South Orleans Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
South Orleans Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Revere Hotel Boston Common
Bay Village
Save 100% on your flight
Price was $1,205, price is now $842 per person
$842
per person
Mar 27 - Apr 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,459, price is now $937 per person
$937
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,657, price is now $1,781 per person
$1,781
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
The Colonnade Hotel Back Bay
Back Bay
Save 100% on your flight
Price was $1,619, price is now $1,088 per person
$1,088
per person
Mar 27 - Apr 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $1,433, price is now $990 per person
$990
per person
Mar 27 - Apr 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
The Verb Hotel
Fenway–Kenmore
Save 100% on your flight
Price was $1,664, price is now $1,159 per person
$1,159
per person
Mar 27 - Apr 1
found 9 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.
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Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
27.85 km from South Orleans
Book a stay at this spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions ...
Chatham Bars Inn
297 Shore Rd Chatham MA
8.01 km from South Orleans
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 ...
Chatham Wayside Inn
512 Main St Chatham MA
8.3 km from South Orleans
Book a stay at this golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
The Mansion at Ocean Edge
2907 Main Street Brewster MA
5.68 km from South Orleans
Book a stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
The Corsair & Cross Rip Oceanfront Resort
41 Chase Ave Dennis Port MA
15.14 km from South Orleans
Book a stay at this beach hotel in Dennis Port. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Sea Street Beach and Cape Cod Theatre ...
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
867 Iyannough Road Hyannis MA
27.05 km from South Orleans
Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. ...
Bayside Resort Hotel
225 Route 28 West Yarmouth MA
24.42 km from South Orleans
Book a stay at this beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Courtyard Resort
125 North St Hyannis MA
26.87 km from South Orleans
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, free parking, and balconies or patios. Popular attractions John F. Kennedy Hyannis Museum ...
Freebird Motor Lodge by Reverie Boutique Collection
553 Main Street West Yarmouth MA
22.98 km from South Orleans
Book a stay at this business-friendly motel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful ...
Edgewater Beach Resort, a VRI resort
95 Chase Avenue Dennis Port MA
14.88 km from South Orleans
Book a stay at this beach aparthotel in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Pleasant Road Beach and Cape Cod ...
Hyannis Plaza Hotel
662 Main Street Hyannis MA
27.43 km from South Orleans
Book a stay at this luxury hotel in Hyannis. Enjoy free parking, an outdoor pool, and a 24-hour front desk. Popular attractions Wackenhammer's Clockwork Arcade ...
Holiday Inn Hyannis by IHG
1127 Iyannough Rd Hyannis MA
27.59 km from South Orleans
Stay at this hotel in Hyannis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Anchor In Distinctive Waterfront Lodging
1 South Street Hyannis MA
26.01 km from South Orleans
Stay at this hotel in Hyannis. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, May 9 - Wed, May 27
LAX
Los Angeles Intl.
BOS
Logan Intl.
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Mon, Aug 3 - Wed, Aug 19
LAX
Los Angeles Intl.
BOS
Logan Intl.
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Tue, May 12 - Wed, May 13
LAX
Los Angeles Intl.
BOS
Logan Intl.
$205 Roundtrip, found 18 hours ago
$205
Roundtrip
found 18 hours ago
Mon, Jun 1 - Tue, Jun 9
PDX
Portland Intl.
BOS
Logan Intl.
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Tue, May 5 - Sat, May 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$214 Roundtrip, found 1 day ago
$214
Roundtrip
found 1 day ago