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Top Holiday Rentals in Raymond

Home is on the original 1926-1930 Route 66 alignment

10.0 out of 10, Exceptional, (87)
"A weekend stay at the Madison House is like a step back in time. The cute and cozy furnishings offer a comforting nostalgia nestled in a quiet neighborhood. The location was perfect for the purpose of our visit. Thanks for the sweet little time warp!"
The price is £114
includes taxes & fees
8 Jul - 9 Jul
Home is on the original 1926-1930 Route 66 alignment

Luxurious Otter Pointe

10.0 out of 10, Exceptional, (23)
"We loved the open indoor kitchen and living room space for gathering. The kids and adults enjoyed the various games in the gameroom and loft. It was also lovely to sit on the back porch in the morning and evening. Jason’s place is well-stocked and beautiful!"
Luxurious Otter Pointe

Private country setting with large indoor pool

9.4 out of 10, Exceptional, (16)
"Greatly enjoyed the property for our holiday get together for family from different directions. The kids especially enjoyed the pool and game room (also the sound system)!One mention would be that the kitchen could use new cooking items, particularly pans and cookie sheets. The bedrooms and bathrooms were quite satisfactory. Overall, it was a great place for our family! Thank you"
Private country setting with large indoor pool

Lake House off Route 66

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay! The Lake House was very clean and met our needs perfectly for our weekend getaway. The property manager was always very responsive! Our dog LOVED the doggy door and the fenced area!"
The price is £164
includes taxes & fees
6 Jul - 7 Jul
Lake House off Route 66

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

10.0 out of 10, Exceptional, (6)
"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!"
The price is £145
includes taxes & fees
30 Jun - 1 Jul
State Street House; 3-br house; PETS WELCOME; Litchfield

Spacious modernized historic home located in downtown Hillsboro.

The price is £159
includes taxes & fees
30 Jun - 1 Jul
Spacious modernized historic home located in downtown Hillsboro.

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

10.0 out of 10, Exceptional, (10)
"Great location, felt like it was home "
The price is £88
includes taxes & fees
30 Jun - 1 Jul
Cozy studio located in small town America, Bunker Hill, IL.

New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving

10.0 out of 10, Exceptional, (2)
"This cabin and grounds are so beautiful! It was a wonderful weekend stay for our family. The cabin was very clean and cozy and the grounds were like our own personal campground. We are already planning another stay next year!"
The price is £278
includes taxes & fees
3 Jul - 4 Jul
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving

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 £134
includes taxes & fees
27 Jul - 28 Jul
Jackson House; Pets Welcome

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

Plainview Vineyard Retreat by StayLage

2.0 star property
The price is £325
includes taxes & fees
6 Jul - 7 Jul
Plainview Vineyard Retreat by StayLage

Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks

9.4 out of 10, Exceptional, (8)
"Very relaxing fun place to stay!"
The price is £278
includes taxes & fees
30 Jun - 1 Jul
Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks

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."
Route 66 house; Litchfield IL; Pets welcome

Charming Hillsboro Home < 1 Mi to Downtown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Much nicer then a motel room."
Charming Hillsboro Home < 1 Mi to Downtown!

Chestnut House; Litchfield, IL; Pets Welcome

9.6 out of 10, Exceptional, (5)
"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 £129
includes taxes & fees
30 Jun - 1 Jul
Chestnut House; Litchfield, IL; Pets Welcome

The Carlinville Cottage

10.0 out of 10, Exceptional, (10)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
The price is £374
includes taxes & fees
6 Jul - 7 Jul
The Carlinville Cottage

Harrison House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (11)
"We loved the house, plenty of space and it was furnished with everything we could need. Highly recommend!"
The price is £138
includes taxes & fees
13 Jul - 14 Jul
Harrison House; Litchfield, IL; Pets welcome

Edwards House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (17)
"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!"
Edwards House; Litchfield, IL; Pets welcome

Charming Hillsboro Home < 1 Mi to Downtown!

2.0 star property
Charming Hillsboro Home < 1 Mi to Downtown!

Historic Blackman-Evans Home

6.0 out of 10, (1)
"I rated this stay a 3/5 star because I was not sent the password or directions for the house/stay and had been trying to get a hold of the house owner, VRBO, and Expedia people for hours before I had received a helpful phone call. I was calling consistently from 8:00pm-12:00am the night I was supposed to begin my stay, we were put on hold for a long period of time with the VRBO people, but finally the house owners received our multiple messages and unlocked the house at midnight. The house...
Historic Blackman-Evans Home
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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Frequently asked questions

Can I find a holiday rental in Raymond?

Yes, there are holiday rentals close to the most popular sights in Raymond, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Raymond has a good selection of bars. Make sure you have time to check out the golf courses and lake views during your trip.

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

The Carlinville Cottage: This holiday home rental outside of Raymond has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Raymond?

While you're exploring the area, Lake Lou Yeager and Piney Creek Ravine - State Natural Area are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Raymond Shoal Creek Golf Course and Litchfield Museum and Route 66 Welcome Center.

What are holiday rentals like in Raymond?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Raymond. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.