Montgomery Holiday Rentals from €82: Search Short-Term Rentals

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Our top choices for Montgomery holiday rentals

A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

1. Modern Hudson Valley Apt 202 - King/Queen/Twin

Montgomery

Shelby A.

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

2. Luxury 3BR with King Beds in Montgomery Village

Montgomery

Barbara M.

includes taxes & fees

28 Sept - 29 Sept

A wooden cabin with a covered deck, outdoor seating, and a fire pit.

3. Historic Cabin with Pool & Fire Pit

Montgomery

Sarah A.

includes taxes & fees

29 Sept - 30 Sept

A person ascending a stone staircase with a wooden railing, leading to a cabin with a dark exterior and a wooden deck.

4. Lux Cabin on Farm, River, Animals, Projector

Montgomery

includes taxes & fees

30 Sept - 1 Oct

A modern kitchen with white cabinetry, a central island with stools, a built-in oven, and a stainless steel refrigerator.

5. New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!

Montgomery

Kyle F.

includes taxes & fees

28 Sept - 29 Sept

A spacious living room with a sofa, armchairs, and a coffee table. A kitchen with modern appliances is visible in the background.

6. Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Montgomery

Richard D.

includes taxes & fees

13 Oct - 14 Oct

A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

7. Hay Loft Apartment in Barn - Goshen

Goshen

A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

8. Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Wallkill

Chris W.

includes taxes & fees

27 Sept - 28 Sept

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Top Montgomery Hotel Reviews

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent

"I felt right at home! A quiet, very clean room with plenty of parking. Hotel is conveniently close to the highway entrance. I enjoyed my stay and the breakfast."

Hampton Inn by Hilton New Paltz

10/10 Excellent

"I prefer a known quantity to unique, and Hampton Inn provides a fresh, clean hotel, a delicious breakfat bar with lots of hot and cold choices, and it was quiet. We swam in the pool twice in the afternoon during our 5 day stay, and had it to ourselves. I missed having a hot tub, as this property has the indoors pool but no tub."

SureStay Plus Hotel by Best Western Highland Poughkeepsie

8/10 Good

"Staff member Ashley was friendly and helpful on check in. The room was clean and well kept. There was shampoo, conditioner, lotion and bar soaps in the bathroom along with a sufficient amount of towels. The shower water was hot and the pressure was average. The king bed was spacious, but not comfortable. There is a mattress protector that makes noise as you move and the mattress itself is not firm enough to support the back. I did find myself tossing and turning in the night because of the discomfort of the mattress, bit of humidity on the room and definitely because of the noise from the roadway. The breakfast runs from 6:30-9:30. It isn't a full menu, but it will do the trick in the morning. Sample items are eggs, sausage, waffles, fruit, yogurt, muffins, juice, breads, cereal, coffee, tea, hot chocolate. Overall pretty good stay."

Find out more about Montgomery

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 €82 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, 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 14 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.

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Check prices for these dates

Our top choices for Montgomery holiday rentals

1. Modern Hudson Valley Apt 202 - King/Queen/Twin