Olean Holiday Rentals | Rent By Owner

Olean Holiday Homes

Apartment

Bring a Pet: Historic Downtown Olean Apartment

10.0

Exceptional

(3 Reviews)

2 Bedrooms 1 Bath 4 Guests 800 ft²

US $212/Night 7 Nights - US $1,486

View Deal

Charming Historic Home ~ 1 Mi to Dtwn Olean!

House

Charming Historic Home ~ 1 Mi to Dtwn Olean!

8.7

Fabulous

(3 Reviews)

4 Bedrooms 3 Baths 8 Guests 5005.22 ft²

US $452/Night 7 Nights - US $3,164

View Deal

Bed & Breakfast

Old Library Inn Olean NY

9.2

Exceptional

(37 Reviews)

1 Bedroom 1 Bath

US $163/Night 7 Nights - US $1,142

View Deal

Price Dropped

Bed & Breakfast

Old Library Inn - J.R.R. Tolkien Room

10.0

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 2 Guests 5500 ft²

US $148/Night 7 Nights - US $1,036

View Deal

Bed & Breakfast

Old Library Inn - Historic Olean NY

8.3

Excellent

(37 Reviews)

9 Bedrooms 8 Baths 20 Guests 291.97 ft²

US $135/Night 7 Nights - US $945

View Deal

Bed & Breakfast

Victoria Mansion 1895, Near SBU - AA Milne Room!

9.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 2 Guests 5500 ft²

US $168/Night 7 Nights - US $1,174

View Deal

Apartment

Bring a Pet: Historic Downtown Olean Apartment

2 Bedrooms 1 Bath 4 Guests 796.53 ft²

US $243/Night 7 Nights - US $1,703

View Deal

Bed & Breakfast

Signature Suite, 1895 Victorian Old Library Inn!

9.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 5500 ft²

US $160/Night 7 Nights - US $1,123

View Deal

Hotel

Hampton Inn & Suites Olean, Ny

9.2

Exceptional

(102 Reviews)

1 Bath 368.67 ft²

US $170/Night 7 Nights - US $1,187

View Deal

Cottage

Cozy Country Get Away Suite with a view of the Enchanted Mountains

8.8

Fabulous

(26 Reviews)

1 Bedroom 1 Bath 4 Guests

US $105/Night 7 Nights - US $738

View Deal

Fairfield Inn & Suites by Marriott Olean

Hotel

Fairfield Inn & Suites by Marriott Olean

8.8

Fabulous

(47 Reviews)

4 Baths 336.37 ft²

US $137/Night 7 Nights - US $959

View Deal

Bed & Breakfast

Elegant Old Library Dickens Suite! Family, Near SBU

2 Bedrooms 1 Bath 4 Guests 5500 ft²

US $287/Night 7 Nights - US $2,007

View Deal

More Top-Rated Holiday Homes in Olean Area

Why Choose Rent By Owner for your Olean Holiday Homes?

What makes our Holiday Homes special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Olean

How to Book Your Olean Holiday Homes

What's our booking process?

Our platform allows you to browse a curated selection of holiday homes. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Olean

More Top-Rated Holiday Homes in Olean Area

Common Holiday Homes Amenities

What amenities can you expect?

Our Holiday Homes are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Other Places to Stay in Olean, NY

Frequently Asked Questions About Olean Holiday Rentals

1. What are the top Holiday Homes in Olean?

There are a lot of options in Olean. If you plan on staying in the Olean area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Holiday Homes in Olean:

2. How many Holiday Homes are available in Olean?

Currently, the total number of properties listed by RBO in 2026 is over 39 in the Olean area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Holiday Homes in Olean. 