Discover Your Perfect Oak Summit Vineyard Vacation Homes

Best Vacation Homes in Oak Summit Vineyard

8.4 (49 Reviews)
Bed & Breakfast
Millbrook Country House
  • Air Conditioner
  • Parking
  • View
View Availability
|
9.0 (77 Reviews)
Bed & Breakfast
Millbrook Country House Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability

Why Choose Rent By Owner for your Oak Summit Vineyard 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 Oak Summit Vineyard

When should you plan your Vacation Rentals stay?

choosing the ideal time to visit this destination can enhance your experience and help you make the most of your stay in the region.

Peak Season Highlights

spring
Spring (April to June)

During spring, the area blossoms with vibrant foliage and pleasant weather, making it an ideal time to enjoy outdoor activities and scenic vineyard views.

Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
autumn
Fall (September to November)

In fall, the region displays stunning autumn colors, perfect for picturesque walks and wine tasting experiences amidst the vineyards.

Average Temperature Daytime: 55-70°F - Nighttime: 35-50°F

Off-Season Highlights

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Winter (December to February)

Winter offers a quieter retreat with cooler temperatures, providing a peaceful setting to enjoy cozy accommodations and scenic winter landscapes.

Average Temperature Daytime: 30-45°F - Nighttime: 15-25°F
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Late Summer (July to August)

During late summer, the area experiences warmer days and fewer visitors, offering a more relaxed visit amidst the vineyard surroundings.

Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F

Weekly Weather Forecast for Oak Summit Vineyard

How to Book Your Oak Summit Vineyard 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 Oak Summit Vineyard

More Top-Rated Vacation Rentals in Oak Summit Vineyard 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 swimming pool to relax and cool off during your stay.
  • Take advantage of spacious outdoor decks or patios perfect for dining and gatherings.
  • Utilize the well-maintained outdoor grilling areas for barbecues in the fresh air.
  • Explore scenic walking or hiking trails accessible directly from the property.
  • Benefit from beautifully landscaped gardens and outdoor seating areas to unwind amid nature.
  • Make use of outdoor recreational equipment such as kayaks or paddleboards, if available.
  • Relish the peaceful setting with outdoor fire pits ideal for evening relaxation.

Top Attractions Around Oak Summit Vineyard

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities and local attractions that showcase the area's natural beauty and cultural heritage, making your stay in these vacation rentals truly memorable.

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Family Activities

  • Exploring Millbrook Vineyards & Winery: You can enjoy wine tastings and guided tours at one of the region’s renowned vineyards, providing a family-friendly way to experience local viticulture.
  • Visit the Millbrook Community Park: This spacious park offers playgrounds, picnic areas, and open fields where your family can relax and enjoy outdoor activities amidst scenic surroundings.
  • Discover the Dutchess County Rail Trail: Perfect for biking or walking, this trail offers a safe and scenic path suitable for all ages to explore the natural beauty of the area.
  • Attend local farm markets and festivals: Seasonal markets and events provide engaging experiences with fresh produce, local crafts, and family-friendly entertainment in the region.
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Adult Activities

  • Wine Tasting Tours: Indulge in exquisite tastings at local vineyards, experiencing the region's renowned wine offerings firsthand.
  • Scenic Hiking Trails: Explore picturesque trails through the area’s lush landscapes, perfect for a peaceful outdoor adventure.
  • Art and Cultural Galleries: Discover the vibrant arts scene with visits to galleries showcasing regional talent and craftsmanship.
  • Farmers’ Markets and Gourmet Shops: Savor fresh local produce and artisanal products at nearby markets and specialty stores.

Oak Summit Vineyard Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local wineries: Take advantage of the region’s renowned vineyards by scheduling tastings and tours to fully experience the area's rich viticulture heritage.
  • Plan outdoor activities: Make the most of the scenic outdoors with activities like hiking or biking in nearby trails to enjoy the natural beauty of this destination.
  • Discover nearby towns: Spend time visiting charming nearby villages and towns to immerse yourself in the local culture and unique regional flavors.
  • Check seasonal events: Stay updated on local festivals and seasonal happenings to enhance your stay with authentic regional experiences.

Transportation Options

  • Private Car Services: Local private car services offer convenient and comfortable transportation to explore the scenic region surrounding your vacation rental in Oak Summit Vineyard.
  • Rental Cars: Renting a car provides flexibility for discovering nearby attractions and navigating the picturesque countryside at your own pace.
  • Public Transportation: Regional bus services connect you to towns and amenities within the area, making it a practical option for budget-conscious travelers staying here.
  • Taxis and Rideshare Services: Taxis and rideshare options like Uber or Lyft provide quick and easy access to local destinations around Millbrook without the need for personal vehicle ownership.

Local Customs Options

  • Wine Tasting Etiquette: When visiting local vineyards, it's customary to sample wines responsibly and show appreciation for the vintners' craftsmanship.
  • Farm-to-Table Customs: Embracing the region's culinary traditions involves supporting local farmers by enjoying fresh, seasonal produce during your stay.
  • Community Events: Participating in local festivals or gatherings allows you to experience the area's cultural heritage firsthand while respecting community customs.
  • Environmental Respect: Visitors are encouraged to preserve the natural beauty of the region by practicing eco-friendly habits during outdoor activities and vineyard visits.

Frequently Asked Questions About Oak Summit Vineyard?

1. What are the top vacation rentals in Oak Summit Vineyard?

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

2. How many Rentbyowner vacation rentals are available in Oak Summit Vineyard?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 48 in the Oak Summit Vineyard 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 Oak Summit Vineyard. 

3. What is the cancellation policy for booking a vacation rental in this region?

Cancellation policies vary by property, so it’s important to review the specific listing details or contact the property owner directly to understand the terms and any potential fees associated with canceling your reservation.

4. How can I find the most accurate availability and pricing for my stay?

Availability and rates are updated frequently on the listing page. To ensure you have the latest information, check the calendar and contact the host if you have specific dates or special requests.

5. Are there any additional fees I should be aware of before confirming my booking?

Additional fees such as cleaning, service charges, or security deposits may apply, depending on the property. These details will be clearly outlined in the listing; reviewing them beforehand helps avoid surprises.

6. What amenities and features can I expect at a vacation rental here?

Most properties offer a range of amenities designed to enhance your stay, like Wi-Fi, kitchen facilities, and outdoor spaces. Exact features are listed on each property’s page, so review these details to match your needs.

7. What should I do if I need assistance during my stay in this destination?

For support during your visit, reach out to the property owner or local contact provided in your reservation details. They can assist with any issues or questions that arise during your stay.

Best Vacation Homes in Oak Summit Vineyard