Cottage holiday rentals in Bend
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Top-rated cottage rentals in Bend
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Bend
Cottage rentals with a hot tub
Cottage in Bend
4.94 out of 5 average rating, 67 reviewsCozy 3 bedroom house, hot tub, near Sun River
12–19 Sep
Cottage in Sisters
4.95 out of 5 average rating, 19 reviewsSteps to Downtown & Amazing Views-Hot Tub/Pool/AC
18–25 Mar
Cottage in Redmond
4.88 out of 5 average rating, 48 reviewsCome Stay and Play at Little Les Cheneaux Retreat
16–23 Nov
Cottage in Sisters
4.95 out of 5 average rating, 20 reviewsCottage Live/Play in the Heart of Downtown Sisters
28 Oct – 4 Nov
Cottage in Bend
Cottage life at Tetherow Resort + HOT TUB, Trails
5–12 Apr
Cottage in Old Bend
4.93 out of 5 average rating, 187 reviewsHistoric Downtown, Private Hot Tub, High Demand
15–22 Jan
Cottage in Bend
4.87 out of 5 average rating, 104 reviewsTrendy West Side, Walk to Breweries, Hot Tub
19–26 Nov
Cottage in Bend
4.93 out of 5 average rating, 131 reviewsOne Block to Downtown, Hot Tub, Private Home, Yard
18–25 Nov
Pet-friendly cottage rentals
Cottage in Bend
4.98 out of 5 average rating, 82 reviewsThe Tumalo House
27 Jan – 3 Feb
Cottage in Bend
5.0 out of 5 average rating, 5 reviews1BR with firepit & covered porch - walk to brews
23–30 Jan
Cottage in Bend
4.98 out of 5 average rating, 51 reviewsDog-Friendly Ranch Cottage w/Trails: 13 Mi to Bend
1–8 Dec
Cottage in Bend
Adorable + comfy! 24hr staff, HOT TUB, dogs
2–9 Nov
Cottage in Bend
Popular cottage at Tetherow! Hot Tub + comfy beds
21–28 Sep
Cottage in Bend
Cute cottage! Hot Tub + near mountain and trails
27 Nov – 4 Dec
Cottage in Bend
Popular 2-bedrm at Tetherow, comfy+clean, dogs ok
19–26 Feb
Cottage in Bend
Cozy cottage by mtn! 24hr staff, HOT TUB, dogs ok
24 Jun – 1 Jul
Private cottage rentals
Cottage in Sunriver
4.95 out of 5 average rating, 39 reviewsCozy Charmer with River Access, 5mins to Village
15–22 Oct
Cottage in Bend
4.97 out of 5 average rating, 110 reviewsExceptional Downtown Cottage-Level II EV charger
21–28 Oct
Cottage in Redmond
5.0 out of 5 average rating, 8 reviewsThe West Minister Square Cottage
9–16 Jul
Cottage in Bend
4.85 out of 5 average rating, 41 reviewsOld Bend 1 Bdrm Duplex. 4 Blocks from Dwntwn, Walk
26 Nov – 3 Dec
Cottage in Sisters
4.24 out of 5 average rating, 34 reviewsCharming downtown 1BR with inviting deck
11–18 Sep
Cottage in Bend
4.74 out of 5 average rating, 43 reviewsWalk Everywhere - Old Mill, Box Factory, Downtown.
30 Dec – 6 Jan
Quick stats about cottage rentals in Bend
Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
4.2T reviews
Nightly prices starting at
₹5,004 before taxes and fees
Destinations to explore
- Eugene Holiday rentals
- Sunriver Holiday rentals
- Crater Lake Holiday rentals
- Government Camp Holiday rentals
- Redmond Holiday rentals
- Sisters Holiday rentals
- Black Butte Ranch Holiday rentals
- Albany Holiday rentals
- Rhododendron Holiday rentals
- McKenzie River Holiday rentals
- Portland Holiday rentals
- Seattle Holiday rentals
- Rentals with a sauna Bend
- Rentals with breakfast Bend
- Rentals with a fireplace Bend
- Flat rentals Bend
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- Guest house rentals Bend
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- Family-friendly rentals Bend
- Hotel rentals Bend
- Rentals with pools Bend
- Rentals with lake access Bend
- House rentals Bend
- Rentals with an EV charger Bend
- Pet-friendly rentals Bend
- Rentals with a hot tub Bend
- Townhouse rentals Bend
- Cabin rentals Bend
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- Serviced apartment rentals Bend
- Rentals with an accessible-height toilet Bend
- Rentals with outdoor seating Bend
- Rentals with a firepit Bend
- Apartment rentals Bend
- Monthly Rentals Bend
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