South Orleans Vacation Packages for 2026

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Top Hotel Deals

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

2.5 out of 5
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

Margaritaville Resort Cape Cod

4 out of 5
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

Cape Sands Inn

2.5 out of 5
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

Chatham Bars Inn

5 out of 5
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

Bayside Resort Hotel

3 out of 5
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

Courtyard Resort

2 out of 5
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

The Mansion at Ocean Edge

4 out of 5
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

The Corsair & Cross Rip Oceanfront Resort

2.5 out of 5
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

Chatham Wayside Inn

4 out of 5
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

Hyannis Travel Inn

2.5 out of 5
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

Freebird Motor Lodge by Reverie Boutique Collection

3.5 out of 5
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

Hyannis Plaza Hotel

2.5 out of 5
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

Wequassett Resort and Golf Club

5 out of 5
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 ...
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
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. ...
Comfort Inn Hyannis - Cape Cod

Comfort Inn Hyannis - Cape Cod

2.5 out of 5
259 Main Street Hyannis MA
26.29 km from South Orleans
Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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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.

JetBlue Airways
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
Select JetBlue Airways flight, departing Wed, Apr 22 from Los Angeles Intl. to Logan Intl., returning Tue, May 5, priced at $179 found 5 days ago
Delta
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
Select Delta flight, departing Wed, Apr 15 from Los Angeles Intl. to Logan Intl., returning Mon, Apr 27, priced at $179 found 5 days ago
United
Thu, Mar 12 - Tue, Mar 17
LAX
Los Angeles Intl.
BOS
Logan Intl.
$185 Roundtrip, found 4 days ago
$185
Roundtrip
found 4 days ago
Select United flight, departing Thu, Mar 12 from Los Angeles Intl. to Logan Intl., returning Tue, Mar 17, priced at $185 found 4 days ago
Southwest Airlines
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
Select Southwest Airlines flight, departing Fri, Jan 16 from Los Angeles Intl. to Logan Intl., returning Sat, Jan 17, priced at $199 found 4 days ago
American Airlines
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
Select American Airlines flight, departing Wed, Mar 18 from Los Angeles Intl. to Logan Intl., returning Mon, Mar 23, priced at $199 found 1 day ago