Gilsum Vacations from $437

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Your Gilsum Vacation

With a Gilsum vacation package, say goodbye to endless planning and hello to stress-free adventure. Every detail of your escape has been taken care of before you depart, so you can enjoy each moment discovering this fantastic city. Make your trip to Gilsum even more exciting by going sightseeing. Granite Gorge, Brentwood Golf Course and Walpole Mountain View Winery are some of the major attractions worth exploring. Your dream Gilsum vacation is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your style.

The Latest Gilsum vacation packages

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $524, price is now $437 per person
$437
per person
Feb 25 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $2,513, price is now $1,972 per person
$1,972
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $2,296, price is now $1,875 per person
$1,875
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8/10 Very Good! (219 reviews)
We really enjoyed our stay at the Mountain Lodge at Okemo, it was clean and our room was newly renovated and very cute. Would definitely recommend!!

Reviewed on Oct 6, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,060, price is now $877 per person
$877
per person
Feb 25 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $870, price is now $742 per person
$742
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
7.6/10 Good! (1,002 reviews)
Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street.

Reviewed on Dec 21, 2025

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Gilsum 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
$87 nightly
The price is $96 total per night from Jan 5 to Jan 6
$96 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
7.6/10 Good! (1,001 reviews)
Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street.

Reviewed on Dec 21, 2025

The Covered Bridge Inn
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
$125 nightly
The price is $138 total per night from Jan 3 to Jan 4
$138 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
8.4/10 Very Good! (747 reviews)
Comfortable room

Reviewed on Dec 28, 2025

Comfort Inn & Suites Brattleboro I-91
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $84 total per night from Jan 5 to Jan 6
$84 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Staff was courteous

Reviewed on Dec 23, 2025

The Putney Inn
See all 367 properties in Gilsum
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 Gilsum Vacation Packages

Gilsum Essential Information

Language
English
Currency
U.S dollars
Population
830
Top Sights
Colonial Theatre, Granite Gorge and Walpole Mountain View Winery

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Frequently asked questions

How much does a Gilsum vacation package cost?
You'll find cheap prices from $437 on Expedia for your Gilsum break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Gilsum costs.
What are the cheapest months to go to Gilsum?
You can typically find lower prices and better availability in October, November and December. Explore our cheap Gilsum vacation packages and you could score some great off-season discounts.
How many days is enough for Gilsum?
With a well-planned schedule, you can easily tick off the most popular Gilsum attractions in a few days. But if you'd like to venture off the beaten track or go on day tours, consider booking your Gilsum vacation for longer.
How to find the best Gilsum package deals?
Start your search for a Gilsum package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Gilsum package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Gilsum adventure underway.
Is it cheaper to book a Gilsum vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Gilsum vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Gilsum?
If you're planning a spur-of-the-moment Gilsum trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Gilsum vacation packages?
Set off on your dream escape to Gilsum with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.