Search Deals onSurfside Vacation Packages
Surfside Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Riverview Resort
Save 100% on your flight
per person
Apr 11 - Apr 15
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this 3-star aparthotel in South Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Hyannis Harbor and Cape Codder Water Park are located nearby.
Sunbird Cape Cod Resort
Save 100% on your flight
per person
May 13 - May 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hyannis Harbor and Cape Codder Water Park are located nearby.
Sea Mist Resort
Save 100% on your flight
per person
Apr 11 - Apr 15
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this 3-star business-friendly aparthotel in Mashpee. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Mashpee Commons and Cape Cod Children's Museum are located nearby.
Lighthouse Inn
Save 100% on your flight
per person
May 23 - May 27
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star beach hotel in West Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Hyannis Harbor and Bass River Lighthouse are located nearby.
Holly Tree Resort
Save 100% on your flight
per person
Apr 11 - Apr 15
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this 3-star aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Hyannis Harbor and Cape Codder Water Park are located nearby.
Chatham Bars Inn
Save 100% on your flight
per person
Apr 11 - Apr 15
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chatham Seaside Links and Chatham Fish Pier are located nearby.
Homewood Suites by Hilton Boston/Canton, MA
Save 100% on your flight
per person
May 13 - May 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Legacy Place and F1 Boston are located nearby.
The Westin Waltham-Boston
per person
May 25 - May 31
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Waltham. Enjoy breakfast (surcharge), room service, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lexington Battle Green and Walden Pond are located nearby.
Surfside Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Surfside Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Apr 3 - Mon, Apr 7
LAX
Los Angeles Intl.
BOS
Logan Intl.
$176 Roundtrip, found 5 days ago
$176
Roundtrip
found 5 days ago
Tue, Sep 16 - Tue, Sep 30
PDX
Portland Intl.
BOS
Logan Intl.
$202 Roundtrip, found 3 days ago
$202
Roundtrip
found 3 days ago
Sun, May 25 - Wed, May 28
LAX
Los Angeles Intl.
BOS
Logan Intl.
$220 Roundtrip, found 3 days ago
$220
Roundtrip
found 3 days ago
Mon, May 26 - Tue, Jun 3
LAX
Los Angeles Intl.
HYA
Barnstable Municipal
$734 Roundtrip, found 3 days ago
$734
Roundtrip
found 3 days ago
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