South Orleans Vacations from $596
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Your South Orleans Vacation
Well known for its coastal scenery and spectacular views, South Orleans is a fantastic getaway destination. Lock in one of our South Orleans vacation packages and uncover all that this exciting city has to offer. If your trip to South Orleans includes some sightseeing, drop by popular attractions like Nauset Beach, Skaket Beach and Rock Harbor Beach. Stop dreaming and start doing. Browse the range of options on Expedia today and finally put your South Orleans vacation plans into gear!
The Latest South Orleans Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel 1620 Plymouth Harbor
Plymouth Downtown Waterfront District
Save 100% on your flight
Price was $892, price is now $596 per person
$596
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.2/10 Very Good! (1,001 reviews)
Very clean and great location
Some noise due to construction
Reviewed on Apr 17, 2026
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Save 100% on your flight
Price was $3,429, price is now $2,100 per person
$2,100
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon
Reviewed on May 8, 2025
The Hotel Portsmouth
Downtown
Save 100% on your flight
Price was $1,323, price is now $896 per person
$896
per person
Jul 19 - Jul 25
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (1,000 reviews)
I loved the decor! The room was clean and well appointed, staff were friendly, and the location was great.
Reviewed on May 3, 2026
Nantucket Inn
Save 100% on your flight
Price was $2,199, price is now $1,497 per person
$1,497
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (670 reviews)
The staff was fantastic, everything was very well maintained, and the shuttle into town was so
helpful! Highly recommend.
Reviewed on May 6, 2026
Where to stay in South Orleans
Find the best South Orleans areas and neighborhoods for the activities you enjoy most. Learn more about South Orleans
East Orleans
1 out of top 10 points of interest in this area
East Orleans is noteworthy for its beaches, and you can make a stop at top attractions like Nauset Beach and Cape Cod National Seashore.
South Orleans Hotel Deals
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $231 total per night from May 17 to May 18
$231 total
May 17 - May 18
Total with taxes and fees
8.6/10 Excellent! (559 reviews)
👌
Reviewed on May 6, 2026
Bayside Resort Hotel
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $153 total per night from May 10 to May 11
$153 total
May 10 - May 11
Total with taxes and fees
8.8/10 Excellent! (1,537 reviews)
Good
Reviewed on May 1, 2026
Chatham Bars Inn
297 Shore Rd Chatham MA
$434 nightly
The price is $496 total per night from May 10 to May 11
$496 total
May 10 - May 11
Total with taxes and fees
9.2/10 Wonderful! (823 reviews)
Beautiful! Restaurant was okay.
Reviewed on May 7, 2026
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.
Discover the most popular places to visit in South Orleans
Skaket Beach
4.5/5(18 reviews)
Warm, clear waters make this beach destination ideal for casual swimming, watersports or a restorative rest on the white sandy shore.
Jonathan Young Windmill
Jonathan Young Windmill is just one of the places to see in Orleans, so why not enjoy the other things to explore during your travels? Stroll along the beautiful beaches or seek out the hiking trails.
Orleans Bowling Center
Enjoy a trip to Orleans Bowling Center and popular activities like hiking in Orleans. Stroll along the area's beautiful beaches, or simply savor its seafood restaurants.
Things to do
Explore a world of travel with Expedia
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- Hotels near Cape Rep Theatre
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- Hotels near Jonathan Young Windmill
- Hotels near Brewster Historical Society Museum
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- Hotels near Ocean Edge Golf Club
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- North Chatham Hotels
- Captain's Cove Golf Course
- Captains Golf Course
- Nickerson State Park
- Orleans Bowling Center
- Academy Playhouse
- Orleans Historical Society Meeting House Museum
- Orleans Vacations
- Cape Rep Theatre
- Caleb Nickerson House
- Fox Hill
- Crosby Mansion
- Jonathan Young Windmill
- Visit East Orleans
- Visit Orleans
- Skaket Beach
- Crosby Landing Beach
- Cape Escape Adventure Golf
- Chatham Marconi Maritime Center
- Church of the Transfiguration Orleans
- Ocean Edge Golf Club
- East Harwich Vacations
- Adventure Chatham
- The E Spa
- Visit North Chatham
- Visit East Harwich
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.