We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Winston Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
50 rentals in Winston.
Sort by:
Tripadvisor Sort

Glampingtent 3 has a double bed and twin bed ! Cot also great for a family

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Glamping Tent I, Located On 80 Acre Ranch , Helena Mt

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Lee's Bunkhouse on Saddle Mountain

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Bay's End-Scenic lakeside cabin/lodge at the end of Magpie Bay on Canyon Ferry

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Historic Unique 1890's Log Cabin At Canyon Ferry Lake

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Breathtaking Views, Canyon Ferry Lakefront!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

'The House on Hauser' New Lakefront Home 5 Bedroom, 2 Master Suites, 4 Bathrooms

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Updated single level townhouse

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

The west shore getaway on Canyon Ferry.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Staubach Creek Ranch, Great Mountain Vistas in Big Sky Country

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Winston rentals sent straight to your email!

Hillsdale Hideaway - Centrally Located

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

SADDLE MOUNTAIN ESCAPE

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Awesome Location, Spacious Home, Perfect for All Sizes of Groups

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Montana TING -5star vacation home in the heart of Montana

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Lakefront Cabin on Candlelight

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena Accommodations: THE DEARBORN

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Twin Peaks Lakefront Property 4200 sq ft.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

We are pet friendly plese check with owners about pets

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Secluded Mountaintop Home ~11 Miles to Helena

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena's Best Weekly/Monthly Rental!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Recently Renovated Family Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena Accommodations: THE STILLWATER

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena Accommodations: THE BIGHORN

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena Accommodations: The Beaverhead

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena Accommodations: THE JEFFERSON

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena Accommodations: The Boulder

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Historic Log Cabin at Canyon Ferry Lake

Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

2-bedroom ~ near hospital and Capitol complex ~

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

2 bedroom flat with full kitchen ~ Close to the State Capitol complex ~

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena Accommodations: THE BLACKFOOT

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Glamping Tent II, Located On 80 Acre Ranch , Helena Mt

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

TING a 5-star luxury vacation home in the heart of Montana. A very special place

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Helena Accommodations: THE CLARK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena Accommodations: The Yellowstone

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Helena Accommodations: THE ST. REGIS

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

You and Fido welcome here!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Small Cabin with Big Canyon Ferry Lake Views

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

GREAT FAMILY DESTINATION! 2 LOVELY UNITS, POOL, PARKING

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

GREAT STAY! ONE COMFY UNIT! POOL, PARKING

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

GREAT ACCOMMODATION! 2 UNITS, POOL, PARKING

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

RARE FIND! 1 COZY AND CLEAN UNIT! POOL, PARKING

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

BREATHTAKING VIEW! ONE AMAZING UNIT! POOL, PARKING

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

LOVELY PLACE! ONE WONDERFUL UNIT! POOL, PARKING

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

LOVELY HOTEL! 2 GREAT UNITS, POOL, PARKING

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

RARE FIND! 2 MAJESTIC UNITS, POOL, PARKING

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

RELAXING AND CALMING DESTINATION! ONE CHIC UNIT! POOL, PARKING

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

BEAUTIFUL ESCAPE! 2 AWESOME UNITS, POOL, PARKING

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

GREAT DEAL! 3 Wonderful Units, Near Attractions, Pool, Hot tub

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Perfect Vacation Or Weekend Getaway in the Little Belt Mountains, near York

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

NEW! Secluded Helena Escape on Trout Creek w/ View

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
1
Frequently Asked Questions about Winston