Family-friendly holiday rentals in Madras

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Top-rated family-friendly rentals in Madras

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Home in Bend

4.9 out of 5 average rating, 196 reviews

Light-Filled 5BR, Great location!

Our corner home sits on a tree-lined block within a family neighborhood with two private parks and walking paths. While snow-capped peaks can be enjoyed from our windows, the home is conveniently located in town on the desirable Westside. Our spacious 3300 sf home is central to Bend's many amenities. Phil's Trail, a mountain biking Mecca, is just seven minutes away past Mount Washington and Skyliners Drive, the main cross streets of our neighborhood. Broken Top Country Club and golf course is adjacent to the neighborhood off of Mount Washington Drive. The Bend Athletic Club is six minutes away on Mount Washington. Cascade Lakes Scenic Byway, the gateway to Mount Bachelor, is also off of Mount Washington Drive. Skiing and recreational areas at Mount Bachelor can be reached in less than 30 minutes. Historic Downtown Bend is just over five minutes away by car and within easy walking or biking distance. The Old Mill District, which has a spectrum of dining, entertainment and shopping opportunities is also only minutes away by car. The Southern Crossing bridge which links us to Old Mill also leads to the Deschutes River. Within two minutes (1/2 mile away) are neighborhood conveniences at Northwest Crossing, as well grocery stores, pharmacies, restaurants, and bike and ski shops off of Century Drive and Galveston. For rock climbers, Smith Rock State Park in Terrebonne is just 45 minutes away. Sleeping arrangements: comfortably sleeps 10 (on beds, not sofas) Bedroom 1: King bed with sofa/futon and master bath Bedroom 2: King bed with window sitting area Bedroom 3: Queen bed Bedroom 4: Queen bed Bedroom 5: 2 twin beds total (no mattresses in trundles) Dining areas: Rectangular dining table with seating for 10-12 Oval dining table with seating for 6 Island bar with seating for 3 Great room living area: 2 large sofas 2 large arm chairs 2 leather chairs 2 upholstered benches/ottomans Seats 10-12 with additional seating nearby Amenities: Free Wifi High definition cable and 4 TVs Hot tub Game room with board games, books and Wii Air hockey table Table tennis (ping pong table) Foosball table Consumables provided: shampoo, conditioner, body gel, hand soap, dish soap, sponge, aluminum foil, plastic wrap, laundry detergent Parking: Garage parking for one large vehicle or plenty of bike storage Parking for two cars in driveway Corner home with plenty of street parking Thank you for your interest! **No pets. No smoking. No parties. No exceptions. ***Maximum occupancy of 10 for rates listed. 11th and 12th person possible with owner agreement and $25/per person per night. *****One week minimum booking during the Holiday period in December through New Year's. 3-night minimum booking during High Season in the months of June through August. If there is a gap in between bookings, a shorter reservation is definitely possible.

Guest favourite

Home in Black Butte Ranch

4.89 out of 5 average rating, 152 reviews

Family retreat on Black Butte Ranch

Perfect space for a family vacation to enjoy the beautiful outdoors. Lots of space to relax and feel at home. Two double bedrooms and kids bunk room with three bathrooms. Two living spaces with entertainment options. A home office area with a wi-fi booster. Very close to Glaze Meadow pool complex, tennis courts, golf course and the games area. We welcome a dog but ask you are confident they are well behaved. There are carpets upstairs and we appreciate those dogs who pee and poop outside!

Guest favourite

Cabin in Sunriver

4.88 out of 5 average rating, 226 reviews

The Sunriver Hive

My home is close to family-friendly activities. You’ll love the house because of the views, the location, the ambiance, and the outdoor space. The deck is expansive and perfect for enjoying the sun, or take a dip in the hot tub! The house is good for couples, families (with kids), and groups of 9 or less. Take advantage of the water toys we include for use for free, or go for a bicycle ride! The world is yours! Check in is 4 PM (Inquire about early check in availability). Checkout 11AM.

Guest favourite

Home in Sunriver

4.96 out of 5 average rating, 113 reviews

Pet friendly, upscale home, AC, sleeps 8

Our beautiful 1900 sq. ft. Home, is the perfect spot for your vacation. Our kitchen has every gadget, and upscale appliances to create gourmet meals. King master upstairs, and 2 queen bedrooms down, share a bathroom. We have bikes and ping pong and TV in the garage. A Weber BBQ on the deck, with a sparkling, bubbling hot tub. Decks face both east and west, so morning sun, and evening sunsets. Dog friendly! (2 dog limit). Warm up by our big fireplace after a fun day skiing at Mt. Bachelor.

Guest favourite

Home in Bend

4.94 out of 5 average rating, 171 reviews

5 Minute Drive to Downtown Bend, Dog Friendly

Centrally located in Bend, we're just minutes away from shopping, restaurants, downtown, Old Mill, and Mt Bachelor. We're thoughtfully stocked with cooking supplies (pots, pans, utensils, seasoning), Smart TVs with cable, coffee, and tea. All rooms have top-rated memory foam mattresses. Washer/Dryer in home. Towels, linens, shampoo, soap all provided. Fire pit and Gas Grill in fenced in back yard. Cleaned by a professional cleaning service after each stay. Parking limited to 5 cars.

Guest favourite

Flat in Sisters

4.94 out of 5 average rating, 162 reviews

Contemporary apartment in Sisters, OR. USA

A contemporary 2 bedroom apartment in a quiet neighborhood just 4 blocks from Sisters main street. Minutes from music venues, festival locations, trails, and popular biking routes. Sisters has art, music, movie theater, good coffee, beer, restaurants, and boutique shopping. Village Green is close by. Superb biking, hiking, skiing, fly fishing, and outdoor opportunities abound year round. The apartment is perfect for couples, solo adventurers, business travelers, and families.

Guest favourite

Home in Bend

4.92 out of 5 average rating, 145 reviews

5 BR, Hot Tub, Fireplace close to Mt Bach & town

Enjoy the peace and quiet surrounded by trees, in our fully remodeled tri-level home. It's on 1 acre on the south end of Bend, just minutes from the Old Mill, downtown, Drake & Riverbend Park. Only 15 min from Sunriver and 30 min from Mt Bachelor. 5 BR home that sleeps 12 with 8 beds. It has a deck, hot tub, a fully-stocked kitchen, fireplace, comfortable beds, cable TV, & Wi-Fi! Everything you need for a relaxing and enjoyable vacation. DCCA#1470

Superhost

Home in Bend

4.77 out of 5 average rating, 114 reviews

1 Mile to Downtown from the Orchard District

Welcome to Bend! Whether you're biking, hiking, skiing, fishing, enjoying the water, or sipping on great beer, you're sure to have an unforgettable time from our centrally located home. After completing a renovation in June 2018, we've created a warm, modern ambiance that's less than 1 mile from the heart of Bend. This space is perfect for a family retreat, a group of friends, or a family seeking the comfort of a home while away. Now, get out and play!

Guest favourite

Home in Bend

4.97 out of 5 average rating, 156 reviews

Old Mill Charm

Thank you for visiting Old Mill Charm! Whether you are here to explore or simply relax we are happy to host you. My husband and I have lived here several years and work hard to make sure the house is stocked with everything you need. This 3 bed, 2 bath home is right down the street from The Old Mill/Amphitheater! The front porch is a great spot for listening to concerts while the fully fenced backyard is a favorite for pets.

Guest favourite

Flat in Bend

4.98 out of 5 average rating, 102 reviews

Amazing West Side* Walk Everywhere * Dog Friendly

The location of this home is just exceptional for visiting Bend. You will be in the heart of the wonderful and popular West Side. We built the home specifically to be used as a vacation rental. We would love to make sure you have a great experience visiting Bend and staying in our home so please let us know what we can do to make sure you have a 5 star experience.

Guest favourite

Home in Terrebonne

4.97 out of 5 average rating, 113 reviews

4BR/3Bth, Bend Country Pastoral 9 Mt View, 9 acres

Plan your vacation getaway and escape the destination resorts at our quiet & peaceful 4 BR, 3 Bath, lodge home retreat on 9 private acres north of Bend, "in the country but not far away". Beautiful 9 Cascade Mt view overlooking a corner of the legendary Deschutes R.; enjoy area Skiing, Golfing, Fishing, Hiking, Rock Climbing, Biking, Micro Breweries, & more.

Holiday rentals for every style

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Popular amenities for Madras family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Home in Sunriver

4.88 out of 5 average rating, 155 reviews

Great 3 Bedroom Sunriver Home w/8 SHARC/REC Passes

Guest favourite

Chalet in Redmond

4.91 out of 5 average rating, 174 reviews

Eagle Crest Luxury Chalet w/Private Hot Tub&Garage

Superhost

Home in Bend

4.87 out of 5 average rating, 374 reviews

Charming east side house, with hot tub.

Guest favourite

Townhouse in Bend

4.94 out of 5 average rating, 125 reviews

Closest to Bachelor. 8 min to town. Spa. DogsOk!

Guest favourite

Home in Old Bend

4.97 out of 5 average rating, 192 reviews

Lava Flo, Historic gem on Lava Road, pets, hot tub

Guest favourite

Townhouse in Sunriver

4.94 out of 5 average rating, 324 reviews

Relaxing Sunriver Retreat | Hot Tub & SHARC Passes

Guest favourite

Home in Sunriver

4.85 out of 5 average rating, 269 reviews

Private & fenced, hot tub, river near by, pets

Guest favourite

Flat in Bend

4.94 out of 5 average rating, 858 reviews

The Garden Apt-Hot Tub Fireplace AC 250+ Mbps

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Family- and pet-friendly home rentals

Guest favourite

Cottage in Bend

4.94 out of 5 average rating, 416 reviews

An Urban Base to Bend's Adventures!

Guest favourite

Home in Bend

4.95 out of 5 average rating, 157 reviews

Separate Apt in Beautiful Westside Bend

Guest favourite

Home in Old Bend

4.96 out of 5 average rating, 171 reviews

Bend River West Loft

Guest favourite

Guest suite in Bend

4.91 out of 5 average rating, 347 reviews

Cozy Studio! Walk to NW Crossing and Shevlin Park

Guest favourite

Home in Sunriver

4.93 out of 5 average rating, 234 reviews

A Little Peace of Paradise, A/C & 8 SHARC Passes

Guest favourite

Guest house in Bend

4.97 out of 5 average rating, 547 reviews

Live the Pastoral Idyll in a Warm and Inviting Guesthouse

Guest favourite

Cottage in Bend

4.95 out of 5 average rating, 328 reviews

Adorable West Side Cottage, Great Location!

Superhost

Home in Bend

4.87 out of 5 average rating, 358 reviews

The Birdseye House

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Family-friendly home rentals with a pool

Guest favourite

Home in Bend

4.97 out of 5 average rating, 197 reviews

Romantic Guest House w/Hot Tub, Pool, Tennis Court

Guest favourite

Apartment in Bend

4.86 out of 5 average rating, 264 reviews

Mt. Bachelor Village Condo - Near Town & River

Guest favourite

Home in Sunriver

4.93 out of 5 average rating, 178 reviews

Sunriver Getaway: Hot Tub & Game Room

Guest favourite

Home in Sisters

4.94 out of 5 average rating, 232 reviews

Private Peaceful Cabin in Sisters!

Superhost

Cabin in Sisters

4.91 out of 5 average rating, 129 reviews

Red Clover Cabin at Black Butte Ranch

Guest favourite

Guest suite in Bend

4.94 out of 5 average rating, 232 reviews

Bungalow at The Parks

Superhost

Home in Sunriver

4.91 out of 5 average rating, 116 reviews

Rustic Luxury in Sunriver with A/C, Spa, SHARC

Guest favourite

Home in Bend

4.97 out of 5 average rating, 213 reviews

Midtown Mid-Century w/Pool & Hot Tub Near Downtown

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Quick stats about holiday rentals that are family-friendly in Madras

Total rentals
20 properties
Nightly prices starting at
$54 SGD before taxes and fees
Total number of reviews
210 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Rio Distinctive Mexican Cuisine, Madras Cinema 5 and Pepe's Mexican Restaurant

Family-friendly holiday rentals in Madras

Top-rated family-friendly rentals in Madras

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Madras family-friendly rentals

Family-friendly home rentals with a hot tub

Home in Sunriver

Chalet in Redmond

Home in Bend

Townhouse in Bend

Home in Old Bend

Townhouse in Sunriver

Home in Sunriver

Flat in Bend

Family- and pet-friendly home rentals

Cottage in Bend

Home in Bend

Home in Old Bend

Guest suite in Bend

Home in Sunriver

Guest house in Bend

Cottage in Bend

Home in Bend

Family-friendly home rentals with a pool

Home in Bend

Apartment in Bend

Home in Sunriver

Home in Sisters

Cabin in Sisters

Guest suite in Bend

Home in Sunriver

Home in Bend

Quick stats about holiday rentals that are family-friendly in Madras

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

Destinations to explore