Dorchester Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Dorchester vacation rentals

Exterior
Harrison House; Litchfield, IL; Pets welcome

Vacation Home in Litchfield

Harrison House; Litchfield, IL; Pets welcome
10.0 out of 10, Exceptional, (16)
"Cozy house, great amenities, and the hosts responded to questions quickly. Definitely will be staying again!"
United States
Jennifer G.
The price is ￥16,804
￥27,122 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Harrison House; Litchfield, IL; Pets welcome
Terrace/patio
Cozy studio located in small town America, Bunker Hill, IL.

Apartment in Bunker Hill

Cozy studio located in small town America, Bunker Hill, IL.
10.0 out of 10, Exceptional, (14)
"Very comfortable, cozy, and quaint decor. Lovely gardens. Made to feel welcome by host."
United States
Rayma P.
The price is ￥11,297
￥19,456 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy studio located in small town America, Bunker Hill, IL.
Fridge, microwave, oven, stovetop
Edwards House; Litchfield, IL; Pets welcome

Vacation Home in Litchfield

Edwards House; Litchfield, IL; Pets welcome
10.0 out of 10, Exceptional, (21)
"Perfect place to stop on road trip to Arkansas. Had everything I needed. "
United States
Jon L.
The price is ￥16,318
￥26,440 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Edwards House; Litchfield, IL; Pets welcome
Interior
Route 66 house; Litchfield IL; Pets welcome

Vacation Home in Litchfield

Route 66 house; Litchfield IL; Pets welcome
9.8 out of 10, Exceptional, (19)
"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 ￥16,318
￥26,440 total
includes taxes & fees
Dec 24 - Dec 25
Route 66 house; Litchfield IL; Pets welcome
Interior
Jackson House; Pets Welcome

Vacation Home in Litchfield

Jackson House; Pets Welcome
10.0 out of 10, Exceptional, (18)
"The home was clean, in a central location of Litchfield, spacious, and we appreciated that the host allowed pets! would recommend this VRBO to anyone visiting the Litchfield area."
United States
Shelby B.
The price is ￥18,044
￥28,269 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Jackson House; Pets Welcome
Living area
State Street House; 3-br house; PETS WELCOME; Litchfield

Vacation Home in Litchfield

State Street House; 3-br house; PETS WELCOME; Litchfield
10.0 out of 10, Exceptional, (14)
"Great location. Wonderful owner"
United States
David E.
The price is ￥21,809
￥34,920 total
includes taxes & fees
Jan 4 - Jan 5, 2026
State Street House; 3-br house; PETS WELCOME; Litchfield
Iron/ironing board, free WiFi, bed sheets
Light Filled Loft on Town Square

Apartment in Carlinville

Light Filled Loft on Town Square
2.0 star property
10.0 out of 10, Exceptional, (1)
"This space is beautiful and everything I hoped it would be for our photo shoot!"
United States
Trista B.
The price is ￥23,849
￥38,411 total
includes taxes & fees
Dec 24 - Dec 25
Light Filled Loft on Town Square
Fridge, microwave, oven, stovetop
The Carlinville Cottage

Vacation Home in Carlinville

The Carlinville Cottage
10.0 out of 10, Exceptional, (17)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
United States
Casey C.
The price is ￥34,518
￥79,148 total
includes taxes & fees
Dec 24 - Dec 25
The Carlinville Cottage
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

Hampton Inn & Suites St. Louis/Alton

Hampton Inn & Suites St. Louis/Alton

10/10 Excellent
"The staff were very professional and friendly. The breakfast had a great selection."
Melissa 2-night trip
Posted 2 days ago
Hampton Inn & Suites St. Louis/Alton

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:

  • View our selection of featured holiday rentals in Dorchester
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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?

Jackson House; Pets Welcome: This vacation home rental near Dorchester is located on a lake and has a patio, a selection of books, and air-conditioning to put you at ease 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, Piney Creek Ravine - State Natural Area and Lake Ka-Ho 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 Beaver Dam State Park.

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.