Sullivan Vacations from $547
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Your Sullivan Vacation
With a Sullivan vacation package, say goodbye to endless planning and hello to an effortless adventure. Every detail of your escape has been taken care of before departing, so you can spend more time discovering this fantastic city. Eager to do some sightseeing? A trip to Sullivan isn't complete without visiting Granite Gorge, Brentwood Golf Course and other major attractions. Don't delay visiting this destination any longer. Your perfect Sullivan vacation is only a few clicks away with Expedia.
The Latest Sullivan vacation packages
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
$547
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (958 reviews)
The red carpet was stained in the room, the bathroom ceiling was peeling with brown dots along the ceiling, dark, dull hallways. The down town did not have much to offer, Staff where very friendly and helpful.
Reviewed on Aug 28, 2026
Deerfield Valley Inn
$736
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
9.4/10 Exceptional! (131 reviews)
We returned to this place on a quick 2-day/last minute get away. Owner is new from last time. Nice people; helpful and made a very good breakfast. Only issue we really had was the plumbing. Our room had some kind of venting issue with the sink/toilet/shower. Toilet bubbled and would go down at times; sink would go slow/stop at times; shower also stopped up and went down very slow. Told the owner about it and hopefully they can get it fixed. But overall, pleasant stay.
Reviewed on Aug 17, 2026
The Shire Woodstock
$1,043
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (978 reviews)
We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along.
The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the
view although this wasn't a game changer.
Reviewed on Aug 27, 2026
Sullivan Hotel Deals
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$128 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"It was good!"
Reviewed on Aug 25, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$83 nightly
$91 total
Sep 2 - Sep 3
Total with taxes and fees
6.8/10 (46 reviews)
"It was dirty. The sink, bathroom, tub, floors. All dead bugs all over. TV was great. But a very musty smell in room. My sheets were not dry when we went to bed."
Reviewed on Aug 26, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$160 nightly
$175 total
Aug 30 - Aug 31
Total with taxes and fees
8.6/10 Excellent! (968 reviews)
"The red carpet was stained in the room, the bathroom ceiling was peeling with brown dots along the ceiling, dark, dull hallways. The down town did not have much to offer, Staff where very friendly and helpful."
Reviewed on Aug 28, 2026
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.
Find the Best Sullivan Vacation Packages
Sullivan Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 800 |
Top Sights | Colonial Theatre, Granite Gorge and Walpole Mountain View Winery |
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Frequently asked questions
How much does a Sullivan vacation package cost?
You can pick up a vacation package to this popular destination from $547 on Expedia. But how much your vacation to Sullivan costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Sullivan?
You can generally find lower prices and better availability in October, November and December. Take a look at our cheap Sullivan vacation packages and you could score some excellent off-season deals.
How many days is enough for Sullivan?
Usually, a handful of days is enough to visit the main attractions during your Sullivan vacation. However, if you'd like to have time to kick back or go on day trips, think about extending your trip.
How to find the best Sullivan package deals?
Begin your search for a Sullivan package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Sullivan package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Sullivan getaway off to a flying start.
Is it cheaper to book a Sullivan vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can customize your Sullivan getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Sullivan?
If you've got your Sullivan travel dates locked in, book early to grab some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Sullivan vacation packages?
If you're anything like us, you love traveling the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Sullivan trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
