Dorchester Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Dorchester

Downtown Midcentury Home- Walk to Everything!
10.0 out of 10, Exceptional, (19)
"Could not have been more pleased. Quality home, spacious, easy access, and walking to down town area. Owner accommodated our request to come a little early to decorate for a birthday. Great to gather around the big dining table and the outside patio. Not a complaint but it would be great to have a couple extra fold up chairs for outside. That is a lovely area as well. Everyone raved about their bed - comfort. We loved the Nespresso coffee too. And maybe there was a coffee pot but we didn’t see...
Downtown Midcentury Home- Walk to Everything!
Cozy loft in a small town; walking distance to the popular restaurant BG’s!
10.0 out of 10, Exceptional, (1)
"Came to Bunker Hill to visit family and needed a little more room. Cozy spot near family and restaurants. Very well stocked and comfy bed and pillows."
The price is CA $110
CA $178 total
includes taxes & fees
Jun 23 - Jun 24
Cozy loft in a small town; walking distance to the popular restaurant BG’s!
Harrison House; Litchfield, IL; Pets welcome
10.0 out of 10, Exceptional, (10)
"Ultra clean, very cutely decorated, and furnished with waters, clean utensils, wonderful beds, and a comfy living room arrangement. We were in town for Mother's Day and we were the envy of the family in this home! It was a lot of fun, normally a place to stay out of town is kind of a wash, you always compromise on something, but not here! If you're staying in Litchfield for whatever reason, give this house a look! Especially for the Picker's Market, every second Sunday, it's right up the road!...
The price is CA $156
CA $246 total
includes taxes & fees
Jun 24 - Jun 25
Harrison House; Litchfield, IL; Pets welcome
Cozy Historic Downtown Edwardsville Charmer
10.0 out of 10, Exceptional, (2)
"This was such a nice home, perfect for my family's stay in the area. We appreciated having access to the full kitchen, dining room and living room to make our stay comfortable."
Cozy Historic Downtown Edwardsville Charmer
Lake House off Route 66
Lake House off Route 66
The Carlinville Cottage
10.0 out of 10, Exceptional, (2)
"Our second stay at the Carlinville Cottage and we will be back!"
The price is CA $272
CA $647 total
includes taxes & fees
Jun 26 - Jun 27
The Carlinville Cottage
Jackson House; Pets Welcome
10.0 out of 10, Exceptional, (6)
"We were there for a wedding--home was roomy and comfortable. Would stay there again."
The price is CA $158
CA $235 total
includes taxes & fees
Jun 20 - Jun 21
Jackson House; Pets Welcome
Edwards House; Litchfield, IL; Pets welcome
10.0 out of 10, Exceptional, (12)
"I enjoyed staying a night at this property in a friendly peaceful family neighborhood in Litchfield. The hosts were very responsive and friendly, and as evidenced in the house they put a lot of effort into making it a nice place for guests to stay, it’s perfect for a single or a couple, the interior was updated throughout, they selected furniture and fixtures that fit appropriately in the spaces so although it’s a smaller home, it didn’t feel super cramped, and created an environment that was...
The price is CA $143
CA $223 total
includes taxes & fees
Jun 23 - Jun 24
Edwards House; Litchfield, IL; Pets welcome
Route 66 house; Litchfield IL; Pets welcome
10.0 out of 10, Exceptional, (12)
"Cute little place we were visiting our grandchildren who live in the area and we all had a great time the house is well decorated so cute and everything you need is there. We will check to see if this place is available every time we visit the grandchildren."
Route 66 house; Litchfield IL; Pets welcome
Chestnut House; Litchfield, IL; Pets Welcome
9.0 out of 10, Wonderful, (2)
"The house was very nice and we had a relaxing stay. We will definitely consider staying here again if we stay in the area."
The price is CA $151
CA $234 total
includes taxes & fees
Jul 12 - Jul 13
Chestnut House; Litchfield, IL; Pets Welcome
Lincoln House; Litchfield, IL; Pets welcome
10.0 out of 10, Exceptional, (13)
"Proprty was well stocked for everything we could possibl y need during our stay. Clean comfortible accommodations. Host is very attentive to guests."
Lincoln House; Litchfield, IL; Pets welcome
Victorian Carlinville home on Rt. 66
10.0 out of 10, Exceptional, (7)
"Awesome place for a group of friends to relax and unwind for a few days after a particularly difficult holiday season!"
Victorian Carlinville home on Rt. 66
Kirkham Train House; PETS WELCOME
Kirkham Train House; PETS WELCOME
Class A RV, 30', Gas Engine, HVAC, Generator, Fridg and Stove, Coffee Maker.
Class A RV, 30', Gas Engine, HVAC, Generator, Fridg and Stove, Coffee Maker.
1 Bedroom Furnished Basement Apartment
1 Bedroom Furnished Basement Apartment
Sunny Mid-Century Modern duplex with a garage
Sunny Mid-Century Modern duplex with a garage
The Lazy Shanty at Shale Lake #2 pet-friendly
The price is CA $192
CA $237 total
includes taxes & fees
Jun 24 - Jun 25
The Lazy Shanty at Shale Lake #2 pet-friendly
Alton Illinois Intimate Events Venue
Alton Illinois Intimate Events Venue
Don't see what you're looking for?
See all available 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.

Other types of properties in Dorchester you may be interested in

Best Western Plus Parkway Hotel
2.5 star property
8.4 out of 10, Very good, (1006)
"The elevator was out of order the entire week. "
The price is CA $122
CA $140 total
includes taxes & fees
Jun 25 - Jun 26
Best Western Plus Parkway Hotel
Super 8 by Wyndham Staunton
2.0 star property
8.6 out of 10, Excellent, (651)
"There is a Dairy Queen Next door to the properties"
The price is CA $103
CA $114 total
includes taxes & fees
Jun 19 - Jun 20
Super 8 by Wyndham Staunton
Hampton Inn & Suites St. Louis/Alton
2.5 star property
9.0 out of 10, Wonderful, (461)
"Staff was friendly and always happy to help. Will definitely stay there again. "
The price is CA $174
CA $198 total
includes taxes & fees
Jul 7 - Jul 8
Hampton Inn & Suites St. Louis/Alton
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.

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 $110 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 can I see and do in Dorchester?

While you're exploring the area, Beaver Dam State Park 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.

Recent reviews of Dorchester properties
Expedia verified reviews