Springfield Holiday Houses

A sign for the African American History Museum in Springfield and Central Illinois.

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Our top choices for Springfield holiday homes

A modern kitchen with stainless steel appliances, white cabinetry, and a window with a view of the outdoors.

1. Oldtown Guesthouse

Oldtown

Don B.

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a large bed, a nightstand, a window, and a view of the outdoors.

2. Sun Valley Overlook A-Frame | Wow Views + Hot Tub

Augusta

Tom H.

includes taxes & fees

24 Sept - 25 Sept

A garden with a variety of flowers and plants, a wooden structure, and a white fence.

3. Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cumberland

Toni R.

includes taxes & fees

28 Sept - 29 Sept

A two-story house with a front porch, a garage, and a large lawn.

4. Country Roads Cottage - Amish Living Reimagined in WV - HOT TUB

Augusta

Everett E.

includes taxes & fees

28 Sept - 29 Sept

A hot tub under a covered area with string lights, surrounded by a natural landscape and a wooden structure in the background.

5. Farmhouse in the South Branch River Valley with idyllic views and country charm

Romney

AnnaDella J.

includes taxes & fees

24 Sept - 25 Sept

An outdoor hot tub with a fire, a wicker basket with bread, and a bottle of wine.

6. Luxury Nomadic Yurt Romantic Getaway with Sauna and Hot Tub on private 8 acres

Keyser

Cole D.

includes taxes & fees

29 Sept - 30 Sept

A living room with a sofa, a coffee table, and a patterned rug.

7. Newly renovated 1905 house, within walking distance to all downtown attractions!

Cumberland

includes taxes & fees

5 Oct - 6 Oct

A hot tub with two glasses of red wine on a wooden tray.

8. GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV

Berkeley Springs

Matthew C.

includes taxes & fees

27 Sept - 28 Sept

A deck with a white railing, a table, and a view of a forested landscape.

9. Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale

La Vale

"This was a really lovely place to stay on a quick trip to Cumberland. It’s in a quiet neighborhood with a great Mountain View off the back deck. The property was clean and the owner was communicative. Convenient to town and the scenic railroad. The only complaint I have was the thermostat was auto set to a temp that was too high for the summer, and I had to wake up twice to make it cooler. Other than that it really is exactly as advertised and I would stay again."

Kasey G.

includes taxes & fees

5 Oct - 6 Oct

A rustic cabin with a wooden deck and stairs leading to the entrance.

10. Wooded Nest, Cozy 3BR Chalet Near Spas & Hiking

Berkeley Springs

Brittany W.

includes taxes & fees

28 Sept - 29 Sept

A room with a wooden ceiling and large windows.

11. Cozy Mountain Retreat with Hot Tub & Fire Pit

Great Cacapon

includes taxes & fees

28 Sept - 29 Sept

A hot tub on a balcony with a tent in the background.

12. Cozy Chalet & Luxe Domes Retreat w/Stunning Views

Augusta

includes taxes & fees

5 Oct - 6 Oct

A spacious living area with a stone fireplace, wooden ceiling beams, and a large window overlooking a deck.

13. Family-Friendly Cabin – Games, Fire Pit, & Nature!

Berkeley Springs

"We had a family gathering over Christmas and this was the perfect place for us! The house was beautiful! It was clean, spacious, very comfortable and the kitchen had all the things needed to cook meals for a group.The great room (on the main level) was a wonderful place to sit and relax, read or visit and the downstairs was a fantastic place to play games and watch TV. The property is large, wooded, very quiet and private. The house has lots of outdoor space, a nice screened in porch and two...

Christy B.

includes taxes & fees

28 Sept - 29 Sept