South Orleans Vacations

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

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South Orleans Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Boston/Woburn

Hilton Boston/Woburn

3.5 out of 5
Save 100% on your flight
Price was $732, price is now $490 per person
$490
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star business-friendly hotel in Woburn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attraction Burlington Mall is located nearby.

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was $2,697, price is now $1,418 per person
$1,418
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and Copley Square are located nearby.

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Save 100% on your flight
Price was $1,183, price is now $683 per person
$683
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $3,576, price is now $2,272 per person
$2,272
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star 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.

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,195, price is now $1,405 per person
$1,405
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a health club. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,117, price is now $2,047 per person
$2,047
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star 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.

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Top Hotel Deals

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd, Hyannis, MA
27.85 km from city center
Stay at this 4-star 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 ...
Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28, West Yarmouth, MA
24.66 km from city center
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 ...
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
24.42 km from city center
Stay at this 3-star beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Hyannis Harbor Hotel

Hyannis Harbor Hotel

3.5 out of 5
213 Ocean St, Hyannis, MA
26.57 km from city center
Stay at this 3.5-star business-friendly hotel in Hyannis. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff in our ...
Hyannis Inn

Hyannis Inn

2 out of 5
473 MAIN ST, Hyannis, MA
26.91 km from city center
Stay at this motel in Hyannis. Enjoy free WiFi, free parking, and a garden. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ...
Aiden by Best Western Cape Cod - West Yarmouth

Aiden by Best Western Cape Cod - West Yarmouth

3 out of 5
476 Route 28, West Yarmouth, MA
23.39 km from city center
Stay at this 3-star business-friendly hotel in West Yarmouth. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and ...
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

3 out of 5
135 Route 28, West Yarmouth, MA
24.75 km from city center
Stay at this 3-star 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. ...
Captains Quarters Motel & Conference Center

Captains Quarters Motel & Conference Center

2 out of 5
5000 State Highway/Route 6, Eastham, MA
12.56 km from city center
Book a stay at this business-friendly hotel in Eastham. Enjoy free WiFi, free parking, and a conference center. Our guests praise the helpful staff and the clean ...
Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
18 North St, Hyannis, MA
26.54 km from city center
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 ...
Viking Shores Motor Inn

Viking Shores Motor Inn

2 out of 5
5200 State Highway Rte 6, Eastham, MA
12.84 km from city center
Stay at this motel in Eastham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Nauset ...
Red Jacket Beach Resort

Red Jacket Beach Resort

3.5 out of 5
1 South Shore Drive, South Yarmouth, MA
22.7 km from city center
Stay at this 3.5-star beach hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. ...
Best Western Cape Cod Hotel

Best Western Cape Cod Hotel

2.5 out of 5
1470 Iyannough Rd. Rt 132, Hyannis, MA
28.21 km from city center
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 ...
Holiday Inn Hyannis by IHG

Holiday Inn Hyannis by IHG

3 out of 5
1127 Iyannough Rd, Hyannis, MA
27.59 km from city center
Stay at this 3-star hotel in Hyannis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the property condition ...
The Villages at Ocean Edge

The Villages at Ocean Edge

3.5 out of 5
One Villages Drive, Brewster, MA
5.73 km from city center
Stay at this 3.5-star beach resort in Brewster. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
662 Main Street, Hyannis, MA
27.43 km from city center
Book a stay at this luxury hotel in Hyannis. Enjoy free parking, an outdoor pool, and a 24-hour front desk. Popular attractions Hyannis Harbor and Cape Cod Melody ...
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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.

American Airlines
Fri, Oct 31 - Wed, Nov 12
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Oct 31 from Los Angeles Intl. to Logan Intl., returning Wed, Nov 12, priced at $217 found 4 days ago
Delta
Tue, Oct 28 - Thu, Oct 30
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 28 from Los Angeles Intl. to Logan Intl., returning Thu, Oct 30, priced at $217 found 3 days ago
Spirit Airlines
Thu, Oct 30 - Sun, Nov 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Oct 30 from Los Angeles Intl. to Logan Intl., returning Sun, Nov 2, priced at $222 found 3 days ago
United
Fri, Oct 31 - Wed, Nov 12
LAX
Los Angeles Intl.
BOS
Logan Intl.
$222 Roundtrip, found 4 days ago
$222
Roundtrip
found 4 days ago
Select United flight, departing Fri, Oct 31 from Los Angeles Intl. to Logan Intl., returning Wed, Nov 12, priced at $222 found 4 days ago
JetBlue Airways
Fri, Oct 31 - Wed, Nov 5
LAX
Los Angeles Intl.
BOS
Logan Intl.
$249 Roundtrip, found 3 days ago
$249
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, Oct 31 from Los Angeles Intl. to Logan Intl., returning Wed, Nov 5, priced at $249 found 3 days ago