Eastside Vacation Packages

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Top Holiday Package Deals in Eastside

Price found within the past 48 hours. Click for updated prices.
La Playa Inn

La Playa Inn

2.5 out of 5
Santa Barbara Beach
Price was CA $1,365, price is now CA $1,194 per person
CA $1,194
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Santa Barbara (SBA)
9.6/10 Exceptional! (1,004 reviews)
Friendly, helpful staff. Clean and well designed room.

Reviewed on Sep. 1, 2025

The Milo

The Milo

3.5 out of 5
Santa Barbara Beach
Price was CA $2,081, price is now CA $1,762 per person
CA $1,762
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Santa Barbara (SBA)
8.4/10 Very Good! (1,415 reviews)
Great location just no central Ac so the ac unit is loud and upstairs guess were very loud

Reviewed on Sep. 5, 2025

Riviera Beach House

Riviera Beach House

3.5 out of 5
Santa Barbara Beach
Price was CA $1,541, price is now CA $1,308 per person
CA $1,308
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Santa Barbara (SBA)
8.4/10 Very Good! (1,003 reviews)
It was an amazing weekend get away for me, my Husband and dog. Much needed!

Reviewed on Sep. 2, 2025

Drift Santa Barbara, a Member of Design Hotels

Drift Santa Barbara, a Member of Design Hotels

3.5 out of 5
Downtown Santa Barbara
Price was CA $1,592, price is now CA $1,369 per person
CA $1,369
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Santa Barbara (SBA)
8.4/10 Very Good! (370 reviews)
What is so special about the Drift are the people. Everyone from folks at the coffee shop, check in team, to the GM Jacqueline are so lovely and provide excellent customer service! So completely above and beyond to make my stay wonderful! I love the streamline design of the rooms, the yoga mat in every room, and the coffee every morning at Dawn! There are bikes and surf boards to borrow and enjoy in SB. Make sure you check out the yoga studio too! Also, the location is perfect for exploring, especially all of the vintage shops and The Funk Zone! I highly recommend staying at The Drift, and hope to check out their other properties.

Reviewed on Jul. 27, 2025

Hotel Californian

Hotel Californian

5 out of 5
Santa Barbara Beach
Price was CA $2,445, price is now CA $2,146 per person
CA $2,146
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Santa Barbara (SBA)
9.2/10 Wonderful! (905 reviews)
Gabby (manager) and the rest of her staff did everything to make our 10th wedding anniversary something special. I truly plan on making this trip to SB and staying at Hotel Californian an annual trip. The proximity to the beach was incredible. The rooftop pool has an incredible view. I took my time selecting a hotel that would make this a special weekend. And there was definitely some concern prior to arriving that my expectations would not be met. But with Gabby’s guidance, our stay felt special and classy. I would highly recommend staying here.

Reviewed on Aug. 30, 2025

Where to stay in Eastside

Find the best Eastside areas and neighborhoods for the activities you enjoy most. Learn more about Eastside
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Montecito

1 out of top 10 points of interest in this area
4.5/5(4 area reviews)

Celebrity-favored Montecito offers backcountry hiking trails and attractions like Lotusland and El Fureidis. Easily accessible via State Route 192 and the U.S. 101 Freeway, it's well-connected to Santa Barbara County.

Find hotels in Montecito

Eastside Hotel Deals

Best Western Plus Carpinteria Inn

Best Western Plus Carpinteria Inn

3.5 out of 5
4558 Carpinteria Ave, Carpinteria, CA
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Sep 22 to Sep 23
CA $187
CA $215 total
Sep 22 - Sep 23
includes taxes & fees
Best Western Plus Carpinteria Inn
Best Western Plus Pepper Tree Inn

Best Western Plus Pepper Tree Inn

3 out of 5
3850 State St, Santa Barbara, CA
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Sep 28 to Sep 29
CA $222
CA $254 total
Sep 28 - Sep 29
includes taxes & fees
Best Western Plus Pepper Tree Inn
Avania Inn of Santa Barbara

Avania Inn of Santa Barbara

2.5 out of 5
128 Castillo St, Santa Barbara, CA
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Oct 7 to Oct 8
CA $251
CA $298 total
Oct 7 - Oct 8
includes taxes & fees
Avania Inn of Santa Barbara
See all 1,516 properties in Eastside
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

Frequently asked questions

How much does an Eastside vacation package cost?
The most affordable Eastside package is CA $1,194, so your dream trip can become a reality — without the high price tag. Bundle flights, hotels, car rentals and more to build a package that matches your traveling style.
How do I get a cheap travel package to Eastside?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, flights, rental cars and activities — we've got them all covered. Pick and choose the combination that best suits you and watch your savings stack up. We know a package deal is never a one-size-fits-all. That's why Expedia offers over 550 airlines and 1,000,000 hotels globally, which lets you customize your Eastside vacation.
Where should I stay in Eastside?
Travelers come from all over the world to experience Mission Santa Barbara and Santa Barbara County Courthouse in Eastside. Book yourself a room close to these must-see attractions and visit them at your leisure.
What are the top hotels in Eastside?
Reserve a room at Charming And Cozy Cottage With Terrace. It's one of this neighborhood's most in-demand properties. Another top option in Eastside is Scenic Studio.
How far in advance should I book my Eastside vacation?
Your best bet is to book early. Air carriers typically release flights up to 12 months prior to departure, and this is when you can pick up some rock-bottom prices. Just been told you need to take some vacation time next week? No problem! Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Eastside travel package include?
With Expedia, you can select a combination of hotels, car rentals and flights to build your ideal Eastside package. Once you've made your booking, you can add on the fun things like sightseeing tours and activities. Remember — the more you bundle, the more discounts you'll get!
What should I know before booking an Eastside travel package?
Our prices are already low. However, you'll grab even more savings if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and a great range of choice.
Can I choose my airline with an Eastside Expedia vacation package?
With a vacation package, you're always in charge. Whether you'd like to fly to Eastside in economy or first class, simply choose from the available airline options. Expedia has access to more than 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Eastside vacation package?
Whether it's your hotel, flight or rental car, yes, you can amend or cancel it. Locked in your Eastside vacation package in the last 24 hours? You may be able to make any changes for free. For older bookings, you may incur a fee from your hotel, airline or car rental company. For further information, head to our Customer Service Portal. We're here to help you every step of the way.

Discover the most popular places to visit in Eastside

Santa Barbara County Courthouse showing heritage architecture and a luxury hotel or resort

Santa Barbara County Courthouse

See the best views of Santa Barbara and enjoy a stunning variety of architectural styles at the city’s historic courthouse.

Santa Barbara County Courthouse
Leadbetter Beach

Leadbetter Beach

If a restful vacation is part of your travel plans, Leadbetter Beach might be the perfect place to seek out during your trip to Santa Barbara. While you're in the area, stroll along the marina.

Leadbetter Beach

Santa Barbara Bowl

Enjoy a show at Santa Barbara Bowl, a storied theater in Santa Barbara. Wander the beautiful beaches and seaside in the area.

Santa Barbara Bowl

Things to do

Santa Barbara Trolley Tour

Santa Barbara Trolley Tour

CA $38
per adult
86% of travellers recommend
Santa Barbara Trolley Tour
Come see Santa Barbara like you never have heard tales of death and bring the city's history back to life.

Santa Barbara Ghosts Tour

CA $44
per adult
Santa Barbara Ghosts Tour
Private Harbor Cruise on Electric Boat in Santa Barbara

Private Harbor Cruise on Electric Boat in Santa Barbara

CA $260
per traveller
Private Harbor Cruise on Electric Boat in Santa Barbara
See all activities in Santa Barbara
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.