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Montgomery Vacation Rentals

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Check prices for these dates

Tonight
Jun 21 - Jun 22
Tomorrow
Jun 22 - Jun 23
Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6

Vacation Rentals in Montgomery

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (111)
"Great place and host!"
The price is ￥27,498
￥43,617 total
includes taxes & fees
Jun 30 - Jul 1
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8
Terrace/patio

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8

10.0 out of 10, Exceptional, (3)
"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

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

9.8 out of 10, Exceptional, (16)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is ￥37,682
￥48,717 total
includes taxes & fees
Jun 22 - Jun 23
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (294)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is ￥58,793
￥77,013 total
includes taxes & fees
Jun 24 - Jun 25
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Trails Head Cabin
Exterior

Trails Head Cabin

9.8 out of 10, Exceptional, (84)
"The Trails Head Cabin was a wonderful getaway for the weekend! It was very clean and nestled in a great area. We enjoyed exploring the trails right next door as well as going up the road for dinner and drinks at Brew."
The price is ￥17,750
￥31,468 total
includes taxes & fees
Jun 25 - Jun 26
Trails Head Cabin
Trails Head Tiny House
Exterior

Trails Head Tiny House

9.0 out of 10, Wonderful, (14)
"A lovely tiny house, great hosts "
The price is ￥10,344
￥18,119 total
includes taxes & fees
Jun 23 - Jun 24
Trails Head Tiny House
Spacious Getaway! 7BR w Park & pool Scenic Views
Smart TV, fireplace, computer monitors

Spacious Getaway! 7BR w Park & pool Scenic Views

8.0 out of 10, Very Good, (1)
Spacious Getaway! 7BR w Park & pool Scenic Views
The Studio at the Inn at High Falls
Exterior

The Studio at the Inn at High Falls

8.0 out of 10, Very Good, (25)
"This was a very nice place, great value and comfortable. I would definitely return."
The price is ￥16,368
￥39,353 total
includes taxes & fees
Jun 24 - Jun 25
The Studio at the Inn at High Falls
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (44)
"A wonderful host with a beautiful & comfortable home. All the necessities, plus more! A must stay at. "
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Modern penthouse suite in a restored grain tower with private roof deck.
Exterior

Modern penthouse suite in a restored grain tower with private roof deck.

10.0 out of 10, Exceptional, (21)
"Wonderful stay!"
The price is ￥49,103
￥78,592 total
includes taxes & fees
Jun 30 - Jul 1
Modern penthouse suite in a restored grain tower with private roof deck.
Cozy Cabin with Sauna & Firepit!
Terrace/patio

Cozy Cabin with Sauna & Firepit!

9.4 out of 10, Exceptional, (28)
"Excellent "
Cozy Cabin with Sauna & Firepit!
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
Exterior

Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

10.0 out of 10, Exceptional, (6)
"We booked this home as additional housing for a corporate retreat. It was very close to the meeting location, as well as Main Street in the nearby town. Home was very clean and beautifully decorated. We traveled there during single digit temps and it was warm and cozy inside. Host is very responsive to questions and inquiries as well. Highly recommend if you are traveling to this area. "
The price is ￥52,592
￥114,043 total
includes taxes & fees
Jun 27 - Jun 28
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
Hot Tub, Pool, 2 Firepits | Near Mohonk Preserve + Wineries | Cragswood Lodge
Smart TV

Hot Tub, Pool, 2 Firepits | Near Mohonk Preserve + Wineries | Cragswood Lodge

Hot Tub, Pool, 2 Firepits | Near Mohonk Preserve + Wineries | Cragswood Lodge
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Terrace/patio

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

10.0 out of 10, Exceptional, (3)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Glamping Tent & Campsite by Minnewaska State Park
Outdoor dining

Glamping Tent & Campsite by Minnewaska State Park

8.8 out of 10, Excellent, (3)
"We had a great time. The tent and toilet were clean. We appreciated the water provided and the cookware. The only thing to note is that there is a bit of walking on a rocky trail before reaching the campsite (not next to the parking spot). The river was fun to explore but can be difficult for younger kids to get to. The campsite is close to Minnewaska State Park, very convenient. "
The price is ￥12,439
￥22,079 total
includes taxes & fees
Jun 25 - Jun 26
Glamping Tent & Campsite by Minnewaska State Park
Higashi: New Paltz family home with King bed minutes to downtown
Fridge, microwave, oven, stovetop

Higashi: New Paltz family home with King bed minutes to downtown

9.8 out of 10, Exceptional, (14)
"Great location and home that is fully stocked with anything you need while away from home. Plenty of space for big families and just a few min from town. The owner was very responsive and was available to us as needed. Can’t wait to stay again! "
Higashi: New Paltz family home with King bed minutes to downtown
Cabin in the heart of the Hudson Valley, Cabin 2
Property grounds

Cabin in the heart of the Hudson Valley, Cabin 2

9.2 out of 10, Wonderful, (14)
"The cabin was very cute cozy and clean! Perfect for a weekend getaway "
The price is ￥15,858
￥25,607 total
includes taxes & fees
Jun 22 - Jun 23
Cabin in the heart of the Hudson Valley, Cabin 2
Inn at High Falls
Fridge, microwave, oven, stovetop

Inn at High Falls

9.4 out of 10, Exceptional, (8)
"Great place for hiking!"
The price is ￥36,373
￥82,127 total
includes taxes & fees
Jun 22 - Jun 23
Inn at High Falls
Cabin in the heart of the Hudson Valley, Cabin 4
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

9.0 out of 10, Wonderful, (23)
"The cabin was great. We drove to Beacon (15min) and spent a day. We plan to return in the Spring/Summer. "
The price is ￥14,273
￥23,736 total
includes taxes & fees
Jun 22 - Jun 23
Cabin in the heart of the Hudson Valley, Cabin 4
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Fridge, microwave, oven, stovetop

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.2 out of 10, Good, (16)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
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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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?

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8: This vacation home rental outside of Montgomery is located on a lake and offers a barbecue grill, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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. You’ll find favorite places to visit like LEGOLAND® New York and Woodbury Common Premium Outlets in the larger area.

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.