues all was as described...however sent 2 notes via vrbo but rec'd no response and ryan apologized...so all good...if needed place up that way again would stay."
The price is CA $294
CA $389 total
includes taxes & fees
May 27 - May 28
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
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!
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is CA $149
CA $223 total
includes taxes & fees
May 27 - May 28
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior
The Studio at the Inn at High Falls
8.4 out of 10, Very good, (17)
"Love staying at The Studio at the Inn at High Falls. It truly is my new home away from home. Soo Clean, Comfortable and incredible friendly helpful people who own and work there. Again Thank you Frank and too a New Year. Patricia"
The price is CA $171
CA $355 total
includes taxes & fees
Jun 2 - Jun 3
The Studio at the Inn at High Falls
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
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is CA $149
CA $223 total
includes taxes & fees
May 27 - May 28
Cabin in the heart of the Hudson Valley, Cabin 2
1 bedroom, free WiFi
Cozy Cottage with a Pond 2
6.8 out of 10, (9)
"Safe quiet clean the only thing was the power went out (quick fix though) and the bed was so hard it hurt my back "
The price is CA $137
CA $178 total
includes taxes & fees
May 27 - May 28
Cozy Cottage with a Pond 2
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
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. "
The price is CA $178
CA $377 total
includes taxes & fees
May 28 - May 29
Cozy family-friendly home!
Interior
Royal Garden Main Cabin
Royal Garden Main Cabin
Fridge, microwave, oven, stovetop
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
6.4 out of 10, (5)
"This host is very irresponsible knowing 8 months in advanced about the reservation and not having the pool ready or even communicating that the pool would not be ready for use is just unexceptable. Also property has many things wrong with it. The oven doesn't work, the gas tank for the grill was left empty, all shower heads need to be replaced, the tv and mini Fridge in the basement bedroom dont work, the power outlet in the master bedroom doesn't work and the wall fixture above jacuzzi is just...
The price is CA $697
CA $1,321 total
includes taxes & fees
May 27 - May 28
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Beach
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (35)
"I needed a place in Wallkill NY to stay. This VRBO was perfect!"
The price is CA $176
CA $318 total
includes taxes & fees
Jun 11 - Jun 12
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
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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.

Montgomery Vacation Rental Travel Info

Other types of properties in Montgomery you may be interested in

In-room safe, desk, iron/ironing board, free cribs/infant beds
Super 8 by Wyndham Montgomery Maybrook
2.5 star property
6.4 out of 10, (1005)
"It was clean. The bed was comfy. Only thing is i was across from the Utility room. Got woken up at 830am when i didn't need to. No big deal. I turned the tv on to drown out the ladies having a full conversation right in front of my door. The bathroom was clean. Tub a little Squeaky but manageable. Frig and microwave was good. "
The price is CA $115
CA $130 total
includes taxes & fees
May 27 - May 28
Super 8 by Wyndham Montgomery Maybrook
Exterior
Holiday Inn Express & Suites Montgomery, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (539)
"Nice and clean hotel with nice amenities like Dove toiletry products. "
The price is CA $164
CA $190 total
includes taxes & fees
May 30 - May 31
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, (1006)
"Love the place"
The price is CA $212
CA $327 total
includes taxes & fees
Jun 6 - Jun 7
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Montgomery?

Yes, you can find vacation rentals where you'll be only 11.2 mi (18 km) from LEGOLAND® New York, providing a secluded option if you want a quieter place to stay. 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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This vacation home rental outside of Montgomery is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Montgomery?

Choose from 8 Expedia vacation rentals in Montgomery for a memorable vacation.

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 favorite places to visit like LEGOLAND® New York and Woodbury Common Premium Outlets in the larger area.

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.

Recent reviews of Montgomery properties
Expedia verified reviews