Discover Your Perfect Guilford Vacation Homes

Best Vacation Homes in Guilford

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Guilford Luxury Rentals

See More Guilford Luxury Vacation Rentals
Find More Guilford Villas, Resorts, & Rentals on BedroomVillas

Why Choose Rent By Owner for your Guilford 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 Guilford

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience by aligning your plans with the region’s best weather and local events, ensuring you enjoy all that Guilford has to offer through your ideal vacation rentals.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

This is when the area experiences warm weather and lush landscapes, making it ideal for outdoor activities and exploring nature. Booking your vacation rentals during this period ensures a vibrant and active atmosphere.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
autumn
Early Fall (September to October)

During these months, the region showcases stunning fall foliage and comfortable temperatures, perfect for sightseeing and scenic drives. Securing your accommodations early guarantees a memorable visit here during this picturesque season.

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

Off-Season Highlights

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Mid Winter (January to February)

The quiet winter months bring cooler temperatures and fewer visitors, offering a peaceful retreat. This is an excellent time to enjoy cozy stays in the area’s vacation rentals with less crowding.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Late Fall (November to December)

As the year winds down, this off-peak period features cooler weather and a tranquil environment. It’s a great opportunity to find attractive deals on local vacation rentals while enjoying the calm of the season.

Average Temperature Daytime: 45-55°F - Nighttime: 35-45°F

Weekly Weather Forecast for Guilford

How to Book Your Guilford 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 Guilford

More Top-Rated Vacation Rentals in Guilford 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 a fully equipped patio or picnic area, perfect for meals al fresco amid the scenic surroundings.
  • Take advantage of spacious yards or gardens that provide ample space for relaxation or outdoor activities.
  • Make the most of private decks or balconies offering picturesque views of the region’s charming landscape.
  • Benefit from access to outdoor swimming pools, ideal for cooling off during warm days here.
  • Experience the convenience of outdoor fire pits or fireplaces, great for gathering and enjoying evenings under the stars.
  • Explore walking trails or landscaped pathways directly from your rental for scenic strolls around the area.
  • Utilize outdoor recreational equipment such as kayaks, paddleboards, or bicycles available for explore this destination’s natural beauty.

Top Attractions Around Guilford

What attractions are nearby?

Here in Guilford, Connecticut, you can enjoy a variety of outdoor activities and scenic attractions just moments from your vacation rental, making it an ideal destination for exploring the natural beauty and charming local sites of the region.

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Family Activities

  • Guilford Green: Explore the vibrant community atmosphere and enjoy family-friendly events in the heart of this charming town.
  • : Discover engaging storytimes and educational activities designed to inspire young minds in a welcoming library setting.
  • Hyland House Museum: Step into local history with interactive exhibits and tours that appeal to both children and adults interested in the area's past.
  • Champlain-Jamestown Park: Spend quality time outdoors, where spacious picnic areas and playgrounds provide a perfect backdrop for family recreation.
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Adult Activities

  • Visit the Guilford Green: Enjoy a leisurely stroll around this historic town square, lined with charming shops and cafes that reflect the area's New England charm.
  • Explore the Fairview Cemetery: Discover the region’s history by wandering through this peaceful cemetery, featuring notable gravestones and scenic views.
  • Go hiking at Guilford Hills Park: Experience the natural beauty of the area with trails that offer serene landscapes and opportunities for outdoor recreation.
  • Enjoy water activities at Long Island Sound: Spend your day kayaking, paddleboarding, or relaxing on the shoreline along the picturesque coastline nearby.

Other Places to Stay in Guilford, CT

Hyland House Museum
Hyland House Museum Vacation Rentals
Henry Whitfield State Museum
Henry Whitfield State Museum Vacation Rentals
Bishops Orchard and Winery
Bishops Orchard and Winery Vacation Rentals
Chaffinch Island State Park
Chaffinch Island State Park Vacation Rentals
Guilford Art Center
Guilford Art Center Vacation Rentals
More Places to Stay Near Guilford

Guilford Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Heritage: Take time to visit the historic sites and landmarks in the area to gain a deeper understanding of its rich history and culture.
  • Plan Outdoor Adventures: Utilize nearby parks and scenic spots for hiking, biking, or simply enjoying the natural beauty that makes the region unique.
  • Savor Regional Cuisine: Indulge in local dining options to experience authentic flavors and regional specialties during your stay.
  • Choose Prime Locations: Select vacation rentals situated near popular attractions or tranquil waterfronts for convenient access and memorable experiences.

Transportation Options

  • Guilford Train Station: This station offers convenient rail services connecting to major cities, making it easy for you to explore the surrounding region without hassle.
  • Interstate 95: As a primary highway nearby, it provides straightforward road access for travelers driving to and from this destination or venturing further along the coast.
  • Local Bus Services: Several regional bus routes serve the area, offering an affordable transportation option for getting around here and reaching nearby towns.
  • Taxi and Rideshare Services: Reliable taxi companies and rideshare options are readily available locally, ensuring seamless transfers for your adventures in this part of Connecticut.

Local Customs Options

  • Tea Time Traditions: You might find locals enjoying afternoon tea, a cherished custom reflecting the area's historic New England charm.
  • Maritime Heritage: Engaging with the region’s maritime customs, such as waterfront gatherings and boat parades, offers a glimpse into its seafaring history.
  • Celebration of Local Artisans: Supporting handcrafted goods during seasonal markets is a common way residents honor their talented local artisans here.
  • Seasonal Harvest Festivals: Participating in fall and summer festivals centered around regional produce allows you to experience authentic local traditions.

Frequently Asked Questions About Guilford?

1. What are the top vacation rentals in Guilford?

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

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2026 is over 74 in the Guilford 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 Guilford. 

4. What is the cancellation policy for vacation rentals in Guilford, Connecticut?

Cancellation policies vary by listing, so you should review the specific property's terms before booking. For detailed information on refunds and cancellation procedures, contact the property owner directly.

5. How do I know if a vacation rental in Guilford has all the essential amenities I need?

Each listing provides a comprehensive list of amenities included. To ensure the property meets your needs, carefully read the property details or reach out to the host for any specific questions.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are typically outlined in the listing. Be sure to review the full cost breakdown before finalizing your reservation.

7. What is the process for checking in and out of a vacation rental in this area?

Check-in and check-out procedures are specified on each listing, often with flexible options. Contact the property owner for precise instructions or to arrange special arrangements if needed.

8. How can I confirm the availability of a vacation rental in Guilford during my travel dates?

Availability is shown on each listing, but it’s recommended to contact the property owner directly to verify current availability and secure your reservation for your chosen dates.