Greenfield Vacation Packages

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Your Greenfield Vacation

Our Greenfield vacation packages allow you to customize your own adventure. Tailor your getaway to your style and interests and make every moment count in this fabulous city. If taking in sights is part of the plan during your trip to Greenfield, stop by big attractions like Magic Wings Butterfly Conservatory, Greenfield Beach and Greenfield Community College. Browse Expedia's extensive range of travel options and start planning your ideal vacation to Greenfield now.

Top Greenfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
We LOVED this hotel! It's so beautiful, the amenities were amazing, very walkable, so safe, amazing gym and pool. Great Dandelion coffee shop with snack options. Staff were so friendly. Rooms are spacious, very nicely decorated, comfortable, quiet. I could rave about this property for days. I look forward to recommending this place and to stay here again in the future. Thank you for an amazing stay!

Reviewed on Jul. 3, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful interior design

Reviewed on Jul. 3, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (1,999 reviews)
Great location at rental car center

Reviewed on Jul. 3, 2025

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
Aug 17 - Aug 24
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (1,475 reviews)
Bathroom needed updating. The train was pretty loud and woke us up.

Reviewed on Jul. 2, 2025

Ready to book your vacation to Greenfield?

 

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Greenfield Hotel Deals

Hampton Inn & Suites Greenfield
Hampton Inn & Suites Greenfield
2.5 out of 5
184 Shelburne Rd, Greenfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jul 13 to Jul 14
CA $218
CA $244 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (812 reviews)
"It is the perfect location for the Green River Festival"

Reviewed on Jun. 22, 2025

Hampton Inn & Suites Greenfield
Lovely 2nd Floor Apartment
Lovely 2nd Floor Apartment
Greenfield
The price is CA $162 per night from Jul 28 to Jul 29
CA $162
CA $278 total
Jul 28 - Jul 29
includes taxes & fees
9.8/10 Exceptional! (28 reviews)
"Great space for a visit with family in the Greenfield/Deerfield area. The apartment was comfortable and clean. The communication with the property manager/owner was easy and timely using the VRBO app. No issues at all. It is definitely a walk up so keep that in mind if stairs are a challenge."

Reviewed on Jul. 1, 2025

Lovely 2nd Floor Apartment
Charming 4 bedroom house with Views, 200 acres, Private Schools, Ski, Hiking
Charming 4 bedroom house with Views, 200 acres, Private Schools, Ski, Hiking
Leyden
10/10 Exceptional! (3 reviews)
Absolutely stunning - even better than described!
"This property was truly exceptional. The listing doesn’t do it justice - the space is even more beautiful and expansive in person. It was perfect for our dynamic family, giving everyone room to spread out and still feel connected. Everything was immaculately clean, well-maintained (dare I say even ..."

Reviewed on Jun. 26, 2025

Get rates
Charming 4 bedroom house with Views, 200 acres, Private Schools, Ski, Hiking
See all 533 properties in Greenfield
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.

All Inclusive Vacations

All Inclusive Vacations

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Frequently asked questions

How much does a Greenfield vacation package cost?
Offering excellent value package deals from CA $948 on Expedia, you'll be pleasantly surprised at how much a vacation to Greenfield costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Greenfield?
If you'd like to snag a cheap Greenfield vacation package, consider travelling in January, April and December. You're likely to find better prices on hotels and airfares during these months --- ideal for a budget-friendly break.
How many days is enough for Greenfield?
You can easily see all the top sights in Greenfield in a few days, including the must-see Poet's Seat Tower. If you want an extended Greenfield vacation, check out what kind of day trips and activities are available close by.
Is it worth booking a vacation package to Greenfield?
Greenfield is a good vacation destination with attractions like Greenfield Beach among the many things to keep you entertained. Whether you're travelling with the family or planning a trip with friends, a Greenfield vacation promises fun for everyone.
How to find the best Greenfield package deals?
Finding a cheap Greenfield package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Greenfield package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Greenfield vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalize your Greenfield getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Greenfield?
If you've got your Greenfield vacation dates finalized, book early to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Greenfield?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Greenfield.
  2. Plan your budget wisely: Besides the price of your accommodations, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that may come up during your trip to Greenfield.
  3. Decide your trip length: Think about how long you want to spend discovering Greenfield. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Greenfield vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.