Holiday rentals with a fireplace in Lake Oswego

Beautiful townhome on bike trail with river views

Welcome to Miles Street, a unique 2200 sq ft bright and airy 2 bedroom 4 story townhome on Portland's 26 mi riverfront trail with Willamette river views. An entertainer's dream with open concept 4th floor kitchen, dining and living room with fireplace, balcony, and river views. Two 3rd floor bedrooms including master with fireplace and balcony, & bathroom with heated floors, open shower & soaking tub. 5th floor rooftop deck has gas grill & firepit table with view of the Willamette and Mt. Hood.

A Cute, Clean, & Comfy SW Portland Guest Apartment

Jasper House is a very clean, pet friendly one bedroom "in-law" apartment in Garden Home. Located on a quiet Culdesaq. Easy access to 217 and I-5. The perfect West side location, close to everything. Great for business and pleasure travelers a like! No additional pet fees for those traveling with pets! This 450 sq ft apartment has a private deck, cozy sitting room w/double futon, 40" TV w/Roku, dining table & kitchenette. The bedroom has a comfy King bed & vanity/desk. We have A/C as well!

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

La Casa with Luxury Amenities

Nestled in the Lake Oswego area, this home offers easy access to numerous wine tasting spots, shopping destinations, and downtown Portland, serving as an ideal starting point for exploring the PNW. The main living area of this 3-bedroom, 1.5-bathroom home features a fully furnished and modern gourmet kitchen, complete with a gas range, granite countertops, and double oven, making entertaining effortless and enjoyable. *Complimentary pass to shop at adidas employee store

Secret Garden Guesthouse!!

Secret garden guesthouse is located 1 mile from downtown Lake Oswego and 2 miles from Lewis and Clark. Ideal hideaway for parents weekend, visiting the college, or guest lecturers. Also great location for exploring the amazing city of Portland and its surrounds. 50 minutes to Mt Hood, 40 minutes to wine country! Located in SW Portland and just a few miles from downtown Portland food scene. 1 mile from Lake Oswego. Friendly pets are welcome with a $40 pet fee.

Bear Lodge - Heart of Wine Country

Bear Lodge is a beautiful little cabin with its own private patio. We have built this beautiful BnB with love & creativity & we are eager to share with our guests! We built it in 2019 and it is totally self-contained. This place is great for couples, solo adventurers, business travelers, and families. NOTE: This SPACE is shared with owners on property. We also have a second rental on site as well (please see Elk Place-Heart of Wine Country). NO Pets Allowed.

Chateau Chardonnay:Tuscan home in NW wine country

Equipped with two HEPA air filtration systems that work continuously to filter and sanitize the air, this home is a clean and safe space to relax and enjoy nature! The house sits on 4 acres in the picturesque Oregon wine country. The back deck looks out over a lush back yard that cascades down to a lazy creek. Gaze out the large kitchen window to the paver patio, vibrant lawn and rimmed with beautiful mature landscaping, koi pond and fountain.

Rustic Barn | Country Getaway

Nestled atop Parrett Mountain is our countryside barn ready for you to enjoy! Conveniently located to many vineyards, and a picturesque drive to close by cities. This space offers a fully stocked kitchen and plush bedding (1 Queen/ 1 Double). Come and slow down with our rural pace of life, unique accommodations and say hi to the mini cows. Check out our photos to imagine yourself in this peaceful paradise.

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautiful cozy cabin that is heated exclusively by a wood stove, on the edge of a magical old growth cedar forest on our 11 acre farm and vineyard. Relax on the deck built into the trees, and sleep peacefully in the loft bed, as you soak in the nature around you. The cute out house is just down the path and the cedar hot tub/ outdoor shower is next to the garden.