Vacation rentals with a kayak in Willamette Valley

4.96 out of 5 average rating, 464 reviews

A vibrant red couch is placed against a light-colored wall, accented by dynamic artwork mounted above it. A soft white throw blankets a nearby chair, complemented by a wooden side table and a lamp casting a warm glow. Natural light enters through a window, enhancing the lively decor.

Guest suite in Portland

Underground Art Suite

Spacious underground art suite/apartment in the sunlit basement of our 1926 bungalow in the lively SE Foster Powell Neighborhood. We partner with local artists to bring rotating artwork to the space. Enjoy a relaxing guest suite with a private entrance, parking and access to nearby food carts, restaurants, bars, galleries, and shops featuring local wares art & food. The space is a newly finished one bedroom modern guest suite with full kitchen, located in a quiet yet fun and funky neighborhood.

4.95 out of 5 average rating, 413 reviews

Guest suite in Milwaukie

River Forest Lake Apt w/hot tub. HOT find!

*No smoking, no parties, no drugs or pets on premises* total/Max 4 guests; included in this total are infants/children, no more than 2 or3 children under 12, as long as only 4 total guests. FYI: Incline driveway Welcome to our newly remodeled daylight basement apartment. Tucked into the quiet peaceful River Forest neighborhood of Milwaukie on River Forest Lake. Conveniently located to shopping, restaurants, hwy 99, freeways to Portland, Oregon City, historic Sellwood, the Gorge, Mt Hood, etc.

4.98 out of 5 average rating, 205 reviews

Treehouse in Mt Hood

Beautiful, Magical, Treehouse

"Glamping at its' best"! 16' x 16' TreeHouse, suspended between 3 large fir trees, queen size bed, loft w/2 twin beds, composting toilet, much more, situated on 20 acres with a pond. Gas heater, mini-fridge, microwave, coffee pot. IMPORTANT: this is a Tree House! Going up the spiral staircase is an adventure in itself, so pack small bags (or packs) (large suitcases are not appropriate). Be sure to look at the pictures & read our reviews... that provides the most information. Happy Travels!

4.94 out of 5 average rating, 110 reviews

The exterior of a modern home is showcased, featuring a wooden pergola adorned with string lights that create a warm ambiance. A patio area includes seating and a grill, surrounded by lush greenery and forested terrain.

Home in Washougal

Forest+River Haven @ Timber Moon Cabin w/ Hot Tub

Timber Moon is a modern Washougal River Getaway. Nestled in over 10 acres of Washington State Forest with secluded access to the Washougal River out your back door. You'll instantly feel the rhythm of nature when you arrive. Just a beautiful one hour drive from Portland. ✴ Hot Tub at the edge of the forest ✴ Dougan Falls 10 min walk ✴ Naked Falls 5 min drive ✴ Yacolt Burn State Forest 1 mile away ✴ Columbia River Gorge 15 min drive ✴ Starlink high Speed WiFi ✴ Pet Friendly *Please note

4.87 out of 5 average rating, 174 reviews

Three kayaks in vibrant hues of purple, red, and blue are arranged against a wooden fence, partially shaded by a tree. The surrounding area features reddish-brown mulch and dappled sunlight filtering through the leaves.

Guesthouse in Milwaukie

Milwaukie Riverfront Guest House

Incredibly majestic river-front guest house. This is the ultimate romantic getaway and peaceful retreat. Large windows and double french doors look out on the Willamette river from the cottage living room and loft sleeping area. It includes a semi-private rocky beach, and a large manicured lawn with fire pit. Kayaks are available for use, and guests are welcome to bring their own too! The guesthouse has its own drive-way, and is completely separate from the main-house grounds for privacy.

4.95 out of 5 average rating, 170 reviews

A serene garden scene captures early morning fog enveloping vibrant fall foliage. Lush greenery is interspersed with colorful autumn leaves, providing a peaceful backdrop. The landscape features a variety of shrubs and trees, adding depth and texture to the tranquil environment.

Guest suite in Milwaukie

Riverside Cottage Apartment.

Charming cottage apartment on a hill next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

Guesthouse in Springfield

A sprawling orchard scene is presented, featuring a large tree with exposed branches. In the foreground, a wooden table sits under the tree, surrounded by a grassy area. Rolling hills and a row of trees stretch across the background, depicting a serene natural landscape.

4.95 out of 5 average rating, 110 reviews

Large Private Studio with Mountain Views

Forget your worries in this spacious and serene space. Located next to the Mohawk River and a nature preserve, the property is perfect for relaxing or enjoying nature. It features a queen sized bed, gas fireplace and 200 sq ft deck. The studio is minutes away from the freeway and access to downtown Eugene, shopping, and exploration. Bring your bike, walking shoes, and binoculars to enjoy the trails, paths and nature or just relax on the deck or river hammock.

4.99 out of 5 average rating, 139 reviews

A modern kitchen and living area feature rich wooden cabinets and stainless steel appliances. A round area rug defines the seating space, which includes a gray couch and an ottoman. Pendant lights hang above the kitchen island, providing both task lighting and ambiance.

Home in Independence

Town n Country

Modern farm cottage located on our 2 acre lifestyle block for you to relax and enjoy our farm scenery. On the property we have chickens, rooster and ducks that roam freely. We want you to enjoy your stay and we welcome you here at the cottage. Cottage sleeps 4 guest max. If you need anything or there is a problem we are close by in the main house on the property. We take great pride in our cottage. Everything laundered and cleaned after each guest.

4.9 out of 5 average rating, 212 reviews

A spacious living area features light wood flooring and natural light from large windows. A comfortable rocking chair and a decorative armchair are positioned on a patterned area rug. The room provides access to a private garden through glass doors, with soft curtains lending an inviting touch.

Guest suite in Salem

Garden studio apt

Light and roomy, opening onto garden, this apartment is private, quiet and secure. The spacious bedroom/ sitting room opens onto a private garden patio that can be enjoyed year-round. The bookshelf-lined den with a couch, TV, dining area, and gas fireplace is welcoming. The apartment includes a kitchen/laundry room and bathroom. Close to downtown and to bike and walking trails. Special pricing available for monthly or longer stays.

5 out of 5 average rating, 107 reviews

A serene lakeside scene is captured, featuring a rowboat and a yellow kayak neatly resting against the shoreline. Lush green trees are reflected in the still water, enhancing the natural beauty of the surroundings.

Home in Oregon City

The Secluded Lodge at Highland Park

Fabulous lodge style home on 5 park-like acres with a small lake, outdoor fireplace, game room and tv room. Just 30 min from Portland and the airport. Sleeps 10. Main level; master with king bed and bath, one bedroom with twin beds, (can be converted to king), one bedroom with queen bed, two baths. Upstairs, one bedroom with king bed and bath, one room with queen hideabed, shared bath.

4.95 out of 5 average rating, 205 reviews

Guesthouse in Tigard

The Cottage at River Run!

Welcome to the Cottage at River Run! Your private oasis nestled on 1.8 acres backing the Tualatin River. This cottage comfortably sleeps eight with an upper loft area with a full bed and two twin beds and views of the river! The lower level has a private deck, kitchen, 3/4 bath, queen Murphy bed and full sofa bed.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Willamette Valley kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 17 reviews

A spacious living room features a comfortable sectional sofa, inviting relaxation. A decorative coffee table sits in front of it, complemented by a small plant. A wall clock and a framed artwork add character, while a door leads to the outside, enhancing the open feel.

Home in Salem

South Salem getaway

EmilyRating, 5 stars1 month ago

Stayed here for a weekend with some friends to explore Willamette Valley wineries. Super convenient location and a really accommodating space for a group. We didn’t end up cooking at all but the kitchen is certainly very well equipped to do so. Also the backyard and entryway with a dog door made it a really easy space to have a pup in.

5 out of 5 average rating, 3 reviews

A modern farmhouse is nestled among tall trees, featuring large windows that illuminate the exterior with a warm glow. The structure showcases a natural wood facade and a charming roof, while outdoor lighting adds to the inviting ambiance of the retreat.

Home in Estacada

Mt. Hood Retreat on Private Mountain Lake

RezaRating, 5 stars1 week ago

This was my second time staying on Jeremy’s magical property, and this time we brought the whole family! We rented both the main house and guest house for a weekend getaway, and the experience was absolutely unforgettable. The main house is warm, inviting, and incredibly spacious—perfect for gathering everyone under one roof. The design is thoughtful and full of charm, with cozy corners, a well-stocked kitchen, and comfortable beds throughout. We cooked, laughed, and shared meals around the dining table, then relaxed by the fire or explored the beautiful surroundings. The private lake, forest trails, wildflowers, and peaceful energy of this place make it feel like your own private nature retreat. We saw all kinds of critters, made bonfires, and enjoyed being completely unplugged. It was everything we hoped for and more. Jeremy’s hospitality is unmatched, and this property continues to be a favorite. We can’t wait to return again.

4.96 out of 5 average rating, 23 reviews

A clear view of Dexter Lake is presented, with lush greenery lining the shore. Trees and vegetation create a natural backdrop, while distant houses are visible along the water's edge. The calm blue water reflects the sky, enhancing the serene environment.

Home in Lowell

Lake Front - incredible views of Dexter Lake and o

TraceyRating, 5 stars2 weeks ago

The lake house was absolutely beautiful. Plenty of room for all of us. The fire pit was wonderful we made s’mores. There was kayaks, canoe, and paddle boards. I would definitely rent from here again in the future. It was absolutely peaceful and wonderful. And Linda was absolutely a delight to work with. I will recommend to my friends and family. If you want an awesome getaway, peaceful, and quiet the place for you not to mention the absolutely beautiful view.

4.94 out of 5 average rating, 66 reviews

A charming two-story home features a welcoming front staircase leading to the entrance. The house showcases a white exterior with contrasting dark trim. Lush greenery and a well-maintained pathway enhance the inviting appearance, while large windows allow natural light to fill the interior.

Home in Camas

Camas Lakehouse With Private Hot Tub

NicoleRating, 5 stars1 week ago

We loved our family’s stay. The owners accommodated us and made us feel comfortable and welcome. The home is beautifully and comfortably furnished and designed.

4.89 out of 5 average rating, 93 reviews

A wooden deck is framed by tall trees, featuring a potted plant with vibrant flowers. Beyond the deck, a glimpse of the lake can be seen through the trees, enhancing the natural surroundings. A gas barbecue is positioned on the deck for outdoor cooking.

Home in Veneta

Beautiful PrivateWaterfront Retreat

GailRating, 5 stars9 months ago

We had a wonderful family gathering at Randy's lake house, spending tons of time in the water and enjoying the kayaks and stand up paddle boards. We are big game players so both the beautiful patio table and the dining room got lots of use. So nice to be close to amenities in town but get to go back to a lovely natural setting. Thanks for sharing your place with us!

4.94 out of 5 average rating, 115 reviews

The front exterior of a one-level home is displayed, featuring a well-manicured lawn and a tree beside a concrete walkway. The house showcases light gray siding with white accents, a dark front door, and a two-car garage with a textured door. Clear blue skies frame the scene.

Home in Battle Ground

Chic home-explore outdoors PNW/Hike/Fish/wineries

OlgaRating, 5 stars1 week ago

I enjoyed my stay, beautiful home

4.83 out of 5 average rating, 24 reviews

The blue historic house features two stories with a wraparound porch. Bushes are neatly trimmed along the pathway, leading to the entrance. A grassy lawn adds to the outdoor space, complemented by the surrounding trees providing shade.

Home in Dayton

Ole Tyme B&B Warm setting with a country feel.

ElizabethRating, 5 stars6 months ago

Thank you Heath, you were a gracious host and it helped us in transition to our new house. Princess was the sweetest goat.

4.91 out of 5 average rating, 69 reviews

A hot tub is positioned on a deck, offering a view of a vibrant sunset beyond a modern home. Trees frame the scene, with soft lighting adorning the structure. The silhouette of a spiral staircase adds depth to the setting.

Home in Happy Valley

RoofTop FirePit, HotTub & Outdoor Theater

KristenRating, 5 stars1 day ago

The most magical, relaxing and beautiful Airbnb I have ever stayed in absolute perfection view from the tower, and the fire pit is incredible. The hot tub is beautiful. There’s this incredible Koi pond with hammock chairs. most relaxed. I’ve been in months. The hostesses are just absolutely delightful friendly people. Could recommend this spot more. Can’t wait to have an excuse to come up and stay again.

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Cabin rentals with a kayak

4.98 out of 5 average rating, 464 reviews

An aerial view captures the cabin nestled among tall trees, with a spacious deck overlooking the river. The surrounding landscape features a mix of lush greenery and pebbled beach, creating a serene natural setting.

Cabin in Tillamook

Mid-Century Riverfront Cabin - Seclusion Awaits!

KavenRating, 5 stars3 weeks ago

very nice and beautiful just like the pictures. 5 visitors from Korea had a wonderful time! It took less than 25 mins to the west coast. Willing to visit again!

5 out of 5 average rating, 67 reviews

A peaceful deck overlooks the gently flowing creek, surrounded by lush greenery and tall trees. Two red chairs are positioned invitingly beside the water, offering a serene spot to relax and enjoy nature. Twinkling lights are visible in the distance, adding to the tranquil ambiance.

Cabin in Rhododendron

Creekside Mt. Hood Cabin, hot tub, fire pits-cozy!

MeganRating, 5 stars2 weeks ago

Stay here!! The cabin is absolutely amazing! so relaxing to sit out in the many seating areas, surrounded by plants and listening to the stream. The cabin is also immaculately clean and cozy. Kate is a super helpful host and has thought of everything. This is a rare listing where it was actually better in person. You won't be disappointed!

Cabin in Mount Hood Village

4.96 out of 5 average rating, 73 reviews

Cozy Cottage near Mt. Hood

JacindaRating, 5 stars1 week ago

Such a great little cottage. We stayed a couple nights while on a long road trip to catch up on laundry and unwind a bit. This place was perfect. And the Heated Bathroom Floors…… Didn’t know how much I needed that in my life 🤣 Thanks Katie