2022 Fall Vacation Packages | September, October & November Vacations | Caribbean Vacation Deals

Flamingo Cancun Resort

Montreal Cancun, Mexico

All Inclusive

Room

Sep 28, 2022 (7 days)

Sep 28, 2022 (7 days) Room

Get 50 Miles

was $2,124 Save 52%

$1,019PP

taxes & fees

Holiday Inn Resort Montego Bay Toronto Montego Bay, Jamaica

All Inclusive

Room

Sep 25, 2022 (7 days)

Sep 25, 2022 (7 days) Room

Get 53 Miles

was $2,139 Save 50%

$1,079PP

taxes & fees

Sol Torremolinos Don Pedro Toronto Torremolinos, Spain

Only Breakfast

Sol Room

Nov 03, 2022 (8 days)

Nov 03, 2022 (8 days) Sol Room

Book with Deposit

Get 67 Miles

was $2,659 Save 49%

$1,349PP

taxes & fees

Book with Deposit

Palladium Costa Del Sol Toronto Benalmadena, Spain

Only Breakfast

Deluxe Room

Nov 03, 2022 (8 days)

Nov 03, 2022 (8 days) Deluxe Room

Book with Deposit

Get 71 Miles

was $2,789 Save 48%

$1,439PP

taxes & fees

Book with Deposit

Hotel Plus St. Johns Montreal Havana, Cuba

Breakfast and Dinner Only

Room Sea View

Oct 01, 2022 (7 days)

Oct 01, 2022 (7 days) Room Sea View

was $1,788 Save 43%

$1,018PP

taxes & fees

Melia Puerto Vallarta Toronto Puerto Vallarta, Mexico

All Inclusive

Melia Gardenview Room

Sep 26, 2022 (7 days)

Sep 26, 2022 (7 days) Melia Gardenview Room

Get 50 Miles

was $1,595 Save 37%

$1,005PP

taxes & fees

Trs Turquesa Hotel Montreal Punta Cana, Dominican Republic

All Inclusive

Junior Suite Garden Pool View

Oct 26, 2022 (6 days)

Oct 26, 2022 (6 days) Junior Suite Garden Pool View

Book with Deposit

Get 76 Miles

was $2,174 Save 29%

$1,539PP

taxes & fees

Book with Deposit

Aston Waikiki Circle Calgary Honolulu, Hawaii

No Meals/Drinks

Partial Oceanview Room

Sep 25, 2022 (7 days)

Sep 25, 2022 (7 days) Partial Oceanview Room

Get 75 Miles

was $2,032 Save 25%

$1,516PP

taxes & fees

Decameron La Marina Toronto Riviera Nayarit, Mexico

All Inclusive

Room

Sep 26, 2022 (7 days)

Sep 26, 2022 (7 days) Room

Get 50 Miles

was $1,255 Save 20%

$1,005PP

taxes & fees

Blue Bay Villas Doradas Ottawa Puerto Plata, Dominican Republic

All Inclusive

Room

Oct 18, 2022 (7 days)

Oct 18, 2022 (7 days) Room

Book with Deposit

Get 53 Miles

was $1,249 Save 14%

$1,079PP

taxes & fees

Book with Deposit

Melia Punta Cana Beach Wellness Resort Adults

Toronto Punta Cana, Dominican Republic

All Inclusive

Deluxe Room

Sep 25, 2022 (6 days)

Sep 25, 2022 (6 days) Deluxe Room

Get 65 Miles

was $1,509 Save 13%

$1,309PP

taxes & fees

Binniguenda Huatulco

Toronto Huatulco, Mexico

All Inclusive

Deluxe Room

Dec 03, 2022 (7 days)

Dec 03, 2022 (7 days) Deluxe Room

Book with Deposit

Get 76 Miles

was $1,749 Save 12%

$1,539PP

taxes & fees

Book with Deposit

Encore At Wynn Las Vegas Toronto Las Vegas, Nevada

No Meals/Drinks

Encore Resort King

Dec 04, 2022 (6 days)

Dec 04, 2022 (6 days) Encore Resort King

Book with Deposit

Get 52 Miles

$1,050PP

taxes & fees

Book with Deposit

Les Suites Hotel Ottawa

Toronto Ottawa, Canada

No Meals/Drinks

Premiere 1 Bedroom Suite

Sep 29, 2022 (7 days)

Sep 29, 2022 (7 days) Premiere 1 Bedroom Suite

Get 58 Miles

$1,165PP

taxes & fees

Hilton Puerto Vallarta Resort Kelowna Puerto Vallarta, Mexico

All Inclusive

Partial Oceanview Room

Oct 31, 2022 (6 days)

Oct 31, 2022 (6 days) Partial Oceanview Room

Book with Deposit

Get 74 Miles

$1,496PP

taxes & fees

Book with Deposit

Malaga Alameda Centro Affliated By Melia Montreal Malaga

No Meals/Drinks

Standard Double

Dec 15, 2022 (8 days)

Dec 15, 2022 (8 days) Standard Double

Book with Deposit

Get 71 Miles

was $2,338 Save 39%

$1,429PP

taxes & fees

Book with Deposit

Hcc Regente Toronto Barcelona, Spain

Only Breakfast

Room

Oct 11, 2022 (7 days)

Oct 11, 2022 (7 days) Room

Book with Deposit

Get 73 Miles

was $1,659 Save 11%

$1,479PP

taxes & fees

Book with Deposit

Barcelona Apolo Affiliated By Melia Toronto Barcelona, Spain

No Meals/Drinks

Standard Room

Oct 19, 2022 (7 days)

Oct 19, 2022 (7 days) Standard Room

Book with Deposit

Get 77 Miles

was $1,739 Save 11%

$1,549PP

taxes & fees

Book with Deposit

Hcc Lugano Toronto Barcelona, Spain

Only Breakfast

Room

Oct 11, 2022 (7 days)

Oct 11, 2022 (7 days) Room

Book with Deposit

Get 69 Miles

was $1,559 Save 11%

$1,389PP

taxes & fees

Book with Deposit

Hcc Taber Toronto Barcelona, Spain

Only Breakfast

Room

Oct 11, 2022 (7 days)

Oct 11, 2022 (7 days) Room

Book with Deposit

Get 70 Miles

was $1,599 Save 11%

$1,419PP

taxes & fees

Book with Deposit

Hcc Montblanc Toronto Barcelona, Spain

Only Breakfast

Room

Oct 11, 2022 (7 days)

Oct 11, 2022 (7 days) Room

Book with Deposit

Get 71 Miles

was $1,619 Save 11%

$1,439PP

taxes & fees

Book with Deposit

Hcc St Moritz Toronto Barcelona, Spain

Only Breakfast

Room

Oct 11, 2022 (7 days)

Oct 11, 2022 (7 days) Room

Book with Deposit

Get 75 Miles

was $1,699 Save 11%

$1,519PP

taxes & fees

Book with Deposit

Royal National Hotel Toronto London, UK

Only Breakfast

Room Twin

Sep 29, 2022 (6 days)

Sep 29, 2022 (6 days) Room Twin

Get 72 Miles

was $1,489

$1,449PP

taxes & fees

Tavistock Hotel Toronto London, UK

Only Breakfast

Room Twin

Sep 29, 2022 (6 days)

Sep 29, 2022 (6 days) Room Twin

Get 74 Miles

was $1,529

$1,489PP

taxes & fees

President Hotel Toronto London, UK

Only Breakfast

Room Double

Sep 29, 2022 (6 days)

Sep 29, 2022 (6 days) Room Double

Get 75 Miles

was $1,549

$1,509PP

taxes & fees

Bedford Hotel

Toronto London, UK

Only Breakfast

Room Twin

Sep 29, 2022 (6 days)

Sep 29, 2022 (6 days) Room Twin

Get 79 Miles

was $1,629

$1,589PP

taxes & fees

Riu Plaza The Gresham Hotel Toronto Dublin, Ireland

Only Breakfast

Room Queen

Nov 21, 2022 (7 days)

Nov 21, 2022 (7 days) Room Queen

Book with Deposit

Get 58 Miles

$1,179PP

taxes & fees

Book with Deposit

Mexico: Acapulco Cancun Los Cabos Puerto Vallarta Riviera Maya

Kore Tulum Retreat And Spa Resort

Montreal Riviera Maya

All Inclusive

Luxury Jacuzzi Suite Gardenview

Sep 28, 2022 (7 days)

Sep 28, 2022 (7 days) Luxury Jacuzzi Suite Gardenview

Get 63 Miles

was $3,035 Save 58%

$1,275PP

taxes & fees

Ocean Riviera Paradise

Montreal Riviera Maya

All Inclusive

Junior Suite

Sep 28, 2022 (7 days)

Sep 28, 2022 (7 days) Junior Suite

Get 51 Miles

was $2,304 Save 55%

$1,029PP

taxes & fees

Platinum Yucatan Princess All Suites And Spa Montreal Riviera Maya

All Inclusive

Deluxe Junior Suite

Sep 28, 2022 (7 days)

Sep 28, 2022 (7 days) Deluxe Junior Suite

Get 64 Miles

was $2,554 Save 50%

$1,289PP

taxes & fees

Catalonia Riviera Maya And Yucatan Beach Montreal Riviera Maya

All Inclusive

Room Gardenview

Sep 28, 2022 (7 days)

Sep 28, 2022 (7 days) Room Gardenview

Get 50 Miles

was $1,744 Save 42%

$1,019PP

taxes & fees

Akumal Bay Beach And Wellness Resort Montreal Riviera Maya

All Inclusive

Junior Suite

Sep 27, 2022 (7 days)

Sep 27, 2022 (7 days) Junior Suite

Get 68 Miles

was $2,354 Save 41%

$1,379PP

taxes & fees

Dreams Tulum Resort And Spa Toronto Riviera Maya

All Inclusive

Deluxe Gardenview Double

Sep 29, 2022 (6 days)

Sep 29, 2022 (6 days) Deluxe Gardenview Double

Get 59 Miles

was $1,879 Save 37%

$1,189PP

taxes & fees

Hideaway At Royalton Riviera Cancun Montreal Riviera Maya

All Inclusive

Luxury Junior Suite

Sep 27, 2022 (7 days)

Sep 27, 2022 (7 days) Luxury Junior Suite

Get 73 Miles

was $2,284 Save 36%

$1,469PP

taxes & fees

El Dorado Seaside Palms Montreal Riviera Maya

All Inclusive

Junior Suite

Sep 28, 2022 (7 days)

Sep 28, 2022 (7 days) Junior Suite

Get 73 Miles

was $2,282 Save 35%

$1,479PP

taxes & fees

Royalton Riviera Cancun Montreal Riviera Maya

All Inclusive

Luxury Junior Suite

Sep 27, 2022 (7 days)

Sep 27, 2022 (7 days) Luxury Junior Suite

Get 67 Miles

was $2,066 Save 34%

$1,359PP

taxes & fees

The Yucatan Resort Playa Del Carmen

Ottawa Riviera Maya

All Inclusive

Room King

Nov 07, 2022 (6 days)

Nov 07, 2022 (6 days) Room King

Book with Deposit

Get 59 Miles

was $1,755 Save 33%

$1,184PP

taxes & fees

Book with Deposit

Riu Playacar Montreal Riviera Maya

All Inclusive

Room

Sep 22, 2022 (7 days)

Sep 22, 2022 (7 days) Room

Get 61 Miles

was $1,735 Save 29%

$1,235PP

taxes & fees

Iberostar Quetzal Toronto Riviera Maya

All Inclusive

Room

Sep 29, 2022 (6 days)

Sep 29, 2022 (6 days) Room

Get 56 Miles

was $1,559 Save 27%

$1,139PP

taxes & fees

Iberostar Paraiso Beach Toronto Riviera Maya

All Inclusive

Room

Sep 29, 2022 (6 days)

Sep 29, 2022 (6 days) Room

Get 58 Miles

was $1,599 Save 27%

$1,169PP

taxes & fees

Hm Playa Del Carmen Toronto Riviera Maya

Only Breakfast

Room

Sep 29, 2022 (7 days)

Sep 29, 2022 (7 days) Room

Get 50 Miles

was $1,355 Save 25%

$1,015PP

taxes & fees

Catalonia Royal Tulum Beach And Spa

Toronto Riviera Maya

All Inclusive

Superior Room

Oct 13, 2022 (6 days)

Oct 13, 2022 (6 days) Superior Room

Book with Deposit

Get 67 Miles

was $1,699 Save 21%

$1,349PP

taxes & fees

Book with Deposit

Cuba: Cayo Coco Cayo Largo Havana Holguin Varadero

Grand Aston Cayo Paredon Beach Resort Montreal Cayo Coco

All Inclusive

Deluxe Main Building

Nov 13, 2022 (7 days)

Nov 13, 2022 (7 days) Deluxe Main Building

Book with Deposit

was $1,858 Save 38%

$1,158PP

taxes & fees

Book with Deposit

Melia Jardines Del Rey Toronto Cayo Coco

All Inclusive

Classic Room

Nov 19, 2022 (7 days)

Nov 19, 2022 (7 days) Classic Room

Book with Deposit

was $1,545 Save 35%

$1,005PP

taxes & fees

Book with Deposit

Cayo Guillermo Resort Kempinski Montreal Cayo Coco

Only Breakfast

Deluxe Pool View

Sep 25, 2022 (7 days)

Sep 25, 2022 (7 days) Deluxe Pool View

was $2,318 Save 31%

$1,598PP

taxes & fees

Pullman Cayo Coco

Toronto Cayo Coco

All Inclusive

Deluxe Gardenview Room

Oct 23, 2022 (7 days)

Oct 23, 2022 (7 days) Deluxe Gardenview Room

Book with Deposit

was $1,349 Save 26%

$999PP

taxes & fees

Book with Deposit

Tryp Cayo Coco

Ottawa Cayo Coco

All Inclusive

Tryp Room

Oct 20, 2022 (7 days)

Oct 20, 2022 (7 days) Tryp Room

Book with Deposit

was $1,289 Save 22%

$999PP

taxes & fees

Book with Deposit

Memories Caribe Beach Resort Ottawa Cayo Coco

All Inclusive

Superior Room

Oct 20, 2022 (7 days)

Oct 20, 2022 (7 days) Superior Room

Book with Deposit

was $1,289 Save 22%

$999PP

taxes & fees

Book with Deposit

Hotel Colonial Cayo Coco Ottawa Cayo Coco

All Inclusive

Room

Dec 13, 2022 (7 days)

Dec 13, 2022 (7 days) Room

Book with Deposit

was $1,249 Save 18%

$1,029PP

taxes & fees

Book with Deposit

Gran Muthu Rainbow Cayo Guillermo

Toronto Cayo Coco, Cuba

All Inclusive

Junior Suite

Oct 09, 2022 (7 days)

Oct 09, 2022 (7 days) Junior Suite

Book with Deposit

was $1,235 Save 18%

$1,015PP

taxes & fees

Book with Deposit

Hotel Camino Del Mar Toronto Cayo Coco

All Inclusive

Room

Dec 06, 2022 (7 days)

Dec 06, 2022 (7 days) Room

Book with Deposit

was $1,229 Save 15%

$1,049PP

taxes & fees

Book with Deposit

Hotel Playa Coco

Sault Sainte Marie Cayo Coco

All Inclusive

Room

Dec 13, 2022 (7 days)

Dec 13, 2022 (7 days) Room

Book with Deposit

was $1,115 Save 10%

$1,005PP

taxes & fees

Book with Deposit

Hotel Mojito

Sault Sainte Marie Cayo Coco, Cuba

All Inclusive

Room

Dec 13, 2022 (7 days)

Dec 13, 2022 (7 days) Room

Book with Deposit

was $1,115 Save 10%

$1,005PP

taxes & fees

Book with Deposit

Hotel Playa Paraiso Sault Sainte Marie Cayo Coco

All Inclusive

Junior Suite

Dec 13, 2022 (7 days)

Dec 13, 2022 (7 days) Junior Suite

Book with Deposit

was $1,125 Save 10%

$1,015PP

taxes & fees

Book with Deposit

Gran Muthu Imperial

Winnipeg Cayo Coco

All Inclusive

Room

Sep 22, 2022 (7 days)

Sep 22, 2022 (7 days) Room

was $1,039

$1,009PP

taxes & fees

Iberostar Selection Playa Pilar

Winnipeg Cayo Coco

All Inclusive

Double Room

Sep 22, 2022 (7 days)

Sep 22, 2022 (7 days) Double Room

was $1,059

$1,029PP

taxes & fees

Grand Muthu Cayo Guillermo

Winnipeg Cayo Coco

All Inclusive

Room

Sep 29, 2022 (7 days)

Sep 29, 2022 (7 days) Room

was $1,019

$999PP

taxes & fees

Dominican Republic: La Romana Puerto Plata Punta Cana Samana Santo Domingo

Whala Bayahibe

Montreal La Romana

All Inclusive

Room

Oct 05, 2022 (7 days)

Oct 05, 2022 (7 days) Room

Get 50 Miles

was $1,865 Save 46%

$1,005PP

taxes & fees

Viva Wyndham Dominicus Beach

Montreal La Romana

All Inclusive

Dominicus Village Hotel Room

Oct 05, 2022 (7 days)

Oct 05, 2022 (7 days) Dominicus Village Hotel Room

Get 50 Miles

was $1,895 Save 46%

$1,015PP

taxes & fees

Grand Paradise Samana Montreal Samana

All Inclusive

Deluxe Gardenview Room

Oct 21, 2022 (7 days)

Oct 21, 2022 (7 days) Deluxe Gardenview Room

Book with Deposit

Get 50 Miles

was $1,833 Save 45%

$1,009PP

taxes & fees

Book with Deposit

Be Live Collection Canoa Adults Club Montreal La Romana

All Inclusive

Junior Suite

Sep 23, 2022 (7 days)

Sep 23, 2022 (7 days) Junior Suite

Get 60 Miles

was $2,205 Save 45%

$1,205PP

taxes & fees

Catalonia Bayahibe Montreal La Romana

All Inclusive

Comfort Room

Sep 23, 2022 (7 days)

Sep 23, 2022 (7 days) Comfort Room

Get 62 Miles

was $2,145 Save 41%

$1,255PP

taxes & fees

Bahia Principe Luxury Bouganville Montreal La Romana

All Inclusive

Junior Suite Deluxe

Sep 28, 2022 (7 days)

Sep 28, 2022 (7 days) Junior Suite Deluxe

Get 61 Miles

was $1,996 Save 38%

$1,239PP

taxes & fees

Dreams Dominicus La Romana

Toronto La Romana

All Inclusive

Deluxe Tropical View Double

Sep 22, 2022 (7 days)

Sep 22, 2022 (7 days) Deluxe Tropical View Double

Get 77 Miles

was $2,405 Save 35%

$1,555PP

taxes & fees

Bahia Principe Grand El Portillo

Montreal Samana

All meals, snacks included daily, unlimited Beverages (Alcoholic and Non-Alcoholic)

Chambre

Oct 04, 2022 (7 days)

Oct 04, 2022 (7 days) Chambre

Get 54 Miles

was $1,671 Save 34%

$1,099PP

taxes & fees

Be Live Collection Canoa Toronto La Romana

All Inclusive

Deluxe Room

Sep 27, 2022 (7 days)

Sep 27, 2022 (7 days) Deluxe Room

Get 51 Miles

was $1,545 Save 33%

$1,035PP

taxes & fees

Bahia Principe Luxury Samana Montreal Samana

All Inclusive

Superior Room No Balcony

Oct 18, 2022 (7 days)

Oct 18, 2022 (7 days) Superior Room No Balcony

Book with Deposit

Get 62 Miles

was $1,841 Save 32%

$1,249PP

taxes & fees

Book with Deposit

Viva Wyndham V Samana

Montreal Samana

All meals, snacks included daily, unlimited Beverages (Alcoholic and Non-Alcoholic)

Chambre V

Oct 13, 2022 (7 days)

Oct 13, 2022 (7 days) Chambre V

Book with Deposit

Get 66 Miles

was $1,903 Save 30%

$1,339PP

taxes & fees

Book with Deposit

Bahia Principe Grand Cayacoa

Toronto Samana

All Inclusive

Standard Room

Nov 07, 2022 (7 days)

Nov 07, 2022 (7 days) Standard Room

Book with Deposit

Get 55 Miles

was $1,477 Save 25%

$1,109PP

taxes & fees

Book with Deposit

Catalonia Royal La Romana

Toronto La Romana

All Inclusive

Superior Room

Sep 27, 2022 (7 days)

Sep 27, 2022 (7 days) Superior Room

Get 73 Miles

was $1,825 Save 19%

$1,475PP

taxes & fees

Viva Wyndham Dominicus Palace Toronto La Romana

All Inclusive

Superior Room

Sep 23, 2022 (7 days)

Sep 23, 2022 (7 days) Superior Room

Get 52 Miles

was $1,195 Save 12%

$1,055PP

taxes & fees

Bahia Principe Grand La Romana Toronto La Romana

All Inclusive

Junior Suite Superior

Sep 22, 2022 (7 days)

Sep 22, 2022 (7 days) Junior Suite Superior

Get 58 Miles

was $1,329 Save 11%

$1,179PP

taxes & fees

Jamaica: Whitehouse Montego Bay Negril Ocho Rios Runaway Bay

Holiday Inn Resort Montego Bay Toronto Montego Bay

All Inclusive

Room

Sep 25, 2022 (7 days)

Sep 25, 2022 (7 days) Room

Fall Vacations