Holiday rentals in Upland

4.9 out of 5 average rating, 167 reviews

Flat in Muncie

Central Location. Very comfy & clean with view.

RhondaRating, 5 stars1 month ago

Cicely and company were very responsive when I had questions, including a request for a last minute extension. This spot is cozy and lovely. It’s close to downtown restaurants and shops. It’s very quiet—all I heard at night were train whistles, which I find comforting. It served as a peaceful sanctuary for me during a very difficult family visit. I would definitely stay here again. I can’t recommend it highly enough.

4.99 out of 5 average rating, 215 reviews

Riverwood Rest Stop next to Ruoff & Koteewi Park

RobynRating, 5 stars1 month ago

What a unique home in a peaceful location, complete with a sweet and friendly cat host! We appreciated the fun deco, the comfortable atmosphere and the beautiful views of the river out of the big picture windows. Lots of special touches from Krista (snacks, flowers, themed deco) and she was proactive and responsive to communication. Highly recommend! We would love to stay in a warmer month to make use of the kayaks next time too!

4.94 out of 5 average rating, 18 reviews

Home in Pendleton

Super Charming Modern Cottage

JamieRating, 5 stars5 months ago

The home is lovely and comfortable. It had everything we needed and was very clean. The neighborhood is quiet. I wish we had more time to enjoy the peaceful back yard. It was beautiful! When I had a question Brenda responded quickly. If you need a place to stay in Pendleton, I highly recommend.

4.99 out of 5 average rating, 117 reviews

Flat in Wabash

Lovely rural 1-bedroom rental unit - The Bluebird

JeanetteRating, 5 stars1 week ago

While we had to cancel our stay right after we got there we could not of been more happy. Very clean, great location and private. Christa was very understanding and worked with me through all of this. She is quick to respond and kind.

4.98 out of 5 average rating, 96 reviews

Sea Lake Creatures

RhondaRating, 5 stars8 months ago

We really enjoyed our stay. The house is so fun and beautiful. There is art everywhere. We were always discovering something new. The place was super clean and tidy. The patio, garden and hosting were great to relax in. The kitchen was well stocked, the bathrooms were clean and the bedrooms were comfortable and roomy. We would stay there again most definitely!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Upland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Upland's top sights

Ivanhoes13 locals recommend

Taylor University9 locals recommend

Payne's Restaurant6 locals recommend

Other great holiday rentals in Upland

Superhost

4.8 out of 5 average rating, 5 reviews

Cozy 4-Bedroom Family Retreat in Noblesville, IN

AkealRating, 5 stars2 weeks ago

Stay was nice! Nice quiet private neighborhood and the house itself was extremely spacious and accommodating to my needs. Will book again!

5 out of 5 average rating, 66 reviews

Home in Fairmount

Vintage Farmhouse Charm

MelissaRating, 5 stars2 weeks ago

This was the family’s second stay with Sara at Grace Farm. We love the well stocked kitchen to prepare meals for the crew, the beds are comfy, three bathrooms is definitely a plus, and there are places for small groups to have conversations and catch up without talking over others. We love meeting in this lovely setting.

5 out of 5 average rating, 25 reviews

Cottage in Cicero

Lake front Cottage on Morse Reservoir w/ Boat Slip

JeffRating, 5 stars9 months ago

We had a great stay! Morse lake is always beautiful and there is plenty to do near by. The rental has been well maintained and updated and has everything you need. This a perfect size for two families.

Superhost

4.83 out of 5 average rating, 23 reviews

Charming Riverfront Home | kayaks/fire pit

EmilyRating, 5 stars3 weeks ago

Great place, super clean, super friendly host!! It was a great spot to relax after basketball games. Will definitely seek this spot out again if we return for a tournament again!

Superhost

Home in Cicero

4.85 out of 5 average rating, 39 reviews

Lakehouse Oasis on Morse Reservoir—Private Getaway

alisonRating, 5 stars6 months ago

Great location and amazing food around a walkable town. Christopher was great with communication when some of our travel plans changed. The venue was perfect and everyone enjoyed the family vacation and wedding weekend

4.99 out of 5 average rating, 124 reviews

Home in Anderson

Historic Eighth Guest house

ErnieRating, 5 stars3 days ago

Absolutely gorgeous place to stay! So peaceful and relaxing. Beautiful inside and out! Michelle is an excellent host! 10/10 recommend

4.88 out of 5 average rating, 41 reviews

Comfy Plum Prairie Home & Yard

BarbaraRating, 5 stars2 weeks ago

Comfortable beds. One bedroom had a 1/2 bath connected to the room. The full bath with tub/shower was on the opposite side of the house, so was not too convenient for using the restroom during the night. We appreciated both regular and decaf coffee and tea.