Vacation Rentals in The Windjammer Gallery, Hamilton: Compare 10+ Sites & Save

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200 Best Vacation Rentals in The Windjammer Gallery (Starting from $143)

Bermuda Vacation Retreat
Bermuda Vacation Retreat
House
Chelston, PG, Bermuda
1.3k from The Windjammer Gallery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$800
Average price / night
Check Availability
CR - Just bring your suitcases
CR - Just bring your suitcases
Apartment
Pembroke, Bermuda
0.3k from The Windjammer Gallery center

AC, Heater, Internet, No Smoking

1 Bedroom2 Guests
New to Booking
$358
Average price / night
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Frognal Apartment
Frognal Apartment
Apartment
North Shore Village, DV, Bermuda
1.8k from The Windjammer Gallery center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms4 Guests
9.5

Superb

15 reviews

$400
Average price / night
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CR Apartment with amazing view.
CR Apartment with amazing view.
Apartment
Pembroke, Bermuda
0.6k from The Windjammer Gallery center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

1 Bedroom3 Guests
New to Booking
$452
Average price / night
Check Availability
AIRBAB Moon Gate East
AIRBAB Moon Gate East
Apartment
Mount Pleasant, PG, Bermuda
2.5k from The Windjammer Gallery center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms6 Guests
9.4

Superb

19 reviews

$207
Average price / night
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Charming 2-bedroom apartment with WiFi and AC in Devonshire
Charming 2-bedroom apartment with WiFi and AC in Devonshire
Apartment
Devonshire, Bermuda
0.9k from The Windjammer Gallery center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.2

Superb

11 reviews

$260
Average price / night
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AIRBAB Moon Gate West
AIRBAB Moon Gate West
Apartment
Mount Pleasant, PG, Bermuda
2.6k from The Windjammer Gallery center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms6 Guests
8.7

Fabulous

26 reviews

$280
Average price / night
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ED 9 King bed Hamilton and pool access
ED 9 King bed Hamilton and pool access
Apartment
Pembroke Parish, Bermuda
1.0k from The Windjammer Gallery center

AC, Heater, Internet, Kitchen, No Smoking, Pool, TV

1 Bedroom3 Guests
New to Booking
$448
Average price / night
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Blue Horizons Guest House
Blue Horizons Guest House
House
The Windjammer Gallery, Hamilton, Bermuda
2.8k from The Windjammer Gallery center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

5 Bedrooms13 Guests
7.6

Good

92 reviews

$333
Average price / night
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Pembroke Villa - Business and Vacation Destination minutes from central Hamilton
Pembroke Villa - Business and Vacation Destination minutes from central Hamilton
Apartment
Pembroke, HM 09, Bermuda
1.2k from The Windjammer Gallery center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms7 Guests
10.0

Exceptional

37 reviews

$500
Average price / night
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Sandpiper Apartments
Sandpiper Apartments
Apartment
Mount Pleasant, WK, Bermuda
3.1k from The Windjammer Gallery center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

14 Bedrooms7 Guests
9.0

Fabulous

169 reviews

$325
Average price / night
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Wild Bird, Paget - Pool, Twizy charger, Kitchenette -  non smoking property
Wild Bird, Paget - Pool, Twizy charger, Kitchenette - non smoking property
House
Paget, PG06, Bermuda
1.2k from The Windjammer Gallery center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
9.8

Exceptional

67 reviews

$251
Average price / night
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Cosy Bermuda House
Cosy Bermuda House
Apartment
Pembroke, HM, Bermuda
3.2k from The Windjammer Gallery center

Balcony/Terrace, Air Conditioner, Pet Friendly, Guest Services, Internet, Pool, Transportation/Shuttle

4 Bedrooms7 Guests
New to Booking
$310
Average price / night
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Pembroke Villa - Business and Vacation Home
Pembroke Villa - Business and Vacation Home
House
Pembroke Parish, Bermuda
1.2k from The Windjammer Gallery center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
10.0

Exceptional

9 reviews

$866
Average price / night
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7 Arches
7 Arches
Apartment
The Windjammer Gallery, Hamilton, Bermuda
4.0k from The Windjammer Gallery center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

5 Bedrooms12 Guests
6.5

Good

16 reviews

$975
Average price / night
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Entire Private Vacation Villa  3 Bedrooms Pool nr Beach in Bermuda.
Entire Private Vacation Villa 3 Bedrooms Pool nr Beach in Bermuda.
House
Paget, PG06, Bermuda
1.3k from The Windjammer Gallery center

AC, Barbecue, Breakfast Available, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$1019
Average price / night
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Wade's Garden Inn
Wade's Garden Inn
Apartment
The Windjammer Gallery, Hamilton, Bermuda
6.0k from The Windjammer Gallery center

Parking, Kitchen, Breakfast, Air Conditioner, Wheelchair Accessible, Internet, Laundry

3 Bedrooms6 Guests
9.9

Exceptional

9 reviews

$143
Average price / night
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Tranquil, Roomy Getaway - Close to City of Hamilton
Tranquil, Roomy Getaway - Close to City of Hamilton
Apartment
Pembroke, Bermuda
1.3k from The Windjammer Gallery center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$609
Average price / night
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Southern Views
Southern Views
House
Southampton, SN, Bermuda
6.2k from The Windjammer Gallery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms39 Guests
10.0

Exceptional

1 reviews

$1672
Average price / night
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Smugglers Cove - Walk to City of Hamilton
Smugglers Cove - Walk to City of Hamilton
House
Pembroke Parish, HM06, Bermuda
1.3k from The Windjammer Gallery center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
10.0

Exceptional

54 reviews

$329
Average price / night
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Rosemont Guest Suites
Rosemont Guest Suites
Apartment
41 Rosemont Avenue, Pembroke Parish, HM08, Bermuda
1.3k from The Windjammer Gallery center

AC, Barbecue, Breakfast Included, Business Services, Frontdesk 24 Hour, Housekeeping, Internet, Kitchen, Laundry

8.6

Fabulous

189 reviews

$433
Average price / night
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Chic Paget Studio Near Hamilton & Railway Trail
Chic Paget Studio Near Hamilton & Railway Trail
Apartment
Paget, PG 06, Bermuda
1.4k from The Windjammer Gallery center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

1 Bedroom3 Guests
New to Booking
$300
Average price / night
Check Availability
Ideal for Business travelers ...easy walk into the center of Hamilton
Ideal for Business travelers ...easy walk into the center of Hamilton
Apartment
Pembroke, Bermuda
1.4k from The Windjammer Gallery center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

1 Bedroom2 Guests
10.0

Exceptional

3 reviews

$261
Average price / night
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Oceanfront Interior designed Beach House, Grape Bay Beach in Paget
Oceanfront Interior designed Beach House, Grape Bay Beach in Paget
House
Paget, PG 06, Bermuda
1.4k from The Windjammer Gallery center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$1254
Average price / night
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Cottage Priv. Pool & Tennis Beach 5 min Central
Cottage Priv. Pool & Tennis Beach 5 min Central
Cottage
Paget, DV04, Bermuda
1.5k from The Windjammer Gallery center

AC, Balcony, Barbecue, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
10.0

Exceptional

23 reviews

$356
Average price / night
Check Availability
ED 12 - Pool, king bed, Hamilton Bermuda
ED 12 - Pool, king bed, Hamilton Bermuda
Apartment
Pembroke Parish, Bermuda
1.6k from The Windjammer Gallery center

AC, Heater, Internet, Kitchen, No Smoking, Pool, TV

1 Bedroom2 Guests
New to Booking
$391
Average price / night
Check Availability
ED 15 Pool, Queen bed, Hamilton Bermuda
ED 15 Pool, Queen bed, Hamilton Bermuda
Apartment
Pembroke Parish, Bermuda
1.7k from The Windjammer Gallery center

AC, Heater, Internet, No Smoking

1 Bedroom2 Guests
8.0

Good

1 reviews

$387
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in The Windjammer Gallery.

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Frequently Asked Questions

You can explore 200 verified vacation rentals in The Windjammer Gallery. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in The Windjammer Gallery vary depending on the season, property size, and location. Rates typically start from around $143 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in The Windjammer Gallery include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in The Windjammer Gallery welcome pets. Currently, 16 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in The Windjammer Gallery often include amenities such as Fireplace/Heating, Balcony/Terrace, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.