South Orleans Vacation Packages for 2026

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South Orleans Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

Save 100% on your flight
$1,081
per person
Nov 15 - Nov 19
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
I will never stay at another place in Boston. Perfect. Felt like Vegas.

Reviewed on Sep 9, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
$1,373
per person
Nov 15 - Nov 19
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Everything about this hotel is wonderful! We would definitely stay here again.

Reviewed on Sep 8, 2026

Raffles Boston

Raffles Boston

Back Bay
Save 100% on your flight
$1,281
per person
Nov 15 - Nov 19
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

Back Bay
Save 100% on your flight
$1,517
per person
Nov 15 - Nov 19
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Great hotel in great location. Staff earned five star status.

Reviewed on Sep 6, 2026

The Langham, Boston

The Langham, Boston

Downtown Boston
Save 100% on your flight
$1,208
per person
Nov 15 - Nov 19
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
We loved it.

Reviewed on Sep 7, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
Save 100% on your flight
$1,800
per person
Oct 18 - Oct 22
found 22 hours ago
Roundtrip flight included
Raleigh (RDU) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
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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. ...
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 ...
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. ...
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. ...
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 ...
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. ...
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 ...
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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.

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