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Chatham Windmill Vacation Packages

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Chatham Windmill Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star hotel in Chelsea. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
YOTEL Boston

YOTEL Boston

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
The Boston Hotel

The Boston Hotel

2 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Fenway Park and Harvard Square are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this eco-certified hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the restaurant and the bar in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Popular attractions Copley Square and Boston Common are located nearby.
The Dagny Boston

The Dagny Boston

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star historic hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and TD Garden are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 28
Roundtrip flight included
Chicago (ORD) 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 Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
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 helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 28
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
XV Beacon

XV Beacon

5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 28
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, 24-hour room service, and a fitness center. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. 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.

3-4 Night Vacations in Chatham Windmill

Price found within the past 48 hours. Click for updated prices.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jun 21 - Jun 24
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 4 - Jul 8
Roundtrip flight included
Chicago (ORD) to Boston (BOS)

Chatham Windmill Last Minute Hotel Deals

Greyfinch Chatham Inn
Greyfinch Chatham Inn
3 out of 5
946 Main Street (Rte 28), Chatham, MA
Stay at this 3-star motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions ...
Greyfinch Chatham Inn
Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. ...
Chatham Bars Inn
Chatham Wayside Inn
Chatham Wayside Inn
3.5 out of 5
512 Main St, Chatham, MA
Stay at this 3.5-star golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Chatham Wayside Inn
The Hawthorne
The Hawthorne
2 out of 5
196 Shore Rd, Chatham, MA
Book a stay at this beach hotel in Chatham. Enjoy free WiFi, free parking, and a private beach. Popular attractions Chatham Seaside Links and Mayo House are ...
The Hawthorne
Old Harbor Inn
Old Harbor Inn
3.5 out of 5
22 Old Harbor Rd., Chatham, MA
Stay at this 3.5-star B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gallery Antonia and Veterans Field are located ...
Old Harbor Inn
Surfside Inn Chatham
Surfside Inn Chatham
2.5 out of 5
25 Holway St, Chatham, MA
Book a stay at this beach B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chatham Lighthouse and Chatham Windmill are ...
Surfside Inn Chatham
Queen Anne Inn
Queen Anne Inn
4 out of 5
70 Queen Anne Rd, Chatham, MA
Stay at this 4-star business-friendly hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Monomoy Theatre and Veterans Field ...
Queen Anne Inn
Captain's House Inn
Captain's House Inn
4 out of 5
369 Old Harbor Road, Chatham, MA
Stay at this 4-star B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chatham Fish Pier and Chatham Shark Center are located ...
Captain's House Inn
See all 3,048 properties in Chatham Windmill
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.

Book the perfect getaway to Chatham Windmill

With Hotwire, booking your next trip to Chatham is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Chatham Windmill while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Chatham Windmill flight and hotel package for as low as $390.

Living it up in Chatham means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Chatham Windmill, Chatham vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Chatham Windmill for some of the best accommodations and flight deals.

FAQs about cheap Chatham Windmill packages:

How to get cheap vacation deals to Chatham Windmill?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $175.

How much are Chatham Windmill packages?

Vacation packages to Chatham Windmill vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $390.

How to find cheap car rentals near Chatham Windmill?

Hotwire partners with some of the most reliable car rental companies in Chatham to bring you the best car rental deals in Chatham Windmill for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Chatham Windmill now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chatham Windmill right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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