Photo by ViajandoconAna Rustrian

Montgomery Holiday Rentals

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Holiday Rentals in Montgomery

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

9.8 out of 10, Exceptional, (50)
"Our family had a truly wonderful winter holiday stay - our kids (3 and 5) loved having the books and toys available to use. The location was super convenient to hiking, snow tubing and indoor playareas. House was clean and the beds were very comfortable - we slept great especially after using the hot tub!"
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Trails Head Cabin

9.8 out of 10, Exceptional, (76)
"We had a wonderful stay! The property managers were wonderful. We stayed the night for a birthday celebration and they made the experience extra special. Will definitely return!"
The price is AU$324
includes taxes & fees
25 Mar - 26 Mar
Trails Head Cabin

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (107)
"Spectacular view and very convenient to USMA. "
The price is AU$381
includes taxes & fees
25 Mar - 26 Mar
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

9.6 out of 10, Exceptional, (39)
"A wonderful host with a beautiful & comfortable home. All the necessities, plus more! A must stay at. "
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

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

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is AU$465
includes taxes & fees
25 Mar - 26 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

2.0 out of 10, (1)
"There was rats inside the house and there was no amenities like toilet paper. And host was very unresponsive."
Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

The Philip Johnson Wolfhouse

10.0 out of 10, Exceptional, (3)
"This house is an architectural gem with great views to the Hudson river and very close to Dia Beacon and really nice hikes. We were a group of 7 and really enjoyed our time together during our stay. Jeremy was really nice and accommodating. I highly recommend this house."
The Philip Johnson Wolfhouse

Ski, hike or just relax. Historic grist mill sleeps 12. Stay in history!

9.6 out of 10, Exceptional, (42)
"Good place for a family gathering. Plenty of sleeping accommodations and bathrooms. Very clean and charming"
Ski, hike or just relax. Historic grist mill sleeps 12. Stay in history!

Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

2.0 star property
9.4 out of 10, Exceptional, (3)
"This home was newly renovated and very clean. Would stay there again."
The price is AU$718
includes taxes & fees
11 Mar - 12 Mar
Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is AU$622
includes taxes & fees
25 Mar - 26 Mar
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Beautiful Private Stone Home in the Hudson Valley

10.0 out of 10, Exceptional, (139)
"We had a wonderful time together. Room for everyone. We were 11. Clean and spacious. We would stay there again."
Beautiful Private Stone Home in the Hudson Valley

MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

9.6 out of 10, Exceptional, (9)
"We felt well taken care of- the house was warm with the fireplace going when we arrived and when it snowed the driveway was plowed and the sidewalk shoveled. The showers were hot and the beds so cozy! Would recommend to others! "
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (281)
"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 AU$429
includes taxes & fees
11 Mar - 12 Mar
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!

10.0 out of 10, Exceptional, (6)
"We enjoyed our stay! Very spacious, bigger than the pictures make it seem! Nice large backyard with a good amount of privacy. "
The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (2)
"My family and I had a fantastic stay! The house was even more beautiful and spacious than we expected, making it the perfect home base for our weekend trip to Mount Peter. It was clean, cozy, and had everything we needed for a comfortable and relaxing stay. My parents live nearby in Warwick and this will definitely be my go-to VRBO recommendation for anyone visiting the area. We can’t wait to come back!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Mountain View escape

10.0 out of 10, Exceptional, (46)
"Can’t wait to go back, if I could move this home to Myrtle Beach I would. Fantastic communication with homeowner, great location. Homeowner keeps the home stocked with goodies, extra plus! Very cozy and Quiet it’s a 10 Star "
Mountain View escape

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

10.0 out of 10, Exceptional, (32)
"Nice."
The price is AU$362
includes taxes & fees
4 Mar - 5 Mar
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Cozy Escape -Strong Wi-Fi -Prime Location

The price is AU$498
includes taxes & fees
19 Mar - 20 Mar
Cozy Escape -Strong Wi-Fi -Prime Location

Yuzu-stunning mountain views family home with a hot tub and a camper, sleeps 15

10.0 out of 10, Exceptional, (6)
"We were looking for a place to stay close to our extended family for the Christmas holiday. The Yuzu was a perfect option. Spacious, clean and easy check in. The hot tub was an added bonus! Would recommend for anyone staying in the area."
Yuzu-stunning mountain views family home with a hot tub and a camper, sleeps 15
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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Other types of properties in Montgomery you may be interested in

Holiday Inn Express & Suites Montgomery by IHG

2.5 star property
8.8 out of 10, Excellent, (689)
"Customer service "
The price is AU$178
includes taxes & fees
14 Mar - 15 Mar
Holiday Inn Express & Suites Montgomery by IHG

Super 8 by Wyndham Montgomery Maybrook

2.5 star property
6.4 out of 10, (1000)
" Great service,rooms were very clean"
The price is AU$114
includes taxes & fees
30 Mar - 31 Mar
Super 8 by Wyndham Montgomery Maybrook

The Kartrite Resort & Indoor Waterpark

4.0 star property
8.0 out of 10, Very good, (1253)
"We had a great time for presidents weekend"
The price is AU$448
includes taxes & fees
6 Mar - 7 Mar
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.

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?

Beautiful Private Stone Home in the Hudson Valley: This holiday home rental outside of Montgomery is located in the mountains, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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?

Thomas Bull Memorial Park and Orange County Arboretum are a couple of lovely local spots to get outside and enjoy nature. While here, City Winery Hudson Valley and Highland Lakes State Park are other places worth a visit.

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.