Dorset Vacations from $492

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Your Dorset Vacation

Say bye-bye to the worries of planning and hello to a Dorset vacation package. With the finer details organized before you leave, you can focus on discovering the best of this city, starting with Bromley Mountain, which is great for views, families and nature. Every trip to Dorset needs a well-thought-out itinerary. Fill yours with major attractions such as Manchester Designer Outlets, Battenkill River and Southern Vermont Arts Center. Your ideal Dorset vacation is just clicks away. Explore flights, accommodations and more on Expedia for an adventure that's tailored to suit your travel style.

The Latest Dorset vacation packages

Price found within the past 48 hours. Click for updated prices.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $829, price is now $492 per person
$492
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $988, price is now $580 per person
$580
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
18.8/10 Exceptional! (13 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....

Reviewed on Oct 20, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $815, price is now $556 per person
$556
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
17.6/10 Exceptional! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open

Reviewed on Nov 12, 2025

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Save 100% on your flight
Price was $734, price is now $530 per person
$530
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
19.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!

Reviewed on Nov 10, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $728, price is now $538 per person
$538
per person
Feb 19 - Feb 23
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
18.4/10 Exceptional! (1,005 reviews)
Everything about our stay was perfect! The lady at check-in was super friendly, the room was extremely clean and modern. Definitely recommend The Landing!

Reviewed on Nov 23, 2025

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Discover the most popular places to visit in Dorset

Dorset Playhouse

4.5/5(7 reviews)

You can enjoy a show at Dorset Playhouse during your trip to Dorset. Discover the mountain views in this quaint area.

Dorset Playhouse

Dorset Hotel Deals

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$194 nightly
The price is $214 total per night from Dec 1 to Dec 2
$214 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (814 reviews)
Staff was great. Our room was okay… broken blinds and lots of scuffs on walls

Reviewed on Nov 16, 2025

Kimpton Taconic Hotel by IHG
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $203 total per night from Dec 7 to Dec 8
$203 total
Dec 7 - Dec 8
Total with taxes and fees
7.4/10 Good! (570 reviews)
Courteous staff Clean room

Reviewed on Nov 22, 2025

The Equinox Golf Resort & Spa
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $140 total per night from Dec 14 to Dec 15
$140 total
Dec 14 - Dec 15
Total with taxes and fees
9.6/10 Exceptional! (1,002 reviews)
It was great. The room was wonderful and the staff great.

Reviewed on Nov 23, 2025

Hampton Inn and Suites Manchester
See all 1,980 properties in Dorset
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 Dorset Vacation Packages

Dorset Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Population
250
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Bromley Mountain Ski Resort, Emerald Lake State Park and Dorset Playhouse

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Frequently asked questions

How much does a Dorset vacation package cost?
You can pick up a vacation package to this destination from $492 on Expedia. However, how much your vacation to Dorset costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Dorset?
If you're hoping to book a cheap Dorset vacation package, consider traveling in March, April and November. You'll usually find better rates on hotels and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Dorset?
The ideal length of your Dorset vacation depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to hit all the major attractions and explore some hidden spots along the way.
How to find the best Dorset package deals?
Use Expedia's filter tool to find some tempting Dorset package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Dorset package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Dorset vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights individually. Better still, you can personalize your Dorset escape to match your exact needs. Pick 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 Dorset?
If you've got your Dorset travel dates finalized, book as soon as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Dorset vacation packages?
Set off on your dream escape to Dorset with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until your next 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 cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snap up travel deals before they sell out.

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