Holiday houses in Cumberland

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Top-rated holiday rentals in Cumberland

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Top Guest favourite
The kitchen features a large wooden island with a white base, surrounded by black stools. Wood ceiling beams complement the light wood cabinetry and black appliances. Natural light streams through the windows, highlighting the modern sink and contemporary fixtures.
Home in Greenwood
4.97 out of 5 average rating, 118 reviews

Cheerful & cozy farmhouse 2 bedroom home

Kick back and relax in this stylish space that is right down the street from Old Greenwood & less than 20 mins to Downtown Indianapolis. This tastefully updated home exudes "peaceful and cozy" w/ 2 bedrooms w/ brand new luxury king sized mattresses, 1.5 baths w/ walk-in tile shower, charming living room w/55" TV, Fiber internet, front load washer and dryer, dining table for 4+ bar seating, and a tranquil backyard space that is fully fenced, (dog friendly for an extra $75 cleaning fee, NO CATS).

Guest favourite
A charming historic home with a two-story structure displays a combination of deep purple and mustard yellow siding. An American flag hangs from the porch, which features decorative woodwork and inviting entry steps surrounded by landscaped gardens.
Home in Greenfield
4.94 out of 5 average rating, 123 reviews

Updated Historic Home, in the Heart of Greenfield

A one-of-a-kind historic gem located three blocks from Downtown Greenfield on Main Street and only a 35-minute drive to downtown Indianapolis. Enjoy the entire downstairs of this completely upgraded late 1800's wooden frame home featuring all original wood flooring and beautiful antique furniture pieces. Filled with modern luxuries; including 3 flat screen tv's with streaming services included, an upgraded 8 burner gas stove, dishwasher, full-size washer and dryer, and outdoor barbecue grill.

Guest favourite
A spacious guest suite is illuminated by natural light from large windows. A cozy seating area is visible beside a desk and a wall-mounted television. Attractive bedding with striped patterns adorns a sizable bed, complemented by a plush carpet and tasteful decor.
Guest suite in Greenfield
4.91 out of 5 average rating, 105 reviews

Peaceful & Luxurious Suite

Our guest suite is close to Indpls--approx. 20 min from downtown. You’ll love our place because of the quiet & serene environment that's just outside of the city. We sit on an acreage close to the I70/Mt Comfort Road Exit making for quick access to and from the interstate. Our suite is in the front corner of our home. It has a private entrance with porch. It looks out into a garden that has a pond with fountain along with seating under a pergola. It has high ceilings and is very spacious.

Top Guest favourite
The entryway features a brick façade with a green front door and a welcoming door mat. A tall sign displaying 'WELCOME' stands beside the door, complemented by potted greenery for a touch of nature.
Home in Indianapolis
4.93 out of 5 average rating, 129 reviews

Cozy 3 bedroom home

Spacious 3 bedroom 2 bathroom ranch home. Large fenced backyard with mature trees and fire pit. Spacious patio. Fully furnished with high speed wifi. Full size washer and dryer. Great place to stay if attending Ruoff, which is only 15 minutes away. Close to geist reservoir and Wolfies restaurant. 6 minute drive to Walmart, Kroger, Kohls and other shopping plazas. 5 minute drive to Daniel's Vineyard which offers live music and different drink specials. Keyless entry to make checkins easy.

Top Guest favourite
A spacious living area features muted gray walls and a large picture window dressed in patterned curtains. A recliner couch, accented with decorative pillows, is paired with a Moon Pod therapeutic bean bag chair. A wooden coffee table is centered on a patterned area rug.
Apartment in Indianapolis
4.94 out of 5 average rating, 175 reviews

Your Comfy Indy Suite

Safe, peaceful suburban neighborhood. Only 15 minutes from downtown Indy. Easy drive to IUPUI, Convention Center, Lucas Oil Stadium. Free parking at your door. Great for long term stays. Fully stocked kitchen. Free laundry facilities. Padded office chair and fast Wi-fi at your laptop workstation. 55" Vizio 4K HDR Smart TV. Moon Pod Zero Gravity Chair for therapeutic relaxation. Queen-size Sealy Plush Pillowtop hybrid mattress, with 2 standard foam pillows and 2 MyPillows.

Top Guest favourite
The dining area features a round wooden table surrounded by six chairs, providing space for group meals. A chandelier hangs above, and a stone fireplace adds character. A cozy living room is visible in the background with comfortable seating and large windows allowing natural light.
Home in Bargersville
4.98 out of 5 average rating, 181 reviews

Cozy Cottage 14 mi. S of Indy In Bargersville, IN

Relax and unwind in this spacious three bedroom, one bath ranch home situated on one acre. The house is on about 1/2 the acre. The house is situated in Bargersville, Indiana in Johnson County, IN on the southern edge of Greenwood located in Center Grove Area. The garage area is not accessible. Vivint Home Security system with doorbell camera. I will email your unique code once you complete reservation. Central a/c & heat. Bedroom off kitchen has window a/c. We live about 1/4 mile away.

Top Guest favourite
A spacious bed is centered against a warm-toned accent wall, framed by two bedside lamps. The bed is layered with a decorative throw, adding texture to the neutral bedding. A simple wall hanging complements the decor, enhancing the serene ambiance of the room.
Home in Irvington
4.9 out of 5 average rating, 335 reviews

Private Irvington Carriage House

This spacious, newly renovated carriage house comfortably sleeps 4. Private entrance leads to a meticulously cleaned, peaceful abode- only 10 minutes to downtown Indy!! Enjoy walks with a cup of coffee to take in all of Historic Irvington, or simply relax in this quiet retreat and enjoy the only table shuffleboard in a private rental in all of Indianapolis! A fully stocked kitchen allows for longer stays. We offer no-contact check-in, but we are nearby to help out if needed.

Top Guest favourite
An expansive yard is featured, bordered by mature trees and lush grass. A concrete driveway leads to the charming bungalow-style suite on the right, showcasing a well-maintained exterior with traditional features. A neighboring structure and a natural landscape complete the tranquil country setting.
Guest suite in Indianapolis
4.91 out of 5 average rating, 164 reviews

THE CUMBERLAND/Indianapolis, Indiana

"Country Living with City Convenience" 15 minutes from the town of Greenfield 15 minutes from The Academy Volleyball Club 23 minutes from Gainbridge Fieldhouse / Lucas Oil Stadium / Convention Center 25 minutes from downtown Indianapolis 28 minutes from Ruoff Music Center 29 minutes from Indianapolis Motor Speedway 30 minutes from Clowes Memorial Hall (Butler University) 31 minutes from Indianapolis International Airport 35 minutes from Grand Park Sports Campus

Top Guest favourite
A spacious bedroom is featured with a plush area rug and sloped ceilings. A large bed, adorned with a textured blanket, is accompanied by a comfortable armchair and a side table. Natural light filters in through a window, illuminating the room.
Guest suite in Greenfield
4.96 out of 5 average rating, 217 reviews

Greenfield CountryCottage-minutes to downtown Indy

Beautiful, relaxing country cottage room is a perfect place to stay for your business trip or vacation. We provide clean and comfortable furnishings, along with a kitchenette and coffee bar. You will have total privacy, including a private driveway and entrance. Relax on the balcony with your morning coffee or after a busy day. Our room is located on a 2nd story with a private stairway to the entrance. Special discount on stays 3 days or more!

Top Guest favourite
A modern kitchen is presented, featuring dark cabinetry and professional-grade stainless steel appliances. Open shelves display glassware and decorative items. A patterned rug contrasts with the light hardwood floor. A view into the adjoining living area can be seen, with natural light filtering through a window.
Home in Glendale
4.99 out of 5 average rating, 103 reviews

Designer 2 bedroom, 1 acre retreat in the city.

Welcome to the Honeysuckle Homestead. This is a completely updated 2 bedroom, 1.5 bathroom cottage with designer updated decor, nestled on a 1 acre wooded lot. Enjoy a peaceful morning on the trails or cooking a meal in a fully stocked kitchen. Adventure minutes away to Broadripple Avenue, Keystone Fashion Mall, Butler University, or a 15 minute drive to downtown Indianapolis. Quiet, safe neighborhood with ample parking and local ownership.

Top Guest favourite
A spacious bedroom is illuminated by natural light, featuring a large bed adorned with a colorful floral bedspread. A ceiling fan adds to the comfort, while a small dining area with a table and chairs is positioned nearby. The entrance to a bathroom is visible through an open door.
Home in Westfield
4.95 out of 5 average rating, 153 reviews

10 Min to Grand Park | Family-Friendly Quiet Area!

Nestled in a safe and beautiful neighborhood in the heart of Westfield, our home offers the perfect balance of peace and convenience. The area is quiet, welcoming, and ideal for unwinding after a full day of activities, yet close enough to everything you might want to explore during your stay. Tree-lined streets, friendly neighbors, and a calm atmosphere make this an ideal retreat for both short visits and longer stays.

Top Guest favourite
An open-concept living space features a large, grey sectional sofa with a vibrant orange throw pillow. A rustic coffee table sits in front, and the kitchen area includes modern appliances. A dining table, barstools, and two desks provide ample space for activities, complemented by natural lighting from multiple windows.
Guest suite in Indianapolis
4.99 out of 5 average rating, 763 reviews

La Cochera Indy East - No Cleaning Fee!

Contemporary, clean carriage house on a large East Indianapolis property. Private keypad entrance with easy self check-in and on-site parking for up to two cars. Comfortably sleeps the whole family with a king bed and a stylish queen-size sofa bed. Important details: • No parties or events • Local guests require prior approval • Early check-in available for $35 (when possible) • $20–$40 linen fee for use of sofa bed

Popular amenities for Cumberland holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Marion County
  5. Cumberland