Discover Your Perfect Middletown Springs Vacation Homes

Middletown Springs Large Vacation Homes

See More Family Vacation Rentals in Middletown Springs on FVR

Why Choose Rent By Owner for your Middletown Springs 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 Middletown Springs

When should you plan your Vacation Rentals stay?

Timing your visit to this charming region can enhance your experience, so consider planning your stay during the seasons when outdoor activities and local events are at their peak, ensuring a memorable vacation in Middletown Springs, Vermont.

Peak Season Highlights

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Summer (June to August)

During the warm summer months, you can enjoy pleasant weather that makes outdoor activities and exploring the scenic views of this destination a delight.

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

This time of year offers stunning foliage and comfortable temperatures, making it ideal for enjoying the vibrant scenery and outdoor excursions in the region.

Average Temperature Daytime: about 65°F to 70°F - Nighttime: roughly 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

In the winter months, the area transforms into a peaceful retreat, perfect for those seeking tranquility and cozy accommodations away from the crowds.

Average Temperature Daytime: around 20°F to 35°F - Nighttime: near 0°F to 15°F
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Spring (March to May)

As the region awakens from winter, you can enjoy fewer crowds and blooming landscapes that create a serene atmosphere for your stay.

Average Temperature Daytime: about 45°F to 55°F - Nighttime: roughly 30°F to 40°F

Weekly Weather Forecast for Middletown Springs

How to Book Your Middletown Springs 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 Middletown Springs

More Top-Rated Vacation Rentals in Middletown Springs 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 outdoor dining with picnic tables and barbecue grills available on the property’s spacious grounds.
  • Take advantage of scenic views from private decks or porches designed for relaxation and soaking in the natural beauty.
  • Access well-maintained gardens or landscaped yards that offer tranquil spaces for reading or unwinding outdoors.
  • Utilize outdoor fire pits or fireplaces perfect for cozy evenings under the stars in this peaceful region.
  • Make use of private or shared pools for a refreshing swim during your stay here.
  • Explore nearby hiking or walking trails directly from your rental, ideal for adventure seekers in the area.
  • Relax in outdoor lounge areas equipped with comfortable seating to enjoy the fresh air and scenic surroundings.

Top Attractions Around Middletown Springs

What attractions are nearby?

Within this charming region, you can explore outdoor activities such as hiking, biking, and nature walks, offering an authentic Vermont experience just steps from your vacation rental.

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Family Activities

  • Middlebury College Museum of Art: Discover engaging art exhibitions and family-friendly activities, offering an enriching experience for visitors of all ages.
  • Skiing at Killington Resort: Enjoy skiing or snowboarding at this nearby resort, perfect for active families seeking outdoor fun during the winter months.
  • Chester Mountain Trail: Embark on a scenic hike with your family along this trail, which provides stunning views and a gentle trek suitable for all skill levels.
  • Vermont State Fair: Attend seasonal events like the state fair, where rides, games, and local food vendors create memorable moments for families visiting the area.
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Adult Activities

  • Hiking at Mount Equinox: Explore scenic trails and enjoy panoramic views from Mount Equinox, just a short drive from here, offering an outdoor adventure amid the area's natural beauty.
  • Visit Manchester’s Art Galleries: Discover local art scenes and cultural exhibits in the nearby town of Manchester, perfect for a relaxed yet enriching day out.
  • Wine Tasting Tour: Indulge in tasting sessions at regional vineyards, providing a delightful experience that highlights the region's burgeoning wine industry.
  • Historical Sites Exploration: Delve into the area's heritage by visiting historic landmarks and museums, offering insight into the region's rich past and development.

Middletown Springs Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the region’s cozy eateries and farm-to-table restaurants to enjoy authentic flavors unique to this destination.
  • Plan Outdoor Activities: Discover the area's scenic parks, walking trails, or nearby natural attractions for an immersive experience in the region’s beautiful landscape.
  • Connect with the Community: Engage with local events or markets to gain a deeper understanding of the area’s culture and traditions during your stay.
  • Utilize Your Vacation Rental’s Amenities: Maximize comfort and convenience by making full use of the amenities offered at your rental property here, ensuring a relaxing visit.

Transportation Options

  • Regional Airport: The closest major airport offers convenient domestic flights, making your journey to this destination straightforward and hassle-free.
  • Train Services: Amtrak's line runs nearby, providing scenic train routes that connect you comfortably to the region’s charming towns and cities.
  • Bus Transportation: Local bus services serve the area, offering an economical way to explore the region without the need for a private vehicle.
  • Car Rentals: Numerous rental agencies in town provide flexible transportation options, allowing you to discover the surroundings at your own pace.

Local Customs Options

  • Community Gatherings: Embrace the local spirit by participating in seasonal festivals and town meetings that foster a close-knit atmosphere in this area.
  • Respect for Nature: Visitors are encouraged to observe eco-friendly practices, as outdoor activities here reflect a deep appreciation for the region’s natural beauty.
  • Historical Reverence: Appreciating the area's heritage through preservation of historic sites and traditions enriches your experience here.
  • Local Cuisine Etiquette: Savor regional flavors at gatherings and eateries while respecting customary manners that highlight the region’s hospitality.

Frequently Asked Questions About Middletown Springs?

1. What are the top vacation rentals in Middletown Springs?

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

2. Which vacation homes in Middletown Springs are best for families?

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

3. How many Rentbyowner vacation rentals are available in Middletown Springs?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 73 in the Middletown Springs 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 Middletown Springs. 

4. What is the cancellation policy for vacation rentals in Middletown Springs, Vermont?

The cancellation policy varies by property. To find specific details, please review the listing carefully or contact the property owner directly for the most accurate information.

5. How do I ensure my booking is secure when reserving a vacation rental in this area?

Reservations are made through a trusted booking platform that provides secure payment options. For additional assurance, review the property's reviews and communicate with the owner if needed before finalizing your reservation.

6. Are there any restrictions or house rules I should be aware of when staying in a vacation rental here?

Each property has its own set of house rules and restrictions. These details are typically listed on the property page, but it's recommended to confirm with the owner directly to ensure a smooth stay.

7. What amenities are usually included in the vacation rentals in this region?

Most rentals offer essential amenities such as Wi-Fi, kitchen facilities, and parking. However, for specific amenities like hot tubs or fireplaces, always check the individual listing or ask the owner before booking.

8. How do I find the best vacation rental deals in Middletown Springs, Vermont?

To secure competitive rates, compare available listings, read guest reviews, and consider flexible travel dates. Reaching out to property owners for any ongoing promotions can also help you find the best value for your stay.