Winchester Vacation Packages 2026 from $850

Winchester flight + hotel vacation packages

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

Hotel Ivy Boston Common

Bay Village

Save 100% on your flight

$850

per person

Jul 19 - Jul 23

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

Free WiFi in public areas, luggage storage, and a safe deposit box are available at this hotel. There's locker space and multilingual staff can provide around-the-clock assistance.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

$2,587

per person

Aug 2 - Aug 8

found 5 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the sauna, bar/lounge, and limo/town car service.

The Atlas Hotel

Allston

Save 100% on your flight

$1,141

per person

Jul 16 - Jul 23

found 9 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the laundry service and WiFi in public areas. A communal living room, luggage storage, and concierge services are also on offer.

enVision Hotel Boston Everett

$851

per person

Jul 21 - Jul 26

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

A gym is featured at this hotel, along with self parking. WiFi in public areas is free. Traveling for business? Take advantage of the business center, express check-in, and conference center.

By the Sea Guests Bed & Breakfast & Suites

Save 100% on your flight

$1,018

per person

Jun 26 - Jun 30

found 13 hours ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Top Winchester hotels deals

Seaport Hotel Boston

1 Seaport Lane Boston MA

Free Cancellation

Reserve now, pay when you stay

$261 nightly

$304 total

May 25 - May 26

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the steam room, bar/lounge, and concierge services.

Pool

Pet friendly

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$242 nightly

$282 total

May 25 - May 26

Total with taxes and fees

A full-service spa, 4 restaurants, and an outdoor pool are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, poolside bar, and snack bar/deli.

Pool

Hot Tub

The Revolution Hotel

40 Berkeley Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$167 total

May 25 - May 26

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.

Pet friendly

Free WiFi

The Godfrey Hotel Boston

505 Washington Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$268 nightly

$312 total

May 25 - May 26

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a business center, and a coffee shop are also offered.

Pet friendly

Restaurant

Hilton Boston Back Bay

40 Dalton St Boston MA

Free Cancellation

Reserve now, pay when you stay

$236 nightly

$275 total

May 21 - May 22

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, express check-in, and express check-out are also offered.

Free WiFi

Restaurant

Harborside Inn Of Boston

185 State St Boston MA

$199 nightly

$232 total

May 25 - May 26

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on offer.

Free WiFi

Restaurant

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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.

Popular places to visit

Fenway Park

4.5/5(2,543 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Harvard University

4.5/5(1,983 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Boston Common

4.5/5(4,846 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Frequently asked questions

How much are vacation packages to Winchester?

Treat yourself to a memorable travel experience in Winchester with a vacation package starting at just $850. Reserving your flights, hotels and tours with Travelocity is so simple. And even better, our great deals will leave you with extra cash for fun.

Where can I get the best vacation package deals for Winchester?

You can pick up awesome Winchester package deals with Travelocity. Select from as many as 400 partner airlines and 1,000,000 properties worldwide and turn your travel dreams into reality.

Why should I purchase my Winchester vacation package via Travelocity?

You'll not only enjoy big savings, but you'll also have access to our 24/7 support, high-quality service and a Price Match Guarantee. Wander across the world, discover hidden sights and make lifelong memories — we'll take care of the important details.

Can I save on my Winchester car rental if I bundle it with hotels and flights?

Combining your hotel, flight and car into a Winchester vacation package is the easiest way to land the best deal. Plus, having your own rental car gives you freedom to get to all those famous sights you want to see. Sitting 40 mi away from Winchester, Plymouth Rock is one attraction that should be on your itinerary. Buckle up and make a day trip of it.

Which airport is best for Winchester?

Many people fly into Logan Intl. Airport (BOS), 9 mi southeast of downtown Winchester. Others prefer T.F. Green Airport (PVD) (55 mi away from central Winchester) or Manchester-Boston Regional Airport (MHT) (35 mi away from central Winchester).

What is there to do in Winchester?

Snap up the excellent photo-ops at Winter Pond, one of the most well-known attractions in Winchester. There's plenty more to uncover in this exciting destination, so give yourself enough time to visit some of its hidden gems.

Where should I stay when visiting Winchester?

Many people spend their nights at the Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93. It's sure to be a good base for your Winchester getaway.