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Montgomery Holiday Rentals

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Check prices for these dates

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Holiday Rentals in Montgomery

Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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 HK$1,463
HK$2,394 total
includes taxes & fees
15 Oct - 16 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (39)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
The price is HK$2,015
HK$2,605 total
includes taxes & fees
2 Nov - 3 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (26)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
The price is HK$848
HK$1,369 total
includes taxes & fees
15 Oct - 16 Oct
Cabin in the heart of the Hudson Valley, Cabin 2
Terrace/patio
Cove - King Bed Escape w/Hot Tub, Unit A
Cove - King Bed Escape w/Hot Tub, Unit A
Cove - King Bed Escape w/Hot Tub, Unit A
Exterior
Trails Head Cabin
Trails Head Cabin
9.8 out of 10, Exceptional, (93)
"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 HK$910
HK$1,636 total
includes taxes & fees
15 Oct - 16 Oct
Trails Head Cabin
Dining tables
Chestnut on Willow Lake
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 HK$3,112
HK$4,526 total
includes taxes & fees
15 Oct - 16 Oct
Chestnut on Willow Lake
Children’s area
Hickory on Willow Lake
Hickory on Willow Lake
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is HK$3,306
HK$4,775 total
includes taxes & fees
15 Oct - 16 Oct
Hickory on Willow Lake
Exterior
Rustic Cabin in Fishkill!
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 HK$1,774
HK$2,809 total
includes taxes & fees
1 Nov - 2 Nov
Rustic Cabin in Fishkill!
Interior
The Perfect Essential Getaway!
The Perfect Essential Getaway!
9.6 out of 10, Exceptional, (5)
"Owner was very responsive and accommodating on the app when I had questions. Place was great."
The price is HK$7,196
HK$9,918 total
includes taxes & fees
16 Oct - 17 Oct
The Perfect Essential Getaway!
Interior
Large,Cozy,Bright Apartment, Business Themed.
Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (14)
"Very cozy stay with responsive host"
The price is HK$3,151
HK$5,266 total
includes taxes & fees
15 Oct - 16 Oct
Large,Cozy,Bright Apartment, Business Themed.
Property grounds
The Woodbury Cottage
The Woodbury Cottage
9.0 out of 10, Wonderful, (26)
"A cozy place to stay. "
The Woodbury Cottage
Interior
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
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!
Exterior
Trails Head Tiny House
Trails Head Tiny House
9.0 out of 10, Wonderful, (19)
"Host was very friendly and helpful. "
The price is HK$553
HK$969 total
includes taxes & fees
15 Oct - 16 Oct
Trails Head Tiny House
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
10.0 out of 10, Exceptional, (1)
"Great host"
The price is HK$2,483
HK$6,134 total
includes taxes & fees
27 Oct - 28 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Outdoor dining
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
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
Interior
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
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
Fridge, microwave, oven, stovetop
Beautiful Barn on 7 Acres - Get Away from it All
Beautiful Barn on 7 Acres - Get Away from it All
9.4 out of 10, Exceptional, (33)
"Had a great time in this super unique and well cared for space"
Beautiful Barn on 7 Acres - Get Away from it All
Exterior
Mountain View escape
Mountain View escape
10.0 out of 10, Exceptional, (67)
"This was such a lovely place to stay! Great location and beautiful setting. "
Mountain View escape
Fridge, microwave, oven, stovetop
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
2.0 star property
9.4 out of 10, Exceptional, (22)
"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 HK$2,567
HK$4,080 total
includes taxes & fees
15 Oct - 16 Oct
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Smart TV, fireplace, books, computer monitors
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
10.0 out of 10, Exceptional, (2)
"From the moment we arrived, we knew we had picked a gem. The house is absolutely lovely—tastefully decorated, comfortable, and full of charm. Every room feels fresh and inviting, and it’s clear the owners take great pride in maintaining their space.Cleanliness was outstanding throughout. We were especially touched by how genuinely friendly and responsive the owner was. From our first inquiry to the check-out process, they were prompt, helpful, and always checked to make sure we were comfortable....
The price is HK$3,431
HK$6,847 total
includes taxes & fees
15 Oct - 16 Oct
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Our third time staying here. Always clean, quiet and comfortable. The staff are always friendly."
Cynthia 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen

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!

Frequently asked questions

Are there holiday rentals in Montgomery?

Yes, there are holiday rentals in Montgomery close to Orange County Arboretum, 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Montgomery offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Montgomery?

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

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 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.