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.
Comfort Inn Randolph - Boston

Comfort Inn Randolph - Boston

$750
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Randolph. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Blue Hills Reservation and South Shore Plaza are located nearby.
Staff was helpful. Room was clean and inexpensive.

Reviewed on Sep 23, 2026

Encore Boston Harbor

Encore Boston Harbor

Save 100% on your flight
$1,645
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
Save 100% on your flight
$1,790
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Holiday Inn Express & Suites Boston - Cambridge by IHG

Holiday Inn Express & Suites Boston - Cambridge by IHG

East Cambridge
Save 100% on your flight
$1,196
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

West End
Save 100% on your flight
$1,738
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Central location, close to train station

Reviewed on Sep 25, 2026

The Inn on Arsenal

The Inn on Arsenal

$791
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Stay at this hotel in Watertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Everything on the surface looked really nice really clean once I saw the bedsheets up close and not so nice. Comforter and sheets that nasty stains

Reviewed on Sep 25, 2026

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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. ...
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. ...
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 ...
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 ...
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 ...
Hyannis Travel Inn

Hyannis Travel Inn

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 ...
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. ...
Riviera Beach Resort

Riviera Beach Resort

327 South Shore Drive South Yarmouth MA
21.11 km from South Orleans
Book a stay at this beach hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and a private beach. Our guests praise the helpful staff and the clean rooms ...
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 ...
Hyannis Plaza Hotel

Hyannis Plaza Hotel

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 Cape Cod Melody Tent and Main ...
Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

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 24-hour fitness center. Our guests praise the helpful staff in ...
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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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