Your Whitby Vacation

Our Whitby vacation packages let you customize your own adventure. Tailor your journey to your interests and needs and make every moment count in this lively city. A trip to Whitby is a superb opportunity to sightsee. Be sure to visit big-name attractions such as Sandy Point Beach, Whitby Beach and Pumpkin Bluff Beach. Expedia will help you escape your routine. Tailor your vacation to Whitby to match your travel style, whatever that may be!

Top Whitby Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Windsong on the Reef

Grace Bay

CA $3,130

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Providenciales (PLS)

9.2/10 Wonderful! (1,051 reviews)

Very nice views, excellent location, beautiful rooms… our stay was very special, we were celebrating our wedding anniversary and the staff were very helpful making our stay very special: they decor our room and gave us a celebration gift! Fully recommended! We will go back again soon!

Reviewed on May 22, 2026

Long Bay Beach Club

Long Bay Hills

CA $11,669

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Providenciales (PLS)

10/10 Exceptional! (3 reviews)

Dream Villas Provo

Blue Hills

CA $3,503

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Providenciales (PLS)

9.2/10 Wonderful! (64 reviews)

Beautiful beachfront stay! Clean, relaxing, and perfect for a peaceful getaway.

Reviewed on May 8, 2026

Beachfront at Windsong on the Reef

Grace Bay

CA $4,212

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Providenciales (PLS)

9.2/10 Wonderful! (138 reviews)

We loved our stay in a 1br oceanfront jr suite! Beautiful view, clean and well appointed room and property. Staff was great, esp waiters Samuel and Jamesley. Nice details like Bulgari products and Frette towels. Loved the food and view from rooftop bar and restaurant Pelago. We recd and $18 per person daily breakfast credit that helped offset the overall very high food costs in T&C. Nice reef in front to snorkel and saw turtles as nearby Smith’s Reef.

Reviewed on May 23, 2026

Bungalows at Windsong on the Reef

Grace Bay

CA $3,574

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Providenciales (PLS)

9/10 Wonderful! (91 reviews)

Wonderful property with exceptional service. Our three bedroom bungalow was spacious and well maintained.

Reviewed on May 23, 2026

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Whitby Hotel Deals

Pelican Beach Hotel

Pelican Beach Drive Whitby North Caicos

CA $400

CA $489 total

May 28 - May 29

includes taxes & fees

9.4/10 Exceptional! (124 reviews)

"Amazing staff"

Reviewed on Apr 28, 2026

Private Beachfront Luxury Estate with Infinity Pool & Concierge incl – Sleeps 16

North Caicos Turks and Caicos Islands

10/10 Exceptional! (191 reviews)

"From start to finish, our stay at this villa was excellent and exactly what we hoped it would be. The house was awesome and and no trouble accommodating our family of 11. The concierge met us at the dock and escorted us to the house and helped us get situated. A big shout-out to Regina! And the owner ..."

Reviewed on May 19, 2026

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Caicos Cottage, 2bd/2bath Beachfront Villa w/pool on Whitby Beach

Caicos Islands Caicos Islands

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See all 1,452 properties in Whitby

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.