Rye Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The air conditioner sound like a truck trailer was in your room

Reviewed on Jul. 11, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 4
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Not bad at all, but nothing special

Reviewed on Jul. 13, 2025

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?

 

Choose your dates

Rye Hotel Deals

Ogunquit - The Milestone
Ogunquit - The Milestone
2 out of 5
687 Main Street, Ogunquit, ME
The price is CA $185 per night from Jul 16 to Jul 17
CA $185
CA $202 total
Jul 16 - Jul 17
includes taxes & fees
8.8/10 Excellent! (1,097 reviews)
"Nice room, close to beach, nice pool, reasonable rates"

Reviewed on Jul. 12, 2025

Ogunquit - The Milestone
Cliff House Maine
Cliff House Maine
4.5 out of 5
591 Shore Road, Cape Neddick, ME
The price is CA $1,011 per night from Jul 23 to Jul 24
CA $1,011
CA $1,159 total
Jul 23 - Jul 24
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"Everything about this location is five stars"

Reviewed on Jul. 6, 2025

Cliff House Maine
Anchor Inn and Cottages Wells-Ogunquit
Anchor Inn and Cottages Wells-Ogunquit
2.5 out of 5
424 Post Rd, Wells, ME
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Jul 14 to Jul 15
CA $183
CA $214 total
Jul 14 - Jul 15
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"The rooms were clean and comfortable. The staff was extremely helpful and knew you by name. The pool was beautiful and clean. It’s in a middle location so quick to get to Wells beaches and Ogunquit. Will definitely come back."

Reviewed on Jul. 11, 2025

Anchor Inn and Cottages Wells-Ogunquit
See all 2,630 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

Family Vacations

Discover the most popular places to visit in Rye

St. Andrew's-by-the-Sea

Learn about the local history of Rye with a stop at St. Andrew's-by-the-Sea. Wander the beautiful beaches and seaside in the area.

St. Andrew's-by-the-Sea

Rye Airfield

Catch an event at Rye Airfield during your trip to Rye. Amble around this family-friendly area's beautiful beaches or attend a sporting event.

Rye Airfield

Frequently asked questions

How much does a Rye vacation package cost?
You'll find cheap prices from CA $705 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.