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.
Hotel Ivy Boston Common
Bay Village
Save 100% on your flight
Price was $1,879, price is now $1,083 per person
$1,083
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Save 100% on your flight
Price was $5,654, price is now $3,663 per person
$3,663
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this beach guesthouse in East Wareham. Enjoy free WiFi, a private beach, and free bicycles on site. Popular attractions Onset Bay Center - Buzzards Bay Coalition and Onset Beach are located nearby.
Eurostars The Boxer
West End
Save 100% on your flight
Price was $1,984, price is now $1,374 per person
$1,374
per person
Jul 14 - Jul 19
found 24 hours ago
Roundtrip flight included
Kansas City (MCI) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $2,216, price is now $1,606 per person
$1,606
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury 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 Faneuil Hall Marketplace and New England Aquarium are located nearby.
The Godfrey Hotel Boston
Downtown Boston
Save 100% on your flight
Price was $1,648, price is now $1,208 per person
$1,208
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Colonial Acres Resort
Save 100% on your flight
Price was $2,651, price is now $1,967 per person
$1,967
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this hotel in West Yarmouth. Enjoy free parking, a fitness center, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis 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 ...
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 24-hour fitness center. Our guests praise the helpful staff in ...
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. ...
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 ...
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 ...
Red Jacket Beach Resort
1 South Shore Drive South Yarmouth MA
22.76 km from South Orleans
Book a stay at this beach hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Parker Beach Lodge
192 S Shore Dr South Yarmouth MA
21.79 km from South Orleans
Stay at this hotel in South Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular ...
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. ...
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. ...
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 Harbor Hotel
213 Ocean St Hyannis MA
26.57 km from South Orleans
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Chatham Tides
394 Pleasant St South Chatham MA
9.74 km from South Orleans
Book a stay at this beach motel in South Chatham. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
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.
Tue, Sep 8 - Tue, Sep 15
PDX
Portland Intl.
BOS
Logan Intl.
$227 Roundtrip, found 3 hours ago
$227
Roundtrip
found 3 hours ago
Fri, May 29 - Tue, Jun 2
PDX
Portland Intl.
BOS
Logan Intl.
$237 Roundtrip, found 15 hours ago
$237
Roundtrip
found 15 hours ago
Tue, Sep 8 - Tue, Sep 15
PDX
Portland Intl.
BOS
Logan Intl.
$237 Roundtrip, found 3 hours ago
$237
Roundtrip
found 3 hours ago
Mon, Oct 5 - Sat, Oct 10
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, found 14 hours ago
$237
Roundtrip
found 14 hours ago
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
BOS
Logan Intl.
$254 Roundtrip, found 4 days ago
$254
Roundtrip
found 4 days ago