Chalet holiday rentals in Sisters

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Top-rated chalet rentals in Sisters

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Guest favourite

Chalet in Redmond

4.98 out of 5 average rating, 166 reviews

Knotty Pine Oasis on Eagle Crest Ridge Golf Course

KristinaRating, 5 stars2 weeks ago

We had a wonderful stay at the Knotty Pine Oasis! The cabin was clean, cozy, and exactly as described, perfect for a few peaceful days away. We spent our days exploring Bend and the surrounding area, and then coming back each evening to unwind, grill, and enjoy the beautiful weather. Even though the cabin is near the golf course, it still felt very private and relaxing. We loved sitting outside watching golfers pass by while enjoying the calm surroundings. The neighborhood was great for evening walks, and everything about our stay was just easy and enjoyable. Scott was incredibly responsive and helpful, which we really appreciated. Highly recommend this spot if you're looking for a quiet, comfortable getaway in a beautiful area! We hope to be back again!

Guest favourite

Chalet in Redmond

4.89 out of 5 average rating, 64 reviews

19th Hole Chalet at Eagle Crest

19th Hole Chalet is a family friendly place to relax. Located on the 15th fairway of the Ridge Course you will enjoy a peaceful setting and beautiful views from the deck, where you can BBQ or soak in the private hot tub. 10 people can comfortably sleep in the 3-bedroom, 2-bath vacation home with vaulted ceilings, floor-to-ceiling windows, central heat, air conditioning, and ceiling fans. The chalet includes a fully stocked kitchen plus 10 passes to the 3 pools, sports center gyms, & game room

Superhost

Chalet in Redmond

4.92 out of 5 average rating, 50 reviews

Juniper Ridge Chalet at Eagle Crest Resort

Experience the beauty of Central Oregon with a stay at the Juniper Ridge Chalet in Eagle Crest Resort. This family-friendly 3-bedroom, 2-bath vacation rental is the perfect destination to call home while you explore and enjoy the resort's recreation areas, three golf courses, spa amenities, indoor and outdoor pools, and nearby hiking trails. After a full day of adventure unwind in your own private hot tub on the back deck, curl up next to the wood-burning fireplace, or enjoy a family game night!

Superhost

Chalet in Crooked River Ranch

4.87 out of 5 average rating, 52 reviews

Classic Timber Framed Chalet

Our Classic Timber Framed Chalet the perfect place to call your home away from home. A main floor master bedroom with king bed & separate sleeping loft are perfect for families or groups. The full kitchen makes the Chalet the complete package for your next vacation rental. Pet Friendly (Pet fee required, max 2 pets) And the views! Take in the expansive views across the 14th hole of the CRR Golf Course and marvel at the towering canyon walls & mountains in the background from your private deck.

Guest favourite

Chalet in Bend

4.92 out of 5 average rating, 104 reviews

Chalet del Sol - Hot Tub - Ping Pong - Fire pit

Welcome to the cozy Chalet del Sol just South of Old Mill District and close to the hiking trails. What this home offers: ☞ Entire property to yourself ☞ Hot tub ☞ BBQ & Blackstone ☞ Ping Pong Table ☞ Master w/king bed upstairs ☞2nd bedroom downstairs queen bed ☞3rd bedroom is a loft w/queen & 2 twins ☞Two full bathrooms ☞ Fast WIFI ☞ Garage ☞ Fully equipped chef’s kitchen ☞ 65” Smart TV w/ Netflix ☞ Lots of Parking → 4 plus cars ☞ Private yard ☞ Washer + dryer ☞ Ductless heating and cooling

Top guest favourite

Chalet in Redmond

4.98 out of 5 average rating, 43 reviews

Perfect Central Oregon Chalet

Centrally located between all of the amazing things that the Redmond, Sisters, Bend area has to offer. Bring the whole family to our cozy Eagle Crest vacation chalet. The cabin can sleep up to eight with three bedrooms, a loft and two bathrooms. Washer & dryer, gas fireplace, and perfect deck area provide everything you need for fun. Eagle Crest offers - dining options, bike paths, 3 pools, 3 golf courses, tennis/pickle ball courts, gyms and hot tubs, the only problem will be needing more time!

Guest favourite

Chalet in Bend

4.87 out of 5 average rating, 45 reviews

Quaint chalet with hot tub and fire pit

Come enjoy this spacious and serene space nestled in the Three Rivers. Relax in the hot tub after your activity filled days, be it hiking the trails, exploring lava cave, or enjoying the waterfalls nearby. We are located less than 25 mins from downtown Bend and Mt Bachelor and 10 mins away from Sunriver Resorts. Stay connected with the goings on around town with our high speed internet. We have plenty of cozy throws & pillows and a fully stocked kitchen which makes for a great retreat!

Guest favourite

Chalet in Redmond

5 out of 5 average rating, 9 reviews

Robin Hood Retreat w/ Level 2 EV Charging station

Welcome to Robin Hood Retreat where the "Sherwood forest" meets the alpine meadow of the Central Oregon Cascade mountain range of Eagle Crest Resort. You'll find Robin Hood on the 14th fairway of the Eagle Crest Ridge golf course. A wonderful central location for river floats, water skiing, hiking, snow skiing, hanging out at one of the 3 pools Eagle crest has to offer, playing tennis or pickle ball indoor or outdoor, or just enjoying the beautiful, peaceful golf course views.

Guest favourite

Chalet in Sunriver

4.94 out of 5 average rating, 101 reviews

Skyliner Chalet ~ Heart of Sunriver ~ Hot Tub ~ AC

The Skyliner Chalet at 23 White Elm is the ideal spot for your next Sunriver vacation. Whether in winter (hot tub) or summer (AC), Sunriver offers endless opportunities for activity, or taking a break and relaxing with your favorite book. The chalet has two bedrooms, two baths and a separate loft area. Centrally located near the hustle and bustle, but just enough removed to enjoy less crowded bike paths and a significant open space surrounding the property.

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Family-friendly chalet rentals

Guest favourite

Chalet in Redmond

4.91 out of 5 average rating, 175 reviews

Eagle Crest Luxury Chalet w/Private Hot Tub&Garage

LaneyRating, 5 stars2 weeks ago

Stayed here for a baseball tournament and it was perfect! Had everything we needed, great location, beautiful location, clean and overall a 5 star stay!

Guest favourite

Chalet in Redmond

4.97 out of 5 average rating, 319 reviews

Wow Holy Cow Chalet

EllaRating, 5 stars3 weeks ago

Nancy gave us an amazing stay! Great home, great location, and left lots of recommendations in her booklet at the house! Great host and great place to stay all around!

Guest favourite

Chalet in Redmond

4.88 out of 5 average rating, 24 reviews

Eagle Crest Resort Condo with Mountain Views!

LionneRating, 5 stars10 months ago

We had a great stay in the house of Sue! We especially loved the view from the deck on the river. Although the house is on a resort, it is really quiet, because it is on the edge of the resort. But it is still easy to enjoy the pools and sport facilities on the park, with even one pool within a short walking distance. The house itself is really comfortable and all the amenities are there. Sue is a great host, she was very responsive.

Guest favourite

Chalet in Redmond

4.98 out of 5 average rating, 166 reviews

Knotty Pine Oasis on Eagle Crest Ridge Golf Course

KristinaRating, 5 stars2 weeks ago

We had a wonderful stay at the Knotty Pine Oasis! The cabin was clean, cozy, and exactly as described, perfect for a few peaceful days away. We spent our days exploring Bend and the surrounding area, and then coming back each evening to unwind, grill, and enjoy the beautiful weather. Even though the cabin is near the golf course, it still felt very private and relaxing. We loved sitting outside watching golfers pass by while enjoying the calm surroundings. The neighborhood was great for evening walks, and everything about our stay was just easy and enjoyable. Scott was incredibly responsive and helpful, which we really appreciated. Highly recommend this spot if you're looking for a quiet, comfortable getaway in a beautiful area! We hope to be back again!

Chalet in Redmond

4.81 out of 5 average rating, 32 reviews

Clean & bright chalet on the golf course (no pets)

GuadalupeRating, 5 stars8 months ago

Beautiful home, we had a wonderful stay. Julie and Ashish were very responsive, helpful and accommodating. We had everything we needed and the kids had a lot of fun, we all enjoyed our stay.

Top guest favourite

Chalet in Prineville

4.92 out of 5 average rating, 97 reviews

Juniper Ridge Retreat

NickiRating, 5 stars2 weeks ago

This house is perfect for all ages and events. It had everything you would possibly need. The view are unbelievable. If I was to come back it will definitely be starting here again.

Guest favourite

Chalet in La Pine

4.95 out of 5 average rating, 118 reviews

Elk View Lodge - Private Luxury Family Retreat

AlyshaRating, 5 stars17 months ago

Elk View Lodge did not disappoint. It comfortably fit our group of 4 adults and 8 children. We had loads of beautiful snow outside and a cozy and pristine home inside for our long weekend away! Michelle was incredibly responsive and helpful. We will definitely be coming back— hopefully next time for a summertime trip to explore all the hiking, biking and rafting in the area.

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Chalet holiday rentals in Sisters

Top-rated chalet rentals in Sisters

Holiday rentals for every style

Popular amenities for chalet rentals in Sisters

Family-friendly chalet rentals

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