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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Rentals in Montgomery

3 bedroom house. AC in Village of Montgomery. Safe location. Gourmet kitchen.
Microwave, oven, stovetop, dishwasher

3 bedroom house. AC in Village of Montgomery. Safe location. Gourmet kitchen.

2.0 star property
3 bedroom house. AC in Village of Montgomery. Safe location. Gourmet kitchen.
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is ￥27,809
￥45,517 total
includes taxes & fees
Oct 2 - Oct 3
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (36)
"Great place for a quiet stay"
The price is ￥38,487
￥49,421 total
includes taxes & fees
Nov 1 - Nov 2
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Interior

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

9.8 out of 10, Exceptional, (12)
"We were very comfortable and enjoyed our stay. We enjoyed the deer and bunnies!"
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Fridge, microwave, oven, stovetop

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (17)
"The property was perfectly secluded while being close to town. We observed lots of wildlife including deer, a woodchuck family, and a turtle laying eggs! The house was roomy and comfortable with just enough upscale elegance that made us feel pampered."
The price is ￥54,833
￥82,395 total
includes taxes & fees
Oct 2 - Oct 3
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Chestnut on Willow Lake
Dining tables

Chestnut on Willow Lake

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is ￥59,168
￥85,552 total
includes taxes & fees
Oct 7 - Oct 8
Chestnut on Willow Lake
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (308)
"We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Interior

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

9.6 out of 10, Exceptional, (47)
"House had everything you could ever need. Such a great location "
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Charming Cottage in the Heart of the Shawangunks
Fridge, microwave, oven, stovetop

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (16)
"The gatehouse was a perfect spot for a girls trip getaway. Secluded enough, but close to some local activities and restaurants! Cozy vibe and place had everything we needed!"
Charming Cottage in the Heart of the Shawangunks
The Woodbury Cottage
Property grounds

The Woodbury Cottage

8.8 out of 10, Excellent, (25)
"A cozy place to stay. "
The Woodbury Cottage
Trails Head Cabin
Exterior

Trails Head Cabin

9.8 out of 10, Exceptional, (91)
"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."
The price is ￥14,578
￥28,078 total
includes taxes & fees
Oct 2 - Oct 3
Trails Head Cabin
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (23)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is ￥31,803
￥78,146 total
includes taxes & fees
Oct 21 - Oct 22
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Rustic Cabin in Fishkill!
Exterior

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is ￥33,881
￥53,150 total
includes taxes & fees
Nov 1 - Nov 2
Rustic Cabin in Fishkill!
Trails Head Tiny House
Exterior

Trails Head Tiny House

9.0 out of 10, Wonderful, (19)
"Host was very friendly and helpful. "
The price is ￥11,848
￥19,926 total
includes taxes & fees
Oct 7 - Oct 8
Trails Head Tiny House
Romantic spot above restaurant., ideal for the gourmet
Exterior

Romantic spot above restaurant., ideal for the gourmet

10.0 out of 10, Exceptional, (3)
"Hosts communicated well, the room was spacious and clean, and the restaurant downstairs is spectacular. "
The price is ￥22,188
￥28,615 total
includes taxes & fees
Oct 12 - Oct 13
Romantic spot above restaurant., ideal for the gourmet
Large,Cozy,Bright Apartment, Business Themed.
Interior

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is ￥59,908
￥100,820 total
includes taxes & fees
Oct 7 - Oct 8
Large,Cozy,Bright Apartment, Business Themed.
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Smart TV, video games, DVD player, foosball

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

9.4 out of 10, Exceptional, (39)
"Very nice location and spacious house.Bbq grill could be better"
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Smart TV, fireplace, books, computer monitors

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck

10.0 out of 10, Exceptional, (1)
"We had an amazing stay at this beautiful home! The views overlooking the lake and mountains are absolutely breathtaking—better than I could have imagined. The house itself is gorgeous, well-maintained, and equipped with everything needed for a comfortable stay. On top of that, the host was incredibly responsive and made sure everything was perfect. If you’re looking for a peaceful retreat with unbeatable scenery and top-notch hospitality, this is the place to be. I can't wait to return!"
The price is ￥76,083
￥144,400 total
includes taxes & fees
Oct 28 - Oct 29
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Terrace/patio

Our home is perfect for relaxing and having lots of fun, with near by activity’s

9.8 out of 10, Exceptional, (6)
"My family and I had a great time at this property. Located on a beautiful property. Very relaxing and coordinating with the property owner was very easy. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s
The Studio at the Inn at High Falls
Exterior

The Studio at the Inn at High Falls

8.2 out of 10, Very Good, (30)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
The price is ￥16,641
￥39,844 total
includes taxes & fees
Oct 7 - Oct 8
The Studio at the Inn at High Falls
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

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

10/10 Excellent
"This is such an awesome place to bring the family to unwind.The kids love to hangout at the pool and it’s easy to get to your room after swimming."
Devya 1-night trip
Posted 22 hours ago
The Kartrite Resort & Indoor Waterpark

Find out more about Montgomery

Find out more about Montgomery

Search for holiday rentals in Montgomery on Expedia! You can easily find your home rentals, villas, holiday apartments in Montgomery using one of the methods below:

  • View our selection of featured holiday rentals in Montgomery
  • Use the map to find apartments and other holiday homes in the Montgomery neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montgomery while they last

Look no further and take a look at our great range of rental properties in Montgomery!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Montgomery?

Yes, you can find vacation rentals in Montgomery near Orange County Arboretum, or you can choose a more secluded option if you're looking for extra privacy while you relax. 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?

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi: This vacation home rental outside of Montgomery is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Montgomery?

Choose from 12 Expedia vacation rentals in Montgomery for a memorable vacation.

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. 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.