New Ashford Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Your New Ashford Vacation

With a vacation package to New Ashford, say goodbye to travel planning and hello to hassle-free adventure. Every detail of your journey has been taken care of before departing, so you can enjoy each moment experiencing this interesting city. Any trip to New Ashford needs a well-designed itinerary. Fill yours with major attractions such as Jiminy Peak Mountain Resort, Mount Greylock and Brodie Mountain. Expedia has what you need to escape your routine. Tailor your vacation to New Ashford to match your travel style, whatever that may be.

Top New Ashford Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
per person
Sep 7 - Sep 13
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
8.6/10 Excellent! (1,862 reviews)
The room was massive and had all kitchen needs met

Reviewed on Jul. 18, 2025

Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
per person
Sep 7 - Sep 13
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
9.2/10 Wonderful! (530 reviews)
Really nice modern units and layout. Loved the car charger for our EV. We stayed in and cooked, as there were minimal food options in the area. Lovely stay and we will be back!

Reviewed on Jun. 7, 2025

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
per person
Sep 7 - Sep 13
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
The friendliness and excellent service received from the staff. While we stayed at the Yankee, we expected a delivery from UPS and the staff at the registration ensured that we would be informed as soon as it arrived at the Yankee. There was a delay from UPS and it caused us some stress. The Yankee staff made sure we were kept informed of the delivery. Their concern was greatly appreciated. Thank you.

Reviewed on Jul. 18, 2025

Element Lenox Berkshires

3 out of 5
per person
Sep 7 - Sep 13
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
No reviews

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New Ashford Hotel Deals

The Springs Motel

The Springs Motel

2 out of 5
94 U.S. 7, New Ashford, MA
The price is CA $146 per night from Jul 23 to Jul 24
CA $146
CA $161 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (51 reviews)
"Love this renovated motel. They made it cute and trendy"

Reviewed on Jul. 15, 2025

The Springs Motel
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Jul 21 to Jul 22
CA $118
CA $147 total
Jul 21 - Jul 22
includes taxes & fees
8.6/10 Excellent! (1,887 reviews)
"The room was massive and had all kitchen needs met"

Reviewed on Jul. 18, 2025

Vacation Village in the Berkshires
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $328 per night from Jul 22 to Jul 23
CA $328
CA $367 total
Jul 22 - Jul 23
includes taxes & fees
9.6/10 Exceptional! (469 reviews)
"Hrwat"

Reviewed on Jul. 11, 2025

The Williams Inn
See all 827 properties in New Ashford
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

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a New Ashford vacation package cost?
Offering great value package deals from CA $679 on Expedia, you'll be surprised at how little a vacation to New Ashford costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to New Ashford?
To score cheap New Ashford vacation packages, plan your trip outside of busy periods like public holidays and major events. You'll generally find better availability and lower prices for flights and hotels.
How many days is enough for New Ashford?
With a well-planned itinerary, you can easily visit the most popular New Ashford attractions in a handful of days. But if you want to discover hidden spots or take day trips, think about booking your New Ashford vacation for longer.
How to find the best New Ashford package deals?
Use Expedia's filter tool to find some great New Ashford package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for New Ashford package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a New Ashford vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the flexibility to create a tailored New Ashford vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to New Ashford?
Land incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu New Ashford break.
How to plan a trip to New Ashford?

  1. Pick your travel dates: The things you'd like to do in New Ashford and your favourite season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to experiences and flights. Your hotel will likely be the largest expense during your trip to New Ashford.
  3. Decide how long to go for: Now that you're up to speed on New Ashford, you can work out the right length of your vacation. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customized New Ashford vacation package.

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