Dorchester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (22 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 CA $103
CA $165 total
includes taxes & fees
Nov 16 - Nov 17
Cozy studio located in small town America, Bunker Hill, IL.
A room with a wooden wall, a sofa, a round table, a chair, a window with curtains, and a door.

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

Beaver Inn - Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
Plainview
10.0 out of 10, Exceptional, (2 reviews)
"We were able to return to stay a few more days, and the cabin work perfectly for us. The kitchen has everything you need and all of the cookware was cleaned in great condition. The fridge, oven and dishwasher looked like they were brand new and everything worked exactly as expected. The bathroom has a tub which has a large "rain" type of shower head and there is plenty of hot water. The proximity to Beaver Dam is probably one of my favorite things about the house because my family loves to...
United States
Toni G.
The price is CA $223
CA $254 total
includes taxes & fees
Nov 15 - Nov 16
Beaver Inn - 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.

3. Edwards House; Litchfield, IL; Pets welcome

Edwards House; Litchfield, IL; Pets welcome
Litchfield
10.0 out of 10, Exceptional, (30 reviews)
"Very cozy, cute house!"
United States
Star
The price is CA $219
CA $328 total
includes taxes & fees
Nov 13 - Nov 14
Edwards House; Litchfield, IL; Pets welcome
A modern kitchen with a dark wood floor, a white cabinet, a black bar stool, and a wooden table.

4. 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 CA $205
CA $310 total
includes taxes & fees
Nov 14 - Nov 15
Route 66 house; Litchfield IL; Pets welcome
A two-story house with a front porch, a green door, and the number 408 on the right side.

5. Harrison House; Litchfield, IL; Pets welcome

Harrison House; Litchfield, IL; Pets welcome
Litchfield
9.8 out of 10, Exceptional, (22 reviews)
"Loved this property. Will def be staying again. "
United States
Amanda G.
The price is CA $235
CA $349 total
includes taxes & fees
Nov 13 - Nov 14
Harrison House; Litchfield, IL; Pets welcome
A spacious room with a large bed, a dining table, and a television.

6. Light Filled Loft on Town Square.

Light Filled Loft on Town Square.
Carlinville
10.0 out of 10, Exceptional, (20 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is CA $325
CA $434 total
includes taxes & fees
Nov 16 - Nov 17
Light Filled Loft on Town Square.
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.

7. 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, (21 reviews)
"Great place in a quiet charming town."
United States
William
The price is CA $304
CA $442 total
includes taxes & fees
Nov 13 - Nov 14
State Street House; 3-br house; PETS WELCOME; Litchfield
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island with bar stools.

8. The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (23 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 CA $311
CA $645 total
includes taxes & fees
Nov 16 - Nov 17
The Carlinville Cottage
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 CA $544
CA $908 total
includes taxes & fees
Nov 10 - Nov 11
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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Dorchester Hotel Reviews

A building with a covered entrance, stone pillars, and a bench outside.
Holiday Inn Express & Suites Litchfield West by IHG

Holiday Inn Express & Suites Litchfield West by IHG

Holiday Inn Express & Suites Litchfield West by IHG
Litchfield

8/10 Good

My only complaint is the internet as a customer it should connect as soon as I come on the property As with many holiday inn sites you have to continually reconnect, very annoying
Canada
Scott
Reviewed May 8, 2019
Holiday Inn Express & Suites Litchfield West by IHG

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dorchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dorchester vacation rentals we have selected for you start as low as CA $84 per night. Entering your travel dates in the search wizard 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.