Vacation rentals in Olean

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Top-rated vacation rentals in Olean

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Guest favorite

Guesthouse in Olean

4.84 out of 5 average rating, 107 reviews

Cozy Country Get Away Suite

If you're passing through town on your travels or a local looking for a private get away, this is the perfect place to kick back, relax and enjoy some peace and quiet. You can sit by the fire, look across to see fireflies in the field or tilt your head back to have an amazing star-gazing experience. A one of a kind property to make memories with friends, family, or for a special romantic get away. Access to 93 acres with trails to walk or mountain bike on, fields to wander through and wildlife.

Sep 12 – 19

G$17,319 GYD per night

Guest favorite

Loft in Olean

4.96 out of 5 average rating, 108 reviews

Joe's Cozy Loft

Joe's Cozy Loft is now under new management! Expect the same great accommodations and amenities as before but with seamless and Superhost service. Your stay with us includes wifi, off street parking after business hrs, a luxurious 2 person jet tub, laundry capabilities, a private deck with grill and more. We are a short walk or drive to many local restaurants and taverns. We are nestled in the heart of the the Enchanted Mountains with easy access to Ellicottville skiing, Buffalo and much more!

Jul 1 – 8

G$21,715 GYD per night

Guest favorite

Condo in Ellicottville

4.95 out of 5 average rating, 269 reviews

Loft Condo in Wildflower

This is a ground level loft condo that is bright, clean and nicely updated. We are minutes from the Holiday Valley Resort and a short walk to the Village of Ellicottville. This condo offers AC for the summer and a gas fireplace for the winter. We have complimentary coffee and tea with cream and sugar on site. Kitchen is equipped with some spices, oils and cookware. We also supply clean linens and towels. This place is great for 2 to 6 guest for family or close friends with 3 beds and a futon .

Jan 16 – 23

G$22,257 GYD per night

Guest favorite

Home in Allegany

4.97 out of 5 average rating, 118 reviews

Stylish 3-bedroom home near Ellicottville, NY

Stylish, entire residential 3 bedroom/ 1 bath home. Close to Ellicottville/skiing -30 mins., St. Bonaventure University, Cutco, Rock City Park, Allegany State Park, kayak launch, biking, and walking trail. Niagara Falls is a 1.5-hour drive, Zippo 30 minutes. Walmart and movie theater are 2 miles away. Many restaurants are nearby. A seasonal 2 screen drive-in movie theater-20 min. drive. 2 queen beds , 1 double bed, and a chair converts to a twin size bed. Fully equipped kitchen.

May 3 – 10

G$23,516 GYD per night

Guest favorite

Cottage in Olean

4.84 out of 5 average rating, 165 reviews

Artists cottage - mid century

View birds, wildlife in an old forest along the Allegany River from the porch, deck or large picture windows. Relax, renew, read a book, create, write, paint, unplug. (fast Wi Fi, 32 inch TV and echo dot) Families and dog owners will like the large yard (no fence, warning ticks and Lyme disease in the area). My grandmother designed the cottage around a vintage house trailer (tiny house). There are many unique and cleaver features. Family mementos through history are on display.

May 21 – 28

G$25,283 GYD per night

Guest favorite

Guest suite in Olean

4.99 out of 5 average rating, 196 reviews

Quiet, Comfortable and Spacious!

Quiet, Comfortable and Spacious Enjoy our bright and spacious guest suite with a private entrance. It also includes a private bath, a relaxing sitting area and off-street parking, along with the following: Coffee maker Microwave Small Refrigerator Wifi Roku TV Outdoor sitting area Walking distance to St. Bonaventure University (.3 mile) and the Allegheny River Rec. Trail (.2 mile), and half a mile to a large shopping plaza. 25 minutes from Holiday Valley and Allegany State Park.

Jun 30 – Jul 7

G$17,921 GYD per night

Guest favorite

Home in Rixford

4.91 out of 5 average rating, 190 reviews

Rustic log cabin with all the amenities

Less than an hour from Ellicottville's Holiday Valley (downhill) and Allegany State Park (x-country) and the 500,000 acres of Allegheny National Forest For the non-adventurous type wishing to get away for some peace and quiet, this is a cozy hideaway where one can enjoy the winter beauty. Within an hour's drive: Kinzua Bridge State Park, the Pennsylvania elk in the Benezette area, the World War ll Museum in Eldred, and the Seneca Allegany Casino in Salamanca.

Dec 4 – 11

G$20,381 GYD per night

Guest favorite

Cottage in Hinsdale

4.98 out of 5 average rating, 45 reviews

The Cottage House

The Cottage House in Hinsdale is cozy and private. Featuring a country setting, you'll enjoy a private backyard covered patio. This small but comfortable cottage has a queen size bed in a cozy bedroom with a television, desk area, and access to the outside patio and hillside view. The full size bathroom has a walk in shower, suitable for all handicap guests. The full kitchen is completely equipped for preparing meals at the island. Also enjoy the coffee/wine nook.

May 29 – Jun 5

G$23,600 GYD per night

Guest favorite

Apartment in Olean

4.89 out of 5 average rating, 355 reviews

Centrally located| Convienant| Cozy|1850 charmer#2

This farmhouse chic decorated home was built in 1850 and is Centrally located to the newly renovated downtown Olean! Charming decor with many modern updates! All the luxuries of a home. Close to St. Bonaventure University, 20 minutes to the Seneca allegany casino and 30 minutes to Ellicottville, NY. Lots of local restaurants nearby and in walking distance to the Four Mile Brewery. Perfect for any stay and meant to meet all your traveling needs!

Nov 13 – 20

G$19,150 GYD per night

Guest favorite

Barn in Cuba

4.97 out of 5 average rating, 117 reviews

Stylish & Inviting, Close to lake, 1BR-Sleeps 2

This unique place has a style all its own. This 1BR space "delivers" when it comes to comfort and convenience. Comes with a fully equipped kitchen and all the amenities to make your stay as comfortable and easy as possible. Has a deck if you would like to just relax or enjoy a meal. This cozy space is on the second story so if you have a hard time with stairs sadly we aren't the place for you. Try us out, you won't be disappointed!!

Mar 7 – 14

G$19,855 GYD per night

Guest favorite

Apartment in Port Allegany

4.98 out of 5 average rating, 144 reviews

Two bedroom apartment

Well-appointed, two bedroom apartment. Hardwood floors through out. All of the comforts of home are included. There's even a play loft for children! Country setting with lovely views of the surrounding hills and pond. Set in the heart of the Allegheny Mountains. Near by attractions include Allegany State Park(31 miles), Kinzua Bridge(22 miles), Cherry Springs State Park (32 miles), Ellicottville NY, ski country (47 miles)

Aug 29 – Sep 5

G$28,606 GYD per night

Guest favorite

Guest suite in Great Valley

4.93 out of 5 average rating, 324 reviews

Comfy studio nestled in the woods (New Listing)

Nestled in the forest only seven minutes’ drive from Holiday Valley, this contemporary style self-contained studio apartment is the perfect weekend getaway for skiing and nature-loving couples. With every luxury and convenience, you can home cook meals or barbecue on the deck overlooking the creek, with nothing but forest beyond. Relax and watch a movie on our LCD screen or use high speed Starlink internet.

Nov 29 – Dec 6

G$22,452 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Olean vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Olean's top sights

Beef-N-Barrel Restaurant18 locals recommend

Perkins Restaurant & Bakery3 locals recommend

Tasta Pizza5 locals recommend

TOPS3 locals recommend

Ried's Food Barn4 locals recommend

Rafi's Platter3 locals recommend

Other great vacation rentals in Olean

Superhost

Apartment in Olean

4.85 out of 5 average rating, 47 reviews

The Palace - Lovely 2-bedroom unit - free parking

Nov 17 – 24

G$29,465 GYD per night

Guest favorite

Cottage in Hinsdale

5.0 out of 5 average rating, 33 reviews

Old barn to modern cottage in 250 private acres

Dec 18 – 25

G$28,816 GYD per night

Guest favorite

Apartment in Olean

4.95 out of 5 average rating, 41 reviews

Henley Hideaway

May 31 – Jun 7

G$19,520 GYD per night

Guest favorite

Guest suite in Olean

4.97 out of 5 average rating, 34 reviews

Lower Level Apartment

Nov 6 – 13

G$26,565 GYD per night

Guest favorite

Home in Olean

4.95 out of 5 average rating, 22 reviews

The Quiet Getaway

Oct 21 – 28

G$18,763 GYD per night

Guest favorite

Home in Olean

5.0 out of 5 average rating, 17 reviews

Stunning Home near Ellicottville

Aug 31 – Sep 7

G$35,792 GYD per night

Guest favorite

Chalet in Olean

5.0 out of 5 average rating, 60 reviews

Chalet of Quietness

Oct 18 – 23

G$38,613 GYD per night

Guest favorite

Tiny home in Shinglehouse

4.98 out of 5 average rating, 50 reviews

Cozy 1-bedroom tiny house cabin in rural PA

Dec 15 – 22

G$19,460 GYD per night

Show all

Quick stats about vacation rentals in Olean

Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
G$10,445 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Olean have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Olean. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Olean?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Olean have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Olean. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Olean?
Yes! Work meets play with ease at over 10 vacation rentals in Olean featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Olean?
Olean has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly vacation rentals in Olean?
Four-legged friends are welcome in Olean. Choose from more than 10 vacation rentals for guests traveling with pets.
Do apartment rentals in Olean have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Olean. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Olean?
Experience the best of Olean with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Vacation rentals in Olean

Top-rated vacation rentals in Olean

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Olean vacation rentals

Stay near Olean's top sights

Other great vacation rentals in Olean

Apartment in Olean

Cottage in Hinsdale

Apartment in Olean

Guest suite in Olean

Home in Olean

Home in Olean

Chalet in Olean

Tiny home in Shinglehouse

Quick stats about vacation rentals in Olean

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Olean have air conditioning?

What are the most popular amenities for Apartment Rentals in Olean?

Do apartment rentals in Olean have wifi?

Are there vacation rentals with a dedicated workspace in Olean?

Are there family-friendly vacation rentals in Olean?

Are there pet-friendly vacation rentals in Olean?

Do apartment rentals in Olean have a kitchen?

How much does it cost to stay in apartment rentals in Olean?

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