Best Vacation Homes in Montgomery
Cottage
10.0(46 Reviews)
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $224/Night
7 Nights - US $1,566
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
12 Guests
2066.67 ft²
Oceanfront
Skiing- Fireplace/Heating
Pool
US $245/Night
7 Nights - US $1,713
Bed & Breakfast
9.8(89 Reviews)
1 Bedroom
1 Bath
Hot Tub
Spa- Skiing
- Fireplace/Heating
US $274/Night
7 Nights - US $1,920
Apartment
10.0(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
Internet
Child Friendly
US $208/Night
7 Nights - US $1,453
House
9.7(19 Reviews)
4 Bedrooms
3 Baths
6 Guests
2002.09 ft²
- Skiing
- Balcony/Terrace
- Parking
Air Conditioner
US $225/Night
7 Nights - US $1,577
Bed & Breakfast
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
320 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $370/Night
7 Nights - US $2,590
Bed & Breakfast
10.0(1 Review)
1 Bedroom
1 Bath
5 Guests
598 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Breakfast
US $381/Night
7 Nights - US $2,668
House
9.8(87 Reviews)
2 Bedrooms
1 Bath
6 Guests
600 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $219/Night
7 Nights - US $1,531
Montgomery Luxury Rentals
Cabin
10.0(17 Reviews)
4 Bedrooms
1 Bath
7 Guests
2100 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $853/Night
7 Nights - US $5,970
House
4 Bedrooms
1 Bath
7 Guests
2098.96 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $726/Night
7 Nights - US $5,082
Ski Chalet
9.8(9 Reviews)
5 Bedrooms
3 Baths
16 Guests
3250 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $682/Night
7 Nights - US $4,776
Ski Chalet
7.6(5 Reviews)
6 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Internet
US $642/Night
7 Nights - US $4,493
House
9.5(2 Reviews)
4 Bedrooms
3 Baths
9 Guests
2400.35 ft²
- Hot Tub
- Spa
- Pet Friendly
- Parking
US $631/Night
7 Nights - US $4,417
House
10.0(6 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $553/Night
7 Nights - US $3,873
Ski Chalet
9.8(10 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
US $529/Night
7 Nights - US $3,701
House
8.4(15 Reviews)
3 Bedrooms
2 Baths
6 Guests
2816 ft²
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $519/Night
7 Nights - US $3,633
Montgomery Pet Friendly Vacation Rentals
House
10.0(77 Reviews)
3 Bedrooms
2 Baths
10 Guests
3000 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $446/Night
7 Nights - US $3,124
Cabin
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $307/Night
7 Nights - US $2,146
House
9.5(4 Reviews)
4 Bedrooms
3 Baths
8 Guests
1851.39 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $357/Night
7 Nights - US $2,497
Ski Chalet
9.8(39 Reviews)
3 Bedrooms
2 Baths
8 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $428/Night
7 Nights - US $2,998
House
9.8(21 Reviews)
4 Bedrooms
2 Baths
9 Guests
2400 ft²
- Hot Tub
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $386/Night
7 Nights - US $2,700
New
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $385/Night
7 Nights - US $2,697
House
10.0(20 Reviews)
4 Bedrooms
3 Baths
8 Guests
1850 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $284/Night
7 Nights - US $1,989
Montgomery Large Vacation Homes
House
9.6(48 Reviews)
3 Bedrooms
2 Baths
10 Guests
1451 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $413/Night
7 Nights - US $2,893
Bed & Breakfast
9.6(55 Reviews)
13 Bedrooms
10 Baths
32 Guests
328.3 ft²
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $279/Night
7 Nights - US $1,953
Ski Chalet
10.0(11 Reviews)
5 Bedrooms
3 Baths
12 Guests
2067 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $395/Night
7 Nights - US $2,765
Ski Chalet
9.8(29 Reviews)
5 Bedrooms
2 Baths
11 Guests
2400 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $436/Night
7 Nights - US $3,049
House
9.6(48 Reviews)
3 Bedrooms
1 Bath
10 Guests
1451 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $352/Night
7 Nights - US $2,465
House
9.2(48 Reviews)
5 Bedrooms
1 Bath
10 Guests
1400 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $311/Night
7 Nights - US $2,177
House
5.0(2 Reviews)
3 Bedrooms
1 Bath
10 Guests
1410 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $385/Night
7 Nights - US $2,693
House
9.8(9 Reviews)
4 Bedrooms
2 Baths
10 Guests
3200 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $1,120/Night
7 Nights - US $7,840
Why Choose Rent By Owner for your Montgomery Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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?
To ensure an unforgettable getaway, consider visiting during the region's peak seasons or quieter shoulder months, allowing you to experience the best of what this destination has to offer while enjoying the comfort and convenience of suitable vacation rentals.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you'll enjoy extended daylight hours and vibrant outdoor activities in the region, making it an ideal time for exploring scenic landscapes and enjoying outdoor pursuits.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn brings stunning foliage and crisp air, attracting visitors who want to experience the area's natural beauty at its peak. This season is perfect for scenic drives and outdoor adventures amidst colorful scenery.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
The winter months offer a quieter atmosphere with snow-covered landscapes, ideal for those seeking peaceful retreats and winter sports in this destination.
Average Temperature Daytime: 20°F to 35°F - Nighttime: 5°F to 15°F
Spring (March to May)
In early spring, the area begins to wake up from winter, creating a calm setting before the busy summer season. It’s a good time for enjoying the budding scenery without the crowds.
Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°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
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 outdoor seating areas perfect for relaxing and taking in the scenic natural surroundings
- Take advantage of private or shared outdoor fire pits for cozy evenings under the stars
- Benefit from well-maintained gardens or landscaped yards to enhance your outdoor experience
- Explore nearby hiking trails directly accessible from your rental property
- Make use of spacious decks or patios ideal for outdoor dining or morning coffee
- Experience outdoor recreational activities such as fishing or kayaking if available nearby
- Park your vehicle conveniently on the premises with ample driveway or outdoor parking options
Top Attractions Around Montgomery
What attractions are nearby?
Nearby, you can explore outdoor activities such as hiking and scenic drives in this charming area, offering a perfect way to enjoy the natural beauty and tranquil surroundings of Montgomery, Vermont.
Family Activities
- Montgomery State Park: Enjoy a family picnic and scenic hiking trails amidst the natural beauty of this popular park in the region.
- Vermont Ski & Snowboard Museum: Discover the history of winter sports with engaging exhibits perfect for a family outing during your stay here.
- Northern Vermont University: Participate in culturally enriching events and activities that add educational fun to your trip with the family.
- Local Farmers' Markets: Explore fresh local produce and handcrafted goods, offering a taste of the area's vibrant community spirit for all ages.
Adult Activities
- Exploring the Montpelier Art Walk: You can enjoy a leisurely stroll through the local art scene, discovering galleries and studios that showcase Vermont’s vibrant creative community.
- Hiking in the Green Mountain National Forest: The region offers scenic trails where you can immerse yourself in nature, taking in breathtaking views just a short drive from your accommodation.
- Visiting local farms and markets: Experience authentic regional flavors by exploring farmers' markets and farm tours that highlight the area's rich agricultural heritage.
- Relaxing at local spas and wellness centers: Unwind with rejuvenating treatments designed to complement your outdoor adventures and enhance your stay here.
Other Places to Stay in Montgomery, VT
Montgomery Center
Green Mountains
Montgomery Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the area's natural beauty by engaging in hiking, biking, or snowshoeing, which are perfect ways to enjoy the landscape around your vacation rentals.
- Visit seasonal attractions: Be sure to check out popular seasonal events and festivals that offer authentic experiences and deepen your connection with this destination.
- Plan your dining experiences: Discover the region's charming eateries and farm-to-table restaurants that showcase the local flavors and fresh ingredients.
- Book with trusted providers: Secure your stay through reputable vacation rentals that prioritize comfort and reliability, ensuring a stress-free visit to here.
Transportation Options
- Montgomery Center Airport: This regional airport offers convenient flights for travelers heading to the area, with easy access to local vacation rentals and outdoor adventures.
- Montgomery Bus Services: Local bus transportation provides a practical way to explore the region without relying on a car, connecting you to key attractions and amenities.
- Rental Cars: Several rental car agencies operate nearby, allowing you to customize your travel schedule and explore Montgomery and its scenic surroundings at your own pace.
- taxis and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft are available locally, giving you flexible transport solutions for short trips or hassle-free arrivals.
Local Customs Options
- Fiddlehead Picking: You’ll find that harvesting fiddleheads is a cherished local tradition during the spring, and participating respects the area's sustainable foraging practices.
- Farmers’ Markets: Visiting the farmers’ markets here offers a glimpse into the region’s agricultural roots and supports local producers in the community.
- Seasonal Festivals: Engaging in seasonal festivals allows you to experience the region’s vibrant community spirit and celebrate its rich local culture.
- Respect for Nature: It’s customary here to show reverence for the natural landscape, often reflected in outdoor etiquette and conservation efforts practiced by residents and visitors alike.
Montgomery Vacation Rental Frequently Asked Questions
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:
- Rustic Vermont Barn Home Near Jay Peak w/Pizza Oven
- Charming cottage by Jay Peak
- Cozy apartment that’s conveniently located just on the edge of town.
- Pet-Friendly Home w/Deck: 4 Mi to Jay Peak Resort
- Upscale Montgomery Cabin, Near Jay Peak Resort!
- Jay Peak VT 5BR Chalet
- Winter wonderland near Jay Peak
- Beautiful chalet close to Jay Peak resort
- SnowDream Chalet - Jay Peak 4 miles!
- Stay near Jay Peak at your own private cabin with 18 brookside acres!
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 62 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, Vermont?
Cancellation policies vary depending on the property listing. You should review the specific policy outlined on the listing page or contact the property owner directly to understand the terms and any potential fees or refund options for your stay in this region.
5. How do I know if my booking for a vacation rental in Montgomery, Vermont is secure?
Booking through trustworthy listings ensures your reservation is protected. You can verify the security measures by checking the listing details and communicating with the host. The platform also offers secure payment options to safeguard your transaction when reserving a property here.
6. Are there any additional fees I should be aware of when booking a vacation rental in this destination?
Additional fees such as cleaning fees, service charges, or local taxes may apply and are detailed in the listing. It’s recommended to review these charges before completing your booking to ensure transparency for your stay in this area.
7. What amenities are typically available in vacation rentals in Montgomery, Vermont?
Most properties here come equipped with essential amenities like Wi-Fi, kitchen facilities, heating, and parking. To find accommodations with specific features, review each listing carefully or contact the host directly for confirmation about amenities that are important to you.
8. How far in advance should I book a vacation rental in this part of Vermont during peak season?
Availability varies, but it’s advisable to book several months ahead, especially during high-demand seasons. Early reservations help secure your preferred property and ensure a smooth planning process for your visit to this scenic region.
Montgomery Top Rated Vacation Rentals
Ski Chalet
3 Bedrooms
3 Baths
8 Guests
2000 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $791/Night
7 Nights - US $5,535
Ski Chalet
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $375/Night
7 Nights - US $2,625
Apartment
2 Bedrooms
1 Bath
4 Guests
- Pool
- Kitchen
- Internet
- Child Friendly
US $250/Night
7 Nights - US $1,750
