South Chatham Vacations

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South Chatham Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
$968
per person
Dec 23 - Dec 29
found 3 hours ago
Roundtrip flight included
San Francisco (SFO) 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.
Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
$1,619
per person
Dec 23 - Dec 29
found 3 hours ago
Roundtrip flight included
San Francisco (SFO) 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 Boston Harbor and Boston Common are located nearby.
Iris Hotel Boston

Iris Hotel Boston

Coolidge Corner
Save 100% on your flight
$1,306
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Fenway Park and Harvard Square are located nearby.
Good location, staff were incredibly helpful, the room was lovely too. This is my second time stopping at the hotel, and if I return to Boston in the future, this will be the first I look to book.

Reviewed on Sep 29, 2026

Raffles Boston

Raffles Boston

Back Bay
Save 100% on your flight
$2,082
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

Back Bay
$1,074
per person
Dec 23 - Dec 29
found 3 hours ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Perfect location in Back Bay. Used Logan Express from/to airport and drop off walkable distance from 800 Boylston. The green line right outside front door. The bed were comfortable, helpful staff. Will definitely return !

Reviewed on Sep 29, 2026

Bricco Suites

Bricco Suites

North End
$1,129
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Popular attractions Faneuil Hall Marketplace and Boston Harbor are located nearby.
Room was super clean, bed and pillows were extremely comfortable. Perfect location in north end, as well as walking distance to Downtown. Felt very safe. Would 1000% stay here again (:

Reviewed on Sep 29, 2026

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Top Hotel Deals

Chatham Tides

Chatham Tides

394 Pleasant St South Chatham MA
1.61 km from city center
Book a stay at this beach motel in South Chatham. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA
23.84 km from city center
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
19.53 km from city center
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. ...
Lighthouse Inn

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA
12.54 km from city center
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
24.3 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 ...
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA
19.96 km from city center
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. ...
The Villages at Ocean Edge

The Villages at Ocean Edge

One Villages Drive Brewster MA
9.94 km from city center
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
6 km from city center
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
9.37 km from city center
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
21.62 km from city center
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
21.83 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 ...
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

216 Main St West Yarmouth MA
19.49 km from city center
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
15.37 km from city center
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
19.86 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 ...
Hyannis Plaza Hotel

Hyannis Plaza Hotel

662 Main Street Hyannis MA
22.58 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 Cape Cod Melody Tent and Main ...
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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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