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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.
The price is ￥11,331
￥19,514 total
includes taxes & fees
Oct 5 - Oct 6
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.
The price is ￥19,970
￥31,505 total
includes taxes & fees
Oct 11 - Oct 12
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
The price is ￥29,113
￥44,195 total
includes taxes & fees
Oct 1 - Oct 2
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.
The price is ￥35,408
￥52,536 total
includes taxes & fees
Oct 11 - Oct 12
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
The price is ￥24,786
￥29,605 total
includes taxes & fees
Oct 4 - Oct 5
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
The price is ￥18,727
￥29,021 total
includes taxes & fees
Oct 1 - Oct 2
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.
The price is ￥34,621
￥79,385 total
includes taxes & fees
Oct 30 - Oct 31
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.
The price is ￥19,042
￥29,688 total
includes taxes & fees
Oct 5 - Oct 6
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.
The price is ￥59,014
￥104,201 total
includes taxes & fees
Oct 4 - Oct 5
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 9 hours ago
Comfort Inn Alton near I-255

Find out more about Dorchester

Search for holiday rentals in Dorchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Dorchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Dorchester!

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.