Discover Your Perfect Flag Hill Winery Vacation Homes

Best Vacation Homes in Flag Hill Winery

|
9.8 (63 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
|
9.6 (283 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
|
9.3 (112 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View

Why Choose Rent By Owner for your Flag Hill Winery Vacation Rental Homes?

What makes our Vacation Rentals special?

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

Best Times to Visit Flag Hill Winery

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this destination ensures you experience its beauty and tranquility at their best, making your stay in the region a memorable and enjoyable getaway.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you'll enjoy lush landscapes and longer daylight hours here, making it an ideal time to explore and indulge in outdoor activities.

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

The vibrant autumn foliage creates a picturesque backdrop for your visit, perfect for scenic drives and outdoor adventures in the region.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

image
Spring (March to May)

As the area awakens from winter, quieter surroundings and blooming scenery offer a peaceful retreat for those seeking tranquility.

Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F
image
Winter (December to February)

This destination transforms into a serene winter wonderland, attracting visitors who appreciate snow-covered landscapes and cozy accommodations.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 10°F to 20°F

Weekly Weather Forecast for Flag Hill Winery

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.

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

  • You can enjoy spacious outdoor seating areas perfect for relaxing and taking in the scenic views of the region.
  • Many properties offer access to charming patios or decks where you can dine al fresco during your stay.
  • Look for accommodations with private gardens or landscaped yards to enhance your outdoor experience here.
  • Outdoor fire pits are commonly available, providing a cozy spot for gatherings on cooler evenings.
  • Some rentals feature outdoor grills, making it easy to enjoy barbecues amidst the natural surroundings.
  • Take advantage of well-maintained walking or hiking paths nearby, ideal for exploring the area's beautiful landscape.
  • If you're seeking outdoor recreation, many properties provide amenities such as tennis courts or swimming pools for active enjoyment.
image
image

Family Activities

  • Wine Tasting Tours: Explore the renowned wine tastings that take place right at the winery, offering a fun and educational experience for families interested in local viticulture.
  • Scenic Vineyard Walks: Take a leisurely stroll through the picturesque vineyards surrounding the area to enjoy nature's beauty and learn about grape cultivation.
  • Picnic Areas: Relax with a family picnic on the scenic grounds, where you can enjoy the fresh air and countryside views typical of this region.
  • Event Participation: Join family-friendly events and seasonal festivals hosted here, providing interactive activities and entertainment suitable for all ages.
image

Adult Activities

  • Wine Tasting Tours: Experience the exquisite varieties available at Flag Hill Winery with guided tastings that highlight the region's renowned viticulture.
  • Enhance your visit by participating in special events that showcase local culinary delights paired perfectly with regional wines.
  • Take a leisurely stroll through the scenic vineyards to learn about grape cultivation and the winemaking process unique to this region.
  • Gain firsthand insight into the art of winemaking through interactive sessions held on-site, perfect for enthusiasts eager to deepen their knowledge.

Flag Hill Winery Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Peak Tasting Seasons: Schedule your stay to coincide with the winery's popular tasting events for an authentic experience of local flavors.
  • Explore Local Food and Wine Pairings: Take advantage of nearby eateries that complement the region's renowned wines to enhance your culinary journey.
  • Book Your Accommodation Early: Secure your preferred vacation rentals in advance, especially during busy weekends or special events at the winery.
  • Discover Scenic Surroundings: Use your stay as a base to explore the area's natural beauty and enjoy leisurely walks through picturesque landscapes.

Transportation Options

  • Driving: You can rent a car and enjoy the flexibility of exploring this area at your own pace, with convenient access from nearby highways.
  • Taxi Services: Professional taxi companies operate in the region, providing reliable transportation for trips to and from local attractions.
  • Rideshare Options: Rideshare services like Uber and Lyft are available here, offering a convenient way to get around without the need for personal vehicle ownership.
  • Public Transit: Local bus routes connect key destinations within the region, making it an economical choice for travelers relying on public transportation.

Local Customs Options

  • Wine Tasting Etiquette: When visiting local wineries here, it’s customary to sample wines responsibly and engage politely with staff to fully appreciate the region's renowned wine culture.
  • Farmers' Market Practices: Supporting local vendors by purchasing fresh produce and handmade goods at regional markets demonstrates respect for the area's agricultural traditions.
  • Community Events: Participating in seasonal festivals or gatherings often involves dressing appropriately and respecting longstanding customs that foster community spirit.
  • Dining Customs: Enjoying meals in the area typically emphasizes sharing dishes family-style and appreciating locally sourced ingredients, embodying the region’s culinary hospitality.

Frequently Asked Questions About Flag Hill Winery?

2. How many Rentbyowner vacation rentals are available in Flag Hill Winery?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 190 in the Flag Hill Winery 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 Flag Hill Winery. 

3. What is the cancellation policy for booking a vacation rental near Flag Hill Winery?

The cancellation policy varies depending on the specific property you choose. It’s best to review the individual listing details or contact the property owner directly to understand the options and any applicable fees.

4. How do I find available dates and book a vacation rental close to Lee, New Hampshire?

You can easily check availability and secure your reservation by using the search function on the listing page. Be sure to confirm the dates and review the booking terms before completing your reservation.

5. Are there any special amenities or features included in vacation rentals around this region?

Every property listing provides detailed information about its amenities and features. For specific offerings, such as Wi-Fi, outdoor spaces, or kitchen facilities, please refer to the individual listing details or contact the host directly.

6. What should I know about checking in and out at a vacation rental near Flag Hill Winery?

Check-in and check-out procedures are outlined in each listing, with flexible options available depending on the property. Contact the host ahead of time if you have specific requirements or need assistance with your arrival or departure times.

7. Is there a minimum stay requirement for booking a vacation rental in this area?

Minimum stay policies can differ between properties. Be sure to review the listing details or reach out to the owner to confirm any minimum night requirements before making your reservation.

Best Vacation Homes in Flag Hill Winery

4.6 (6 Reviews)
House
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities