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Montgomery Holiday Rentals

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Holiday Rentals in Montgomery

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

10.0 out of 10, Exceptional, (1)
"Guido was very responsive and thoughtful! My partner and I stayed with our small dog and it was safe, clean, well stocked and in a beautiful area. Highly recommend to those looking to stay in the area!"
The price is NZ$325
includes taxes & fees
14 July - 15 July
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Serene Hudson Valley Escape in Historic Montgomery with Hottub,Pool,King Suite

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had workers that were erecting a building nearby and needed a play to stay. Our workers had nothing but nice things to stay about the house and the property. They absolutely loved it and would stay again!"
The price is NZ$1,487
includes taxes & fees
13 July - 14 July
Serene Hudson Valley Escape in Historic Montgomery with Hottub,Pool,King Suite

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

9.0 out of 10, Wonderful, (9)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
The price is NZ$308
includes taxes & fees
16 July - 17 July
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is NZ$691
includes taxes & fees
17 July - 18 July
Rustic Cabin in Fishkill!

Chestnut on Willow Lake

9.0 out of 10, Wonderful, (2)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
The price is NZ$959
includes taxes & fees
21 July - 22 July
Chestnut on Willow Lake

Hickory on Willow Lake

9.0 out of 10, Wonderful, (2)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is NZ$1,012
includes taxes & fees
22 July - 23 July
Hickory on Willow Lake

Red Cottage - Lakeside Property!

The price is NZ$969
includes taxes & fees
21 July - 22 July
Red Cottage - Lakeside Property!

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

9.8 out of 10, Exceptional, (22)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is NZ$552
includes taxes & fees
13 July - 14 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is NZ$1,369
includes taxes & fees
13 July - 14 July
West Point Family Retreat, 5 min walk to Thayer!

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is NZ$557
includes taxes & fees
29 July - 30 July
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
The price is NZ$558
includes taxes & fees
6 Aug - 7 Aug
Fabulous 3bdrm Home w/parking!

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
Room for Everyone: Spacious 6BR West Point Retreat

Cozy Escape -Strong Wi-Fi -Prime Location

7.4 out of 10, Good, (3)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
The price is NZ$589
includes taxes & fees
17 July - 18 July
Cozy Escape -Strong Wi-Fi -Prime Location

Family friendly Spacious 4 bedroom 3 bathroom getaway

10.0 out of 10, Exceptional, (4)
"Very easy checkin, great communication from owner. Bring your own travel soap shampoo etc. Store was right down the road for these things so not a big deal. Would rent again in a heartbeat."
Family friendly Spacious 4 bedroom 3 bathroom getaway

Large, Cozy, Bright Business Class Corporate Retreat

9.0 out of 10, Wonderful, (13)
"Very cozy stay with responsive host"
The price is NZ$1,121
includes taxes & fees
13 July - 14 July
Large, Cozy, Bright Business Class Corporate Retreat

complete privacy vacation home [private pool]

9.8 out of 10, Exceptional, (8)
"Our family thoroughly enjoyed our stay. The pool was so big and so much fun!"
The price is NZ$1,894
includes taxes & fees
15 July - 16 July
complete privacy vacation home [private pool]

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

10.0 out of 10, Exceptional, (298)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is NZ$992
includes taxes & fees
18 July - 19 July
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

5BR Home with Sauna & Pool Hot tub Fire pit

The price is NZ$2,400
includes taxes & fees
14 July - 15 July
5BR Home with Sauna & Pool Hot tub Fire pit

Indoor Pool Paradise | 6BR + Huge Decks

The price is NZ$2,751
includes taxes & fees
15 July - 16 July
Indoor Pool Paradise | 6BR + Huge Decks

The Meyer: spacious family home with hot tub minutes to downtown New Paltz

10.0 out of 10, Exceptional, (7)
"Really appreciated the well stocked kitchen and plenty of towels, etc. the hot tub was happiness!"
The price is NZ$645
includes taxes & fees
31 July - 1 Aug
The Meyer: spacious family home with hot tub minutes to downtown New Paltz
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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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?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Montgomery is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Montgomery?

Choose from 11 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.