Sullivan Vacations from $569

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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

Latchis Hotel

2.5 out of 5
Price was $651, price is now $569 per person
$569
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Springfield (VSF)
8.4/10 Very Good! (822 reviews)
Our room was very clean. Comfy bed. Loved the uniqueness of this hotel! Will come again!

Reviewed on Dec 7, 2025

Windham Hill Inn

Windham Hill Inn

4 out of 5
Price was $926, price is now $764 per person
$764
per person
Feb 19 - Feb 24
found 23 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (37 reviews)
The Inn is situated near the top of a mountain and surrounded by other hilltops. There are trails that help you to reconnect with nature. Our room was lovely and comfortable. There is a attention to detail in the decor of this establishment which is both delightful and humorous.

Reviewed on Jul 11, 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $1,962, price is now $1,663 per person
$1,663
per person
Feb 19 - Feb 24
found 23 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.8/10 Excellent! (242 reviews)
Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability

Reviewed on Oct 18, 2025

COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

2 out of 5
Price was $797, price is now $697 per person
$697
per person
Feb 19 - Feb 24
found 23 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
9.2/10 Wonderful! (43 reviews)
I stayed at here on a whim in December ‘25 on an early ski trip to Stratton & Killington, looking for a spot that wouldn’t break the bank. Got a whole lot more than I bargained for! Eggs & bacon for breakfast, super cozy cabin, great hospitality, and good recommendations. New owners Ali & Lane are hard at work investing more and more into the place and I can’t wait to go back in the summer. Highly recommend for anyone seeking an unfussy stay with rustic charm and super-welcoming owner/operators.

Reviewed on Dec 10, 2025

Chalet 239

Chalet 239

2 out of 5
Price was $944, price is now $832 per person
$832
per person
Feb 19 - Feb 24
found 23 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
9.4/10 Exceptional! (87 reviews)
The place was beautiful!! The room was clean and comfortable.

Reviewed on Nov 23, 2025

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Sullivan Hotel Deals

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $87 total per night from Dec 17 to Dec 18
$87 total
Dec 17 - Dec 18
Total with taxes and fees
7.6/10 Good! (1,001 reviews)
Room very nice, comfortable clean

Reviewed on Nov 29, 2025

The Covered Bridge Inn
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $158 total per night from Dec 17 to Dec 18
$158 total
Dec 17 - Dec 18
Total with taxes and fees
8.2/10 Very Good! (925 reviews)
Convenient, clean. Staff was very friendly and helpful. Close to Highway. Keys weren’t working when we returned from a long day out. TV was also not working, but luckily we were in the room for only a short time before heading out for dinner.

Reviewed on Dec 8, 2025

Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $118 total per night from Dec 14 to Dec 15
$118 total
Dec 14 - Dec 15
Total with taxes and fees
8.4/10 Very Good! (738 reviews)
Staff was friendly and pool was nice

Reviewed on Dec 1, 2025

Comfort Inn & Suites Brattleboro I-91
See all 313 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

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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 $569 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.