Montgomery Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Montgomery holiday rentals

1 bedroom, desk, iron/ironing board, free WiFi

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

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful stay. Responded quickly to any issues even if it was a tiny one. Would absolutely stay here again. "
United States
Richard D.
The price is HK$1,158
HK$2,087 total
includes taxes & fees
26 Jan - 27 Jan
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Exterior

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is HK$1,482
HK$2,294 total
includes taxes & fees
5 Feb - 6 Feb
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Fridge, microwave, oven, stovetop

New Farmhouse-Hot Tub, King Beds, Game Room & View

New Farmhouse-Hot Tub, King Beds, Game Room & View
Montgomery
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here! The property is gorgeous and the hosts were helpful and communicative. The house was clean and had everything we needed."
United States
Emily B.
The price is HK$5,557
HK$10,042 total
includes taxes & fees
19 Jan - 20 Jan
New Farmhouse-Hot Tub, King Beds, Game Room & View
Fridge, microwave, oven, stovetop

Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
2.0 star property
Montgomery
The price is HK$2,054
HK$3,683 total
includes taxes & fees
21 Jan - 22 Jan
Luxury 3BR with King Beds in Montgomery Village
Microwave, oven, stovetop, dishwasher

Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (16 reviews)
"We had a great stay!! I booked for a “get ready” spot for my wedding and it was everything I could have dreamed of. Everything was perfect and very clean! Can’t wait to book again Very centrally located near some amazing small boutiques, a couple restaurants. The town seemed like a popular spot on the weekend! "
United States
Tiffani H.
The price is HK$1,175
HK$2,106 total
includes taxes & fees
19 Jan - 20 Jan
Modern Hudson Valley Apt 202 - King/Queen/Twin
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$729
HK$1,478 total
includes taxes & fees
9 Feb - 10 Feb
Cozy 1-bedroom retreat minutes from West Point!
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$811
HK$2,821 total
includes taxes & fees
4 Feb - 5 Feb
House on the Babbling Brook- Quiet 2BR + King Bed!
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (15 reviews)
"Great Unit."
United States
Rudy R.
The price is HK$585
HK$2,010 total
includes taxes & fees
19 Jan - 20 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
3 bedrooms, desk, iron/ironing board, free WiFi

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is HK$725
HK$3,111 total
includes taxes & fees
20 Jan - 21 Jan
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (24 reviews)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
The price is HK$433
HK$1,271 total
includes taxes & fees
20 Jan - 21 Jan
Dream getaway apartment in the foot of Gunks Ridge
Interior

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
The price is HK$926
HK$1,642 total
includes taxes & fees
2 Feb - 3 Feb
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Exterior detail

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,352
HK$3,730 total
includes taxes & fees
21 Jan - 22 Jan
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Smart TV

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is HK$1,158
HK$2,274 total
includes taxes & fees
21 Jan - 22 Jan
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Terrace/patio

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
2.0 star property
Gardiner
10.0 out of 10, Exceptional, (7 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is HK$1,027
HK$1,951 total
includes taxes & fees
21 Jan - 22 Jan
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
1 bedroom

Natural Getaway at Orchard Farm Lakeside Retreat

Natural Getaway at Orchard Farm Lakeside Retreat
2.0 star property
Monroe
The price is HK$757
HK$1,852 total
includes taxes & fees
19 Jan - 20 Jan
Natural Getaway at Orchard Farm Lakeside Retreat
Smart TV

Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (99 reviews)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
The price is HK$842
HK$1,561 total
includes taxes & fees
19 Jan - 20 Jan
Trails Head Cabin
Interior

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (12 reviews)
"The breakfast was lovely!"
United States
Tara
The price is HK$1,224
HK$2,258 total
includes taxes & fees
20 Jan - 21 Jan
Villa Verde B&B, bsm, Greenwood Lake NY
3 bedrooms, desk, iron/ironing board, travel cot

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is HK$608
HK$2,787 total
includes taxes & fees
20 Jan - 21 Jan
Local Artist Inspired | Walk to WestPoint + King Bed
Dining

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
The price is HK$873
HK$1,858 total
includes taxes & fees
19 Jan - 20 Jan
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Interior

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.4 out of 10, Exceptional, (8 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is HK$681
HK$1,194 total
includes taxes & fees
28 Jan - 29 Jan
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Clean and the staff are very nice "
Jeanette 1-night trip
Posted 3 days ago
Hampton Inn Harriman Woodbury

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 an electric kettle, 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?

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.