Jamestown Holiday Rentals

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Our top choices for Jamestown holiday rentals

Kit’s Cabin - Log Cabin Retreat in Indianapolis

Kit’s Cabin - Log Cabin Retreat in Indianapolis
Indianapolis
10.0 out of 10, Exceptional, (30)
"We loved staying in the cabin! It was a nice quiet spot to rest and relax! Would definitely stay again! "
United States
Krista K.
The price is AU$374
includes taxes & fees
4 Jan - 5 Jan 2026
Kit’s Cabin - Log Cabin Retreat in Indianapolis

Earthy Elegance Spacious 2BR 2BA 2 KingBeds GymWFH

Earthy Elegance Spacious 2BR 2BA 2 KingBeds GymWFH
Whitestown
10.0 out of 10, Exceptional, (7)
"Excellent place to stay, has everything you need "
United States
Kevin H.
The price is AU$379
includes taxes & fees
30 Dec - 31 Dec
Earthy Elegance Spacious 2BR 2BA 2 KingBeds GymWFH

Grandma's House - Classic Indy Charm

Grandma's House - Classic Indy Charm
Indianapolis
9.4 out of 10, Exceptional, (6)
"Check in was smooth and everything went great. "
United States
Chad J.
Grandma's House - Classic Indy Charm

Downtown Whitestown Retreat with King Suite, Private Pool & Spacious Backyard

Downtown Whitestown Retreat with King Suite, Private Pool & Spacious Backyard
Whitestown
10.0 out of 10, Exceptional, (3)
"Awesome house and backyard and great area for food and drinks "
United States
Kevin H.
The price is AU$551
includes taxes & fees
4 Jan - 5 Jan 2026
Downtown Whitestown Retreat with King Suite, Private Pool & Spacious Backyard

20 mins DT | Sleeps 9 | Sunrise Glow Spacious Gym

20 mins DT | Sleeps 9 | Sunrise Glow Spacious Gym
Whitestown
10.0 out of 10, Exceptional, (7)
"Very nice and clean apartment in a good location "
United States
chad/kelly m.
The price is AU$372
includes taxes & fees
1 Jan - 2 Jan 2026
20 mins DT | Sleeps 9 | Sunrise Glow Spacious Gym

20 mins DT | Sleeps 9 |Verdant Retreat SpaciousGym

20 mins DT | Sleeps 9 |Verdant Retreat SpaciousGym
Whitestown
10.0 out of 10, Exceptional, (3)
"Great place to stay, has everything you need "
United States
Kevin H.
The price is AU$395
includes taxes & fees
4 Jan - 5 Jan 2026
20 mins DT | Sleeps 9 |Verdant Retreat SpaciousGym

Charming 3-bedroom Country Cottage in Beautiful Brownsburg, IN!

Charming 3-bedroom Country Cottage in Beautiful Brownsburg, IN!
Brownsburg
10.0 out of 10, Exceptional, (11)
"This place was perfect it had everything you needed whether it be weekend or longer. We would definitely stay again. "
United States
Leslie O.
The price is AU$546
includes taxes & fees
1 Jan - 2 Jan 2026
Charming 3-bedroom Country Cottage in Beautiful Brownsburg, IN!

IRIE Living, Refresh Kg 2Bd+Gym+Pool, BRAND NEW!

IRIE Living, Refresh Kg 2Bd+Gym+Pool, BRAND NEW!
Whitestown
10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay, as frequent travelers for softball, we have been all over. This was one of the best we have stayed at. Very clean, great area, pool, gym, and several places to eat and shop around the corner! Highly recommend, if we are in town again we will definitely stay here."
United States
Chrissy R.
The price is AU$371
includes taxes & fees
31 Dec - 1 Jan 2026
IRIE Living, Refresh Kg 2Bd+Gym+Pool, BRAND NEW!

The Cozy Charcoal Cottage - w/Garage

The Cozy Charcoal Cottage - w/Garage
Brownsburg
10.0 out of 10, Exceptional, (6)
"Very nice"
United States
John H.
The price is AU$561
includes taxes & fees
11 Jan - 12 Jan 2026
The Cozy Charcoal Cottage - w/Garage

Decadent Haven Spacious 2BR 2BA King Beds WFH GYM

Decadent Haven Spacious 2BR 2BA King Beds WFH GYM
Whitestown
9.8 out of 10, Exceptional, (8)
"Amazing place to stay, has everything you need for a great trip."
United States
Kevin H.
The price is AU$426
includes taxes & fees
3 Jan - 4 Jan 2026
Decadent Haven Spacious 2BR 2BA King Beds WFH GYM

Opulent Suite Spacious Pond View King Bed WFH Gym

Opulent Suite Spacious Pond View King Bed WFH Gym
Whitestown
10.0 out of 10, Exceptional, (4)
"Amazing place to stay, has everything you need "
United States
Kevin H.
The price is AU$359
includes taxes & fees
2 Jan - 3 Jan 2026
Opulent Suite Spacious Pond View King Bed WFH Gym

Entire house in Speedway! Pool~Big Yard~King Beds

Entire house in Speedway! Pool~Big Yard~King Beds
2.0 star property
Speedway
9.8 out of 10, Exceptional, (8)
"House was great. Lots of comfy beds and great pool."
United States
Teri R.
The price is AU$647
includes taxes & fees
4 Jan - 5 Jan 2026
Entire house in Speedway! Pool~Big Yard~King Beds

Hot Tub - Fire Pit - Shuffleboard - Walk to Track

Hot Tub - Fire Pit - Shuffleboard - Walk to Track
Speedway
9.6 out of 10, Exceptional, (8)
"It was a great weekend with the family and the property was perfect for it"
United States
Jeremy C.
The price is AU$743
includes taxes & fees
29 Dec - 30 Dec
Hot Tub - Fire Pit - Shuffleboard - Walk to Track

Regal Apt with King & Queen Bed for Long-Term Stay

Regal Apt with King & Queen Bed for Long-Term Stay
Whitestown
8.6 out of 10, Excellent, (11)
"The stay was fantastic. Did not have the right code to the lock box or the wifi, but when notified the host got an immediate response. Couch is great, but is not a queen size bed that I could see. Pool area and bbq are were wonderful. Area was great. "
Canada
Penny T.
The price is AU$452
includes taxes & fees
3 Jan - 4 Jan 2026
Regal Apt with King & Queen Bed for Long-Term Stay

Charming 2-bedroom duplex in fabulous Avon with WiFi, AC

Charming 2-bedroom duplex in fabulous Avon with WiFi, AC
Avon
8.0 out of 10, Very good, (2)
"No cooking utensils No lamps to read withBeds were minimally comfortable But very clean and convenient Would stay there again"
United States
Shawn M.
The price is AU$386
includes taxes & fees
29 Dec - 30 Dec
Charming 2-bedroom duplex in fabulous Avon with WiFi, AC

Indy Speedway Retreat: King Beds & Near Downtown

Indy Speedway Retreat: King Beds & Near Downtown
Speedway
10.0 out of 10, Exceptional, (9)
"Brian’s place was a perfect spot for our family to spend time together. It was spotless, beds were comfy and it was fully stocked with all necessities! We would definitely recommend this house for a visit to Indy! "
United States
Joel N.
The price is AU$658
includes taxes & fees
29 Dec - 30 Dec
Indy Speedway Retreat: King Beds & Near Downtown

Sleeps 10/Batting Cage/Theater!

Sleeps 10/Batting Cage/Theater!
2.0 star property
Westfield
10.0 out of 10, Exceptional, (2)
"Great house in a great area for a golf trip!"
United States
Jared M.
The price is AU$877
includes taxes & fees
29 Dec - 30 Dec
Sleeps 10/Batting Cage/Theater!

Off Leash Oasis: Hot Tub, Fire Pit & Pets Welcome!

Off Leash Oasis: Hot Tub, Fire Pit & Pets Welcome!
2.0 star property
Indianapolis
Off Leash Oasis: Hot Tub, Fire Pit & Pets Welcome!

Life-Giving, Quiet retreat only 25 min west of Indpls. Peace, Pace, & Gratitude

Life-Giving, Quiet retreat only 25 min west of Indpls. Peace, Pace, & Gratitude
Coatesville
9.6 out of 10, Exceptional, (13)
"The stay was wonderful and convenient to the Hendricks County Fairgrounds."
United States
Alyson M.
Life-Giving, Quiet retreat only 25 min west of Indpls. Peace, Pace, & Gratitude

The Maureen Whitestown

The Maureen Whitestown
Whitestown
8.0 out of 10, Very good, (1)
"Property was very clean, very nice and just as pictures showed. Note for after booking: The address given is not the address of the property. It is an apartment complex and the unit is in a different building than the address given. We arrived at night at this made it difficult to find. Once we drove around and found the correct building, the code we were given to access the unit did not work. After 15 minutes we were given a new code and that did work. No problems other than that. "
United States
Shelly L.
The Maureen Whitestown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Jamestown Hotel Reviews

Find out more about Jamestown

Everything you need to know about Jamestown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jamestown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jamestown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Jamestown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jamestown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jamestown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jamestown holiday rentals we have selected for you start as low as AU$350 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Jamestown rentals

At Expedia, we put the best Jamestown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jamestown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jamestown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jamestown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Jamestown?

Yes, there are holiday rentals close to the most popular sights in Jamestown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Jamestown has to offer?

Beautiful Hardwood floor House in Indianapolis Indiana: This holiday home rental outside of Jamestown has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Jamestown?

Explore the area and family-friendly sights such as Traders Point Creamery, or get out into nature at a spot like Eagle Creek Park. In the wider area, you’ll find Wabash College and Eagle Creek Golf Club.

What are holiday rentals like in Jamestown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jamestown. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.