Rockingham Vacation Packages

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Your Rockingham Vacation

Memorable adventures await when you lock in a Rockingham vacation package. Whether you're a foodie, art buff or just a traveler who loves to discover new places, there's something for everyone in this lively city. If your trip to Rockingham includes some sightseeing, visit renowned attractions like Vermont Country Store, Bellows Falls Opera House and Jud Hartmann Gallery. Stop dreaming and start doing. Browse the range of options on Expedia today and finally put your Rockingham vacation plans into motion!

Top Rockingham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,502, price is now CA $1,264 per person
CA $1,264
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (858 reviews)
Property beautiful. Rooms very large. Staff very friendly. The only thing that was odd to me was none of our closets had rods to hang clothes on. We were going to a formal wedding, my husband had a suit and I had a long dress to hang up, but the closets had no rods, and we had 3 closets in our room. Had to hang the suit from a door handle and the long dress from the shower rod!

Reviewed on Jun 28, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $2,698, price is now CA $2,097 per person
CA $2,097
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (944 reviews)
Lovely place. We stayed in room 118 with our Lab. It was ideal. Recently updated. Loved looking out over the river and ate our dinner and sipped wine on the deck. Great location for exploring Woodstock. Would return in a heart beat.

Reviewed on Jul 1, 2026

The Vesper

The Vesper

3 out of 5
Price was CA $2,023, price is now CA $1,690 per person
CA $1,690
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
9.2/10 Wonderful! (64 reviews)
Charming, clean and friendly place!

Reviewed on Jul 1, 2026

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was CA $1,902, price is now CA $1,591 per person
CA $1,591
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was CA $1,710, price is now CA $1,441 per person
CA $1,441
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rutland (RUT)
9.2/10 Wonderful! (1,002 reviews)
I really enjoyed the heated pool

Reviewed on Jun 29, 2026

Ready to book your vacation to Rockingham?

 

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Rockingham Hotel Deals

Harvest Barn Inn

Harvest Barn Inn

3 out of 5
16 Webb Terrace Bellows Falls VT
The price is CA $222 per night from Jul 30 to Jul 31
CA $222
CA $242 total
Jul 30 - Jul 31
includes taxes & fees
9.8/10 Exceptional! (268 reviews)
"Easy check in. Had a wonderful stay. Very clean and comfortable. Very friendly and accommodating. Breakfast was 3-course.. .amazing! Beautiful view overlooking the Connecticut River."

Reviewed on Jun 29, 2026

Harvest Barn Inn
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jul 12 to Jul 13
CA $155
CA $168 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"It was clean staff was nice friendly and dressed in uniforms breakfast nice breakfast area was clean i would stay at ascend collection hotel again.. i wish would have done so near bar harbor area but didnt"

Reviewed on Jun 29, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Jul 5 to Jul 6
CA $181
CA $196 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"It was average but not worth the cost"

Reviewed on Jun 30, 2026

Best Western Plus Keene Hotel
See all 1,748 properties in Rockingham
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.
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Stay near popular Rockingham attractions

Vermont Country Store

9.2/10 (382 reviews)
Enjoy an outing to Vermont Country Store during your stay in Rockingham. You can seek out the ski slopes while in the area.
See properties

Frequently asked questions

How much does a Rockingham vacation package cost?
You'll find cheap prices from CA $1,264 on Expedia for your Rockingham escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Rockingham costs.
What are the cheapest months to go to Rockingham?
If you're hoping to book a cheap Rockingham vacation package, consider visiting in September, November and December. You're likely to find lower prices on flights and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Rockingham?
The ideal length of your Rockingham vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to hit all the leading attractions and explore some hidden treasures along the way.
How to find the best Rockingham package deals?
Finding a cheap Rockingham package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Rockingham package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Rockingham vacation as a package?
You can enjoy significant savings on your Rockingham getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Rockingham?
If you have your Rockingham travel dates confirmed, book early to score some terrific deals. With Expedia, you can generally reserve some flights up to a 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 Rockingham?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Rockingham.
  2. Set your budget: Consider expenses like transportation, flights and meals when working out how much to set aside for your trip to Rockingham. Then, select a property that suits your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Decide how long to go away for: Now that you're more familiar with Rockingham, you can figure out the ideal length of your vacation. Put together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Rockingham vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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