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Shelter Island Vacation Packages

Shelter Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Winners Circle Resort by VRI Americas

Winners Circle Resort by VRI Americas

3.5 out of 5
Save 100% on your flight
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
Book a stay at this family-friendly hotel in Solana Beach. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Del Mar Racetrack and Del Mar Fairgrounds are located nearby.
Granger Hotel Gaslamp Quarter

Granger Hotel Gaslamp Quarter

4 out of 5
Save 100% on your flight
per person
Dec 17 - Dec 21
found 8 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
Stay at this 4-star business-friendly hotel in San Diego. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Popular attractions Petco Park and Balboa Park are located nearby.
Fairmont Grand Del Mar

Fairmont Grand Del Mar

5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 3
found 13 hours ago
Roundtrip flight included
Washington (IAD) to San Diego (SAN)
Stay at this 5-star luxury hotel in San Diego. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Torrey Pines Golf Course and Del Mar Racetrack are located nearby.
Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Residence Inn by Marriott San Diego Downtown/Bayfront

Residence Inn by Marriott San Diego Downtown/Bayfront

3 out of 5
per person
Dec 27 - Jan 3
found 13 hours ago
Roundtrip flight included
Washington (IAD) to San Diego (SAN)
Stay at this 3-star business-friendly hotel in San Diego. Enjoy free WiFi, a rooftop terrace, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Petco Park and San Diego Zoo are located nearby.
WorldMark San Diego - Balboa Park

WorldMark San Diego - Balboa Park

3.5 out of 5
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to San Diego (SAN)
Stay at this 3.5-star hotel in San Diego. Enjoy a rooftop terrace, a fitness center, and WiFi (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Petco Park and Balboa Park are located nearby.
Chula Vista Inn

Chula Vista Inn

2.5 out of 5
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to San Diego (SAN)
Stay at this hotel in Chula Vista. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions North Island Credit Union Amphitheatre and Las Americas Premium Outlets are located nearby.
Ramada by Wyndham San Diego National City

Ramada by Wyndham San Diego National City

3 out of 5
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to San Diego (SAN)
Book a stay at this business-friendly hotel in National City. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the clean rooms and the overall value in our reviews. Popular attractions Petco Park and Hotel del Coronado are located nearby.
Days Inn by Wyndham Mission Valley/SDSU

Days Inn by Wyndham Mission Valley/SDSU

2 out of 5
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to San Diego (SAN)
Stay at this hotel in San Diego. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the clean rooms in our reviews. Popular attractions Balboa Park and San Diego Zoo are located nearby.
Hyatt Regency La Jolla

Hyatt Regency La Jolla

4 out of 5
per person
Dec 27 - Jan 3
found 13 hours ago
Roundtrip flight included
Washington (IAD) to San Diego (SAN)
Book a stay at this business-friendly hotel in San Diego. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Westfield UTC and La Jolla Beach are located nearby.
Days Inn by Wyndham Chula Vista/San Diego

Days Inn by Wyndham Chula Vista/San Diego

2.5 out of 5
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to San Diego (SAN)
Stay at this hotel in Chula Vista. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Hotel del Coronado and North Island Credit Union Amphitheatre are located nearby.
Howard Johnson by Wyndham San Diego Sea World

Howard Johnson by Wyndham San Diego Sea World

2 out of 5
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to San Diego (SAN)
Book a stay at this business-friendly hotel in San Diego. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mission Bay and Mission Beach are located nearby.

3-4 Night Vacations in Shelter Island

Price found within the past 48 hours. Click for updated prices.
Winners Circle Resort by VRI Americas

Winners Circle Resort by VRI Americas

3.5 out of 5
Save 100% on your flight
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
InterContinental San Diego, an IHG Hotel

InterContinental San Diego, an IHG Hotel

4 out of 5
Downtown San Diego
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to San Diego (SAN)
Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

4 out of 5
Downtown San Diego
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to San Diego (SAN)
Town and Country San Diego

Town and Country San Diego

4 out of 5
Mission Valley
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to San Diego (SAN)

5-7 Night Vacations in Shelter Island

Price found within the past 48 hours. Click for updated prices.
Motel San Diego - In San Diego (Pacific Beach)

Motel San Diego - In San Diego (Pacific Beach)

2 out of 5
Pacific Beach
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to San Diego (SAN)
Granger Hotel Gaslamp Quarter

Granger Hotel Gaslamp Quarter

4 out of 5
Downtown San Diego
per person
Dec 30 - Jan 4
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to San Diego (SAN)
Kings Inn San Diego

Kings Inn San Diego

2.5 out of 5
Mission Valley
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to San Diego (SAN)
Holiday Inn Express Mira Mesa-San Diego, an IHG Hotel

Holiday Inn Express Mira Mesa-San Diego, an IHG Hotel

2.5 out of 5
Scripps Ranch
per person
Dec 27 - Jan 3
found 13 hours ago
Roundtrip flight included
Washington (IAD) 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
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
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
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
Ramada by Wyndham San Diego Airport
Ramada by Wyndham San Diego Airport
3 out of 5
1403 Rosecrans St, San Diego, CA
Book a stay at this business-friendly hotel in San Diego. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Ramada by Wyndham San Diego Airport
See all 6,687 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 $324.

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 $103.

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 $324.

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.