Holiday houses in Pittsfield

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Top-rated holiday rentals in Pittsfield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A bright living area is presented, featuring a comfortable sofa and loveseat arranged around a wooden coffee table. Natural light filters through the large window, illuminating a patterned area rug beneath. A decorative mirror and potted plant add subtle touches of style.
Home in Quincy
4.95 out of 5 average rating, 117 reviews

Beautiful Renovated Home at 507

Kick back and relax in this calm, stylish space. Amazing location! Directly across the street from Quincy’s finest shopping outlets - TJ Maxx, Kohls, DSG, Kirlins -Hallmark, Old Navy, Carters, to name a few. 3 minutes to Walmart, 5 to Target! 10 minutes to Quincy University, Blessing Hospital, or QMG. Yet, located in a safe, peaceful, and quiet neighborhood, on the edge of town, and just a quick 15 minute(or less) drive to the best food, drinks, and attractions downtown Quincy, IL has to offer!

Top Guest favourite
The cabin's exterior is viewed from a grassy area, showcasing a covered porch with steps leading up to the entrance. Two white doors are framed by light-colored walls, while a red wreath adds a touch of color. The natural surroundings feature trees in the background.
Cabin in Winchester
4.96 out of 5 average rating, 179 reviews

Container Home GREAT Countryside Views COZY Stay

Singing Hills Cabin is the ultimate getaway for fresh air and an unbeatable view of the countryside. Enjoy morning coffee as the sun rises from the large front porch. This newly renovated container home is perfect for small families looking for an outdoor escape or for couples seeking a romantic getaway. It is located on a 40 acre hobby farm, so do not be surprised if you see cows and other wildlife during your stay! The best deer hunting, river access, and restaurants are located minutes away.

Top Guest favourite
The kitchen features white cabinetry and modern black appliances. A spacious countertop offers seating at two metal stools. Natural light filters through the windows, illuminating the wooden flooring and classic tile backsplash.
Home in Hannibal
4.96 out of 5 average rating, 177 reviews

Little House in the Hollow

Enjoy a private peaceful setting that is Conveniently located. Large fenced in yard for the kids and/or pets. Also has a 4 person hotub which is available year-round. The house is fully stocked for convenience. The house also has covered parking, outdoor fire pit, BBQ grill a play place for the kids and more. You will be within walking distance of 2 National Landmarks (Mark Twain Cave, Cameron Cave) as well as our Winery and Giftshop. Located just two miles from Hannibal's Historic District.

Top Guest favourite
The building features a classic architectural style with large bay windows and ornate detailing. The ground floor includes glass storefronts, while the upper level showcases decorative molding and an inviting façade in a warm maroon color.
Loft in Virginia
4.94 out of 5 average rating, 185 reviews

Two Doors Down Loft, Virginia-Lincoln territory!

Located in VIRGINIA, IL-Our fantastic, urban vibed loft sits on the town square across from the town's historical courthouse. We are 30 minutes from Springfield, 15 minutes from Jacksonville and in the middle of Abe Lincoln territory and historical markers. The loft is also surrounded by lovely wineries and wildlife parks. Be sure to thoroughly read our listing to ensure that we'll meet all of your needs in exploring our unique area. Two Doors Down is a hidden gem listed at a super price!

Top Guest favourite
A bright kitchen area is highlighted by light wood cabinetry and a green patterned backsplash. Appliances include a white refrigerator and kitchen essentials situated on shelves. Two upholstered stools are positioned at the kitchen island, complementing the wood flooring and woven rug in the living space.
Loft in Pittsfield
4.91 out of 5 average rating, 86 reviews

Historic Loft on Adams

Charming updated loft-style studio in the heart of quaint downtown Pittsfield. Located within walking distance of restaurants, the historic courthouse, and local bars. This private apartment is perfect for weekend getaways, staycations, or even a cozy home base to work from remotely. The view of our Pike County Courthouse from any window is gorgeous and the historic building has so much character, all in a convenient, central location. This second floor loft is completely private.

Top Guest favourite
A two-story tiny house is positioned at the end of a grassy path, surrounded by native grasses and trees. A rainbow flag gently waves in the breeze, and several trees display autumn foliage, adding color to the serene landscape.
Townhouse in Murrayville
4.98 out of 5 average rating, 325 reviews

Peace on the Prairie Too - Tiny House

Need a break from Politics? Peace on the Prairie accepts all guests for who they are rather than what some might wish them to be. Whether it’s a business trip, romantic time together with your significant other, a family vacation, a girl's time away, a secluded spot to work on your music, writing, art, star gazing, or a reconnection with nature, you'll find your inspiration and renewal in this natural rural setting of 23 acres of restored prairie, timber, and wetlands?

Top Guest favourite
A cozy dining area is highlighted by a wooden table surrounded by four chairs. Antique stained glass windows illuminate the space with soft colors. A small kitchen area is visible in the background, featuring modern appliances and bright cabinetry.
Cabin in Jacksonville
4.98 out of 5 average rating, 377 reviews

Bunkhouse Seventy-Four

Once used by seasonal farm labor in the 1930s, Bunkhouse Seventy-Four is a fully restored historic bunkhouse with all the modern amenities for a comfortable getaway. Perfect for couples, it features a full kitchen, bath, queen bed, a spacious porch, beautiful antique stained glass windows, a private outdoor soaking tub (Apr-Nov) on a 7 acre hobby farm. Also check out our listing, Audrey’s Abode, which is next door. Pets are welcome but we charge a $25 pet cleaning fee.

Top Guest favourite
A single-story home with a welcoming covered porch is displayed. Greenery surrounds the house, and flower pots hang near the entrance. The porch features a pair of outdoor chairs, inviting relaxation. The light-colored exterior is complemented by a well-maintained lawn.
Home in Bowling Green
4.96 out of 5 average rating, 160 reviews

Home away from Home

A relaxing and inviting home away from home with everything that you need for your stay in Bowling Green. During your stay here you will enjoy the smart TV, free Wi-fi, and washer and dryer. A comfortable night’s sleep is a given with a brand new mattress on all three beds (queen bed and two twin beds). Located on the north side of town, you are less than 1 mile from Wood’s Smoked Meats and Bankhead’s Chocolates. This is an ideal base for your Pike County, MO visit.

Top Guest favourite
The historic brick building, featuring a green roof, is surrounded by open grassy areas. Several flags are displayed in front, symbolizing heritage. Multiple sets of stairs lead to various entrances, highlighting the structure's two-story design and outdoor spaces for guests to enjoy.
Home in Pittsfield
4.85 out of 5 average rating, 248 reviews

Florence Guest House

This 1,200 sq. ft. PRIVATE BOOK is a 175 year old building that Abe Lincoln stayed in. Central A/C, Forced air heat, Two decks (one overlooking the Illinois River), burn pit, outside grill, fully equipped kitchen, screened in porch, ample parking, access to the Illinois River/ boat ramp near, tie up on Our Private Lots! NOTE: RECENTLY HAD Guests' wanting to "JUST GET AWAY" for A Time!!! PRIVATE TIME ALONE, Guaranteed!!! NEW KEURIG; BRING YOUR OWN K-CUPS!!!***

Guest favourite
A cozy living area features a black sofa with decorative pillows and a wooden coffee table at its center. Natural light streams through two windows, illuminating the neutral tones and textured decor. A small accent chair and a patterned rug complete the inviting space.
Loft in Winchester
4.94 out of 5 average rating, 144 reviews

The Bike Flat

Visit historic Winchester and explore what our quaint community has to offer! This stylish place to stay is perfect for a quiet getaway and can accommodate groups thanks to its ample space. You can bring the family or plan a getaway with friends. The flat is located above a newly opened bicycle and coffee shop that also offers craft beers and wine. We hope you will consider choosing our rural accommodations for a trendy and relaxing experience!

Guest favourite
A single-story home is set within a grassy area, surrounded by trees exhibiting autumn colors. The structure features a red front door and multiple windows. A building is visible to the right, and the landscape includes a backdrop of cornfields under a clear blue sky.
Farm stay in Coatsburg
4.97 out of 5 average rating, 125 reviews

Your Getaway in the country!

Relax with the whole family at this peaceful place to stay. Our 3 bedroom, 2 bath home is ready for you to enjoy! Peaceful, relaxing & fun times! Outdoor seating & bbq, 3 acres to roam with fishing next door. Plenty of amenities nearby including golfing, fine dining, several local wineries & more. Overnight, weekends, weekly or longer, welcome to The Getaway! Search YouTube for "The Getaway Camp Point Airbnb" to see our property

Guest favourite
A rustic log cabin, set on a grassy area, features a covered porch with rocking chairs. Sunlight filters through the surrounding trees, illuminating the wood exterior and stone steps. A small white cat is seen resting on the porch, adding a charming touch to the serene setting.
Place to stay in Virginia
4.98 out of 5 average rating, 361 reviews

Virginia Lake Getaway/Fishing/Hot Tub/Hammock

Welcome to your charming log cabin located in Virginia, IL. This 1-bedroom, 1-bathroom cabin is designed to provide you with rustic comfort, making your stay truly exceptional. Nestled on a bluff overlooking the serene Virginia Lake, this 1850's log cabin combines historic charm with modern luxuries. Set on 80acres of timber and water for you to explore. Hike, kayak, fish or just relax and enjoy!

Popular amenities for Pittsfield holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Pike County
  5. Pittsfield