Montgomery Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Montgomery

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

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

Fishkill
9.6 out of 10, Exceptional, (48)
"Nice place"
United States
mary B.
The price is HK$2,141
HK$2,730 total
includes taxes & fees
2 Dec - 3 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is HK$3,363
HK$5,380 total
includes taxes & fees
2 Dec - 3 Dec
Large,Cozy,Bright Apartment, Business Themed.
Exterior
Trails Head Cabin

Trails Head Cabin

Rock Hill
9.8 out of 10, Exceptional, (96)
"Great location that's super close to the trailhead, very convenient for those that want to hike in the area! Very easy check-in and reasonably priced. My partner and I had a wonderful time staying here."
United States
Qiuwei Z.
The price is HK$841
HK$1,558 total
includes taxes & fees
4 Dec - 5 Dec
Trails Head Cabin
Interior
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

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

Monticello
9.6 out of 10, Exceptional, (50)
"Amazing spot in the Catskills! Plenty of beds and rooms."
United States
Taurance R.
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,355
HK$3,519 total
includes taxes & fees
2 Dec - 3 Dec
Rustic Cabin in Fishkill!
Exterior
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

Pine Bush
10.0 out of 10, Exceptional, (4)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is HK$960
HK$1,729 total
includes taxes & fees
2 Dec - 3 Dec
TRANQUIL MOUNTAIN SOLITUDE
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is HK$1,464
HK$2,396 total
includes taxes & fees
2 Dec - 3 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!

Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!

New Paltz
10.0 out of 10, Exceptional, (136)
"Great location, comfortable cabin, responsive host!"
United States
Theresa M.
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Terrace/patio
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland
9.4 out of 10, Exceptional, (10)
"Enjoyed the stay. Nice place to relax for a weekend."
United States
Marie J.
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2

Newburgh
9.4 out of 10, Exceptional, (30)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
The price is HK$1,004
HK$1,554 total
includes taxes & fees
2 Dec - 3 Dec
Cabin in the heart of the Hudson Valley, Cabin 2
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

new paltz
9.6 out of 10, Exceptional, (5)
"5 stars!!! 100% recommended and I will be coming back! Host is prompt, attentive, and is great with communication!! No complaints at all!!! "
United States
Fantasia
The price is HK$1,401
HK$5,528 total
includes taxes & fees
3 Dec - 4 Dec
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Interior
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

Kerhonkson
9.8 out of 10, Exceptional, (23)
"Comfortable accommodations. Everything you need for a relaxing holiday "
United States
Susan W.
The price is HK$1,331
HK$2,276 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Exterior
Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B

Ellenville
10.0 out of 10, Exceptional, (2)
"The cabin was clean, and full of all necessities, cookware, etc. we needed. Hot tub was amazing and overall home was very comfortable and cozy. We wish we could have stayed longer! "
United States
Cristina
Tiny Home, King Bed & Hot Tub, Unit B
Outdoor dining
The House In Highland- Secluded Retreat

The House In Highland- Secluded Retreat

Highland
10.0 out of 10, Exceptional, (18)
"Very nice location and private."
United States
Patrick P.
The House In Highland- Secluded Retreat
Children’s area
Hickory on Willow Lake

Hickory on Willow Lake

Fishkill
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
The price is HK$2,997
HK$4,351 total
includes taxes & fees
29 Dec - 30 Dec
Hickory on Willow Lake
Exterior
The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

High Falls
8.0 out of 10, Very good, (32)
"We loved our studio — it was cozy, charming, and fit our needs perfectly. Frank went above and beyond to make us feel comfortable, and his hospitality really stood out. Everything was spotless and well-kept, and we had everything we needed for a relaxing stay. The location was convenient, the space felt welcoming, and little touches made it even more enjoyable. We would definitely stay here again and highly recommend it to anyone looking for a comfortable and stress-free getaway!"
United States
Ya-elle G.
The price is HK$876
HK$2,114 total
includes taxes & fees
2 Dec - 3 Dec
The Studio at the Inn at High Falls
Interior
Luxury 9BR Retreat w/Pool & Hot Tub

Luxury 9BR Retreat w/Pool & Hot Tub

Chester
7.0 out of 10, Good, (2)
"Pool was not open or usable but we were not interested in doing that "
United States
John D.
Luxury 9BR Retreat w/Pool & Hot Tub
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh
9.8 out of 10, Exceptional, (20)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Property grounds
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

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

Wallkill
10.0 out of 10, Exceptional, (70)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
The price is HK$897
HK$1,824 total
includes taxes & fees
2 Dec - 3 Dec
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
4 bedrooms, iron/ironing board, WiFi
Mountain Peak Retreat - Pool - Hot Tub

Mountain Peak Retreat - Pool - Hot Tub

Ellenville
10.0 out of 10, Exceptional, (6)
"beautiful home. felt so comfortable. tje pool n hot tub are awesome. thought it would be great fir family reunion "
United States
Peter D.
The price is HK$3,893
HK$7,725 total
includes taxes & fees
2 Dec - 3 Dec
Mountain Peak Retreat - Pool - Hot Tub
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Check in staff is courteous and friendly."
Sherry A. 1-night trip
Posted 2 days ago
Sleep Inn & Suites Middletown - Goshen

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 a coffee maker, 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 11 Expedia holiday rentals in Montgomery for a memorable holiday.

What can I see and do in Montgomery?

Orange County Arboretum and Thomas Bull Memorial Park 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.