Downtown Bend holiday rentals
We found 318 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Downtown Bend that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, which might include Wi-Fi and a pool. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts – Downtown Bend
Showing deals for:4 Dec - 11 Dec
Excellent
(8 reviews)
Location! Historical District Downtown - Walk everywhere, new 4 Bedroom, 3 Bath
Bend
S$6,967
for 7 nights, 1 home
S$995 per night
includes taxes & fees
Exceptional
(222 reviews)
Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes
Bend
S$2,486
for 7 nights, 1 cottage
S$355 per night
includes taxes & fees
Exceptional
(198 reviews)
RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER
Bend
S$8,439
for 7 nights, 1 home
S$1,206 per night
includes taxes & fees
Exceptional
(95 reviews)
Historic 1917 cottage by the river, walkable to all of downtown Bend!
Bend
S$2,099
for 7 nights, 1 home
S$300 per night
includes taxes & fees
Exceptional
(138 reviews)
Bend Bungalow - a Walk in the Park to Downtown and River!
Bend
S$1,491
for 7 nights, 1 home
S$213 per night
includes taxes & fees
Exceptional
(43 reviews)
Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby
Bend
S$1,378
for 7 nights, 1 home
S$197 per night
includes taxes & fees
Exceptional
(197 reviews)
Riverfront Cottage -Near Drake Park, Walk to Town.
Bend
S$1,740
for 7 nights, 1 home
S$249 per night
includes taxes & fees
Exceptional
(17 reviews)
Mckay Getaway, between Drake Park/Miller's Landing
Bend
S$1,839
for 7 nights, 1 home
S$263 per night
includes taxes & fees
Wonderful
(28 reviews)
Heart of Bend-Walkable, Ping Pong, Billards
Bend
S$3,235
for 7 nights, 1 home
S$462 per night
includes taxes & fees
Exceptional
(28 reviews)
Hillside Haven: Tranquil NW Studio Near the River
Bend
S$1,187
for 7 nights, 1 home
S$170 per night
includes taxes & fees
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Find the best place to stay - Downtown Bend
***NEW*** Charming home located in Downtown Bend!
Sleeps 6 · 2 bedrooms · 1 bathroom
Luxury Rooftop Condo in the Heart of Downtown Bend, Cascade Mountain views
Sleeps 4 · 2 bedrooms · 2 bathrooms
3 Bedroom house 2 blocks from down town Bend
Sleeps 6 · 3 bedrooms · 1 bathroom
Elderberry- Salt Hot Tub, Wood Fireplace, 100+mbps Wifi, Walkable to Downtown
Sleeps 8 · 3 bedrooms · 1 bathroom
Mirror Pond - Cozy Cabin Directly on Mirror Pond - Deschutes River!
Sleeps 6 · 2 bedrooms · 2 bathrooms
Awbrey - Amazing! Steps to Downtown & River, Gorgeous, Newer, A/C
Sleeps 10 · 4 bedrooms · 2+ bathrooms
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Can I find a holiday rental in Downtown Bend?
Yes, there are holiday rentals close to the most popular sights in Downtown Bend, or you can select a more secluded option if you're looking for a relaxing stay.
What can I see and do in Downtown Bend?
Enjoy the outdoors at Deschutes River and Drake Park, or simply take in cultural attractions like Tower Theater and Des Chutes Historical Museum. In the wider area, you'll find Bend Farmers Market and Hayden Homes Amphitheater.
What are holiday rentals like in Downtown Bend?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Downtown Bend. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a family trip.