Sullivan Vacations from $595

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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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $727, price is now $595 per person
$595
per person
Dec 4 - Dec 7
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (VSF)
8.8/10 Excellent! (507 reviews)
Clean room and spacious. Walkable areas around to explore. Would stay again.

Reviewed on Oct 6, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
Price was $1,255, price is now $891 per person
$891
per person
Nov 7 - Nov 11
found 2 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.8/10 Excellent! (823 reviews)
Loved the rockers on the porch

Reviewed on Oct 8, 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was $2,262, price is now $1,939 per person
$1,939
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
9.6/10 Exceptional! (64 reviews)
We loved our stay in Deerfield Valley Inn. One of the best inns in Southern Vermont that we stayed in. The room was spacious, cozy, clean and elegantly decorated with a fireplace. The staff were super friendly and accommodating. The inn was right in the middle of the town so everything was walking distance. Definitely going back and highly recommend for a relaxing getaway.

Reviewed on Sep 25, 2025

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $720, price is now $644 per person
$644
per person
Dec 11 - Dec 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
9.8/10 Exceptional! (90 reviews)
Our stay at the Sinclair Inn Bed and Breakfast was nothing short of amazing. The accommodations were beautifully decorated, blending comfort with charm. The common sitting areas were especially inviting, offering the perfect setting to unwind, play a game, or just visit. Each breakfast was different— thoughtfully prepared, and absolutely delicious. The hosts were gracious and attentive, providing warm hospitality that made us feel both welcome and cared for. The grounds were well-kept, enhancing the sense of peace and quiet that made our stay so relaxing. A truly memorable retreat — we look forward to returning.

Reviewed on Oct 4, 2025

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $715, price is now $607 per person
$607
per person
Dec 4 - Dec 7
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (VSF)
7.8/10 Good! (1,003 reviews)
This place is in need of a serious update. The room was relatively clean and the bed pretty comfortable. The property just looks worn down and neglected.

Reviewed on Oct 8, 2025

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Sullivan Hotel Deals

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
$125 nightly
The price is $136 total per night from Oct 26 to Oct 27
$136 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (914 reviews)
"💞"

Reviewed on Oct 5, 2025

Keene Elm City Hotel, an Ascend Collection Hotel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
$133 nightly
The price is $147 total per night from Oct 9 to Oct 10
$147 total
Oct 9 - Oct 10
Total with taxes and fees
8.4/10 Very Good! (800 reviews)
"Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful."

Reviewed on Sep 28, 2025

Latchis Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
$140 nightly
The price is $154 total per night from Oct 9 to Oct 10
$154 total
Oct 9 - Oct 10
Total with taxes and fees
6.6/10 (1,004 reviews)
"Location and parking are perfect for us. Also the price for the size of the room that we get is definitely fair. We stay here every time I come visit my family."

Reviewed on Oct 6, 2025

Colonial Motel And Spa
See all 323 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.

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 $595 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.