Sea Pines Vacation Packages

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Top Holiday Package Deals in Sea Pines

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 $1,558, price is now CA $841 per person
CA $841
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,637, price is now CA $1,652 per person
CA $1,652
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,300, price is now CA $878 per person
CA $878
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (188 reviews)
It is truly a bed and breakfast. We stayed in the main house in a cozy upstairs updated bedroom overlooking the ocean. Breakfast was served every morning between 8am and 10am. Allowing us to have our coffee and stroll along the beach before our meal. Staff friendly and helpful. We will return again next year

Reviewed on Jun 18, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $2,824, price is now CA $1,924 per person
CA $1,924
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (707 reviews)
It was absolutely charming and beautiful! The view was magnificent, the staff couldn't have been more accommodating and the room was wonderful. I would return to Room 23 over and over again.

Reviewed on Jun 20, 2026

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was CA $1,578, price is now CA $1,147 per person
CA $1,147
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (4 reviews)
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week. We did not have a rental car but the parking garage was easily accessible and secure. We were able to get ubers very easily from the location. The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient. The support staff replied to all our messages in the chat option quickly and were very helpful. The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred. Would recommend this place without hesitation.

Reviewed on Jun 15, 2026

Sea Pines Hotel Deals

Charm on Main by Ocean Edge

Charm on Main by Ocean Edge

2.5 out of 5
2553 Main Street Brewster MA
The price is CA $338 per night from Jun 22 to Jun 23
CA $338
CA $387 total
Jun 22 - Jun 23
includes taxes & fees
9.8/10 Exceptional! (8 reviews)
"Beautifull property that really qualify its name! Charm...!"

Reviewed on Jun 18, 2026

Charm on Main by Ocean Edge
Riviera Beach Resort

Riviera Beach Resort

3 out of 5
327 South Shore Drive South Yarmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $384 per night from Jun 22 to Jun 23
CA $384
CA $488 total
Jun 22 - Jun 23
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Great location Clean rooms Restaurant hours seemed a bit limited"

Reviewed on Jun 18, 2026

Riviera Beach Resort
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 $327 per night from Jun 22 to Jun 23
CA $327
CA $455 total
Jun 22 - Jun 23
includes taxes & fees
8.8/10 Excellent! (598 reviews)
"The property is a waterpark. The only reason anybody would go there would be to use the waterpark. Your book a stay which costs a fortune but yet when you walk down to use the waterpark they charge you per day. My father who was on his 90th birthday drove down to watch my son use a waterslide and ..."

Reviewed on Jun 20, 2026

Margaritaville Resort Cape Cod
See all 5,238 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 $841. 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

4.5/5(4 reviews)

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.