Sea Pines Vacation Packages

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

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Top Holiday Package Deals in Sea Pines

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,765, price is now CA $1,147 per person
CA $1,147
per person
Jul 1 - Jul 5
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Price was CA $2,544, price is now CA $1,522 per person
CA $1,522
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (3,127 reviews)
Everything was great except for the shower, which is too small.

Reviewed on Apr 29, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,579, price is now CA $1,584 per person
CA $1,584
per person
Jul 19 - Jul 24
found 2 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
South End
Price was CA $2,001, price is now CA $1,303 per person
CA $1,303
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,003 reviews)
I had a great experience staying at Staypineapple in the South End. The hotel has a really fun, unique vibe while still feeling clean and well put together. The rooms were cozy but thoughtfully designed, and the bed was honestly one of the most comfortable I’ve slept in. The staff was friendly and welcoming, and the location made it easy to get around Boston and explore nearby restaurants and shops. Small touches like the complimentary coffee and overall atmosphere made the stay feel a little more special. Would definitely stay here again and recommend it to anyone looking for something a bit different from a typical hotel.

Reviewed on Apr 30, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $2,902, price is now CA $1,982 per person
CA $1,982
per person
Jul 1 - Jul 5
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (682 reviews)
Excellent Such a great surprise Amazing view. Great staff, very helpful with restaurant recommendations We loved it

Reviewed on Apr 23, 2026

Sea Pines Hotel Deals

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from May 3 to May 4
CA $173
CA $277 total
May 3 - May 4
includes taxes & fees
8.6/10 Excellent! (554 reviews)
It was stressful that after paying for the hotel we had to wait in line the day of to buy pool tickets to hopefully get them. We were not allowed to purchase them at check in. It was the only reason we booked the trip. If it sold out we would have been out of luck and there wouldn’t have been anything ...

Reviewed on Apr 28, 2026

Margaritaville Resort Cape Cod
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from May 3 to May 4
CA $170
CA $210 total
May 3 - May 4
includes taxes & fees
8.8/10 Excellent! (1,541 reviews)
Noisy

Reviewed on Apr 29, 2026

Bayside Resort Hotel
Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
18 North St Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from May 3 to May 4
CA $112
CA $128 total
May 3 - May 4
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Everything

Reviewed on Apr 28, 2026

Hyannis Travel Inn
See all 4,907 properties in Sea Pines
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.
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Frequently asked questions

How much does a Sea Pines vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Sea Pines from just CA $1,147. And the more you bundle, the more money you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Sea Pines?
Bundle, bundle, bundle. Flights, hotels and rental cars — combine whatever you need into a Sea Pines vacation package to save a pile of cash. Score even better deals when you add extras such as day tours to your booking. But that's not the only good part. You have the flexibility to tailor your vacation your way. We offer more than 550 partner airlines and 1,000,000 properties around the world, so that everyone has an opportunity to travel and fulfill those vacation dreams.
Where should I stay in Sea Pines?
If you're eager to be in the heart of the action, stay close to Cape Cod Museum of Natural History. Many travelers book a hotel around this top tourist attraction.
What are the top hotels in Sea Pines?
Just A Short Distance To A Shared Private Beach and Less Than Half A Mile To The Private Association beach With Fire Pit And Outdoor Shower are among the most sought-after hotels in Sea Pines. Why not check out the facilities and amenities at each and then make a decision?
How far in advance should I book my Sea Pines vacation?
To score rock-bottom prices, book early. Air carriers typically release tickets, along with some of the lowest fares, nearly 12 months prior to departure. Hotels, activities and car rental should also be booked early to avoid disappointment. If you've decided on a last-minute getaway in Sea Pines, there are always plenty of great bargains to be had on Expedia. Book something in today!
What does an Expedia Sea Pines travel package include?
With Expedia, you can select any combination of flights, car rentals and hotels to build your ideal Sea Pines travel package. Once you've made your booking, you can add on the fun things like sightseeing tours and activities. Don't forget, the more you bundle, the more discounts you'll get!
What should I know before booking a Sea Pines travel package?
Whether it's relaxation or adventure you're after, a Sea Pines vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Sea Pines Expedia vacation package?
You sure can. We have more than 550 partner airlines throughout the world, so opt for the carrier that's a good fit for your travel needs.
If I'm not able to travel, can I cancel my Sea Pines vacation package?
Don't stress if you're rethinking your Sea Pines vacation package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We get that life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.

Discover the most popular places to visit in Sea Pines

Breakwater Beach

Breakwater Beach

Swim in the clear, shallow waters of this sandy bay and return at low water to explore a sprawling field of fascinating tidal pools.

Breakwater Beach
Cape Cod Museum of Natural History

Cape Cod Museum of Natural History

When the beauty and natural richness of Cape Cod’s landscape leave you craving to know more, enjoy a tour through the halls of this museum and education center.

Cape Cod Museum of Natural History
Sunset on Paine’s creek beach Cape Cod MA USA

Paine's Creek Beach

Why not spend a carefree afternoon at Paine's Creek Beach during your travels in Brewster? Stroll along the seaside in this relaxing area, or check out its seafood restaurants.

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