Dorchester Holiday Rentals

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Holiday Rentals in Dorchester

Route 66 house; Litchfield IL; Pets welcome

Litchfield
9.8 out of 10, Exceptional, (18)
"Had everything we needed"
United States
Becky M.
The price is NZ$297
includes taxes & fees
15 Nov - 16 Nov
Route 66 house; Litchfield IL; Pets welcome

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

Litchfield
10.0 out of 10, Exceptional, (12)
"My daughters, son-in-law and I found ourselves needing to stay near Hillsboro for my Grandmother’s funeral. Mike and Amy were gracious hosts. We truly felt the love they have for the home. It’s a great location, a quick walk to downtown Litchfield. I highly recommend!"
United States
Joanna M.
The price is NZ$421
includes taxes & fees
16 Nov - 17 Nov
State Street House; 3-br house; PETS WELCOME; Litchfield

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

Litchfield
10.0 out of 10, Exceptional, (2)
"Very clean and beds were extremely comfortable. Very nice space"
United States
Catherine M.
Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield

The Carlinville Cottage

Carlinville
10.0 out of 10, Exceptional, (17)
"Our second stay at the Carlinville Cottage and we will be back!"
United States
Janell M.
The price is NZ$890
includes taxes & fees
11 Nov - 12 Nov
The Carlinville Cottage

Jackson House; Pets Welcome

Litchfield
10.0 out of 10, Exceptional, (17)
"We were there for a wedding--home was roomy and comfortable. Would stay there again."
United States
Donna T.
The price is NZ$320
includes taxes & fees
9 Nov - 10 Nov
Jackson House; Pets Welcome

Edwards House; Litchfield, IL; Pets welcome

Litchfield
10.0 out of 10, Exceptional, (21)
"Perfect situation for those who prefer to stay in a small house rather than hotel. Older but well-maintained neighborhood. Very pleasant and just a few blocks from the downtown area."
United States
Robert N.
The price is NZ$299
includes taxes & fees
22 Nov - 23 Nov
Edwards House; Litchfield, IL; Pets welcome

Victorian Carlinville home on Rt. 66

Carlinville
10.0 out of 10, Exceptional, (11)
"Beautiful spacious Victorian home! Wonderful location and impeccably stocked. Gracious owner. We had a wonderful stay."
United States
Janell M.
Victorian Carlinville home on Rt. 66

Lake House off Route 66

Mount Olive
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...
United States
Jodiq P.
Lake House off Route 66

Harrison House; Litchfield, IL; Pets welcome

Litchfield
10.0 out of 10, Exceptional, (15)
"Everything was in excellent shape and the fenced yard was great for the pups."
United States
Barbara A B.
The price is NZ$305
includes taxes & fees
16 Nov - 17 Nov
Harrison House; Litchfield, IL; Pets welcome

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

Bunker Hill
10.0 out of 10, Exceptional, (14)
"Great location, felt like it was home "
United States
Dawn L.
The price is NZ$220
includes taxes & fees
9 Nov - 10 Nov
Cozy studio located in small town America, Bunker Hill, IL.

1 Bedroom Furnished Basement Apartment Close to Phillips 66

Alton
1 Bedroom Furnished Basement Apartment Close to Phillips 66

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

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

Cozy Historic Downtown Edwardsville Charmer

Edwardsville
9.4 out of 10, Exceptional, (14)
"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."
United States
Desera G.
Cozy Historic Downtown Edwardsville Charmer

Chestnut House; Litchfield, IL; Pets Welcome

Litchfield
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."
United States
Tim P.
Chestnut House; Litchfield, IL; Pets Welcome

Charming 1BR Near Historic Downtown Edwardsville & SIUE

Edwardsville
"Charles is a very conscientious VRBO member who was available when I had difficulty entering. This home has been recently updated and the interior decor is quite attractive and comfortable. The bathroom even has an in floor heating system. The house is located in an older section of town but the entire street of homes are well maintained. The location is super convenient to the university and all the activities in downtown Edwardsville."
United States
Joseph K.
Charming 1BR Near Historic Downtown Edwardsville & SIUE

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

3.0 star property
Litchfield
Home < 3 Mi to Rte 66 & Lake Lou Yaeger!

Sunny Mid-Century Modern duplex with a garage

Edwardsville
Sunny Mid-Century Modern duplex with a garage

Light Filled Loft on Town Square

2.0 star property
Carlinville
The price is NZ$413
includes taxes & fees
20 Nov - 21 Nov
Light Filled Loft on Town Square
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

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$220 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.