Vacation Rentals in Montgomery, NY: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  New York

  5.  Newburgh
  6.  Montgomery

Refine your search

Price per night

Amenity Filter

Rating

27 Best Vacation Rentals in Montgomery (Starting from $149)

Montgomery Modern
Montgomery Modern
Apartment
Montgomery, NY, USA
0.8k from Montgomery center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$253
Average price / night
Check Availability
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.
Apartment
Montgomery, NY, 12549, United States
0.5k from Montgomery center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$267
Average price / night
Check Availability
New Farmhouse, King Beds, Game Room, Hot Tub & View!
New Farmhouse, King Beds, Game Room, Hot Tub & View!
House
Montgomery, NY, USA
2.2k from Montgomery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

6 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$705
Average price / night
Check Availability
Modern Hudson Valley Apt 202 - King/Queen/Twin
Modern Hudson Valley Apt 202 - King/Queen/Twin
Apartment
Montgomery, NY, 12549, United States
0.6k from Montgomery center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom5 Guests
9.8

Exceptional

17 reviews

$267
Average price / night
Check Availability
Cozy Cabin Gateway with Pool and Firepit
Cozy Cabin Gateway with Pool and Firepit
Ski Chalet
Montgomery, NY, USA
3.0k from Montgomery center

Cheap, Accommodations, Pools, Parking, Cabins, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$149
Average price / night
Check Availability
Luxury 3BR with King Beds in Montgomery Village
Luxury 3BR with King Beds in Montgomery Village
House
Montgomery, NY, 12549, United States
1.0k from Montgomery center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms8 Guests
New to Booking
$473
Average price / night
Check Availability
Cardinal Farm - Montgomery, NY
Cardinal Farm - Montgomery, NY
House
Montgomery, NY, 12549, United States
1.8k from Montgomery center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

5 Bedrooms10 Guests
New to Booking
$1228
Average price / night
Check Availability
Cardinal Farm-The Cardinal Suite
Cardinal Farm-The Cardinal Suite
House
Montgomery, NY, 12549, United States
1.8k from Montgomery center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$292
Average price / night
Check Availability
Cardinal Farm-The Bluebird Room
Cardinal Farm-The Bluebird Room
House
Montgomery, NY, 12549, United States
1.8k from Montgomery center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom2 Guests
New to Booking
$237
Average price / night
Check Availability
Cardinal Farm-The Sparrow Room
Cardinal Farm-The Sparrow Room
House
Montgomery, NY, 12549, United States
1.8k from Montgomery center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$237
Average price / night
Check Availability
Cardinal Farm-The Wren Room
Cardinal Farm-The Wren Room
House
Montgomery, NY, 12549, United States
1.8k from Montgomery center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$237
Average price / night
Check Availability
New Farmhouse-Hot Tub, King Beds, Game Room & View
New Farmhouse-Hot Tub, King Beds, Game Room & View
House
Montgomery, NY, 12549, United States
2.2k from Montgomery center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Fitness Equipment

6 Bedrooms16 Guests
10.0

Exceptional

16 reviews

$1304
Average price / night
Check Availability
Lux Cabin on Farm, River, Animals, Projector
Lux Cabin on Farm, River, Animals, Projector
House
Montgomery, NY, 12549, United States
2.3k from Montgomery center

New to Booking
$429
Average price / night
Check Availability
Historic Cabin with Pool & Fire Pit
Historic Cabin with Pool & Fire Pit
Cabin
Montgomery, NY, 12549, United States
2.9k from Montgomery center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Microwave, No Smoking, Pool

1 Bedroom3 Guests
10.0

Exceptional

3 reviews

$208
Average price / night
Check Availability
Serene Hudson Valley Escape in Historic Montgomery with Hottub,Pool,King Suite
Serene Hudson Valley Escape in Historic Montgomery with Hottub,Pool,King Suite
House
Montgomery, NY, 12549, United States
3.0k from Montgomery center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$873
Average price / night
Check Availability
Serene and modern Woodland Retreat, Hudson Valley & Catskills
Serene and modern Woodland Retreat, Hudson Valley & Catskills
House
Montgomery, NY, 12549, United States
3.2k from Montgomery center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$384
Average price / night
Check Availability
3 Bedroom Hot Tub, Huge, Rustic, Wooded, Quiet, Adventurers, Business, Groups.
3 Bedroom Hot Tub, Huge, Rustic, Wooded, Quiet, Adventurers, Business, Groups.
House
Montgomery, NY, 12549, United States
4.5k from Montgomery center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
New to Booking
$479
Average price / night
Check Availability
Field of Boaz - A Contemporary Country Home. Perfect for the whole family! \n
Field of Boaz - A Contemporary Country Home. Perfect for the whole family! \n
House
Walden, NY, 12586, United States
4.6k from Montgomery center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms10 Guests
10.0

Exceptional

25 reviews

$754
Average price / night
Check Availability
Cozy Studio Apartment
Cozy Studio Apartment
Apartment
Montgomery, NY, 12549, United States
6.3k from Montgomery center

AC, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$185
Average price / night
Check Availability
Luxury 10-acre Estate - Heated Pool - Sauna - Fire Pit - Playground - Trail
Luxury 10-acre Estate - Heated Pool - Sauna - Fire Pit - Playground - Trail
House
Montgomery, NY, 12549, United States
8.3k from Montgomery center

AC, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

5 Bedrooms10 Guests
New to Booking
$1015
Average price / night
Check Availability
LOG  CABIN IN ZEN FOREST
LOG CABIN IN ZEN FOREST
Cabin
Wallkill, NY, 12589, United States
8.5k from Montgomery center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

40 reviews

$443
Average price / night
Check Availability
Woodsie - best glamping experience Middletown ny
Woodsie - best glamping experience Middletown ny
House
Middletown, NY, 10941, United States
8.7k from Montgomery center

Barbecue, Extra Bed, TV

1 Bedroom5 Guests
8.0

Good

1 reviews

$218
Average price / night
Check Availability
Cozy Lakeside Retreat
Cozy Lakeside Retreat
House
Walden, NY, 12586, United States
9.0k from Montgomery center

AC, Fireplace, Free Parking, Heater, Microwave, No Smoking, TV

2 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$363
Average price / night
Check Availability
Family Staycation Retreat 7BDR.Sauna.Games.Gym
Family Staycation Retreat 7BDR.Sauna.Games.Gym
House
Campbell hall, NY, 10916, United States
9.1k from Montgomery center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking

7 Bedrooms24 Guests
New to Booking
$1979
Average price / night
Check Availability
Nature Escape - studio in the forest
Nature Escape - studio in the forest
Cabin
Middletown, NY, 10941, United States
9.2k from Montgomery center

Heater, No Smoking

1 Bedroom5 Guests
New to Booking
$224
Average price / night
Check Availability
Pond Paradise: Marvelous 4-bedroom house with AC in charming Campbell Hall
Pond Paradise: Marvelous 4-bedroom house with AC in charming Campbell Hall
House
Campbell Hall, NY, 10916, United States
9.4k from Montgomery center

AC, Barbecue, Dryer, Free Parking, Heater, Laundry, Microwave, No Smoking, TV

4 Bedrooms8 Guests
New to Booking
$443
Average price / night
Check Availability
A Restored Schoolhouse With Movie Theater, Firepit, and Pool
A Restored Schoolhouse With Movie Theater, Firepit, and Pool
House
Rock Tavern, NY, 12575, United States
9.8k from Montgomery center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms8 Guests
9.6

Exceptional

4 reviews

$567
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Montgomery.

Montgomery Vacation Rentals on the Map

Frequently Asked Questions

You can explore 27 verified vacation rentals in Montgomery. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Montgomery vary depending on the season, property size, and location. Rates typically start from around $149 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Montgomery include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Montgomery welcome pets. Currently, 15 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Montgomery often include amenities such as Fireplace/Heating, Wellness Facilities, and Bedding/Linens. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.