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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Montgomery vacation rentals

Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (4 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.
$266 nightly
The price is $301
Jun 14 - Jun 15
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
Fridge, microwave, oven, stovetop

Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
$480 nightly
The price is $487
Jun 15 - Jun 16
Total with taxes and fees
Luxury 3BR with King Beds in Montgomery Village
Fridge, microwave, oven, stovetop

New Farmhouse-Hot Tub, King Beds, Game Room, Golf Sim & incredible view.

New Farmhouse-Hot Tub, King Beds, Game Room, Golf Sim & incredible view.
Montgomery
10.0 out of 10, Exceptional, (18 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.
$1,245 nightly
The price is $1,421
Jun 11 - Jun 12
Total with taxes and fees
New Farmhouse-Hot Tub, King Beds, Game Room, Golf Sim & incredible view.
Property grounds

Lux Cabin on Farm, River, Animals, Projector

Lux Cabin on Farm, River, Animals, Projector
Montgomery
$376 nightly
The price is $425
Jul 7 - Jul 8
Total with taxes and fees
Lux Cabin on Farm, River, Animals, Projector
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.
$274 nightly
The price is $312
Jun 11 - Jun 12
Total with taxes and fees
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
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, (18 reviews)
"Was a great stay and fabulous communication! Highly recommend "
United States
Michael C.
$235 nightly
The price is $268
Jun 14 - Jun 15
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
Property grounds

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (5 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
$204 nightly
The price is $228
Jun 15 - Jun 16
Total with taxes and fees
TRANQUIL MOUNTAIN SOLITUDE
Exterior

Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B
Ellenville
9.6 out of 10, Exceptional, (9 reviews)
"Quiet and lovely for a solo adventure with my dog. "
United States
Darcie B.
$271 nightly
The price is $304
Jun 11 - Jun 12
Total with taxes and fees
Tiny Home, King Bed & Hot Tub, Unit B
Interior

Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (112 reviews)
"Was very pet friendly. "
United States
Kevin
$183 nightly
The price is $205
Jun 11 - Jun 12
Total with taxes and fees
Trails Head Cabin
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (34 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
$234 nightly
The price is $276
Jun 11 - Jun 12
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$234 nightly
The price is $276
Jun 11 - Jun 12
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
Exterior detail

Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views
Wurtsboro
9.8 out of 10, Exceptional, (8 reviews)
"Quiet, comfortable, cute, cleanliness, intimate stay. "
United States
Charise C.
$303 nightly
The price is $339
Jun 11 - Jun 12
Total with taxes and fees
Close to Trails: Studio w/ Water Views
Interior

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

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
new paltz
8.8 out of 10, Excellent, (8 reviews)
"Very clean Good communication with host Close to town & hiking Recommend! "
United States
Jennifer E.
$627 nightly
The price is $702
Jun 11 - Jun 12
Total with taxes and fees
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
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, (138 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
$277 nightly
The price is $327
Jun 15 - Jun 16
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Apartment (0 Bedroom) | Interior

Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views
3.0 star property
Westbrookville
$302 nightly
The price is $342
Jun 11 - Jun 12
Total with taxes and fees
Close to Trails: Studio w/ Water Views
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
$282 nightly
The price is $319
Jun 30 - Jul 1
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (5 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
$615 nightly
The price is $702
Jun 11 - Jun 12
Total with taxes and fees
Chestnut on Willow Lake
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (37 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
$498 nightly
The price is $563
Jun 16 - Jun 17
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
$243 nightly
The price is $287
Jun 15 - Jun 16
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$491 nightly
The price is $541
Jun 11 - Jun 12
Total with taxes and fees
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
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

Resorts World Catskills Casino

Resorts World Catskills Casino

10/10 Excellent
"Our bellman was excellent but the"
Amy 1-night trip
Posted 6 hours ago
Resorts World Catskills Casino

Find out more about Montgomery

Everything you need to know about Montgomery vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montgomery vacation 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 low season months. For more hustle and bustle, you may prefer to visit Montgomery in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montgomery rentals

At Expedia, we put the best Montgomery vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Cozy Cabin with Sauna & Firepit!: This vacation home rental outside of Montgomery offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave.

How many vacation rentals are there in Montgomery?

Choose from 14 Expedia vacation rentals in Montgomery for a memorable vacation.

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. 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.