Winter Rentals in Pembroke:【 GREAT PRICES 】Rent By Owner

Pembroke Winter Rental

Smugglers Cove - Walk to City of Hamilton

Highly Rated

House

Smugglers Cove - Walk to City of Hamilton

10.0

Exceptional

(59 Reviews)

1 Bedroom 1 Bath 2 Guests

US $382/Night 7 Nights - US $2,677

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Hotel

Hamilton Princess & Beach Club A Fairmont Managed Hotel

8.7

Fabulous

(237 Reviews)

10 Baths 569 ft²

US $855/Night 7 Nights - US $5,982

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Price Dropped

Hotel

Royal Palms Hotel

9.8

Exceptional

(569 Reviews)

1 Bath

US $564/Night 7 Nights - US $3,950

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House

Pembroke Villa - Business and Vacation Home

10.0

Exceptional

(10 Reviews)

3 Bedrooms 2 Baths 7 Guests 1400 ft²

US $1,007/Night 7 Nights - US $7,049

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Highly Rated

Hotel

Rosedon Hotel

9.8

Exceptional

(376 Reviews)

1 Bath

US $622/Night 7 Nights - US $4,354

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Apartment

Tranquil, Roomy Getaway - Close to City of Hamilton

9.8

Exceptional

(8 Reviews)

3 Bedrooms 2 Baths 6 Guests

US $546/Night 7 Nights - US $3,825

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Hamilton Princess & Beach Club - A Fairmont Hotel

Highly Rated

Resort

Hamilton Princess & Beach Club - A Fairmont Hotel

9.2

Exceptional

(1003 Reviews)

1 Bath

US $939/Night 7 Nights - US $6,573

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Apartment

Salt & Sage Bermuda Retreat - 3 bedroom, 1.5 bathroom

3 Bedrooms 1 Bath 6 Guests

US $645/Night 7 Nights - US $4,517

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Hamilton Princess - Fairmont Gold Experience

Highly Rated

Hotel

Hamilton Princess - Fairmont Gold Experience

9.2

Exceptional

(58 Reviews)

1 Bath

US $1,163/Night 7 Nights - US $8,138

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Hotel

Lemon and Ginger

9.4

Exceptional

(13 Reviews)

1 Bath

US $112/Night 7 Nights - US $782

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Apartment

Lovely private studio apartment in beautiful garden setting

9.8

Exceptional

(29 Reviews)

1 Bedroom 1 Bath 2 Guests

US $259/Night 7 Nights - US $1,815

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Bed & Breakfast

Edgehill Manor Guest House

7.5

Very Good

(43 Reviews)

11 Bedrooms 3 Baths 8 Guests 175.81 ft²

US $555/Night 7 Nights - US $3,888

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More Top-Rated Winter Rental in Pembroke Area

Why Choose Rent By Owner for your Pembroke Winter Rental?

What makes our Winter Rental special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Pembroke

When should you plan your Winter Rental stay?

Timing your visit to this destination can greatly enhance your experience, as the region's mild winter climate offers ideal conditions for enjoying your vacation here while avoiding peak tourist periods.

Peak Season Highlights

Spring (March to May)

During spring, the region experiences warm temperatures ideal for enjoying outdoor activities and exploring local scenery. It’s a popular time for visitors seeking pleasant weather without the peak crowds.

Average Temperature Daytime: around 70°F to 75°F - Nighttime: about 60°F to 65°F

Summer (June to August)

The summer months bring hot and humid weather, making it perfect for beach outings and water-based adventures. Expect this season to be vibrant with increased tourism in this desirable destination.

Average Temperature Daytime: approximately 85°F to 88°F - Nighttime: roughly 75°F to 78°F

Off-Season Highlights

Fall (September to November)

In fall, the area sees milder temperatures and fewer visitors, providing a peaceful atmosphere for your winter rentals. It’s an excellent time to enjoy the region’s natural beauty with fewer crowds.

Average Temperature Daytime: around 75°F to 80°F - Nighttime: about 65°F to 70°F

Winter (December to February)

During winter, the destination offers cooler weather that still remains mild compared to other regions. This season is favored by travelers looking to escape colder climates and enjoy a tranquil stay.

Average Temperature Daytime: roughly 65°F to 70°F - Nighttime: about 55°F to 60°F

Weekly Weather Forecast for Pembroke

How to Book Your Pembroke Winter Rental

What's our booking process?

Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Pembroke

More Top-Rated Winter Rental in Pembroke Area

Common Winter Rental Amenities

What amenities can you expect?

Our Winter Rental 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 access to private outdoor pools or communal swimming areas for relaxing dips in warm weather.
Benefit from lush, landscaped gardens perfect for leisurely strolls and outdoor photography.
Take advantage of spacious patios or decks ideal for outdoor dining or sunset viewing over the region.
Make use of convenient outdoor grilling stations to host barbecues with friends or family.
Find properties that feature shaded pergolas or covered terraces to stay cool while enjoying the fresh air.
Discover outdoor recreational equipment such as bicycles or kayaks for exploring the area's scenic surroundings.
Relax in well-maintained outdoor lounge areas designed for casual gatherings and enjoying the region's pleasant climate.

Top Attractions Around Pembroke

What attractions are nearby?

During your stay here, you can enjoy a variety of activities nearby, including exploring scenic coastal walks, engaging in water sports such as snorkeling and kayaking, or visiting local parks and cultural sites that showcase the region's rich history and natural beauty.

Family Activities

Clarence Hill Park: Enjoy a day outdoors at this scenic park, perfect for families to have picnics, play sports, and take in beautiful views of the surrounding area.
Horseshoe Bay Beach: Relax on the soft sands of this popular Bermudian beach, ideal for swimming, building sandcastles, or simply soaking up the sun with your loved ones.
Bermuda Aquarium, Museum & Zoo: Discover local marine life and exotic animals, making it an educational and entertaining experience for children and parents alike.
Fort Hamilton: Explore this historic fort offering panoramic views of the coastline, providing a fun and educational outing for the whole family.

Adult Activities

Golfing at Port Royal Golf Course: Spend a day teeing off on this renowned Bermuda golf course, offering stunning sea views and challenging fairways perfect for golf enthusiasts.
Sailing Excursions: Experience the open waters with sailing trips that showcase the area's breathtaking coastline and provide a relaxing way to explore the maritime scenery of Bermuda.
Historical Tours: Discover the rich history of this destination by visiting local landmarks and museums that highlight Bermuda's unique cultural heritage.
Beach Relaxation and Water Sports: Unwind on nearby beaches while enjoying activities like snorkeling, paddleboarding, or simply soaking up the sun in the tranquil surroundings.

Other Places to Stay in Pembroke

Pembroke Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Days Carefully: Take advantage of the area's beautiful natural surroundings by scheduling outdoor activities early in the day to enjoy optimal weather conditions.
Explore Local Cuisine: Sample authentic dishes at nearby eateries to fully immerse yourself in the culinary culture unique to this destination.
Utilize Public Transportation: Make use of available transit options to conveniently explore the region without the hassle of parking or navigating unfamiliar roads.
Book Accommodations in Advance: Secure your preferred winter rentals early through RentByOwner.com to ensure a seamless and stress-free stay in the area.

Transportation Options

Public Bus Service: The region offers an extensive bus network that provides easy and affordable transportation around Pembroke, making it convenient to explore the area during your stay.
Taxi Services: Reliable taxi options are available for quick and direct travel to various destinations within the destination, ensuring a comfortable journey in the area.
Car Rentals: Renting a car gives you the flexibility to navigate here at your own pace, especially beneficial if you're planning to visit nearby attractions or explore beyond the immediate vicinity.
Bike Rentals: For those seeking an eco-friendly and healthy way to see the sights, bike rentals are a popular choice for getting around this part of Bermuda with ease.

Local Customs Options

Respect for the Local Dress Code: Visitors are encouraged to dress modestly and appropriately, especially when attending religious or community gatherings in the area.
Celebration of Heritage through Festivals: Participating in local festivals allows you to experience the region’s rich cultural traditions and fosters a deeper connection with the community.
Environmental Conservation Practices: The community emphasizes eco-friendly habits, such as proper waste disposal and water conservation, which you can observe and adopt during your stay here.
Greeting Etiquette: A friendly greeting and respectful nod are customary when meeting locals, reflecting the region's warm hospitality and welcoming spirit.

Frequently Asked Questions About Pembroke Winter Rentals

1. What are the top Winter Rentals in Pembroke?

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

2. How many Winter Rentals are available in Pembroke?

Currently, the total number of properties listed by RBO in 2026 is over 10 in the Pembroke area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Pembroke. 

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

Cancellation policies vary by property. You should review the specific listing details or contact the owner directly to understand the terms applicable to your booking.

4. Are there any specific requirements or restrictions when booking winter rentals here?

Yes, certain properties may have requirements such as minimum stay durations or age restrictions. Please refer to the individual listing for detailed information or reach out to the owner for clarification.

5. How do I confirm my reservation and what payment methods are accepted?

Reservations are confirmed once the required deposit or full payment is received through the booking platform. Accepted payment methods typically include credit cards and online transfer options; details will be provided during the reservation process.

6. Is there a check-in and check-out process I should be aware of for stay in this destination?

Check-in and check-out procedures are detailed in each property’s listing. Contact the host directly if you need specific instructions or have special arrangements.

7. Are linens, towels, and amenities included in my winter rental?

Most properties offer linens and towels as part of the stay, but amenities can vary. Review the specific listing details or communicate with the owner to ensure your needs are met during your visit.