Historic Route 66 Cottages

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
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

Our top choices for Historic Route 66 cottages

A single-story house with a covered porch, a front door with a red doorbell, and a number '205' on the front.

1. Charming Thomas cottage for 2 with large carport

Thomas

Susan E.

includes taxes & fees

16 Oct - 17 Oct

A single-story house with a garage, surrounded by a grassy lawn and trees.

2. Recently Remodeled Route 66 Retreat! Claremore Gem

Claremore

includes taxes & fees

4 Oct - 5 Oct

A living room with a sofa set, a coffee table, a fireplace, and a TV mounted on a wooden wall.

3. Quaint 2 bedroom cottage in the pines

Fort Valley

Carlos

includes taxes & fees

2 Nov - 3 Nov

A small wooden cabin with a porch, a satellite dish, and a gravel driveway.

4. Dragonfly Meadows Guesthouse

Stoutland

Denise

includes taxes & fees

6 Oct - 7 Oct

A single-story house with a gabled roof, a front porch with two chairs, and a small front yard.

5. New 1 bedroom cottage right off Route 66.

Galena

JJ J.

includes taxes & fees

3 Oct - 4 Oct

A small, single-story building with a dark exterior and a white door, surrounded by a gravel driveway and sparse vegetation.

6. Fireside Retreat

Afton

Andrea H.

includes taxes & fees

5 Oct - 6 Oct

A small, green wooden cabin with a snow-covered roof, surrounded by trees.

7. Secluded cottage on 8 acres at Bell Cow Lake. Come let your cares slip away!

Chandler

Gabriela

includes taxes & fees

30 Oct - 31 Oct

An aerial view of a rural property with two houses, a dirt road, and a lake in the background.

8. Charming 1-bedroom cottage with WiFi and AC near Monkey Island and Grand Lake

Afton

Marty H.

includes taxes & fees

3 Oct - 4 Oct

A covered porch with a view of a lake and distant land.

9. Castaway at CrossTimbers Marina

Sperry

Johannah

includes taxes & fees

15 Oct - 16 Oct

A covered porch with a table and chairs, overlooking a body of water and trees.

10. Eagles Nest at CrossTimbers Marina

Sperry

Angela W.

includes taxes & fees

14 Oct - 15 Oct

A wooden deck with a wooden chair and a stone fireplace.

11. Lake Views & Fall Colors | Cozy Cottage + Kayaks

Jay

Jon J.

includes taxes & fees

4 Oct - 5 Oct

A single-story house with a front porch, a stone foundation, and a red staircase.

12. Remodeled Tulsa House w/ Yard ~ 4 Mi to Downtown!

Tulsa

Alex

includes taxes & fees

4 Oct - 5 Oct

A garden pathway with a wooden fence, potted plants, and a small tree.

13. Historic Guesthouse in Central Oklahoma City

Central Oklahoma City

Scott E.

includes taxes & fees

3 Oct - 4 Oct

A cozy porch with a white bench and a pink table, stone walls, and a view of a grassy field.

14. Granny's House by Coleman Vault

Marionville

Patty O.

includes taxes & fees

4 Oct - 5 Oct

A small, single-story building with a wooden deck and a staircase leading to a door.

15. R&R Retreat w/Lake Access. Grand Lake Grove, OK

Wyandotte

Alena B.

includes taxes & fees

12 Oct - 13 Oct

A covered outdoor area with a view of a large body of water, a white railing, and a round table.

16. Shoreside at CrossTimbers Marina

Sperry

Jeff L.

includes taxes & fees

15 Oct - 16 Oct

A modern house with a deck, large windows, and a pathway leading to the entrance.

17. Wooded Oasis.Free Bottle of Wine+Breakfast+Golf

Caseyville

amy m.

includes taxes & fees

6 Oct - 7 Oct

A kitchen with dark cabinets, a white dishwasher, and a tiled backsplash.

18. Charming 3-bedroom cottage with WiFi and AC in delightful downtown Guthrie

Guthrie

Nancy H.

includes taxes & fees

4 Oct - 5 Oct

A single-story house with a front porch, a front door, and a small front yard.

19. Charming Cozy Cottage with a Brand New Bathroom!

Lebanon

Fred L.

includes taxes & fees

5 Oct - 6 Oct

A wooden deck with two Adirondack chairs, surrounded by lush greenery and trees.

20. KayaksForest ViewFirepitKingLakefront*Gameroom

Grove

Glynn S.

includes taxes & fees

6 Oct - 7 Oct

View all properties

Find holiday rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top Historic Route 66 Hotel Reviews

Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood

8/10 Good

"Property was fine. Looks shabby outside. Room was clean. A little Worn but fine."

Terrace #1 | 2 BR/1BA | Spend Spring in Flagstaff!

10/10 Excellent

"This stay was AWESOME ! The beds were so comfortable, the home was immaculate.m and we felt so incredibly safe so close to Downtown. We had the pleasure of staying here with our puppy and the accessibility to the backyard was absolutely fantastic. Our stay was met with calm and serene every time we stepped foot in the door. Everything that we wanted to explore was walking distance. The host responded quickly with any questions we had. "

Terrace Main | 5BR/3BA | Spend Spring in Flagstaff!

8/10 Good

"The house was ok. There was an issue with the outlets not working in one room, the dishwasher was not secured and would fall forward when the trays were pulled out, and one of the pans in the kitchen needs to be replaced. Other than that, it was fine."

Find out more about Historic Route 66