North Chatham Vacations

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North Chatham Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Omni Parker House

Omni Parker House

Downtown Boston
Save 100% on your flight
$1,016
per person
Oct 29 - Nov 3
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Excellent location! So close to everything within walking distance. They had free ice cream on our last day! Room was huge! The only thing is that a fuse we always blew in our room no matter what we did so it was a bit annoying. They were quick to fix it but slowed us down a bit.

Reviewed on Aug 15, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
$1,463
per person
Oct 29 - Nov 3
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Good Hotels Boston

Good Hotels Boston

South End
Save 100% on your flight
$1,351
per person
Sep 24 - Sep 28
found 15 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, laundry facilities, and bathrobes. Popular attractions Copley Square and Fenway Park are located nearby.
Very nice people and had excellent help!

Reviewed on Aug 7, 2026

Hotel AKA Boston Common

Hotel AKA Boston Common

Downtown Boston
Save 100% on your flight
$1,080
per person
Oct 29 - Nov 3
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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 Boston Common and Faneuil Hall Marketplace are located nearby.
Great staff, Saheed was pleasant and courteous. Lovely room, clean and nice modern furniture. The staff in the restaurant are very attentive and friendly, the bartender Kathleen made excellent mixed drinks and was pleasant to talk to.

Reviewed on Aug 14, 2026

Eurostars The Boxer

Eurostars The Boxer

West End
Save 100% on your flight
$1,062
per person
Oct 29 - Nov 3
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
Save 100% on your flight
$1,253
per person
Oct 29 - Nov 3
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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
29.8 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 ...
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA
26.06 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. ...
Bayside Resort Hotel

Bayside Resort Hotel

225 Route 28 West Yarmouth MA
25.64 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. ...
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

1470 Iyannough Road Hyannis MA
30.22 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 ...
Cape Sands Inn

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA
25.96 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 Harbor Hotel

Hyannis Harbor Hotel

213 Ocean St Hyannis MA
27.76 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 ...
Lighthouse Inn

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA
18.75 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. ...
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

553 Main Street West Yarmouth MA
23.89 km from city center
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 ...
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
23.84 km from city center
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 ...
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA
15.53 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 ...
All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

1199 Route 28 South Yarmouth MA
20.4 km from city center
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 ...
Red Jacket Beach Resort

Red Jacket Beach Resort

1 South Shore Drive South Yarmouth MA
23.23 km from city center
Book a stay at this beach hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
The Villages at Ocean Edge

The Villages at Ocean Edge

One Villages Drive Brewster MA
11.26 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
1.84 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 ...
Hyannis Plaza Hotel

Hyannis Plaza Hotel

662 Main Street Hyannis MA
28.7 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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