Holiday houses in Jamestown

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Top-rated holiday rentals in Jamestown

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

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Guest favourite

Home in Lebanon

Crossroads: Endless entertainment in Lebanon

Stay in a huge, fully remodeled historic home with something to keep everyone happy- golfing, karaoke, 6 arcade games, a Playstation, board games, TVs with ESPN, a pool table, toys & a bar. Cook to your heart's content in our fully stocked kitchen, inc. a Crockpot, coffee bar, blender, 5 types of grills/smokers (outside of course). This is in walking distance to downtown Lebanon and sleeps 12 across 4 bedrooms (plus 3 full bathrooms). There are multiple seating areas and outdoor areas to enjoy.

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 20 reviews

Top Guest favourite

Farm stay in Avon

Avon Farmhouse-Sleeps 14 Game Room, Hot Tub, Pond!

Spacious Family Retreat with Pool, Hot Tub & Game Room – Sleeps 14 | Avon, IN Gather your favorite people and escape to this stunning countryside retreat in Avon, Indiana — where comfort, fun, and relaxation come together on 10 peaceful acres. Designed for families and large groups, this spacious home comfortably sleeps up to 14 guests and offers every amenity you need for a memorable stay — including a private pool, hot tub, game room, and a scenic pond perfect for fishing or quiet reflection.

LocationFamilyParking

5.0 out of 5 average rating, 49 reviews

Guest favourite

The front view of the house showcases a classic white exterior with a welcoming entrance. Lush green shrubs frame the entrance, and a driveway leads to a detached garage seen in the distance. A clear blue sky complements the home's inviting appearance.

Home in Brownsburg

Cozy and Comfortable, great Fall destination!

This house is an old model, but it is a cozy comfortable house and will everything you need for your stay. In Brownsburg it's only minutes from the Indianapolis Raceway Park and the Lucas Oil Raceway. There is plenty of entertainment and food options within driving distance and a couple you can walk to. I have wifi and streaming with a Fire Stick available on the TV. I do not have cable. I have Netflix, Disney, HBO. Feel free to bring your own Streaming Devices to access your own shows.

FamilyValueLayout

4.84 out of 5 average rating, 133 reviews

Guest favourite

The exterior of the A-frame cabin is framed by lush greenery, showcasing a wooden deck with potted plants at the entrance. The black exterior features large windows, allowing natural light to brighten the interior spaces. Gravel pathways lead to the cabin amidst the tranquil wooded surroundings.

Cabin in Rockville

Walker Getaway | A-Frame•Hot Tub•Decks•Lake•Hiking

Escape to Walker Getaway, an updated A-frame cabin on 5 private wooded acres w a creek, hot tub, fire pit and multi-level decks. Located across from Walker Boat Ramp and only 5 minutes from Raccoon Lake Beach. Use the provided Indiana State Park pass to explore nearby Turkey Run and Shades. Fully stocked and family-friendly, it’s perfect for couples, friends, or families looking to relax, recharge, and explore Parke County. Walker Getaway is where modern comfort meets Indiana’s natural beauty.

LocationFamilyCondition

4.99 out of 5 average rating, 106 reviews

Top Guest favourite

The exterior of the primary house is visible, featuring a wooden facade and large windows. A spacious deck area is seen with lounge chairs and a view of the surrounding trees. The detached bunkhouse is located in the background, offering additional accommodation.

Home in Crawfordsville

Cottage on Lake Holiday

This well appointed, nicely finished, heated & cooled, home on Lake Holiday is a great place to get away. Only 15 minutes to Shades State Park & 20 minutes to Turkey Run. In the primary house is a queen bed, air mattress, & 2 full bathrooms. The bunkhouse has 2 queen beds. Please note bunkhouse is detached from the primary house. Guests will have to briefly walk outside to access a bathroom. The outdoor shower is not operable October through April. Lake access is not available for guests.

FamilyValueGetting around

5.0 out of 5 average rating, 14 reviews

Guest favourite

A charming cottage exterior is framed by a blossoming tree in the foreground. The wooden deck features a railing and is accessible through a glass-paneled door. Nearby, lush green grass extends toward an open field in the background, suggesting a serene rural setting.

Farm stay in Thorntown

Heavenly Acres Farm and Learning Center

Experience a relaxing stay, spending time watching chickens happily foraging or barn animals as they graze in the pasture. Take a walk by the creek, taking in the country sunset.Enhance your experience by interacting with the animals during a farm tour or helping with daily chores. We also offer a variety of learning opportunities as we share how we process fiber, health care for animals or maybe a simple hay ride. Here at Heavenly Acres we want to provide you with a unique farm experience.

LocationFamilyBathroom

4.97 out of 5 average rating, 214 reviews

Guest favourite

A charming exterior of the home is displayed, featuring a welcoming front porch with hanging planters. Lush green grass and colorful flower beds surround the property, while a paved path leads up to the entrance. A clear blue sky enhances the inviting appearance.

Home in Lizton

3 Bed + 2 Bath Family Home w/ Game Room

Welcome to our charming home in Lizton, IN! Just minutes from two stunning wedding venues and a short 30-minute drive to downtown Indianapolis, this recent remodel offers comfort and convenience. Enjoy a spacious, fully stocked kitchen with a coffee bar, a cozy living room with a fireplace and TV, a laundry room, and a lovely backyard seating area. With three bedrooms and two baths, our home comfortably accommodates eight guests. Perfect for wedding guests, families, or anyone visiting Indy!

ValueFamilyDecor

4.97 out of 5 average rating, 90 reviews

Guest favourite

A spacious living area is highlighted by a modern fireplace and a large wall-mounted television. Comfortable seating is arranged around a decorative rug, with soft lighting provided by recessed fixtures. A dining area with a wooden table and chairs is visible in the background.

Home in Brownsburg

Charming 3-Bdrm Cottage w/Yard!

This 3-bedroom cottage in a charming country setting is perfect for your trip to Indianapolis. This charming property offers a family friendly retreat for guests. Just minutes from Brownsburg and Avon both featuring wonderful dining experiences. While also near dozens of other attractions! Indianapolis Motor Speedway - 15 miles Lucas Oil Raceway at Indianapolis IRP - 7 miles Downtown Indianapolis - 20 miles Children's Museum of Indianapolis - 17 miles Indianapolis Airport - 21 miles

FamilyLocationQuiet

5.0 out of 5 average rating, 12 reviews

Guest favourite

Home in Brownsburg

Walkable Downtown Home | 3 King Beds + Cozy Charm

Your family will love this centrally located 1920s home with over 3,100 square feet of space to relax and enjoy! This charming 4-bedroom, 3-bathroom house blends classic character with modern comfort. Step outside and you’re just a short walk from all the new Brownsburg has to offer, including great restaurants, local bars, playgrounds, and walking trails. Whether you’re here to explore or simply kick back, this home has everything you need for a comfortable and memorable stay.

LocationFamilyTV

4.92 out of 5 average rating, 26 reviews

Top Guest favourite

A charming exterior of the lodge is featured, showcasing a wooden porch supported by exposed beams. A wedding dress is displayed on a hanger, highlighted against the rustic backdrop. Lush green plants and a decorative bench add to the inviting atmosphere.

Cabin in Crawfordsville

Townsend Lodge at Hidden Hollow Farm

The lodge is a very private/secluded setting located on 62 wooded acres. Everything nature has to offer is just outside the door. Enjoy the trails, garden ponds, or just relax on the porch and listen to the birds sing all day long. Inside you will find all the comforts of home along with fireplace, cabin decor, and walk-in shower with unlimited hot water. Perfect place for a couples romantic getaway or gatherings for holidays, bachelorette/bachelor party, and more.

FamilyValueCheckout

4.94 out of 5 average rating, 271 reviews

Top Guest favourite

The exterior of a two-story guest house is surrounded by autumn foliage, showcasing wooden decking with a railing. The entrance features large windows, allowing natural light to brighten the space. A pathway leads from the front, bordered by seasonal plants.

Guesthouse in Brownsburg

Cozy Guest House in the Big Woods

Guest house located in the rear grounds of main home. Sidewalk access. 20 minute drive to downtown Indy.Full kitchen & 3/4 bath. This means toilet, sink & 42" shower (no tub).Entire house can sleep 1-3. Price is for 2 guests. Add’l fees for add’l guests & pets (no pit bulls) The upstairs has a king bed & down stairs a twin futon. This area is heavily wooded so the occasional critter can be seen & there will be spiders from time to time (part of wooded living).

ValueLocationComfort

4.87 out of 5 average rating, 636 reviews

Guest favourite

A serene countryside landscape is captured at sunset, featuring a lush green field with round hay bales scattered throughout. The sun is setting, casting a warm glow over the expansive horizon, with trees lining the perimeter, providing a peaceful backdrop.

Farm stay in Danville

The Hobbit's Shire on 32 acres near Indianapolis

Welcome to our charming Hobbit’s Shire! Nestled in the countryside, this retreat offers a peaceful and relaxing getaway while still being located close to Indy!!! Enjoy our large backyard and sip your morning coffee on the patio while watching the sunrise or for a wonderful wine experience overlooking the backyard. Book your stay with us for a peaceful retreat or family getaway or an adventure filled vacation and create lasting memories.

LocationValueNearby

4.85 out of 5 average rating, 88 reviews