Dorchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Vacation Rentals in Dorchester

Our top choices for Dorchester vacation rentals

Charming 1BR Near Historic Downtown Edwardsville & SIUE
TV, fireplace

Charming 1BR Near Historic Downtown Edwardsville & SIUE

Charming 1BR Near Historic Downtown Edwardsville & SIUE
Plainview Vineyard Retreat by StayLage
Exterior detail

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 ￥18,250
￥67,296 total
includes taxes & fees
Aug 25 - Aug 26
Plainview Vineyard Retreat by StayLage
Victorian Carlinville home on Rt. 66
Terrace/patio

Victorian Carlinville home on Rt. 66

10.0 out of 10, Exceptional, (8)
"We will stay there again if we're in the area."
Victorian Carlinville home on Rt. 66
Edwards House; Litchfield, IL; Pets welcome
1 bedroom, iron/ironing board, WiFi, bed sheets

Edwards House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (20)
"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 ￥15,282
￥24,761 total
includes taxes & fees
Aug 25 - Aug 26
Edwards House; Litchfield, IL; Pets welcome
Lake House off Route 66
Exterior

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 ￥14,547
￥31,768 total
includes taxes & fees
Aug 26 - Aug 27
Lake House off Route 66
The Carlinville Cottage
Fridge, microwave, oven, stovetop

The Carlinville Cottage

10.0 out of 10, Exceptional, (12)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
The price is ￥32,327
￥73,624 total
includes taxes & fees
Aug 25 - Aug 26
The Carlinville Cottage
Jackson House; Pets Welcome
Fridge, microwave, oven, stovetop

Jackson House; Pets Welcome

10.0 out of 10, Exceptional, (13)
"Overflow holiday guests stayed at this cute, clean, comfortable home. A wonderful experience with exceptionally kind, engaged, owners! "
The price is ￥16,898
￥26,474 total
includes taxes & fees
Aug 25 - Aug 26
Jackson House; Pets Welcome
Harrison House; Litchfield, IL; Pets welcome
Property grounds

Harrison House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (11)
"Everything was in excellent shape and the fenced yard was great for the pups."
The price is ￥17,486
￥27,253 total
includes taxes & fees
Aug 25 - Aug 26
Harrison House; Litchfield, IL; Pets welcome
Cozy studio located in small town America, Bunker Hill, IL.
Property grounds

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

10.0 out of 10, Exceptional, (11)
"Great location, felt like it was home "
The price is ￥10,580
￥18,221 total
includes taxes & fees
Aug 25 - Aug 26
Cozy studio located in small town America, Bunker Hill, IL.
State Street House; 3-br house; PETS WELCOME; Litchfield
Private kitchen

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

10.0 out of 10, Exceptional, (8)
"Even cuter in person! It was the perfect stay for 4 girls traveling from various states. The house was clean, owners were communicative, and check out process was easy. We would stay here again. "
The price is ￥20,425
￥33,171 total
includes taxes & fees
Aug 25 - Aug 26
State Street House; 3-br house; PETS WELCOME; Litchfield
Cozy Historic Downtown Edwardsville Charmer
Private kitchen

Cozy Historic Downtown Edwardsville Charmer

9.6 out of 10, Exceptional, (10)
"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
Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield
Smart TV, fireplace

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

Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield
Route 66 house; Litchfield IL; Pets welcome
Fridge, microwave, oven, stovetop

Route 66 house; Litchfield IL; Pets welcome

10.0 out of 10, Exceptional, (15)
"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 ￥15,282
￥24,761 total
includes taxes & fees
Aug 28 - Aug 29
Route 66 house; Litchfield IL; Pets welcome
Chestnut House; Litchfield, IL; Pets Welcome
Fridge, microwave, oven, stovetop

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
Kirkham Train House; PETS WELCOME
Fridge, microwave, oven, stovetop

Kirkham Train House; PETS WELCOME

Kirkham Train House; PETS WELCOME
1 Bedroom Furnished Basement Apartment Close to Phillips 66
Property grounds

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
Living area

Sunny Mid-Century Modern duplex with a garage

Sunny Mid-Century Modern duplex with a garage
Alton Illinois Intimate Events Venue
Dining

Alton Illinois Intimate Events Venue

Alton Illinois Intimate Events Venue
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

Baymont by Wyndham Litchfield

Baymont by Wyndham Litchfield

10/10 Excellent
"Clean safe for overnight stop"
Dorcas 1-night trip
Posted 1 day ago
Baymont by Wyndham Litchfield

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 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 Beaver Dam State Park 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.