Wine Country Villas - Vacation Rentals in Bend

4BR Riverfront Villa, Quiet and Upscale! From US $270
         

10.0 (102 Reviews)
Villa
  • Air Conditioner
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  • Pool
Villa #5 at Broken Top From US $124
         

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10.0 (1 Review)
House
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  • Pet Friendly
  • Security/Safety
River Ridge 421ab From US $396
         

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New
Villa
  • Air Conditioner
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The Gem Estate by AvantStay | Modern Farmhouse w/Lavender Fields + Hot Tub From US $785
         

Drake Park Villa From US $339
         

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9.0 (2 Reviews)
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  • Security/Safety
  • Sports/Activities
River Ridge 422ab From US $396
         

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New
Villa
  • Air Conditioner
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  • TV

Luxury Places to Stay in Bend

Over 7349+ Luxury Places to Stay in or Near Bend
The Lodge at Highland Farms From US $6,299
         

New
House
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  • View
Dancing Rock "Grandview Lodge" (Caldera Springs) From US $3,140
         

Gorgeous 6BR From US $2,604
         

New
House
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating

Top-Rated Vacation Rentals with a Pool in Bend

Over 3107+ Top-Rated Vacation Rentals with a Pool in or Near Bend
BEAUTIFUL HOME OVERLOOKING THE RIVER-MINUTES TO IT ALL From US $426
         

10.0 (261 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Happiness Just Around The Bend, Caldera Springs, Bend, Oregon From US $553
         

Enjoy Our Family Friendly Home In Tollgate From US $229
         

10.0 (214 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Skyline Lodge, Gorgeous Setting, Walk to Downtown! From US $793
         

10.0 (199 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Bend

Over 2850+ Pet-Friendly Vacation Rentals in or Near Bend
Glaze Meadow 252 From US $169
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
2 Killdeer - Remodeled, EV Charger, Hot Tub, Walk to Village, SHARC, Bikes From US $308
         

Pet Friendly Circle 4 Cabin And People Friendly As Well From US $241
         

See More Pet-Friendly Vacation Rentals in Bend on PetFriendly.io

Large Vacation Homes & Villas in Bend

Over 1832+ Large Vacation Homes & Villas in or Near Bend
Abbot House and Mountain Retreat From US $102
         

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New
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River Ridge 414ab From US $396
         

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New
Villa
  • Air Conditioner
  • Pool
  • TV
Luxury 7 BR Home/BEST RATES!/Hot Tub/SHARC/AC/Wi Fi/Bikes From US $929
         

Wheelchair Accessible Vacation Homes in Bend

Over 307+ Wheelchair Accessible Vacation Homes in or Near Bend
Experience Nature's Spectacle from the Front Row! From US $565
         

10.0 (11 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Steps to Downtown & Amazing Views-Hot Tub/Pool/AC From US $185
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunriver Resort From US $168
         

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9.0 (1074 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
5 Wickiup - Hot Tub, Updated, Ping Pong, SHARC Passes, Bikes From US $237
         

Cozy centrally located 3-BR house w/EV charger & king bed From US $250
         

Bend Varoom and Airbnb Places to Stay Under $200

Over 1712+ Bend Varoom and Airbnb Places to Stay Under $200
Glaze Meadow 7 From US $84
         

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8.0 (3 Reviews)
House
  • Parking
  • Pool
  • Balcony/Terrace
Grants Pass Hillside Retreat w/View Mins from Everything From US $113
         

Classic Otter Cabin: Near Village & SHARC From US $195
         

9.4 (96 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bend Condo w/Deck, Resort-Style Amenities & Views From US $178
         

9.0 (43 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Bend

Over 4680+ Instantly Bookable Vacation Homes in or Near Bend
Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries From US $216
         

About Bend Vacation Rentals

With more than 30 Bend vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Winecountryvillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Bend.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Winecountryvillas Bend, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Bend. Places to stay near Bend are 1297.19 ft² on average, with prices averaging $388 a night.

Winecountryvillas makes it easy and safe to find and compare vacation rentals in Bend with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Bend

Type Count
Villas 23
Vacation Homes 7

Use these Quick Filters to Find a Vacation Rental in Bend

Pro Tip: Winecountryvillas makes it easy to compare the best listings on Winecountryvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winecountryvillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Bend.

Weather in Bend

View the weather forecast for Bend before booking your Bend Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F