Family-friendly holiday rentals in Pendleton

4.93 out of 5 average rating, 122 reviews

A two-story townhome is presented from an elevated angle, showcasing a wooden deck with a railing and steps leading to the entrance. Green foliage and a small tree add natural elements to the landscape, complemented by a blue door and large windows that offer ample light.

Townhouse in Pendleton

Peanut Butter Cup on the Hill, 1.2 mi to Round Up

Enjoy some quiet time in this private townhome playing ping-pong, Wii, board games, or ring darts. Better yet, send the kids to play while you relax on the deck by the fire pit under the lights. Or cozy up by one of the two indoor electric fireplaces. Bedroom 1- Queen bed, walk in closet, dresser, sink and mirror with door to the shared bathroom. Bedroom 2- Queen bed, closet, dresser Basement (bedroom 3)- Queen bed, futon, small closet, bathroom with shower, laundry room, access to game room.

Indoor spacesKitchenOutdoor spaces

A charming exterior view of the property showcases a stone chimney adorned with greenery, blending naturally with the surrounding landscape. A welcoming front door sits under a small archway, framed by lush bushes and manicured grass. Soft lighting highlights the entrance.

4.87 out of 5 average rating, 105 reviews

~Pearl Cottage~

1930’s French cottage for an ADULT ONLY get away NO WORK CREWS/TEAMS. The coffee-breakfast size kitchen is tiny. Features vintage dishes, 30’s silverware and crystal bar service. NOTE: dinning room and kitchen are tiny. The down sofa and working fireplace make the living room a relaxing place to unwind. Bedrooms furnished with velvet headboards from Anthropology, down bedding for a luxurious nights sleep. 4 blocks from the Round Up grounds, parking included. NO children under 13. No pets.

FamilyIndoor spacesGetting around

A single-story home is presented with a light grey exterior, a welcoming front porch, and a neatly landscaped yard featuring green grass and potted plants. A driveway provides access to a garage, while a fenced area is visible to the side.

4.99 out of 5 average rating, 268 reviews

Elegant Western Home 3BR 2BA

Easy to find 3 bedroom 2bath home just a short distance from freeway exit, located in a safe neighborhood with fenced backyard and view of the city. Perfect for guests with children or a relaxing stay for adults. Enjoy being within minutes to local downtown shops, businesses and restaurants, Underground Tours, Children's Museum Round-Up grounds and Happy Canyon. Also located within 6 miles is Wild Horse Casino & Resort. Golfing, Movie theater, Bowling, Family Fun Plex, restaurants and more.

FamilyKitchenCondition

4.95 out of 5 average rating, 499 reviews

A modern structure is depicted with a vibrant red exterior and a contrasting gray base. A prominent garage door is featured at the front, accompanied by a minimalist sign displaying '416.' Gravel surrounds the building, with a clear sky above.

Barn in Pendleton

The 406 Shop

One bedroom, queen size bed, air mattresses available, full bathroom with shower. Park in front of the shop. Full size fridge, microwave, propane BBQ, toaster & Keurig. - Concrete floors throughout, pet friendly. Max 4 guests without approval. RV plug with pull through parking available. Any unregistered guests on property after 11 pm will be charged as an additional occupant. NO UNAUTHORIEZED PARTIES ALLOWED. You will be asked to vacate property and an event fee will be charged.

KitchenIndoor spacesLaundry

4.96 out of 5 average rating, 358 reviews

A welcoming bunkhouse is set amidst lush green grass, with two pink chairs positioned on the front porch. Surrounding trees provide shade, while the structure features a wooden deck and a traditional roof. A sense of tranquility is enhanced by the open outdoor space.

Tiny home in Pilot Rock

McKay Creek Bunkhouse

Welcome to McKay Creek Bunkhouse. We are located on McKay Creek 11 miles from the heart of Pendleton, Oregon. This 1900 bunkhouse is situated near the blue mountains and is recognized by the state of Oregon as part of our century farm which is still a working farm. The bunkhouse is surrounded by a couple of acres of grass and wheat fields. Locate just down from the mouth of McKay Reservoir you may see geese, turkeys and deer to name a few wildlife that visit the area. Come and relax.

KitchenIndoor spacesBarbecue

4.91 out of 5 average rating, 116 reviews

A spacious studio layout is shown, featuring a comfortable bed with light bedding and a gray sofa positioned nearby. Warm lighting emanates from ceiling fixtures, while a small table and decorative items are visible. A TV is mounted on the wall, adding to the cozy atmosphere.

Apartment in Pendleton

Cozy Pendleton Studio Hideaway

Welcome to your cozy Pendleton retreat! Perfect for two, this spacious studio offers all the comforts of home, complete with your own private driveway and entrance. Relax with a movie on the TV or stay connected with high-speed WiFi. The kitchenette is equipped with a microwave, hot plate, toaster oven, and all the essential cooking tools, making it easy to whip up a meal. Whether you're here to explore or unwind, this studio provides a comfortable and convenient base for your stay.

KitchenFamilyQuiet

A well-maintained, two-story home showcases a white exterior with black shutters. A covered porch is adorned with seating, and decorative lanterns are positioned by the entrance. Lush green landscaping surrounds the property, adding a neat appearance to the front yard.

4.97 out of 5 average rating, 266 reviews

Pendleton River Parkway House

When you stay here, you truly feel at home while surrounded by modern farm style furnishings. We are conveniently located along the Umatilla River and less than a five minute walk from the Pendleton Round Up grounds and historical Main Street. This is especially convenient during Round Up or one of the many concerts Pendleton hosts. The property has recently been refurbished including an updated kitchen and bathroom. The backyard is a nice place to sit and enjoy your coffee.

FamilyKitchenDecor

4.93 out of 5 average rating, 311 reviews

Apartment in Pendleton

*Cozy Downtown Stay* (Private apt. Self check-in)

Beautiful, large apartment located in the heart of Pendleton. This beautiful apartment is stylishly decorated with a relaxing feel. It is fully equipped for a long term stay or a short term comfortable stay. Centrally located to multiple bars, restaurants; walking distance from Pendleton underground tours, Umatilla River levy, Pendleton Center for the Arts, children’s museum & a 15 min walk to Pendleton Round-up. Perfect location for people who want explore or simply relax.

Indoor spacesKitchenAir conditioning

4.99 out of 5 average rating, 132 reviews

The exterior of Weston Mountain Lodge showcases warm wooden siding, adorned with large windows that provide ample natural light. A well-kept lawn features colorful flowers, and deck furniture awaits outdoor relaxation. Tall trees surround the property, enhancing the lodge's natural setting and providing a sense of privacy.

Home in Weston

Weston Mountain Lodge in the Blue Mountains

Weston Mountain Lodge is a grand, open space full of natural light that feels intimate and cozy too. A group of friends or families as well as a couple or an individual would all feel at home here. The house and land inspire reflection and serenity. Weston Mountain Lodge feels magical and “other worldly” - a quiet oasis tucked off life’s busy path. The Lodge is a perfect place to disconnect so you can reconnect, where you can build traditions and create lasting memories.

KitchenIndoor spacesHot tub

A welcoming entrance showcases a bright yellow door adorned with a floral wreath. A doormat with the word 'hi!' greets visitors, while a decorative sign reading 'STAY awhile' adds to the inviting atmosphere. Soft gray siding lines the entrance.

4.95 out of 5 average rating, 348 reviews

Stay Awhile - Pet Friendly, Fenced Yard

Welcome to Pendleton! We are excited to have you stay and hope you enjoy this home away from home. Our shabby-chic abode is family and pet friendly, and the perfect space to relax while you stay in our Northeastern Oregon town. Our location places you within minutes of anything you may want to do here or anywhere you may want to be. This 3-bedroom, 1-bath comfortably houses 6 people; Making it perfect for your family or a small group.

KitchenFamilyNearby

4.98 out of 5 average rating, 185 reviews

The kitchen features light-colored cabinetry and a countertop with a double sink. Open shelves display dishware. Appliances include a microwave and a dishwasher. Natural light enters from a nearby window, with floral curtains adding a touch of color. A door leads to the outside.

Cottage in Pendleton

*The Garden House* Adjustable bed•fire pit•Bbq

Welcome to the Garden House Take it easy at this unique and tranquil getaway, this updated two bedroom home with a vintage flair. Gas fireplace, Hi speed internet off street parking with lit entrance. Feel comfortable with Enhanced cleaning and high end bedding. Easy access from Hwy 84 and OR-11. 11 minutes to wildhorse casino and minutes to downtown and Pendleton Round - up Grounds and Happy Cannon.

KitchenFamilyCondition

The exterior of the house exhibits a welcoming blue facade with white trim and a prominent entrance featuring a covered porch. Bright flower pots with pink blooms are placed at the base of the steps, while decorative stones and landscaping enhance the curb appeal.

4.98 out of 5 average rating, 254 reviews

Creekside Cottage with EV Charger

House has a country/farm feel but is located right in town, just minutes away from restaurants, shopping, and the Round-Up grounds. House has a deck with a barbecue grill and back yard which look out over the beautiful McKay Creek. Chickens, cows and pigs on the property. Small horse pasture available. Room for kids to play. Kitchen is fully stocked with everything you need to prepare meals.

FamilyKitchenParking

Popular amenities for Pendleton family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 218 reviews

A cozy living area features two armchairs and a sofa arranged around a coffee table. A gas fireplace is located against a neutral wall, and soft lighting is provided by two table lamps. Large windows allow natural light to brighten the space, complemented by decorative plants.

Home in Milton-Freewater

Vineyard Gypsy - fireplace, hot tub, king bed

Indoor spacesKitchenGetting around

5.0 out of 5 average rating, 140 reviews

A charming bungalow is softly illuminated by warm outdoor lights, highlighting its welcoming façade. A clear pathway leads to the front porch, surrounded by lush green grass and trees, with a vibrant sunset sky adding a touch of color in the background.

Home in College Place

Lux Boho Bungalow in Walla Walla

FamilyKitchenView

4.95 out of 5 average rating, 166 reviews

A modern barn-style structure is set against a colorful sky at sunset. The building features large windows and a distinctive cupola. A windmill stands nearby, and a grassy lawn extends in the foreground, bordered by wooden fencing.

Farm stay in Walla Walla

SpringBranch Bunkhouse. Country living w/ hot tub.

Indoor spacesFamilyAir conditioning

Superhost

An inviting studio space features a large screen suitable for movie streaming, positioned against a blue wall. A comfortable seating area is provided by a plush chair and decorative rug. A bar area with high chairs is located nearby, creating an engaging relaxation spot.

Guesthouse in Kennewick

Theater Themed House w/ Hottub

Indoor spacesFamilyShared spaces

4.85 out of 5 average rating, 678 reviews

4.98 out of 5 average rating, 117 reviews

A stylish living area features a blend of modern and rustic elements, with a large round coffee table and comfortable seating options. A dining table with multiple chairs is visible in the background, complemented by large windows that let in natural light. Greenery is incorporated with a tall plant.

Home in Kennewick

Icon Escape - 3 Bedroom Oasis

Indoor spacesKitchenHospitality

4.98 out of 5 average rating, 178 reviews

An outdoor seating area is positioned under a covered patio, featuring comfortable wicker chairs. A spacious lawn extends beyond the patio, bordered by landscaped beds of various plants and trees. The serene view stretches towards the horizon, with a clear sky above.

Home in Kennewick

Spacious Home Amazing Golf Course & River Views

KitchenFamilyHospitality

4.95 out of 5 average rating, 104 reviews

A cozy bedroom contains a spacious bed dressed in light bedding with a textured throw. A window with blinds allows natural light to fill the space, and a small bedside table with a lamp is positioned next to the bed. Soft, neutral tones create a calming atmosphere.

Cabin in La Grande

Modern Cabin with great views!

FamilyIndoor spacesDecor

Guest suite in College Place

Vibrant purple flowers are featured prominently in the foreground, contrasting with lush greenery in the background. A birdbath is visible among the garden elements, with a decorative pot containing vibrant blooms adding charm to the serene outdoor space.

Highland Hideout

FamilyKitchenShared spaces

4.98 out of 5 average rating, 245 reviews

Family- and pet-friendly home rentals

Farm stay in Milton-Freewater

Unique Cabin•Very Comfortable•King Bed•Gated

FamilyIndoor spacesLocation

4.99 out of 5 average rating, 153 reviews

4.97 out of 5 average rating, 325 reviews

A private patio area is shown with orange Adirondack chairs positioned near a firepit. Potted plants and greenery are visible, with a spacious yard in the background and trees framing the scene. Soft evening light casts a welcoming glow across the space.

Guest suite in Hermiston

Private apartment in secluded country setting.

Indoor spacesFamilyBreakfast

4.99 out of 5 average rating, 240 reviews

A cabin features warm lighting strung above the deck, illuminating its exterior walls and inviting seating areas. Large windows provide a glimpse into the interiors, while the surrounding space is open and rural, enhancing the peaceful setting at night.

Home in La Grande

Trailside! The Owl’s Nest at Mt Emily Rec Area

Indoor spacesKitchenBackyard

Cabin in Milton-Freewater

A charming cabin is set among lush greenery, surrounded by trees and a well-maintained lawn. A gravel driveway leads to the property, while a wooden fence delineates the yard. Sunlight filters through the trees, highlighting the rustic exterior and natural surroundings.

Beautiful Cabin on a river, close to wine country

FamilyKitchenAmenities

4.98 out of 5 average rating, 105 reviews

4.96 out of 5 average rating, 163 reviews

A cozy bedroom features a spacious white bed with textured bedding. Two decorative wall hangings are positioned above the headboard on a dark gray wall. A small nightstand with a plant adds a touch of greenery, and light is provided by a ceiling fixture and natural light from the window.

Townhouse in Hermiston

2 bed 2 bath- sleeps 4

FamilyKitchenBackyard

4.91 out of 5 average rating, 505 reviews

A welcoming entrance to the retreat is highlighted by a circular sign featuring mountain and tree designs. A hanging planter brims with vibrant purple flowers, while a rustic metallic art piece resembling a sunburst adds character to the earthy-colored wall.

Farm stay in La Grande

Elk Song Inn @ Foothill Retreat-Cozy and spacious

KitchenIndoor spacesLocation

4.9 out of 5 average rating, 173 reviews

A lush garden area showcases a curved stone wall filled with various plants and flowers. A small archway decorated with climbing vines adds character. The background features a cottage with a sloped roof, surrounded by greenery, creating a serene outdoor retreat.

Home in La Grande

Garden Get Away

Indoor spacesKitchenLong stay

Guesthouse in Walla Walla

The COTTAGE at Silver Maple Estates

Indoor spacesFamilyParks

4.98 out of 5 average rating, 269 reviews

Family-friendly home rentals with a pool

4.88 out of 5 average rating, 796 reviews

A wooden deck leads to a spacious luxury tent surrounded by lush greenery on a tranquil property. The tent features a canopy design and is set among vibrant plants, creating a secluded atmosphere. Natural light filters through the surrounding foliage.

Tent in College Place

Hideaway Tent with Pool and Hot Tub

KitchenIndoor spacesLong stay

Superhost

A cedar soaking tub filled with hot springs mineral water is seen, surrounded by wooden walls and an outdoor setting. Green hills are visible in the background, along with a string of lights overhead that create a soft glow.

Yurt in La Grande

Yurt #2, Private Hot Springs Getaway

Indoor spacesFamilyPets

4.9 out of 5 average rating, 1069 reviews

4.99 out of 5 average rating, 203 reviews

A heated pool is surrounded by a spacious patio featuring two loungers with towels draped over them. A tray with wine glasses and a bottle rests nearby. The pool area is framed by lush greenery and colorful patio furniture, creating an inviting outdoor space.

Home in Walla Walla

Heated Pool & Hot Tub - Walk to Town- Dog Friendly

Indoor spacesFamilyCheckout

4.92 out of 5 average rating, 155 reviews

A refreshing pool is surrounded by a spacious, sunlit patio. Lounge chairs are adorned with colorful cushions, providing a comfortable spot for relaxation. A vibrant umbrella offers shade, while a pineapple-shaped float adds a playful touch to the inviting water.

Home in Kennewick

Playtime Paradise! Pool, Video Game Room, Pets OK!

FamilyIndoor spacesAccess

4.97 out of 5 average rating, 139 reviews

An outdoor area is presented with a large dining table surrounded by dark chairs, complemented by a vibrant red umbrella. A heated pool is visible along with lounge chairs positioned nearby. Lush landscaping features a variety of plants and bushes, with a white fence creating a private atmosphere.

Farm stay in Walla Walla

The Farmhouse and Pool in Walla Walla Wine Country

FamilyKitchenCondition

4.9 out of 5 average rating, 115 reviews

A private heated pool sits within a fenced area, surrounded by lush green shrubs. Comfortable lounge chairs are positioned nearby, with a small table featuring drinks and snacks. Clear blue skies and bright sunlight enhance the inviting outdoor space.

Home in Walla Walla

Grant House | Hot Tub + Pool Near Downtown

KitchenIndoor spacesAir conditioning

Guesthouse in Walla Walla

Harvest Cottage · Hot Tub · Bike to 3 Wineries

Indoor spacesKitchenWalkability

5.0 out of 5 average rating, 28 reviews