Dorchester Vacations from $588

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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.
Streeter Mountain Farm

Streeter Mountain Farm

2 out of 5
Price was $604, price is now $588 per person
$588
per person
Jul 4 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Lebanon (LEB)
6/10 (4 reviews)
Hanover Inn Dartmouth

Hanover Inn Dartmouth

4 out of 5
Price was $919, price is now $857 per person
$857
per person
Jul 4 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Lebanon (LEB)
9.6/10 Exceptional! (942 reviews)
Very helpful, friendly staff. Very nice, comfortable room with everything I needed. Would definitely stay again!

Reviewed on May 11, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $757, price is now $706 per person
$706
per person
Jul 4 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Lebanon (LEB)
9/10 Wonderful! (831 reviews)
The accommodations were clean and comfortable, the staff friendly, the on site restaurant had several delicious options, the views were amazing!

Reviewed on Apr 27, 2026

Six South St Hotel

Six South St Hotel

2.5 out of 5
Price was $822, price is now $780 per person
$780
per person
Jul 4 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Lebanon (LEB)
9.4/10 Exceptional! (925 reviews)
Great hotel! Have stayed here a few times visiting our daughter attending Dartmouth. Perfect location. Clean rooms. Friendly staff. Highly recommend it.

Reviewed on May 14, 2026

Dowds Country Inn

Dowds Country Inn

3 out of 5
Price was $691, price is now $658 per person
$658
per person
Jul 4 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Lebanon (LEB)
9.4/10 Exceptional! (208 reviews)
Great breakfast but it’s a noisy rundown kind of place.

Reviewed on Oct 28, 2025

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Discover the most popular places to visit in Dorchester

Rattlesnake Mountain

Rattlesnake Mountain

4.5/5(2 reviews)

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

4.5/5(10 reviews)

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

4/5(4 reviews)

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
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $95 total per night from Jun 7 to Jun 8
$95 total
Jun 7 - Jun 8
Total with taxes and fees
Streeter Mountain Farm
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $158 total per night from May 26 to May 27
$158 total
May 26 - May 27
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Room was nice, good size etc. Mattresses were terrible and the sheets had bleach or detergent residual on them that irritated my skin. I ultimately had to dress to eliminate the skin irritation to be able to sleep. Bad experience for the cost, or otherwise!

Reviewed on May 14, 2026

Fireside Inn & Suites West Lebanon
Hampton Inn White River Junction

Hampton Inn White River Junction

2.5 out of 5
104 Ballardvale Dr White River Junction VT
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $137 total per night from May 25 to May 26
$137 total
May 25 - May 26
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
The hotel was going through renovations.. the whole lobby was a mess and the room smelled paint

Reviewed on May 14, 2026

Hampton Inn White River Junction
See all 873 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.

Find the Best Dorchester Vacation Packages

Dorchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Top Sights
Polar Caves Park, Stinson Lake and Rumney Rock Climbing

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Frequently asked questions

How much does a Dorchester vacation package cost?
Offering excellent value package deals from $588 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.