Photo by ViajandoconAna Rustrian

Holiday Rentals in Montgomery

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Montgomery

Exterior
Trails Head Tiny House
10.0 out of 10, Exceptional, (5)
"It was great"
The price is €120
includes taxes & fees
7 May - 8 May
Trails Head Tiny House
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!
Property grounds
Renovated 1850's Cottage on Storm King Mountain
10.0 out of 10, Exceptional, (7)
"Great location, very clean. Check in was easy and convenient. Will stay there again. Perfect for a family gathering."
Renovated 1850's Cottage on Storm King Mountain
Save an average of 15% on thousands of hotels when you're signed in
Property grounds
Hudson River View Suite-romantic getaway with fireplace/private deck-75 min NYC
10.0 out of 10, Exceptional, (33)
"Very nice property, immaculately clean and very close to the Riverside Art Venue. Both quiet and convenient for my time in Newburgh. I would definitely stay here again."
The price is €169
includes taxes & fees
19 May - 20 May
Hudson River View Suite-romantic getaway with fireplace/private deck-75 min NYC
Fridge, microwave, oven, stovetop
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (27)
"Weather was not so great to be outside but the game room made up for it!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (24)
"The place was amazing! It was a very beautiful place and was close to everything I was needing to do. It was extremely clean and cozy and I would stay again for sure!"
Spectacular Log Home Estate North Wing Apt
Exterior
Mountain View escape
10.0 out of 10, Exceptional, (24)
"We had an excellent stay at this cabin. Check-in and checkout were smooth and easy. The interior was super cozy, well-decorated, and very clean, with an impressively well-stocked kitchen. Almost all the major hikes in the area were 10-15 minutes away, and New Paltz was just as close. Aster was very responsive and gracious as a host, and even allowed us to stay a few extra hours so we could watch the solar eclipse from the backyard. Only regret was not making use of the fire pit."
Mountain View escape
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (16)
"This house is located minutes from the highway making it easy to get to. Its a very scenic and country area so you feel farther away then you are. The house is extremely clean and well appointed it sits up high on a hill so you can enjoy the veiw of the country house across the street which has a small creek and gardens to enjoy theres even a pool to enjoy in summer months and a fire pit .this house was peaceful and perfect for the quick weekend getaway that we all needed. The host Pat was...
The price is €245
includes taxes & fees
6 May - 7 May
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Exterior
Getaway w/ ALL- Pool, Hot Tub, Game Room, Dog Run, Playground, Near Mountains!
10.0 out of 10, Exceptional, (9)
"Had a great time at this house. It is perfect for large groups and had so many great amenities. Doug was extremely responsive and helpful. Highly recommend!"
Getaway w/ ALL- Pool, Hot Tub, Game Room, Dog Run, Playground, Near Mountains!
Outdoor dining
Black Walnut Tree Farm: Farmhouse on 50 Acres
10.0 out of 10, Exceptional, (13)
"Four friends had a wonderful time at Black Walnut Tree Farm. The space was amazing! There was plenty of spaces that we could hang out together, but also we each had areas that we could retreat to. The kitchen was well-stocked ands spacious, the large living room had many comfortable seats around the fire, and there was a great sunroom where we could sit and play games. The grounds were huge and one could easily get lost walking around the property. We all loved the place and are collectively...
Black Walnut Tree Farm: Farmhouse on 50 Acres
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (2)
"The property was beautiful and just as pictured. The host was more than attentive and helpful. He went above and beyond to make sure my stay was fantastic. I highly recommend this property!"
Cozy family-friendly home!
Exterior
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
10.0 out of 10, Exceptional, (103)
"Great comfortable home with all the amenities we could have asked for! Loved the games there to entertain us and the vestigial fireplace to relax at at night. Close by to area hiking and short drive into town!"
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Exterior
Trails Head Cabin
9.8 out of 10, Exceptional, (55)
"Clean and quiet. Beautiful setting."
The price is €187
includes taxes & fees
2 May - 3 May
Trails Head Cabin
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 €257
includes taxes & fees
6 May - 7 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, desk, iron/ironing board, travel cot
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."
The price is €248
includes taxes & fees
6 May - 7 May
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (37)
"This property is beautiful!! Spotless, functional and private. We absolutely loved the experience and will DEFINITELY be back again."
The price is €209
includes taxes & fees
21 May - 22 May
Cozy country efficiency in the Hudson Valley
Exterior
Catskills Cabin over waterfall with views & hot tub
9.8 out of 10, Exceptional, (57)
"We had a wonderful week of relaxing and recharging, such a cozy cabin! The views are amazing! Definitely recommend!"
Catskills Cabin over waterfall with views & hot tub
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (29)
"Family trip with teens and grandma. Beautiful home but unprepared for the gnats outside. Quiet location. Peaceful to sit outside around the fire pit. Kelly quickly responded to all questions and concerns. Kids enjoyed the ping pong table and grandma enjoyed the sunsets. Thank you for a great getaway!"
The price is €361
includes taxes & fees
2 May - 3 May
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (34)
"Comfy place and great communication. Would stay again!"
The price is €328
includes taxes & fees
6 May - 7 May
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Cozy Loft Cabin high above Bashakill Wildlife Refuge
9.6 out of 10, Exceptional, (9)
"Nice"
The price is €170
includes taxes & fees
6 May - 7 May
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Don't see what you're looking for?
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.

Other types of properties in Montgomery you may be interested in

Exterior
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (366)
"Clean and new. Lovely hotel."
The price is €140
includes taxes & fees
6 May - 7 May
La Quinta Inn & Suites by Wyndham Middletown
Exterior
Holiday Inn Express & Suites Montgomery, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (526)
"Reliable "
The price is €135
includes taxes & fees
12 May - 13 May
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, (1000)
"Great family getaway. The Kartrite is vibrant, very clean and the staff is professional and pleasant. The waterpark was an enjoyable experience and I look forward to returning in the summer."
The price is €241
includes taxes & fees
16 May - 17 May
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.

Everything you need to know about Montgomery holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montgomery holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montgomery holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montgomery. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montgomery holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery holiday rentals we have selected for you start as low as €120 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montgomery rentals

At Expedia, we put the best Montgomery holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montgomery rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montgomery holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montgomery. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Montgomery?

Yes, you can find holiday rentals where you'll be only 11.2 mi (18 km) from LEGOLAND® New York, providing a more remote option to escape the hustle and bustle. 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?

Trails Head Tiny House: This holiday home rental outside of Montgomery is situated on a river, and has a BBQ and WiFi to help you feel content during your stay. Kitchen amenities include a stovetop, kitchenware and an electric kettle.

How many holiday rentals are there in Montgomery?

Choose from 8 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.

Recent reviews of Montgomery properties
Expedia verified reviews