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Dorchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Dorchester vacation rentals

A patio area with wicker furniture, a striped umbrella, and potted plants.

1. Cozy studio located in small town America, Bunker Hill, IL.

Cozy studio located in small town America, Bunker Hill, IL.
Bunker Hill
10.0 out of 10, Exceptional, (20 reviews)
"The apartment was very comfortable and cozy. We slept great and it was very nice to have a place to stay in Bunker Hill. "
United States
Erica L.
$117 nightly
The price is $124
Oct 5 - Oct 6
Total with taxes and fees
Cozy studio located in small town America, Bunker Hill, IL.
A two-story house with a front porch, a green door, and the number 408 on the right side.

2. Harrison House; Litchfield, IL; Pets welcome

Harrison House; Litchfield, IL; Pets welcome
Litchfield
10.0 out of 10, Exceptional, (21 reviews)
"Loved this property. Will def be staying again. "
United States
Amanda G.
$189 nightly
The price is $200
Oct 4 - Oct 5
Total with taxes and fees
Harrison House; Litchfield, IL; Pets welcome
A living room with a black leather couch, a wooden coffee table, and a bookshelf. There is a dining area visible through an archway with a wooden table and chairs.

3. State Street House; 3-br house; PETS WELCOME; Litchfield

State Street House; 3-br house; PETS WELCOME; Litchfield
Litchfield
9.6 out of 10, Exceptional, (20 reviews)
"Great place in a quiet charming town."
United States
William
$255 nightly
The price is $270
Oct 1 - Oct 2
Total with taxes and fees
State Street House; 3-br house; PETS WELCOME; Litchfield
A spacious room with a large island kitchen, a cozy seating area with a sofa and armchairs, and a bed with a view of the city through arched windows.

4. Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
Carlinville
10.0 out of 10, Exceptional, (17 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
$315 nightly
The price is $334
Oct 1 - Oct 2
Total with taxes and fees
Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
A modern kitchen with white cabinets, stainless steel appliances, a wooden staircase, and a dining area with a wooden table and chairs.

5. Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.

Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
Plainview
$178 nightly
The price is $188
Oct 4 - Oct 5
Total with taxes and fees
Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
A modern kitchen with white cabinets, a gas stove, and a microwave. There is a dining area with a wooden table and two chairs.

6. Edwards House; Litchfield, IL; Pets welcome

Edwards House; Litchfield, IL; Pets welcome
Litchfield
10.0 out of 10, Exceptional, (29 reviews)
"Very cozy, cute house!"
United States
Star
$174 nightly
The price is $184
Oct 1 - Oct 2
Total with taxes and fees
Edwards House; Litchfield, IL; Pets welcome
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island with bar stools.

7. The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house, our home away from home. We have stayed here many times and we will be back!"
United States
Janell M.
$460 nightly
The price is $473
Oct 30 - Oct 31
Total with taxes and fees
The Carlinville Cottage
A modern kitchen with a dark wood floor, a white cabinet, a black bar stool, and a wooden table.

8. Route 66 house; Litchfield IL; Pets welcome

Route 66 house; Litchfield IL; Pets welcome
Litchfield
10.0 out of 10, Exceptional, (23 reviews)
"Nice little place, check in and communication excellent. Perfect for us when visiting my Dad who lives near by."
United States
Mike O.
$178 nightly
The price is $189
Oct 5 - Oct 6
Total with taxes and fees
Route 66 house; Litchfield IL; Pets welcome
A two-story house with a wrap-around porch, a central entrance with a door, and a chimney.

9. Grand Victorian Carlinville home on Rt. 66.

Grand Victorian Carlinville home on Rt. 66.
Carlinville
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay"
United States
Adam M.
$600 nightly
The price is $662
Oct 1 - Oct 2
Total with taxes and fees
Grand Victorian Carlinville home on Rt. 66.
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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Top Dorchester Hotel Reviews

Comfort Inn Alton near I-255

Comfort Inn Alton near I-255

10/10 Excellent
"Have a great continental breakfast"
Jonathan 3-night trip
Posted 8 hours ago
Comfort Inn Alton near I-255

Find out more about Dorchester

Everything you need to know about Dorchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dorchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dorchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dorchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dorchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Dorchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Dorchester rentals

At Expedia, we put the best Dorchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Dorchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dorchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dorchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Dorchester?

Yes, we offer vacation rentals near the most popular local attractions in Dorchester, or you can select a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Dorchester?

Edwards House; Litchfield, IL; Pets welcome: This vacation home rental near Dorchester offers a patio, a private yard, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Dorchester?

While you're exploring the area, Lake Ka-Ho and Piney Creek Ravine - State Natural Area are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find The Winery at Shale Lake and Litchfield Museum and Route 66 Welcome Center.

What are vacation rentals like in Dorchester?

Vacation rentals are private accommodations you can reserve for a couple days or more in Dorchester. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family trips or small group gatherings.