Dorchester Vacations from $578

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Your Dorchester Vacation

With plenty of highlights as well as hidden gems, this city is best experienced with a Dorchester vacation package. Check out places to stay in Tenney Mountain, which is great for nature, views and hiking. Fill your trip to Dorchester with visits to some of its most popular attractions. First stop? Don't miss Rumney Rock Climbing. Whoever you're heading away with and whatever the size of your budget, your ultimate Dorchester vacation is just a few clicks away with Expedia.

The Latest Dorchester vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn at Weathersfield

The Inn at Weathersfield

4 out of 5
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Greenville (GSP) to Lebanon (LEB)
10/10 Exceptional! (63 reviews)
Not what I expected, room or food.

Reviewed on Aug 7, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
per person
Oct 2 - Oct 5
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Lebanon (LEB)
9/10 Wonderful! (727 reviews)
very spacious. Would have like to use the outdoor pool but was being renovated

Reviewed on Aug 5, 2025

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
per person
Sep 21 - Sep 28
found 24 hours ago
Roundtrip non-stop flight included
Greenville (GSP) to Lebanon (LEB)
9.4/10 Exceptional! (243 reviews)
The staff and the cleaning was wonderful love it

Reviewed on Aug 12, 2025

Spacious Dartmouth College Home on Occum Pond

Spacious Dartmouth College Home on Occum Pond

2 out of 5
per person
Oct 2 - Oct 5
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Lebanon (LEB)
No reviews
Brookside Hideaway, Brook Road Inn

Brookside Hideaway, Brook Road Inn

3.5 out of 5
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Amarillo (AMA) to Lebanon (LEB)
10/10 Exceptional! (1 review)
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Discover the most popular places to visit in Dorchester

New Hampshire, tree tree trees for miles and miles. ❤️

Rattlesnake Mountain

Commune with nature and explore the great outdoors at Rattlesnake Mountain during your travels in Rumney. Discover the mountain views while you're in the area.

Rattlesnake Mountain

Polar Caves Park

Explore the great outdoors at Polar Caves Park, a lovely green space in Rumney. Wander the lakeside or discover the area's mountain views.

Polar Caves Park

Rumney Rock Climbing

You can take time to visit Rumney Rock Climbing during your travels to Rumney. Discover the mountain views while you're in the area.

Rumney Rock Climbing

Dorchester Hotel Deals

Streeter Mountain Farm

Streeter Mountain Farm

2 out of 5
218 Streeter Woods Rd, Rumney, NH
$107 nightly
The price is $117 total per night from Aug 31 to Sep 1
$117 total
Aug 31 - Sep 1
Total includes taxes and fees
"Most dangerous environment for a family. Cabin was remotely located with no electricity and indoor toilet. Photographs posted do not do justice. I paid in full but after looking in person chose not stay because of safety, security and privacy. Staff was friendly."

Reviewed on Nov 22, 2024

Streeter Mountain Farm
The Common Man Inn & Spa

The Common Man Inn & Spa

4 out of 5
231 Main St, Plymouth, NH
$116 nightly
The price is $125 total per night from Aug 19 to Aug 20
$125 total
Aug 19 - Aug 20
Total includes taxes and fees
9/10 Wonderful! (347 reviews)
"Great place and nice people to work with."

Reviewed on Aug 7, 2025

The Common Man Inn & Spa
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $134 total per night from Aug 24 to Aug 25
$134 total
Aug 24 - Aug 25
Total includes taxes and fees
7/10 Good! (1,003 reviews)
Stay at White River Inn
"We had a three day stay. Overall, it was good. Staff was Friendly and helpful. The Pool was extremely cold...but we did it. Selection of Breakfast was minimal...Great Breakfast Staff though. The Hotel needs updating badly. Very worn. Old furniture. sinks don't drain. Floors feel sticky. Bed was comfortable. ..."

Reviewed on Aug 6, 2025

White River Inn and Suites
See all 834 properties in Dorchester
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 Dorchester vacation package cost?
Offering excellent value package deals from $578 on Expedia, you'll be thrilled with how little a vacation to Dorchester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Dorchester?
October, November and December are great times to look for cheap Dorchester vacation packages. Traveling in less busy months means you can generally find better prices on accommodations and flights.
How many days is enough for Dorchester?
The ideal length for your Dorchester vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you enough time to visit all the main sights and explore some hidden treasures along the way.
How to find the best Dorchester package deals?
Bagging a cheap Dorchester package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Dorchester package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Dorchester vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging stays and flights separately. Better still, you can customize your Dorchester trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Dorchester?
Enjoy fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Dorchester trip.
Does Expedia offer Book Now, Pay Later Dorchester vacation packages?
Secure your dream escape to Dorchester with help from our Book Now, Pay Later vacations. No need to save up or wait for your next payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snag great 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.