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.
The Revolution Hotel
South End
Save 100% on your flight
Price was $548, price is now $362 per person
$362
per person
Feb 18 - Feb 23
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Whitney Hotel
Beacon Hill
Save 100% on your flight
Price was $1,254, price is now $752 per person
$752
per person
Feb 18 - Feb 23
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and TD Garden are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,207, price is now $1,403 per person
$1,403
per person
Feb 19 - Feb 24
found 1 hour ago
Roundtrip flight included
Orlando (MCO) 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 Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
Price was $1,365, price is now $876 per person
$876
per person
Feb 18 - Feb 23
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a health club. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Comfort Inn & Suites Logan International Airport
Save 100% on your flight
Price was $570, price is now $380 per person
$380
per person
Feb 18 - Feb 23
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this hotel in Revere. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and TD Garden are located nearby.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $1,705, price is now $1,137 per person
$1,137
per person
Feb 19 - Feb 24
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
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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. ...
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 ...
Cape Sands Inn
149 Main St - RT 28 West Yarmouth MA
24.66 km from South Orleans
Book a stay at this family-friendly motel in West Yarmouth. Enjoy free parking, an outdoor pool, and a sauna. Our guests praise the pool and the helpful staff ...
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 ...
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 ...
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 ...
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 ...
Hyannis Travel Inn
18 North St Hyannis MA
26.54 km from South Orleans
Stay at this hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
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 ...
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 ...
Wequassett Resort and Golf Club
2173 Head of the Bay Road, Route 28 Harwich MA
3.13 km from South Orleans
Book a stay at this luxury resort in Harwich. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Captains Golf Course and Chatham Marconi ...
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.
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
BOS
Logan Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Wed, Apr 15 - Mon, Apr 27
LAX
Los Angeles Intl.
BOS
Logan Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Thu, Mar 12 - Tue, Mar 17
LAX
Los Angeles Intl.
BOS
Logan Intl.
$185 Roundtrip, found 5 days ago
$185
Roundtrip
found 5 days ago
Fri, Jan 16 - Sat, Jan 17
LAX
Los Angeles Intl.
BOS
Logan Intl.
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
Wed, Mar 18 - Mon, Mar 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago