Sullivan Vacations from $404

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $477, price is now $404 per person
$404
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
9.4/10 Exceptional! (118 reviews)
Way overpriced . I’ve stayed in other hotels in the area that included breakfast with hot tubs that are 50% less than this place. The place to put your shoes in the room had mud all over it. Maybe clean it before your next guest.

Reviewed on Mar 2, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,136, price is now $950 per person
$950
per person
Jul 4 - Jul 8
found 24 hours ago
Roundtrip flight included
Houston (IAH) to Springfield (VSF)
8.8/10 Excellent! (929 reviews)
Lovely hotel with views of river and walkable to variety of shops and restaurants

Reviewed on May 12, 2026

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $808, price is now $682 per person
$682
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
10/10 Exceptional! (195 reviews)
Super clean, staff very nice, cabins had kitchens and fireplace that were very nice, but the coffee maker did not work. Nice you could spend just one night but really once there you are going to want to spend at least two. No amenities like pool or gym but they did have the worlds smallest sheep. :) It would be nice if they had a couple of cabins with a jacuzzi tub for after a long drive. It was hard to get to but i think our GPS messed up and took us onto lots of gravel roads to get there so be careful.

Reviewed on May 19, 2026

Chalet 239

Chalet 239

2 out of 5
Price was $546, price is now $464 per person
$464
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
9.4/10 Exceptional! (126 reviews)
Staff very helpful. Everything was very clean

Reviewed on May 17, 2026

Deer Brook Inn

Deer Brook Inn

3 out of 5
Price was $2,797, price is now $2,414 per person
$2,414
per person
Jul 4 - Jul 8
found 24 hours ago
Roundtrip flight included
Houston (IAH) to Springfield (VSF)
10/10 Exceptional! (1 review)
A beautiful location. Hosts were amazing. Clean and tastefully decorated. My only criticism would be to add ports for charging cell phones and computers. Otherwise, it was incredible. We highly recommend this location!

Reviewed on May 24, 2026

Don't see what you're looking for?
See all available trips from Columbus to Sullivan
View all trips

Sullivan Hotel Deals

Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $134 total per night from Jun 7 to Jun 8
$134 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (984 reviews)
"This is the best option in the area and we are big fans of the Hilton family of hotels (we stay there exclusively when this is an option). Everything was as expected for a Hampton Inn, including the workout room, layout of the room, and amenities. Five stars for pillows, hot water, and lack of noise. ..."

Reviewed on May 26, 2026

Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $126 total per night from Jun 2 to Jun 3
$126 total
Jun 2 - Jun 3
Total with taxes and fees
8.6/10 Excellent! (886 reviews)
"Unique hotel. Very quiet - helpful staff though would’ve appreciated a paper receipt at checkout."

Reviewed on May 26, 2026

Latchis 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
$145 nightly
The price is $158 total per night from Jun 11 to Jun 12
$158 total
Jun 11 - Jun 12
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
"This place is a dump Pretty much a motel Looks and smells dirty The curtains in bathroom are filthy The tub is disgusting and black No pride in the upkeep of this property Dirty walls and carpets Exposed outlets Didn’t even clean our room I only stayed here because Hampton inn was sold out NEVERRR ..."

Reviewed on May 25, 2026

Best Western Plus Keene Hotel
See all 340 properties in Sullivan
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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Sullivan vacation package cost?
You can pick up a vacation package to this popular destination from $404 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.