Dorchester Vacations from $292

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The Latest Dorchester vacation packages

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

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $541, price is now $292 per person
$292
per person
Sep 18 - Sep 20
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,661 reviews)
Professional staff. Very helpful

Reviewed on Jul 18, 2026

Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

2 out of 5
Save 100% on your flight
Price was $831, price is now $498 per person
$498
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
10/10 Exceptional! (1 review)
The property was excellent, and the home was very warm and welcoming.

Reviewed on Jun 25, 2026

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $786, price is now $502 per person
$502
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
So much charm. Fantastic hotel with great on site restaurants & bars. The included breakfast was very good. My only complaint was the lack of attention to the pool area. Great little area but not staffed. Expedia stated there was food & drink available at the pool which was not the case. There were also a lot of used towels laying around. Overall fantastic stay & will definitely be booking again.

Reviewed on Jul 17, 2026

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Save 100% on your flight
Price was $678, price is now $450 per person
$450
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,061 reviews)

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Save 100% on your flight
Price was $791, price is now $534 per person
$534
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9/10 Wonderful! (1,984 reviews)

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Dorchester Hotel Deals

Baymont by Wyndham Litchfield

Baymont by Wyndham Litchfield

2.5 out of 5
1405 W Hudson Dr Litchfield IL
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $109 total per night from Jul 19 to Jul 20
$109 total
Jul 19 - Jul 20
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
"Friendly people, very clean!"

Reviewed on Jul 17, 2026

Baymont by Wyndham Litchfield
Best Western Plus Parkway Hotel

Best Western Plus Parkway Hotel

2.5 out of 5
1900 Homer Adams Pkwy Alton IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $106 total per night from Aug 16 to Aug 17
$106 total
Aug 16 - Aug 17
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Great place to stay"

Reviewed on Jul 14, 2026

Best Western Plus Parkway Hotel
The Great Rivers, an Ascend Collection Hotel

The Great Rivers, an Ascend Collection Hotel

3 out of 5
3559 College Avenue Alton IL
Fully refundable
$103 nightly
The price is $118 total per night from Aug 16 to Aug 17
$118 total
Aug 16 - Aug 17
Total with taxes and fees
7.8/10 Good! (790 reviews)
"The hotel was great starting with the staff being accommodating and having a good attitude. The breakfast was good, just needed more fruit and possibly a salad option for those who do not eat meat. Lastly, the room was great! The bath tub needed the no slip markers to prevent accidents. Thank you ..."

Reviewed on Jul 17, 2026

The Great Rivers, an Ascend Collection Hotel
See all 45 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
Top Sights
The Winery at Shale Lake, Beaver Dam State Park and Timber Lakes Golf Course

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Frequently asked questions

How much does a Dorchester vacation package cost?
You can grab a vacation package to this destination from $292 on Expedia. However, how much your vacation to Dorchester costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Dorchester?
You can typically find lower rates and better availability in November, December and January. Browse our cheap Dorchester vacation packages and you could score some great off-season discounts.
How many days is enough for Dorchester?
The ideal length for your Dorchester vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to hit all the leading attractions and explore some hidden treasures along the way.
How to find the best Dorchester package deals?
Start your search for a Dorchester package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Dorchester package deal right away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Dorchester adventure underway.
Is it cheaper to book a Dorchester 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 usually get a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Dorchester vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Dorchester?
If you're planning a spur-of-the-moment Dorchester adventure, browse 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 sensational deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Dorchester vacation packages?
Your Dorchester trip is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to give you that extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.