South Orleans Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

South Orleans Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
enVision Hotel Boston Everett

enVision Hotel Boston Everett

$1,003
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Boston (BOS)
Book a stay at this business-friendly hotel in Everett. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Eurostars The Boxer

Eurostars The Boxer

West End
Save 100% on your flight
$1,370
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) 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.
Omni Parker House

Omni Parker House

Downtown Boston
Save 100% on your flight
$1,333
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Faneuil Hall Marketplace and Boston Common are located nearby.
Hyatt Regency Boston

Hyatt Regency Boston

Downtown Boston
$1,333
per person
Oct 16 - Oct 20
found 21 hours ago
Roundtrip non-stop flight included
Omaha (OMA) 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 Faneuil Hall Marketplace are located nearby.
Lovely hotel, comfortable beds and helpful staff

Reviewed on Sep 3, 2026

The Godfrey Hotel Boston

The Godfrey Hotel Boston

Downtown Boston
$1,501
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) 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.
Staff was very kind and attentive. Good location for Boston Common, restaurants, theaters. Great experience.

Reviewed on Sep 3, 2026

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

Fenway–Kenmore
$1,093
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Boston (BOS)
Stay at this apartment in Boston. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Fenway Park and Copley Square are located nearby.
Great property beautiful vintage building great location

Reviewed on Sep 1, 2026

Don't see what you're looking for?
See all available trips from Columbus to South Orleans
View all trips

Top Hotel Deals

Margaritaville Resort Cape Cod

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 ...
Bayside Resort Hotel

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. ...
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

1470 Iyannough Road Hyannis MA
28.16 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 pool in our ...
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA
24.75 km from South Orleans
Book a stay at this beach hotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the restaurant in our reviews. ...
Cape Sands Inn

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 ...
Lighthouse Inn

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA
18.42 km from South Orleans
Book a stay at this beach hotel in West Dennis. Enjoy free WiFi, free parking, and private plunge pools. Our guests praise the helpful staff in our reviews. ...
Hyannis Harbor Hotel

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, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff in our ...
The Villages at Ocean Edge

The Villages at Ocean Edge

One Villages Drive Brewster MA
5.73 km from South Orleans
Book a stay at this beach resort in Brewster. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
Freebird Motor Lodge by Reverie Boutique Collection

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 ...
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA
15.16 km from South Orleans
Book a stay at this family-friendly motel in Dennis Port. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Chatham Bars Inn

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 ...
The Mariner Resort Cape Cod by The Red Collection

The Mariner Resort Cape Cod by The Red Collection

573 Main Street (Route 28) West Yarmouth MA
22.96 km from South Orleans
Book a stay at this family-friendly hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

216 Main St West Yarmouth MA
24.36 km from South Orleans
Stay at this hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

1199 Route 28 South Yarmouth MA
19.38 km from South Orleans
Book a stay at this business-friendly hotel in South Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Sunbird ANNEX Resort

Sunbird ANNEX Resort

226 Main St West Yarmouth MA
24.38 km from South Orleans
Book a stay at this business-friendly hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Don't see what you're looking for?
See all available properties in South Orleans
View all properties
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.

Frontier Airlines
Delta
American Airlines
Southwest Airlines
JetBlue Airways