Rye Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Rye Vacation

With every last detail planned before you go, our Rye vacation packages mean you can simply focus on having fun. Whether you're based in the neighborhood of South Eliot, which is good for walking, or somewhere else, this lively city promises a wealth of discoveries. If sightseeing is on the cards during your trip to Rye, visit popular attractions like Fort Constitution Historical Site, Market Square and Water Country. A couple of quick clicks is all it takes to create a tailored Rye vacation on Expedia.

Top Rye Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,411, price is now CA $706 per person
CA $706
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,120, price is now CA $1,126 per person
CA $1,126
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,397, price is now CA $1,548 per person
CA $1,548
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,234, price is now CA $1,488 per person
CA $1,488
per person
Jan 14 - Jan 17
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it.

Reviewed on Nov 8, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,542, price is now CA $1,098 per person
CA $1,098
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Coffee machine in our room did not work and unfortunately our room located near the stair exit was not the most quiet. Other than that, was a very nice hotel with lovely staff.

Reviewed on Nov 7, 2026

Rye Beach Vacation

Get ready to live out those summery daydreams on your Rye vacation. Go on a romantic walk, appreciate the sparkling coastal views and pick up unique seashells during your trip to Rye. Situated just 3 kilometres from downtown, Jenness State Beach is the place to be for many sun-seeking travelers. Have a look through our Rye vacation packages and watch your travel budget stretch further!

Ready to book your vacation to Rye?

 

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Rye Hotel Deals

Ashworth by the Sea

Ashworth by the Sea

3 out of 5
295 Ocean Blvd Hampton NH
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Nov 9 to Nov 10
CA $177
CA $231 total
Nov 9 - Nov 10
includes taxes & fees
Ashworth by the Sea
Ogunquit - The Milestone

Ogunquit - The Milestone

2 out of 5
687 Main Street Ogunquit ME
8.8/10 Excellent! (1,629 reviews)
"This motel was clean, quiet and reasonably priced to fit our needs. I have stayed here before and would stay again."

Reviewed on Nov 7, 2026

Get rates
Ogunquit - The Milestone
Anchorage Inn and Resort

Anchorage Inn and Resort

3 out of 5
265 Long Beach Avenue York Beach ME
The price is CA $154 per night from Dec 1 to Dec 2
CA $154
CA $168 total
Dec 1 - Dec 2
includes taxes & fees
Anchorage Inn and Resort
See all 2,654 properties in Rye
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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Stay near popular Rye attractions

A calm harbor with boats, a wooden pier, and houses in the background.

Rye Harbor State Park

You can take time to visit Rye Harbor State Park during your travels to Rye. Wander the beautiful beaches and seaside in the area.
See properties

Frequently asked questions

How much does a Rye vacation package cost?
You'll find cheap prices from CA $706 on Expedia for your Rye escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Rye costs.
What are the cheapest months to go to Rye?
February, March and December are the best times to look for cheap Rye vacation packages. Opting to travel in less busy months means you can typically find better prices on flights and accommodations.
How many days is enough for Rye?
Generally, a handful of days is ideal for a Rye vacation. With a well-organized schedule, you can visit all the top sights like Strawbery Banke Museum, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Rye?
Rye offers everything you need for an amazing escape. Get your Rye vacation off to a flying start by exploring top attractions like Jenness State Beach.
How to find the best Rye package deals?
Start your search for a Rye package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Rye package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Rye getaway off to a flying start.
Is it cheaper to book a Rye vacation as a package?
You can enjoy significant savings on your Rye retreat by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to view the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Rye?
Enjoy fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Rye adventure.
How to plan a trip to Rye?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Rye.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Rye.
  3. Set the duration of your trip: Start by making a list of all the attractions you want to get to in Rye. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Rye vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.