Search Deals on
Shelter Island Vacation Packages

Shelter Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Dallas (DFW) to San Diego (SAN)
Stay at this 3.5-star spa hotel in San Diego. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions USS Midway Museum and Petco Park are located nearby.
Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 7
Roundtrip non-stop flight included
Dallas (DAL) to San Diego (SAN)
Book a stay at this beach resort in San Diego. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Mission Bay and Mission Beach are located nearby.
Westin Carlsbad Resort & Spa

Westin Carlsbad Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip flight included
Portland (PDX) to San Diego (SAN)
Stay at this 4-star golf hotel in Carlsbad. Enjoy free WiFi, 4 restaurants, and room service. Our guests praise the clean rooms in our reviews. Popular attractions LEGOLAND® California and Flower Fields of Carlsbad are located nearby.
Beach Terrace

Beach Terrace

3.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip flight included
Portland (PDX) to San Diego (SAN)
Book a stay at this beach hotel in Carlsbad. Enjoy free breakfast, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® California and Carlsbad State Beach are located nearby.
Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

4 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Dallas (DFW) to San Diego (SAN)
Stay at this 4-star business-friendly hotel in San Diego. Enjoy a rooftop terrace, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Petco Park and USS Midway Museum are located nearby.
Sheraton San Diego Hotel and Marina

Sheraton San Diego Hotel and Marina

4 out of 5
per person
Jun 3 - Jun 7
Roundtrip non-stop flight included
Dallas (DAL) to San Diego (SAN)
Book a stay at this business-friendly hotel in San Diego. Enjoy 3 outdoor pools, 6 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions USS Midway Museum and Petco Park are located nearby.
The Wayfarer San Diego

The Wayfarer San Diego

4 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 7
Roundtrip non-stop flight included
Dallas (DAL) to San Diego (SAN)
Stay at this hotel in San Diego. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Mission Beach and Mission Bay are located nearby.
Omni La Costa Resort & Spa Carlsbad

Omni La Costa Resort & Spa Carlsbad

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip flight included
Portland (PDX) to San Diego (SAN)
Stay at this spa resort in Carlsbad. Enjoy free WiFi, 8 outdoor pools, and 4 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions LEGOLAND® California and Moonlight State Beach are located nearby. Discover genuine guest reviews for Omni La Costa Resort & Spa Carlsbad, in La Costa neighborhood, along with the latest prices and availability – book now.
The Horton Grand, Downtown/Gaslamp Quarter

The Horton Grand, Downtown/Gaslamp Quarter

3.5 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip non-stop flight included
Dallas (DFW) to San Diego (SAN)
Book a stay at this historic hotel in San Diego. Enjoy breakfast (surcharge), a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Petco Park and USS Midway Museum are located nearby.
Inn At The Park

Inn At The Park

3 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip flight included
Portland (PDX) to San Diego (SAN)
Stay at this hotel in San Diego. Enjoy free WiFi, a rooftop terrace, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions San Diego Zoo and Balboa Park are located nearby. Discover genuine guest reviews for Inn At The Park, in Bankers Hill neighborhood, along with the latest prices and availability – book now.
Roam and Board

Roam and Board

1 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 16
Roundtrip non-stop flight included
Detroit (DTW) to San Diego (SAN)
Stay at this golf campground in San Diego. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Mission Bay and Mission Beach are located nearby. Discover genuine guest reviews for Roam and Board along with the latest prices and availability – book now.

3-4 Night Vacations in Shelter Island

Price found within the past 48 hours. Click for updated prices.
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
per person
Jun 22 - Jun 25
Roundtrip flight included
Dallas (DFW) to San Diego (SAN)
Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 7
Roundtrip non-stop flight included
Dallas (DAL) to San Diego (SAN)
Westin Carlsbad Resort & Spa

Westin Carlsbad Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip flight included
Portland (PDX) to San Diego (SAN)

5-7 Night Vacations in Shelter Island

Price found within the past 48 hours. Click for updated prices.
Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 18
Roundtrip non-stop flight included
Detroit (DTW) to San Diego (SAN)
Sheraton San Diego Hotel and Marina

Sheraton San Diego Hotel and Marina

4 out of 5
Harbor Island
Save 100% on your flight
per person
Jun 12 - Jun 18
Roundtrip non-stop flight included
Detroit (DTW) to San Diego (SAN)
The Dana on Mission Bay

The Dana on Mission Bay

3.5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 18
Roundtrip non-stop flight included
Detroit (DTW) to San Diego (SAN)

Shelter Island Last Minute Hotel Deals

Sunrise Inn San Diego
Sunrise Inn San Diego
2 out of 5
1150 Rosecrans St, San Diego, CA
Stay at this business-friendly hotel in San Diego. Enjoy free WiFi, free parking, and 3 beach bars. Our guests praise the helpful staff and the clean rooms in ...
Sunrise Inn San Diego
Kona Kai San Diego
Kona Kai San Diego
4 out of 5
1551 Shelter Island Drive, San Diego, CA
Stay at this 4-star beach hotel in San Diego. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Kona Kai San Diego
Best Western Plus Island Palms Hotel & Marina
Best Western Plus Island Palms Hotel & Marina
3 out of 5
2051 Shelter Island Dr, San Diego, CA
Stay at this hotel in San Diego. Enjoy free WiFi, 2 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions ...
Best Western Plus Island Palms Hotel & Marina
Humphreys Half Moon Inn
Humphreys Half Moon Inn
3.5 out of 5
2303 Shelter Island Dr, San Diego, CA
Book a stay at this business-friendly hotel in San Diego. Enjoy a marina, a nightclub, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
Humphreys Half Moon Inn
Bay Club Hotel & Marina
Bay Club Hotel & Marina
3.5 out of 5
2131 Shelter Island Dr, San Diego, CA
Book a stay at this business-friendly hotel in San Diego. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
Bay Club Hotel & Marina
Best Western Yacht Harbor Hotel
Best Western Yacht Harbor Hotel
2.5 out of 5
5005 N Harbor Dr, San Diego, CA
Stay at this business-friendly hotel in San Diego. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Best Western Yacht Harbor Hotel
Sea Harbor Hotel
Sea Harbor Hotel
2 out of 5
1325 Scott St, San Diego, CA
Stay at this hotel in San Diego. Enjoy free WiFi, a marina, and onsite parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Sea Harbor Hotel
Holiday Inn San Diego-Bayside, an IHG Hotel
Holiday Inn San Diego-Bayside, an IHG Hotel
3 out of 5
4875 N Harbor Dr, San Diego, CA
Book a stay at this business-friendly hotel in San Diego. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the pool and ...
Holiday Inn San Diego-Bayside, an IHG Hotel
See all 6,754 properties in Shelter Island
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.

Book the perfect getaway to Shelter Island

With Hotwire, booking your next trip to Point Loma is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Shelter Island while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Shelter Island flight and hotel package for as low as $424.

Living it up in Point Loma means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Shelter Island, Point Loma vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Shelter Island for some of the best accommodations and flight deals.

FAQs about cheap Shelter Island packages:

How to get cheap vacation deals to Shelter Island?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $74.

How much are Shelter Island packages?

Vacation packages to Shelter Island vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $424.

How to find cheap car rentals near Shelter Island?

Hotwire partners with some of the most reliable car rental companies in Point Loma to bring you the best car rental deals in Shelter Island for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Shelter Island now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Shelter Island right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Discover Other Travel Deals