Colebrook Vacations from $626

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Your Colebrook Vacation

The friendly locals and spectacular views are just the start of the things Colebrook has going for it. Enjoy the very best of this interesting city the way you want with a customized Colebrook vacation package. If your trip to Colebrook includes some sightseeing, drop by famous attractions like Haystack Mountain State Park, Laurel Lanes and Winchester Historical Society. Whatever your travel plans or budget, organizing your ultimate tailored Colebrook vacation is a cinch with Expedia.

The Latest Colebrook vacation packages

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

the Alander

2.5 out of 5
Price was $635, price is now $626 per person
$626
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Pittsfield (PSF)
9/10 Wonderful! (157 reviews)
clean, staff great,food excellent, rooms beautiful, outdside dinning and firepits are wonderful. loved it!!!

Reviewed on Sep 18, 2025

Little Cat Lodge

Little Cat Lodge

2 out of 5
Price was $1,016, price is now $867 per person
$867
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Pittsfield (PSF)
9.4/10 Exceptional! (58 reviews)
Loved staying here. It was a beautiful room, clean and modern. Loved having a balcony to sit on at night. The breakfast was excellent and the service with a smile was great. Would love to come back again.

Reviewed on Aug 10, 2025

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Colebrook Hotel Deals

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundable
$142 nightly
The price is $158 total per night from Sep 23 to Sep 24
$158 total
Sep 23 - Sep 24
Total with taxes and fees
9/10 Wonderful! (727 reviews)
"Check-in and check-out was seamless, the room was spacious,clean, comfortable and well equipped. Swimming pools were well maintained and very clean. The stairs were a bit difficult for seniors…great stay!"

Reviewed on Sep 16, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Oct 2 to Oct 3
$104 total
Oct 2 - Oct 3
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
"Great breakfast buffet."

Reviewed on Sep 15, 2025

Quality Inn
Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St, Simsbury, CT
$204 nightly
The price is $235 total per night from Sep 21 to Sep 22
$235 total
Sep 21 - Sep 22
Total with taxes and fees
9.2/10 Wonderful! (988 reviews)
"Beautiful place, great staff, needs a little updating"

Reviewed on Sep 10, 2025

Simsbury 1820 House
See all 612 properties in Colebrook
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.

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Frequently asked questions

How much does a Colebrook vacation package cost?
You can pick up a vacation package to this destination from $626 on Expedia. However, how much your vacation to Colebrook costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Colebrook?
December, January and February are the best times to search for cheap Colebrook vacation packages. Opting to travel in quieter months means you can usually find reduced prices on accommodations and flights.
How many days is enough for Colebrook?
With a well-planned schedule, you can easily hit the main Colebrook attractions in a few days. But if you'd like to explore off the beaten track or go on day tours, consider booking your Colebrook vacation for longer.
How to find the best Colebrook package deals?
Use Expedia's filters to help you find some fabulous Colebrook package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Colebrook package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Colebrook vacation as a package?
You can enjoy significant savings on your Colebrook break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Colebrook?
If you have your Colebrook travel dates locked in, book as soon as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Colebrook vacation packages?
Secure your perfect trip to Colebrook with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to budget for your trip and snap up travel deals while they last.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.