Crawl Hill Winter Rental

10.0
Exceptional
(129 Reviews)
280 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Cottage
  • Fireplace/Heating
  • Pool
  • Ocean View
CA $380/Night For 7 Nights CA $2,661
9.2
Exceptional
(18 Reviews)
904.17 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Spa
  • Fireplace/Heating
CA $575/Night For 7 Nights CA $4,025
9.4
Exceptional
(492 Reviews)
1 Bathroom
Ocean View Resort
  • Spa
  • Pool
  • Ocean View
CA $1,432/Night For 7 Nights CA $10,027
10.0
Exceptional
(117 Reviews)
450 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
CA $338/Night For 7 Nights CA $2,363
8.5
Fabulous
(108 Reviews)
355.21 ft² 24 Guests 8 Bathrooms
Free Cancellation Resort
  • Private Beach
  • Oceanfront
  • Hot Tub
CA $1,653/Night For 7 Nights CA $11,574
10.0
Exceptional
(81 Reviews)
280 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Fireplace/Heating
  • Pool
  • Ocean View
CA $344/Night For 7 Nights CA $2,408
New
4305.56 ft² 2 Guests 1 Bedroom 1 Bathroom
Free Cancellation Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • View
CA $482/Night For 7 Nights CA $3,376
10.0
Exceptional
(15 Reviews)
16 Guests 8 Bedrooms 7 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Hot Tub
CA $7,731/Night For 7 Nights CA $54,121
10.0
Exceptional
(13 Reviews)
3000 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
CA $4,320/Night For 7 Nights CA $30,237
10.0
Exceptional
(11 Reviews)
6 Guests 1 Bedroom 2 Bathrooms
Ocean View Cottage
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
CA $668/Night For 7 Nights CA $4,676
10.0
Exceptional
(9 Reviews)
9 Guests 5 Bedrooms 4 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Hot Tub
CA $5,395/Night For 7 Nights CA $37,764
10.0
Exceptional
(6 Reviews)
4000 ft² 8 Guests 4 Bedrooms 1 Bathroom
Ocean View House
  • Private Pool
  • Oceanfront
  • Spa
CA $3,085/Night For 7 Nights CA $21,595

Why Choose Rent By Owner for your Crawl Hill Winter Rental?

What makes our Winter Rental 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 Crawl Hill

When should you plan your Winter Rental stay?

Choosing the optimal time to enjoy your winter rentals here can enhance your experience in this destination, as the climate and local events in the area vary throughout the year, making certain seasons more ideal for relaxing and exploring.

Peak Season Highlights

spring
Spring (March to May)

During this period, the region begins to warm up, making it ideal for enjoying outdoor activities and exploring the area's natural beauty.

Average Temperature Daytime: around 70°F (21°C) - Nighttime: around 60°F (16°C)
summer
Summer (June to August)

This high season features warm and humid weather, perfect for beach outings and water sports, attracting many visitors to the area.

Average Temperature Daytime: around 85°F (29°C) - Nighttime: around 75°F (24°C)

Off-Season Highlights

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Fall (September to November)

As temperatures gently cool down, you can enjoy a quieter atmosphere while still experiencing pleasant weather here.

Average Temperature Daytime: around 78°F (26°C) - Nighttime: around 68°F (20°C)
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Winter (December to February)

During this time, the region sees cooler temperatures, making it an ideal choice for those seeking a peaceful winter escape in Bermuda.

Average Temperature Daytime: around 65°F (18°C) - Nighttime: around 55°F (13°C)

Weekly Weather Forecast for Crawl Hill

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

  • Enjoy a private outdoor swimming pool to relax and unwind during your stay.
  • Take advantage of a spacious patio area, perfect for outdoor dining or gathering with family and friends.
  • Explore well-maintained gardens that add natural beauty and tranquility to your accommodation.
  • Benefit from direct access to scenic walking or jogging paths nearby, ideal for outdoor activities.
  • Make use of outdoor furniture and loungers for sunbathing under the warm Bermuda skies.
  • Utilize BBQ grills available for outdoor cooking while enjoying the fresh air and regional scenery.
  • Relax in shaded verandas or porches that provide comfortable spots to appreciate the area's natural surroundings.
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Family Activities

  • Snorkeling at the Coral Reefs: Explore the vibrant underwater world just off the coast, perfect for family adventures during your stay in this region.
  • Visit to a Local Nature Reserve: Discover the area's lush landscapes and native wildlife through guided walks and educational programs suitable for all ages.
  • Beach Day at a Family-Friendly Shore: Relax on the soft sands and enjoy swimming or building sandcastles at one of the region’s popular beaches ideal for families.
  • Boat Excursions: Embark on a scenic boat tour along the coastline to experience breathtaking views and learn about the area’s maritime history with your loved ones.
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Adult Activities

  • Snorkeling at the Coral Reefs: Explore vibrant marine life just off the coast, making it a must-do activity for those staying in the area’s winter rentals.
  • Visit to Bermuda Botanical Gardens: Enjoy a peaceful stroll through lush gardens filled with exotic plants and flowers, perfect for a relaxing day out.
  • Golfing on Local Courses: Tee off at nearby golf courses that offer stunning views and challenging holes, ideal for golf enthusiasts seeking leisure activities.
  • History and Culture Tours: Discover the region’s rich heritage by joining guided tours that highlight Bermuda’s unique history and colonial architecture.

Crawl Hill Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Make the most of your stay by researching popular local spots and booking any excursions early to ensure availability and avoid last-minute surprises.
  • Choose a Convenient Location: Opt for winter rentals that are close to key attractions and beaches to maximize your leisure time and reduce transportation hassles here.
  • Embrace Local Cuisine and Culture: Take the opportunity to enjoy authentic Bermudian dishes and experience local customs, enhancing your overall visit to this destination.
  • Pack Thoughtfully for the Climate: Bring appropriate clothing and essentials for Bermuda's winter weather to stay comfortable during your outdoor adventures in the area.

Transportation Options

  • Renting a Scooter or Bike: Explore the area at your own pace by renting a scooter or bicycle, offering flexibility and ease for navigating local attractions and beaches.
  • Public Transportation (Bus Service): The regional bus system provides an affordable and convenient way to reach popular destinations within Hamilton Parish and beyond.
  • Private Car Rentals: Renting a car gives you the freedom to discover hidden spots around the region, making it ideal for those seeking comfort and independence during their stay.
  • Taxis and Rideshare Services: For quick and reliable transportation, taxis and rideshare options are readily available, ensuring you can comfortably reach your preferred destinations in this part of Bermuda.

Local Customs Options

  • Rum Rebellion Day: This local custom commemorates Bermuda's historical protest against taxation, and participating in community gatherings offers a unique insight into the area's heritage.
  • Gombey Dances: Engaging with vibrant Gombey performances showcases traditional Bermudian dance and music, which are integral to the region’s cultural celebrations.
  • Fishing Traditions: The area has a rich history of fishing, and observing or partaking in local fishing practices provides an authentic connection to the island’s livelihood.
  • Seafood Cuisine: Sampling freshly caught seafood prepared using age-old recipes highlights the importance of culinary customs that are cherished here in this destination.

Frequently Asked Questions About Crawl Hill Winter Rentals

2. How many Winter Rentals are available in Crawl Hill?

Currently, the total number of properties listed by RBO in 2026 is over 41 in the Crawl Hill area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Crawl Hill. 

3. What is the cancellation policy for winter rentals in this area?

The cancellation policy varies depending on the specific listing. You should review the terms provided during your booking process or contact the property owner directly for detailed information.

4. Are there any restrictions or requirements for booking a winter rental here?

Yes, each property may have its own set of rules or requirements, such as minimum stay periods or age restrictions. Please refer to the listing details or reach out to the owner to clarify these conditions.

5. How do I find available winter rentals in this destination for my preferred dates?

You can check availability by entering your desired travel dates on the booking website or contacting the property owner directly for real-time information about open dates.

6. What amenities are typically included with winter rentals in this region?

Most properties offer essential amenities such as Wi-Fi, kitchen facilities, and parking. However, for specifics like pools or additional features, consult the listing details or speak directly with the owner.

7. Is it possible to make special requests or modifications when booking a winter rental here?

Special requests can often be accommodated, but it's best to communicate directly with the property owner beforehand to ensure they can meet your needs.

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9.8
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3000 ft² 18 Guests 5 Bedrooms 5 Bathrooms
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  • Oceanfront
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9.2
Exceptional
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650 ft² 3 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
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  • Pet Friendly
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  • Fireplace/Heating
  • Pool
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CA $3,178/Night For 7 Nights CA $22,243
New
12917 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
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CA $1,432/Night For 7 Nights CA $10,024
New
50 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
CA $648/Night For 7 Nights CA $4,536
10.0
Exceptional
(89 Reviews)
450 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Spa
  • Fireplace/Heating
  • Balcony/Terrace
CA $179/Night For 7 Nights CA $1,254