Deals on vacations and trips to South Orleans
South Orleans flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Lakeside Inn
Save 100% on your flight
Price was $461, price is now $284 per person
$284
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $1,139, price is now $701 per person
$701
per person
Feb 12 - Feb 15
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
A full-service spa, 3 restaurants, and a 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, limo/town car service, and a snack bar/deli are also offered.
The Wylie Inn and Conference Center at Endicott College
Save 100% on your flight
Price was $464, price is now $287 per person
$287
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Boston (BOS)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the conference center and conference space, and free internet in public areas. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
The Cove At Salem
Save 100% on your flight
Price was $449, price is now $303 per person
$303
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room and barbecue grills are also provided.
Top South Orleans hotels deals
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach
Orleans MA
This vacation home features a hot tub and a sauna. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
867 Iyannough Road Hyannis MA
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $116 total per night
$116 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Pool
Breakfast included
Cape Sands Inn
149 Main St - RT 28 West Yarmouth MA
Free Cancellation
Reserve now, pay when you stay
$59 nightly
The price is $68 total per night
$68 total
Dec 5 - Dec 6
Total with taxes and fees
This motel features an indoor pool and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the hot tub and perks like free self parking and free WiFi.
Pool
Hot Tub
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $176 total per night
$176 total
Dec 8 - Dec 9
Total with taxes and fees
This smoke-free resort features a full-service spa, a water park, and 2 restaurants. There's fun for all ages with a lazy river and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the outdoor pool and perks like free self parking and free WiFi.
Pool
Hot Tub
Holly Tree Resort
412 Main St West Yarmouth MA
This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
Red Jacket Beach Resort
1 South Shore Drive South Yarmouth MA
A private beach, 2 restaurants, and an indoor pool are all featured at this traditional hotel. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Bring the family and enjoy the children's club, children's pool, and kid-friendly dining.
On private beach
Pool
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.
Popular places to visit
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.
Frequently asked questions
Photos of local treasures
Browse South Orleans vacation photos for more inspiration