Top Oregon Vacation Homes for the Holiday Season: Cozy Coast & Mountain Stays

The holiday season in Oregon shimmers with cozy charm and scenic wonder. Snow-dusted peaks sparkle beneath bluebird skies, small towns glow with twinkling lights, and the air carries the scent of pine and possibility. In Central Oregon, adventure meets serenity on mountain trails and in fireside lodges, while along the coast, waves crash against rugged cliffs as festive lights dance across seaside streets. Days are filled with skiing, snowshoeing, and boutique shopping; evenings invite slow moments with hot cocoa, warm blankets, and ocean sunsets. From mountain cabins to beachfront escapes, Oregon turns every holiday stay into a celebration of comfort and connection.

This curated collection of Meredith Lodging brings together Oregon’s best winter escapes – five cozy retreats in Central Oregon and five along the Coast. Each home pairs inviting comfort with easy access to the state’s most scenic winter playgrounds. Discover where mountain adventure meets coastal serenity and plan a holiday getaway that’s merry, memorable, and uniquely Oregon.

Central Oregon Holiday Stays: Cozy Cabins, Lodges & Winter Fun

Central Oregon shines during the holidays with its snow-covered trails, festive towns, and endless outdoor adventures. From skiing and snowshoeing to relaxing by a crackling fire, it’s a destination that mixes mountain excitement with cozy small-town charm. If you’re planning a holiday getaway in Bend, Sunriver, or the Mt. Hood area, these five Meredith Lodging rentals offer the perfect mix of comfort, location, and style for your winter escape..

Bend Comfy Condo – Ski House 235, Bend, OR

This bright upper-level retreat in Mt. Bachelor Village Resort blends modern comfort with tranquil woodland views. The open living area features a gas fireplace, Smart TV, and sliding doors leading to a private deck framed by evergreens – perfect for morning coffee or après-ski sunsets. The updated kitchen and cozy dining space make gathering easy after a day exploring Bend or Mt. Bachelor.

Both bedrooms feature Smart TVs and plush linens, and the flexible sleeping layout ensures plenty of space for families or small groups. After dinner, curl up by the fire or step outside for a breath of cool mountain air as snow drifts through the trees.

Holiday Highlight: Cozy Comfort Meets Adventure

A peaceful, light-filled condo with unbeatable access to Bend’s trails, breweries, and slopes. Enjoy the best of winter-skiing, shopping, and stargazing, all from a warm, welcoming home base.

Details:

• Bedrooms: 2
• Bathrooms: 1 full
• Guests: 6
• Pets Allowed: No

Amenities:
Smart TVs • Gas Fireplace • Queen Sleeper Sofa • Community Hot Tub & Pool • Game Room • Fire Pit • Washer/Dryer

Black Bear Lodge – Sunriver, OR

Gather family and friends at Black Bear Lodge, a grand seven-bedroom home designed for connection and comfort. The soaring ceilings, stone fireplace, and rich wood details create that classic lodge atmosphere, while two living areas and a gourmet kitchen make entertaining effortless. Double ovens, dishwashers, and a large dining table let everyone come together for festive meals.

After dinner, relax in the hot tub or enjoy the heated garage game room with ping-pong, foosball, and video games. Six king suites ensure privacy and space for guests, while the bunk room and bonus living area keep the fun going for kids and adults alike.

Holiday Highlight: Celebrate in Style

Spacious, elegant, and filled with amenities, Black Bear Lodge is built for gatherings. Host a reunion, share a holiday feast, and make memories surrounded by forest views and the warmth of a roaring fire.

Details:

• Bedrooms: 7
• Bathrooms: 6 full + 1 half
• Guests: 16
• Pets Allowed: No

Amenities:
Gas Fireplaces • Multiple TVs • Gourmet Kitchen • Game Room • Hot Tub • Bikes & Helmets • SHARC Passes • Laundry • BBQ Deck

Cypress Cabin Retreat – Sunriver, OR

Wrapped in tall pines and rich with rustic character, Cypress Cabin Retreat balances log-cabin charm with sleek, modern design. Vaulted ceilings and reclaimed wood accents add warmth to the open living space, where a large sectional and wood stove invite long, cozy evenings. The custom kitchen and hand-built dining table are perfect for holiday meals, and the covered deck offers a private hot tub for relaxing under winter skies.

Four spacious bedrooms and flexible sleeping areas provide comfort for families and friends alike. Wake up to quiet forest views, explore nearby trails, then return for games, stories, and laughter by the fire.

Holiday Highlight: Rustic Charm, Modern Magic

A picture-perfect cabin for winter retreats. Enjoy handcrafted design, luxurious touches, and the cozy glow of a wood-burning stove, your own slice of holiday serenity in Sunriver.

Details:

• Bedrooms: 4
• Bathrooms: 2 full
• Guests: 10
• Pets Allowed: No

Amenities:

Wood Stove • Smart TVs • Gourmet Kitchen • Private Hot Tub • BBQ Deck • Heated Floors • Washer/Dryer • SHARC Passes

Eazy Inn at Eagle Crest – Redmond, OR

Eazy Inn lives up to its name, a bright, single-level home designed for effortless relaxation. The living room welcomes guests with a gas fireplace and plush seating, while the fully equipped kitchen and circular dining area make holiday meals feel easy and intimate. A private patio opens to open skies and mountain air, with a secluded hot tub perfect for stargazing.

Guests enjoy full access to Eagle Crest Resort amenities: pools, fitness centers, tennis courts, and championship golf. With cozy bedrooms, a quiet study space, and pet-friendly comfort, this home combines convenience and calm in every detail.

Holiday Highlight: Effortless Relaxation

Simple, stylish, and surrounded by resort amenities, this home makes your holiday unwind easy. Sip cocoa in the hot tub, enjoy crisp walks through Eagle Crest, and embrace Oregon’s slower winter rhythm.

Details:

• Bedrooms: 2
• Bathrooms: 2 full
• Guests: 6
• Pets Allowed: Yes

Amenities:

Gas Fireplace • Private Hot Tub • Resort Pools & Fitness Centers • Golf Access • Study/Workspace • Washer/Dryer • BBQ Patio

Firwood Cabin – Mt. Hood Area, OR

Hidden on three forested acres, Firwood Cabin offers peace, privacy, and postcard-perfect mountain views. Its open layout blends vintage fir beams and cozy décor with modern updates, including a fully equipped kitchen and streaming TV. The great room’s gas fireplace keeps the space warm and welcoming, while the large deck and outdoor firepit invite evenings spent under a canopy of stars.

After a day on Mt. Hood’s slopes or nearby trails, relax in the private hot tub surrounded by snow-tipped trees. With pet-friendly amenities and a timeless cabin feel, this mountain retreat is ideal for couples or small families looking for a quiet holiday hideaway.

Holiday Highlight: Serenity Among the Pines

Quiet mornings, mountain views, and nights under a clear Oregon sky – Firwood Cabin delivers a holiday experience filled with peace and natural beauty. It’s a cozy escape where memories come easy.

Details:

• Bedrooms: 2
• Bathrooms: 1 full
• Guests: 4
• Pets Allowed: Yes

Amenities:

Private Hot Tub • Forest Views • Gas Fireplace • Deck with BBQ • Firepit • Washer/Dryer • Streaming TV • Pet Friendly

Oregon Coast Holiday Stays: Seaside Charm & Peaceful Escapes

The Oregon Coast offers a quieter kind of holiday magic – ocean waves, glowing village lights, and cozy cottages made for storm watching. It’s the perfect place to unwind, recharge, and celebrate the season by the sea. From romantic beachside retreats to spacious ocean-view homes for family gatherings, these five Meredith Lodging properties set the scene for a memorable coastal holiday.

Beach Bliss – Rockaway Beach, OR

Just steps from the shore, Beach Bliss is a romantic coastal cottage reimagined for modern comfort. Its vaulted ceilings, soft sea-blue walls, and bright, airy décor create an atmosphere of relaxation from the moment you arrive. Curl up on the white sectional by the electric fireplace or enjoy coffee at the cozy window nook with ocean breezes drifting through. The updated kitchenette is perfect for simple meals in, and an outdoor picnic table invites you to dine al fresco on clear winter days.

The king bedroom features soft linens and a serene ambiance, ideal for slow mornings with the sound of surf and seabirds in the distance. Every detail feels curated for a tranquil escape, whether it’s a couple’s retreat or a solo coastal reset.

Coastal Holiday Highlight: Your Own Slice of Seaside Serenity

Beach Bliss is perfect for travelers craving peace, style, and proximity to the ocean. Enjoy Rockaway’s quiet charm, long walks on the beach, and easy access to local shops and the scenic coastal railway, all from your cozy home by the sea.

Details:

• Bedrooms: 1
• Bathrooms: 1 full
• Guests: 4
• Pets Allowed: Yes

Amenities:

Smart TV • Electric Fireplace • Kitchenette • King Bed • Outdoor Picnic Area • Beach Access • Private Entrance

Breakers Beach House #7 – Neskowin, OR

Breakers Beach House #7 combines Craftsman elegance with the timeless allure of an oceanfront stay. This beautifully furnished three-bedroom home features panoramic windows, a wood-burning fireplace (with wood included), and a chef’s kitchen with quartz counters and stainless steel appliances. Thoughtful touches, art by Oregon photographers, a curated library of books and films, and games for every age, make this a true home away from home.

Two upstairs ocean-view bedrooms let you wake up to waves, while the third offers built-in bunks perfect for families. A private deck with Adirondack chairs overlooks the sand, inviting you to watch sunsets blaze across the horizon.

Coastal Holiday Highlight: Classic Style Meets Oceanfront Comfort

A refined retreat for families or friends who want both charm and ocean views. Cozy up by the fire, share long dinners as storms roll in, and fall asleep to the rhythm of the sea just outside your door.

Details:

• Bedrooms: 3
• Bathrooms: 2 full
• Guests: 6
• Pets Allowed: No

Amenities:

Wood-Burning Fireplace • Ocean Views • Smart TV • Blu-Ray/DVD Player • Fully Equipped Kitchen • Deck with Seating • Beach Access

Cabin at the Beach – Rockaway Beach, OR

The aptly named Cabin at the Beach offers warmth, charm, and space for the whole family. Inside, a vaulted ceiling and plush sectional create a bright, inviting living room ideal for movie nights or board games by the fire. The updated kitchen makes mealtime easy, while the backyard, picnic tables, and firepit bring everyone together outdoors. Upstairs, the loft bedroom, complete with its own private deck, delights kids and adults alike.

Nestled in a quiet neighborhood just three blocks from Nedonna Beach, this home offers both peace and proximity to coastal fun. Spend your mornings beachcombing, your afternoons exploring Rockaway’s shops, and your evenings roasting marshmallows under the stars.

Coastal Holiday Highlight: Family Fun, Oregon-Style

Spacious yet cozy, this cabin makes every moment feel special. Perfect for small groups or families, it offers all the ingredients for an easy, joy-filled coastal holiday, comfort, convenience, and that unmistakable Oregon charm.

Details:

• Bedrooms: 2 + Loft
• Bathrooms: 1 full
• Guests: 6
• Pets Allowed: Yes

Amenities:

TV • Fully Equipped Kitchen • Backyard with Firepit • Loft Deck • Outdoor Dining • Washer/Dryer • Beach Access

Cape View Escape – Pacific City, OR

Perched high on Nestucca Ridge, Cape View Escape lives up to its name with breathtaking panoramas of Haystack Rock and the Pacific coastline. The open-concept great room features vaulted ceilings, a gas fireplace, and floor-to-ceiling windows framing ocean sunsets. The modern kitchen with its breakfast bar and elevated dining table, lets guests cook and dine while soaking in sweeping views.

Downstairs, a media room with foosball and a sectional provides extra entertainment space for families. Multiple decks offer vantage points for whale-watching or toasting to the holidays with friends. It’s a stunning blend of privacy, space, and natural beauty.

Coastal Holiday Highlight: Views Worth Celebrating

Ideal for families and groups seeking a scenic, luxurious getaway. Watch winter waves from the comfort of your deck, explore Pacific City’s dunes, and enjoy the warmth of home in a setting that feels cinematic.

Details:

• Bedrooms: 3
• Bathrooms: 2 full + 1 half
• Guests: 8
• Pets Allowed: No

Amenities:

Gas Fireplace • Ocean Views • Multiple Decks • Foosball Table • Media Room • Fully Equipped Kitchen • BBQ Grill

King Tide – Rockaway Beach, OR

Bright, spacious, and just 68 steps from the sand, King Tide is a picture-perfect Oregon Coast cottage. Tongue-and-groove ceilings and coastal-inspired décor create an airy, inviting space filled with light. The living room features a plush white sectional, Smart TV, and electric fireplace, perfect for cozy movie nights after a beach walk. The kitchen and dining nook are designed for easy gatherings, while the outdoor porch offers Adirondack chairs and a picnic table for fresh-air meals.

Two queen bedrooms provide a restful escape after days spent exploring the coast. Everything here feels fresh, modern, and ready to make your holiday escape unforgettable.

Coastal Holiday Highlight: Where Modern Style Meets Classic Coastal Charm

A gem for couples or small families who love being near the beach. King Tide delivers comfort, design, and proximity to everything, shop local, ride the scenic railway, and end your day with the sound of the surf just beyond your door.

Details:

• Bedrooms: 2
• Bathrooms: 1 full
• Guests: 6
• Pets Allowed: Yes

Amenities:

Smart TVs • Electric Fireplace • Queen Sofa Sleeper • Outdoor Porch • Picnic Table • Beach Access • Private Entrance

Plan Your Oregon Holiday Getaway with Meredith Lodging

No matter where you celebrate the season, beneath snow-dusted pines in Central Oregon or beside the waves along the Oregon Coast – Meredith Lodging has a stay to make your holidays unforgettable. From large group getaways perfect for family celebrations to romantic retreats built for two, our collection of homes is ready to welcome you. Looking for something extra special? Explore our luxury homes, pet-friendly stays, or cozy mountain retreats for a true Oregon experience.

Prefer a little more adventure or relaxation? Browse homes with private hot tubs, game rooms, private pools, golf course views, or peaceful lakefront escapes. Wherever your holiday plans take you, Meredith Lodging has the perfect Oregon home waiting, so you can focus on what matters most: time together, surrounded by the beauty of the season.