Dorchester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Dorchester

Our top choices for Dorchester holiday rentals

Jackson House; Pets Welcome

10.0 out of 10, Exceptional, (15)
"Overflow holiday guests stayed at this cute, clean, comfortable home. A wonderful experience with exceptionally kind, engaged, owners! "
The price is NZ$307
includes taxes & fees
30 Sept - 1 Oct
Jackson House; Pets Welcome

Route 66 house; Litchfield IL; Pets welcome

10.0 out of 10, Exceptional, (16)
"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."
The price is NZ$287
includes taxes & fees
28 Sept - 29 Sept
Route 66 house; Litchfield IL; Pets welcome

The Carlinville Cottage

10.0 out of 10, Exceptional, (13)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
The price is NZ$859
includes taxes & fees
7 Oct - 8 Oct
The Carlinville Cottage

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

10.0 out of 10, Exceptional, (12)
"Great location, felt like it was home "
The price is NZ$211
includes taxes & fees
25 Sept - 26 Sept
Cozy studio located in small town America, Bunker Hill, IL.

Plainview Vineyard Retreat by StayLage

2.0 star property
10.0 out of 10, Exceptional, (1)
"Quiet place to relax after a long day. Clean and will rent again if given the choice. "
The price is NZ$750
includes taxes & fees
24 Sept - 25 Sept
Plainview Vineyard Retreat by StayLage

Cozy Historic Downtown Edwardsville Charmer

9.8 out of 10, Exceptional, (11)
"Wonderful location for what we needed! Comfortable beds and great amenities. Lots of little touches and extras."
Cozy Historic Downtown Edwardsville Charmer

Charming 1BR Near Historic Downtown Edwardsville & SIUE

Charming 1BR Near Historic Downtown Edwardsville & SIUE

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

9.8 out of 10, Exceptional, (10)
"Great house with a really great layout. Great location for accessing the parts of Litchfield we wanted to find. Super responsive host. "
The price is NZ$377
includes taxes & fees
28 Sept - 29 Sept
State Street House; 3-br house; PETS WELCOME; Litchfield

Edwards House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (21)
"Mike and Amy have a beautiful cozy place to stay. My partner and I had a wonderful time and were super comfy during our stay!"
The price is NZ$287
includes taxes & fees
25 Sept - 26 Sept
Edwards House; Litchfield, IL; Pets welcome

Victorian Carlinville home on Rt. 66

10.0 out of 10, Exceptional, (10)
"We will stay there again if we're in the area."
Victorian Carlinville home on Rt. 66

Lake House off Route 66

9.0 out of 10, Wonderful, (2)
"The home itself was fantastic—clean, well-maintained, and exactly as pictured. The host was responsive and friendly, and the location right on the lake made for a relaxing stay. The only downside, and the reason I’m giving 4 stars instead of 5, is that there’s a camper in the front yard with people staying in it. This wasn’t disclosed in the listing, and it made the experience feel a bit less private and more awkward than expected. If that had been communicated up front, it would’ve helped set...
The price is NZ$361
includes taxes & fees
25 Sept - 26 Sept
Lake House off Route 66

Harrison House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (13)
"Everything was in excellent shape and the fenced yard was great for the pups."
The price is NZ$316
includes taxes & fees
25 Sept - 26 Sept
Harrison House; Litchfield, IL; Pets welcome

Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield

Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield

Chestnut House; Litchfield, IL; Pets Welcome

9.0 out of 10, Wonderful, (7)
"The house was very nice and we had a relaxing stay. We will definitely consider staying here again if we stay in the area."
Chestnut House; Litchfield, IL; Pets Welcome

1 Bedroom Furnished Basement Apartment Close to Phillips 66

1 Bedroom Furnished Basement Apartment Close to Phillips 66

Sunny Mid-Century Modern duplex with a garage

Sunny Mid-Century Modern duplex with a garage

Alton Illinois Intimate Events Venue

Alton Illinois Intimate Events Venue

Home < 3 Mi to Rte 66 & Lake Lou Yaeger!

Home < 3 Mi to Rte 66 & Lake Lou Yaeger!

Home < 3 Mi to Rte 66 & Lake Lou Yaeger!

3.0 star property
Home < 3 Mi to Rte 66 & Lake Lou Yaeger!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Dorchester Hotel Reviews

Find out more about Dorchester

Find out more about Dorchester

Everything you need to know about Dorchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dorchester holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Dorchester holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dorchester holiday rentals we have selected for you start as low as NZ$211 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 holiday 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 holiday.

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 holiday rentals in Dorchester?

Yes, there are holiday rentals close to the most popular sights in Dorchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Dorchester has to offer?

Route 66 house; Litchfield IL; Pets welcome: This holiday home rental outside of Dorchester offers a patio, a selection of games and a BBQ 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, Piney Creek Ravine - State Natural Area and Lake Ka-Ho are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Beaver Dam State Park and Litchfield Museum and Route 66 Welcome Center.

What are holiday rentals like in Dorchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dorchester. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip.