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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Montgomery vacation 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.

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 ￥23,300
￥41,990 total
includes taxes & fees
Jan 11 - Jan 12
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

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 ￥22,029
￥35,573 total
includes taxes & fees
Feb 8 - Feb 9
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Microwave, oven, stovetop, dishwasher
Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (15 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 ￥23,645
￥42,384 total
includes taxes & fees
Jan 11 - Jan 12
Modern Hudson Valley Apt 202 - King/Queen/Twin
Fridge, microwave, oven, stovetop
Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
2.0 star property
Montgomery
The price is ￥41,320
￥75,170 total
includes taxes & fees
Jan 25 - Jan 26
Luxury 3BR with King Beds in Montgomery Village
Fridge, microwave, oven, stovetop
New Farmhouse-Hot Tub, King Beds, Game Room & View

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 ￥109,475
￥198,618 total
includes taxes & fees
Jan 15 - Jan 16
New Farmhouse-Hot Tub, King Beds, Game Room & View
Property grounds
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (4 reviews)
"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 ￥23,849
￥40,593 total
includes taxes & fees
Jan 24 - Jan 25
TRANQUIL MOUNTAIN SOLITUDE
Interior
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (32 reviews)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
The price is ￥10,060
￥26,911 total
includes taxes & fees
Jan 11 - Jan 12
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
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 !

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 ￥14,121
￥61,941 total
includes taxes & fees
Jan 12 - Jan 13
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Dining
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

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 ￥17,259
￥37,571 total
includes taxes & fees
Jan 28 - Jan 29
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Terrace/patio
House on the Babbling Brook- Quiet 2BR + King Bed!

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, (5 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥11,768
￥48,421 total
includes taxes & fees
Jan 11 - Jan 12
House on the Babbling Brook- Quiet 2BR + King Bed!
Exterior detail
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (42 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is ￥17,259
￥36,850 total
includes taxes & fees
Jan 20 - Jan 21
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
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

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 ￥15,660
￥32,971 total
includes taxes & fees
Jan 15 - Jan 16
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
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

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 ￥13,980
￥24,335 total
includes taxes & fees
Jan 12 - Jan 13
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior
Dream getaway apartment in the foot of Gunks Ridge

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 ￥10,200
￥27,157 total
includes taxes & fees
Feb 9 - Feb 10
Dream getaway apartment in the foot of Gunks Ridge
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!

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 ￥11,768
￥40,451 total
includes taxes & fees
Jan 12 - Jan 13
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
TV
Cozy 1-bedroom retreat minutes from West Point!

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 ￥14,662
￥29,746 total
includes taxes & fees
Feb 9 - Feb 10
Cozy 1-bedroom retreat minutes from West Point!
Outdoor dining
Stylish & Peaceful Getaway on 3 Private Acres

Stylish & Peaceful Getaway on 3 Private Acres

Stylish & Peaceful Getaway on 3 Private Acres
2.0 star property
Goshen
9.0 out of 10, Wonderful, (12 reviews)
"Great location!"
United States
Alozie E.
The price is ￥45,187
￥68,722 total
includes taxes & fees
Jan 11 - Jan 12
Stylish & Peaceful Getaway on 3 Private Acres
1 bedroom, free WiFi, bed sheets
The Studio at the Inn at High Falls

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, (34 reviews)
"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "
United States
William K.
The price is ￥17,651
￥42,087 total
includes taxes & fees
Jan 11 - Jan 12
The Studio at the Inn at High Falls
Exterior detail
Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.
New Paltz
10.0 out of 10, Exceptional, (7 reviews)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is ￥20,052
￥40,206 total
includes taxes & fees
Jan 11 - Jan 12
Cozy private suite in the heart of beautiful Gardiner.
Fireplace, books
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.4 out of 10, Exceptional, (12 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is ￥12,743
￥29,770 total
includes taxes & fees
Jan 12 - Jan 13
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
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 & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"The staff was extremely friendly!"
Nickea 1-night trip
Posted 4 days ago
Hampton Inn & Suites Poughkeepsie

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 vacation rentals in Montgomery?

Yes, you can find vacation rentals in Montgomery near Orange County Arboretum, or you can choose a more secluded option if you're looking for extra privacy while you relax. Our travelers 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 vacation rentals that Montgomery has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation 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 kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Montgomery?

Choose from 12 Expedia vacation rentals in Montgomery for a memorable vacation.

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 vacation rental in Montgomery like?

Vacation rentals are privately owned properties where you can stay for short or long periods in Montgomery. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.