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Shelter Island Vacation Packages

Shelter Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Surfer Beach Hotel

Surfer Beach Hotel

3 out of 5
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Stay at this 3-star beach hotel in San Diego. Enjoy free WiFi, a beach locale, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mission Beach and Mission Bay are located nearby.
The Wayfarer San Diego

The Wayfarer San Diego

4 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Book a stay at this beach 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.
The Dana on Mission Bay

The Dana on Mission Bay

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Book a stay at this business-friendly hotel in San Diego. Enjoy 2 outdoor pools, a marina, and 2 spa tubs. Our guests praise the pool and the restaurant in our reviews. Popular attractions Mission Beach and Mission Bay are located nearby.
Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
La Jolla Shores Hotel

La Jolla Shores Hotel

3 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Book a stay at this beach hotel in La Jolla. Enjoy a beach locale, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Mission Bay and Mission Beach are located nearby.
Catamaran Resort and Spa

Catamaran Resort and Spa

4 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Book a stay at this beach resort in San Diego. Enjoy free WiFi, a full-service spa, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mission Beach and Mission Bay are located nearby.
Humphreys Half Moon Inn

Humphreys Half Moon Inn

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
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 in our reviews. Popular attractions USS Midway Museum and Petco Park are located nearby.
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Kona Kai San Diego

Kona Kai San Diego

4 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
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 attractions Petco Park and Mission Beach are located nearby.
Bahia Resort Hotel

Bahia Resort Hotel

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Book a stay at this beach resort in San Diego. Enjoy free parking, a beach locale, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Mission Beach and Mission Bay are located nearby.
Ocean Park Inn

Ocean Park Inn

3 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Book a stay at this beach hotel in San Diego. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mission Beach and Mission Bay are located nearby.
Best Western Plus Island Palms Hotel & Marina

Best Western Plus Island Palms Hotel & Marina

3 out of 5
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
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 Petco Park and Mission Beach are located nearby.

3-4 Night Vacations in Shelter Island

Price found within the past 48 hours. Click for updated prices.
Catamaran Resort and Spa

Catamaran Resort and Spa

4 out of 5
Mission Beach
Save 100% on your flight
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Sacramento (SMF) to San Diego (SAN)
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Save 100% on your flight
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Sacramento (SMF) to San Diego (SAN)
Marriott Marquis San Diego Marina

Marriott Marquis San Diego Marina

4 out of 5
Downtown San Diego
Save 100% on your flight
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Sacramento (SMF) to San Diego (SAN)
Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

4 out of 5
Downtown San Diego
Save 100% on your flight
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Sacramento (SMF) to San Diego (SAN)

5-7 Night Vacations in Shelter Island

Price found within the past 48 hours. Click for updated prices.
The Dana on Mission Bay

The Dana on Mission Bay

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
The Wayfarer San Diego

The Wayfarer San Diego

4 out of 5
Mission Beach
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)
La Jolla Shores Hotel

La Jolla Shores Hotel

3 out of 5
La Jolla Shores
Save 100% on your flight
per person
Oct 23 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Diego (SAN)

Shelter Island Last Minute Hotel Deals

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 restaurant ...
Bay Club Hotel & Marina
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
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
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
Comfort Inn San Diego Airport At The Harbor
Comfort Inn San Diego Airport At The Harbor
2.5 out of 5
San Diego
Book a stay at this business-friendly hotel in San Diego. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Comfort Inn San Diego Airport At The Harbor
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 parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Sea Harbor Hotel
Sheraton San Diego Hotel and Marina
Sheraton San Diego Hotel and Marina
4 out of 5
1380 Harbor Island Dr, San Diego, CA
Book a stay at this business-friendly hotel in San Diego. Enjoy 3 outdoor pools, 6 restaurants, and a marina. Our guests praise the pool and the restaurant in ...
Sheraton San Diego Hotel and Marina
Wyndham Garden San Diego Near SeaWorld
Wyndham Garden San Diego Near SeaWorld
3 out of 5
3737 Sports Arena Blvd, San Diego, CA
Book a stay at this business-friendly hotel in San Diego. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff ...
Wyndham Garden San Diego Near SeaWorld
See all 6,688 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 $381.

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 $127.

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 $381.

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.

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