Discover Your Perfect Montgomery Vacation Homes

Montgomery Pet Friendly Vacation Rentals

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8.9 (106 Reviews)
Bed & Breakfast
The Borland House Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
10.0 (2 Reviews)
Apartment
Beaver Dam Escape
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in Montgomery on PetFriendly.io

Why Choose Rent By Owner for your Montgomery Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Montgomery

When should you plan your Vacation Rentals stay?

Understanding the best time to vacation here can help you enjoy the region’s unique charm and convenience when booking your ideal accommodation in Montgomery, New York.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you can enjoy longer daylight hours and vibrant local activities, making it an ideal time to explore this destination’s outdoor scenery.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

The fall season offers stunning foliage and crisp air, perfect for scenic drives and outdoor adventures in the region.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

While the colder winter months bring less crowds, this is a quieter time to enjoy cozy accommodations and peaceful surroundings here.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Spring (March to May)

Early spring marks a transition period with milder weather and fewer visitors, offering a tranquil experience for exploring the area’s natural beauty.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Montgomery

How to Book Your Montgomery Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Montgomery

More Top-Rated Vacation Rentals in Montgomery Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or deck perfect for relaxing and dining al fresco in the region.
  • Make the most of the spacious backyard, ideal for outdoor activities or family gatherings.
  • Take advantage of scenic views from your outdoor seating area, offering a peaceful retreat here.
  • Utilize outdoor grills or barbecue stations to host cookouts in this welcoming destination.
  • Benefit from access to well-maintained gardens or landscaped yards that enhance your stay.
  • Cool off in a refreshing outdoor swimming pool available at select rentals in the area.
  • Explore nearby walking trails, parks, or natural spaces accessible directly from your accommodation.

Top Attractions Around Montgomery

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities, explore local parks, or indulge in scenic nature walks that highlight the natural beauty of this region.

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Family Activities

  • Montgomery Community Pool: Enjoy a relaxing day swimming and splashing with your family at the community pool located nearby, perfect for outdoor fun in the sun.
  • The Orange County Farmers Market: Explore fresh local produce and handmade goods, providing an engaging and delicious outing for families visiting this region.
  • Trailside Museums and Zoo: Discover native animals and enjoy interactive exhibits that make learning about wildlife enjoyable for kids of all ages in this area.
  • Corn Maze Adventures: Experience seasonal outdoor entertainment as you navigate through a family-friendly corn maze, offering adventure right here in the region.
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Adult Activities

  • Visit the Montgomery Historical Society Museum: Discover local history and learn about the area's rich heritage through engaging exhibits and artifacts.
  • Explore the Storm King Art Center: Enjoy a scenic outdoor experience immersed in contemporary sculptures set amidst the natural beauty of this regional art park.
  • Walk along the Wallkill Valley Rail Trail: Experience a peaceful hike or bike ride along this popular trail that offers picturesque views of the surrounding landscape.
  • Attend seasonal festivals and events: Participate in vibrant community gatherings that showcase the local culture and provide entertainment for adults visiting here.

Other Places to Stay in Montgomery, NY

Rock Tavern
Rock Tavern Vacation Rentals
More Places to Stay Near Montgomery

Montgomery Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Markets: Take advantage of the area's culinary scene and local markets to enjoy authentic regional flavors during your stay.
  • Plan Outdoor Activities: Make the most of the natural surroundings by scheduling outdoor activities such as hiking or boating, which showcase the region’s scenic beauty.
  • Discover Cultural Events and Festivals: Check out current festivals and cultural events happening nearby to immerse yourself in the local community vibe.
  • Choose a Prime Location for Your Rental: Select a vacation rental close to key attractions and conveniences in this destination for easy access and a more enriching experience.

Transportation Options

  • Montgomery Transit Service: This local bus service offers convenient routes within the area, making it easy for you to explore Montgomery and its surroundings without hassle.
  • Amtrak Train Station in Beacon: Connecting you to major cities and regional destinations, this station provides reliable rail options just a short drive from your stay here.
  • Private Shuttle Services: Several private transportation providers operate in the region, offering tailored shuttle services for comfortable travel around Montgomery and nearby attractions.
  • Taxi and Rideshare Options: Rideshare apps and taxis are readily available in the area, providing flexible and quick transportation solutions during your visit.

Local Customs Options

  • Traditional Irish Celebrations: You can experience lively Irish festivals here that reflect the region’s rich cultural heritage, especially during local Saint Patrick's Day festivities.
  • Farmers' Markets: Visiting the area’s farmers' markets offers a glimpse into the community’s focus on fresh, locally sourced produce and artisanal goods.
  • Historic Preservation Practices: Respect for historic buildings and sites is evident through community efforts to preserve the area's architectural heritage and traditional craftsmanship.
  • Embracing the region’s natural beauty, outdoor customs like apple picking and fall harvest festivals are popular among both locals and visitors.

Frequently Asked Questions About Montgomery?

1. What are the top vacation rentals in Montgomery?

There are a lot of options in Montgomery. If you plan on staying in the Montgomery area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Montgomery:

2. Which vacation homes in Montgomery are best for families?

If you are looking for a family-friendly vacation home in Montgomery, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Montgomery:

3. How many Rentbyowner vacation rentals are available in Montgomery?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 36 in the Montgomery area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Montgomery. 

4. What is the cancellation policy for vacation rentals in Montgomery, New York?

Cancellation policies vary by listing; please review the specific rental details or contact the property owner directly to understand the terms and any potential fees associated with cancellations.

5. How do I secure my booking for a vacation rental in this region?

To reserve your stay, follow the booking instructions provided on the listing page and communicate with the property owner if needed. Payment methods and confirmation procedures are detailed within each listing.

6. Are there any additional fees I should be aware of when booking in Montgomery, New York?

Additional fees such as cleaning, service charges, or taxes may apply depending on the property. Be sure to read the full listing description or ask the owner for clarity before completing your reservation.

7. What amenities are typically included in vacation rentals here?

Amenities can differ between properties, so check the specific listing for details like Wi-Fi, kitchens, parking, or outdoor spaces. Contact the owner if you have particular needs or questions about available facilities.

8. Is there a minimum stay requirement for booking a vacation home in Montgomery, New York?

Minimum stay requirements vary based on the property and season. Review the listing details or contact the owner directly to confirm the length of stay allowed for your preferred dates.