Photo by Vicki Chandler

Search Vacation Homes in Winchester Bay

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 105 Vacation Homes in Winchester Bay with updated reviews, rates, and availability.

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Exterior

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

10.0 out of 10, Exceptional, (6)
"The cottage is super cute and comfortable just like the listing. Great communication with the owner. The use of the crab trap was awesome. We will book another trip hoping for better crabbing. "
The price is AED 606
AED 1,342 total
includes taxes & fees
12 May - 13 May
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Overlooking Old Town yet In a Secluded Forest Setting
Exterior

Overlooking Old Town yet In a Secluded Forest Setting

8.0 out of 10, Very Good, (117)
"Hunted mushrooms on the property and had a ton of fun! Will for sure stay here again!"
The price is AED 716
AED 1,368 total
includes taxes & fees
12 May - 13 May
Overlooking Old Town yet In a Secluded Forest Setting
*NEW LISTING* Beautiful Lake Area Home, Pet Friendly, Close to Old town Florence & Dunes, Gas Grill
Beach

*NEW LISTING* Beautiful Lake Area Home, Pet Friendly, Close to Old town Florence & Dunes, Gas Grill

9.8 out of 10, Exceptional, (31)
"Spacious home in good location with lovely kitchen. Great house for our family reunion, but could use some maintenance, cleaning and furniture for the deck. "
*NEW LISTING* Beautiful Lake Area Home, Pet Friendly, Close to Old town Florence & Dunes, Gas Grill
Dunecastle - Private Setting and Coastal Views (no direct dune access)
TV, books

Dunecastle - Private Setting and Coastal Views (no direct dune access)

9.4 out of 10, Exceptional, (21)
"A group of us celebrating a couple 40th birthdays had a blast at this giant house! Quiet and away from everyone, yet a close drive to Coos Bay or Charleston bay. "
Dunecastle - Private Setting and Coastal Views (no direct dune access)
New listing! Beautiful lakefront 3 bedroom 3 bath home, private dock, hot tub, pets, gas, grill
Miscellaneous

New listing! Beautiful lakefront 3 bedroom 3 bath home, private dock, hot tub, pets, gas, grill

2.0 star property
9.0 out of 10, Wonderful, (4)
"My family was looking for a quick getaway with our dogs. The lakehouse did not disappoint! There is plenty of space and ammenities, a dog run, and easy to clean floors. We felt right at home and stress free. The from the firepit is breathtaking."
New listing! Beautiful lakefront 3 bedroom 3 bath home, private dock, hot tub, pets, gas, grill
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok
Fridge, microwave, oven, stovetop

Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

9.4 out of 10, Exceptional, (38)
"Great central location for running up and down the coast exploring."
The price is AED 386
AED 1,052 total
includes taxes & fees
12 May - 13 May
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok
Enchanting Coos Bay Sanctuary w/ Lush Views!
Terrace/patio

Enchanting Coos Bay Sanctuary w/ Lush Views!

9.6 out of 10, Exceptional, (16)
"The views & privacy were amazing. Also, easy access to town. Highly recommend!"
Enchanting Coos Bay Sanctuary w/ Lush Views!
Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.
Beach

Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.

9.8 out of 10, Exceptional, (146)
"Lots of space (interior and exterior parking)for 2 adults and 4 teenagers. House is well appointed for a week stay. Only recommendation is upgrading the mattresses. "
Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.
Waterfront retreat with lake views & private hot tub
Outdoor spa tub

Waterfront retreat with lake views & private hot tub

8.2 out of 10, Very Good, (30)
"The house was well supplied and very inviting. The lake view was gorgeous and really made our stay special."
Waterfront retreat with lake views & private hot tub
Beautiful Lake Area Home, Gas Grill - Close to Downtown Florence & Dunes
Beach

Beautiful Lake Area Home, Gas Grill - Close to Downtown Florence & Dunes

9.0 out of 10, Wonderful, (24)
"Main room is bigger than it looks. Bedrooms were differently configured than the listing. Good stay overall, enjoyed it."
Beautiful Lake Area Home, Gas Grill - Close to Downtown Florence & Dunes
Adorable Cottage On The Lake - Boat Access Only, Private Dock, Fire pit, Gas Grill
Beach

Adorable Cottage On The Lake - Boat Access Only, Private Dock, Fire pit, Gas Grill

9.2 out of 10, Wonderful, (19)
"Great place awesome fire pit area"
Adorable Cottage On The Lake - Boat Access Only, Private Dock, Fire pit, Gas Grill
New Listing! Adorable spacious home on a large private lot near the dunes and Old Town Florence.
Property grounds

New Listing! Adorable spacious home on a large private lot near the dunes and Old Town Florence.

7.4 out of 10, Good, (3)
"This was a functional, comfortable property with plenty of cookware. Kids enjoyed foosball//BUT we could not get any tv for evening ""
New Listing! Adorable spacious home on a large private lot near the dunes and Old Town Florence.
Beautiful Lake Retreat with amazing Views! Walk to Siltcoos Lake, Relaxing Deck w/BBQ, pet friendly
Beach

Beautiful Lake Retreat with amazing Views! Walk to Siltcoos Lake, Relaxing Deck w/BBQ, pet friendly

9.6 out of 10, Exceptional, (9)
"Short stay over the weekend but are already planning our next stay at this location."
Beautiful Lake Retreat with amazing Views! Walk to Siltcoos Lake, Relaxing Deck w/BBQ, pet friendly
Dog-friendly home with Siuslaw River views, fireplace & WiFi - near beach & town
Fridge, microwave, oven, stovetop

Dog-friendly home with Siuslaw River views, fireplace & WiFi - near beach & town

8.6 out of 10, Excellent, (34)
"Such a cute rental! Perfect location!"
Dog-friendly home with Siuslaw River views, fireplace & WiFi - near beach & town
Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools

2.0 star property
9.4 out of 10, Exceptional, (3)
"Thank you for a fabulous stay and for being flexible with the checkout time. The house was very clean and comfortable. "
The price is AED 551
AED 1,097 total
includes taxes & fees
1 Jun - 2 Jun
Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools
*New Listing* Beautiful lake view home with shared lake access, gas grill and amazing views
Beach

*New Listing* Beautiful lake view home with shared lake access, gas grill and amazing views

9.6 out of 10, Exceptional, (28)
"Beautiful views of the lake. House was very clean and well equipped, beds were very comfortable. Stay was enjoyed by all four of us. "
*New Listing* Beautiful lake view home with shared lake access, gas grill and amazing views
*NEW LISTING* Beautiful Lake Front Home w/ Hot Tub. Close to Downtown Florence and Dunes
Beach

*NEW LISTING* Beautiful Lake Front Home w/ Hot Tub. Close to Downtown Florence and Dunes

9.6 out of 10, Exceptional, (50)
"Nice property close to honeyman state park "
*NEW LISTING* Beautiful Lake Front Home w/ Hot Tub. Close to Downtown Florence and Dunes
Luxe dog-friendly water-view home with a fireplace, wrap-around balcony
TV, fireplace

Luxe dog-friendly water-view home with a fireplace, wrap-around balcony

9.8 out of 10, Exceptional, (9)
"9 family comfortably stayed for 5 days."
Luxe dog-friendly water-view home with a fireplace, wrap-around balcony
New listing! Beautiful 3 bedroom 3 bath, near lakes, ocean, and dunes, pet friendly, large lot, bbq
Miscellaneous

New listing! Beautiful 3 bedroom 3 bath, near lakes, ocean, and dunes, pet friendly, large lot, bbq

8.0 out of 10, Very Good, (1)
"House was very clean, big yard, perfect for relaxing."
New listing! Beautiful 3 bedroom 3 bath, near lakes, ocean, and dunes, pet friendly, large lot, bbq
Dune Riders Dream - Direct Dune Access - 2 Bdr 1 Ba Sleeps 5
Sun loungers

Dune Riders Dream - Direct Dune Access - 2 Bdr 1 Ba Sleeps 5

9.6 out of 10, Exceptional, (143)
"House is very clean and in a great location for dune access. Lots of space to park and we could've brought our 37 foot 5th wheel and larger side by side trailer and had plenty of parking. Owner/property manager was great to work with. Will definitely stay here again. "
Dune Riders Dream - Direct Dune Access - 2 Bdr 1 Ba Sleeps 5
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Winchester Bay
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester Bay

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Exterior

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

10.0 out of 10, Exceptional, (6)
"The cottage is super cute and comfortable just like the listing. Great communication with the owner. The use of the crab trap was awesome. We will book another trip hoping for better crabbing. "
The price is AED 606
AED 1,342 total
includes taxes & fees
12 May - 13 May
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok
Fridge, microwave, oven, stovetop

Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

9.4 out of 10, Exceptional, (38)
"Great central location for running up and down the coast exploring."
The price is AED 386
AED 1,052 total
includes taxes & fees
12 May - 13 May
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok
Reedsport Coastal Retreat: Adventure Awaits You Near the Ocean
Indoor spa tub

Reedsport Coastal Retreat: Adventure Awaits You Near the Ocean

9.4 out of 10, Exceptional, (9)
"We’ve been looking for a place close to Winchester for work events. This place checked all the boxes and our team enjoyed the stay."
Reedsport Coastal Retreat: Adventure Awaits You Near the Ocean
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.