Discover Your Perfect Highwood Vacation Homes

Best Vacation Homes in Highwood

10.0
Exceptional
(27 Reviews)
4 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $318/Night For 7 Nights US $2,227
10.0
Exceptional
(2 Reviews)
548.96 ft² 3 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Pet Friendly
  • Parking
  • Air Conditioner
US $188/Night For 7 Nights US $1,316
9.8
Exceptional
(374 Reviews)
1 Bathroom
Family Friendly Hotel
  • Fireplace/Heating
  • Breakfast
  • Kitchen
US $137/Night For 7 Nights US $960
10.0
Exceptional
(23 Reviews)
1800 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Hot Tub
  • Spa
  • Fireplace/Heating
US $227/Night For 7 Nights US $1,588
9.2
Exceptional
(6 Reviews)
2701.74 ft² 10 Guests 5 Bedrooms 3 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • View
  • Parking
US $424/Night For 7 Nights US $2,970
10.0
Exceptional
(20 Reviews)
646 ft² 4 Guests 1 Bedroom 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Kitchen
  • Parking
US $122/Night For 7 Nights US $853
10.0
Exceptional
(19 Reviews)
4 Guests 1 Bedroom 1 Bathroom
Family Friendly Cottage
  • Fireplace/Heating
  • Kitchen
  • Parking
US $192/Night For 7 Nights US $1,345
10.0
Exceptional
(8 Reviews)
4 Guests 2 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $190/Night For 7 Nights US $1,329

Highwood Luxury Rentals

10.0
Exceptional
(1 Review)
16 Guests 8 Bedrooms 9 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $1,842/Night For 7 Nights US $12,897
New
10 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Cabin
  • Fireplace/Heating
  • Balcony/Terrace
  • Internet
US $1,342/Night For 7 Nights US $9,396
New
6 Guests 3 Bedrooms 2 Bathrooms
House
  • Pool
  • Internet
  • Child Friendly
US $903/Night For 7 Nights US $6,318
New
645.83 ft² 16 Guests 5 Bedrooms 4 Bathrooms
House
  • Hot Tub
  • Fireplace/Heating
  • Air Conditioner
US $879/Night For 7 Nights US $6,155
New
2744.8 ft² 8 Guests 4 Bedrooms 4 Bathrooms
Free Cancellation House
  • Hot Tub
  • Spa
  • Fireplace/Heating
US $807/Night For 7 Nights US $5,649
New
4004.17 ft² 16 Guests 5 Bedrooms 5 Bathrooms
House
  • Hot Tub
  • Fireplace/Heating
  • Pet Friendly
US $775/Night For 7 Nights US $5,425
10.0
Exceptional
(4 Reviews)
2750 ft² 8 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $732/Night For 7 Nights US $5,122
10.0
Exceptional
(1 Review)
8 Guests 3 Bedrooms 3 Bathrooms
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $729/Night For 7 Nights US $5,103

Highwood Pet Friendly Vacation Rentals

10.0
Exceptional
(3 Reviews)
520 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $187/Night For 7 Nights US $1,306
New
1797.57 ft² 9 Guests 4 Bedrooms 3 Bathrooms
House
  • Fireplace/Heating
  • View
  • Pet Friendly
US $515/Night For 7 Nights US $3,605
8.6
Fabulous
(22 Reviews)
3 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
US $151/Night For 7 Nights US $1,057
10.0
Exceptional
(2 Reviews)
6 Guests 1 Bedroom 1 Bathroom
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $481/Night For 7 Nights US $3,364
New
2002.09 ft² 4 Guests 2 Bedrooms 3 Bathrooms
House
  • Pet Friendly
  • Parking
  • Internet
US $295/Night For 7 Nights US $2,065
10.0
Exceptional
(1 Review)
6 Guests 1 Bedroom 1 Bathroom
Family Friendly Cabin
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $508/Night For 7 Nights US $3,553
9.8
Exceptional
(103 Reviews)
7 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $152/Night For 7 Nights US $1,066
9.6
Exceptional
(108 Reviews)
504 ft² 6 Guests 1 Bedroom 1 Bathroom
Family Friendly Cabin
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $170/Night For 7 Nights US $1,189

Highwood Large Vacation Homes

10.0
Exceptional
(46 Reviews)
2700 ft² 10 Guests 5 Bedrooms 3 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $328/Night For 7 Nights US $2,299
New
1797.57 ft² 13 Guests 4 Bedrooms 2 Bathrooms
House
  • Hot Tub
  • Fireplace/Heating
  • Air Conditioner
US $437/Night For 7 Nights US $3,059
10.0
Exceptional
(17 Reviews)
3993 ft² 16 Guests 5 Bedrooms 5 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Kitchen
US $433/Night For 7 Nights US $3,030
10.0
Exceptional
(15 Reviews)
646 ft² 16 Guests 5 Bedrooms 4 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $392/Night For 7 Nights US $2,744
10.0
Exceptional
(7 Reviews)
10 Guests 5 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $380/Night For 7 Nights US $2,662
9.8
Exceptional
(9 Reviews)
12 Guests 6 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $377/Night For 7 Nights US $2,637
9.6
Exceptional
(35 Reviews)
3000 ft² 12 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $357/Night For 7 Nights US $2,498
9.6
Exceptional
(24 Reviews)
1798 ft² 10 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $307/Night For 7 Nights US $2,151

Why Choose Rent By Owner for your Highwood Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Highwood

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you can enjoy the region's natural beauty and outdoor activities at their best, making your stay in Highwood, Montana a memorable experience tailored to your preferences.

Peak Season Highlights

summer
Summer (June to August)

During these months, the area experiences warm weather ideal for outdoor activities and exploring local scenery. You’ll find that this is the most popular time to visit, so booking your vacation rentals early ensures a comfortable stay.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 50°F to 60°F
autumn
Fall (September to November)

This season offers mild temperatures and vibrant fall foliage, creating a picturesque backdrop for your getaway. It’s a favored time for travelers who want to enjoy the region’s natural beauty without the summer crowds.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

Cooler temperatures make this period perfect for winter sports enthusiasts and those seeking a peaceful retreat. Accommodation rates tend to be lower, offering excellent value during these colder months.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
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Spring (March to May)

As the region transitions from winter, you can experience blooming landscapes and gradually warming days. Visiting during this shoulder season allows for a quieter experience with more availability in your preferred vacation rentals.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Highwood

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor grilling with a private barbecue area to enhance your meals amidst the natural surroundings.
  • Take in the scenic views and fresh air while relaxing on a spacious outdoor patio or deck.
  • Explore nearby trails and enjoy outdoor activities such as hiking or birdwatching right from the property.
  • Make use of a fire pit perfect for cozy evenings under the stars, ideal for gathering with friends or family.
  • Benefit from access to outdoor recreational equipment like kayaks, paddleboards, or bicycles to explore the region.
  • Unwind in a private hot tub or outdoor soaking area, ideal for relaxation after a day of adventure.
  • Experience the beauty of the area with landscaped gardens or outdoor seating areas designed for enjoying nature.
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Family Activities

  • Highwood Creek Trail: Embark on a family-friendly hike along this scenic trail, offering stunning views of the surrounding mountains and opportunities to spot local wildlife.
  • Highwood Lake Park: Spend a relaxing day enjoying picnic areas, gentle waters for paddle boating, and easy trails perfect for young adventurers in this peaceful lakeside setting.
  • Local Wildlife Watching: Visit nearby natural habitats where your family can observe a variety of birds and other native animals in their natural environment.
  • Highwood Historical Museum: Explore the region’s history through engaging exhibits that provide insight into the area's cultural heritage, ideal for enriching family outings.
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Adult Activities

  • Fishing on the Highwood River: Enjoy a tranquil day casting your line in the renowned waters that attract anglers seeking a peaceful Montana experience.
  • Hiking and Nature Walks: Explore scenic trails that wind through the area's natural beauty, offering breathtaking views and opportunities to observe local wildlife.
  • Wildlife Viewing: Experience the region's diverse fauna by visiting nearby parks and preserves to see elk, deer, and various bird species in their native habitat.
  • Photography Excursions: Capture stunning landscapes and vibrant sunsets against the backdrop of Montana's rugged terrain, perfect for photography enthusiasts exploring here.

Highwood Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Outdoor Activities: Take advantage of the area's natural beauty by scheduling outdoor adventures like hiking or fishing to make your stay in this region truly memorable.
  • Book Early for Popular Seasons: Secure your preferred vacation rentals well in advance, especially during peak seasons when demand for accommodations here is at its highest.
  • Explore Local Dining and Shops: Discover authentic regional flavors and unique shops nearby to immerse yourself in the local culture during your visit.
  • Utilize Local Resources: Leverage the knowledge of hosts or property managers to find hidden gems and insider tips that can enhance your experience here.

Transportation Options

  • Driving your own vehicle: You can easily explore the area at your own pace by driving your car, with several well-maintained roads connecting Highwood to nearby attractions and amenities.
  • Local taxi services: Reliable taxi options are available for convenient transportation within the region, helping you reach local dining, shopping, or scenic spots effortlessly.
  • Rental cars: Renting a car provides flexibility and comfort as you discover the scenic landscapes and outdoor activities in this part of Montana.
  • Public transportation: Limited bus services operate in the area, offering a cost-effective way to travel around and access key points of interest during your stay.

Local Customs Options

  • Local Hospitality:** You’ll find that warm welcomes and friendly conversations are a cherished part of the community here in Highwood, Montana, making your stay feel truly local.
  • Traditional Dining Customs:** Dining etiquette often involves sharing hearty meals with neighbors, reflecting the region’s appreciation for community and good company.
  • Outdoor Respect:** Respect for the natural surroundings is an important custom in the area, where outdoor activities like fishing and hiking are integral to the local lifestyle.
  • Community Events:** Participating in local gatherings or celebrations offers a wonderful way to immerse yourself in the area's rich cultural traditions during your visit.

Highwood Vacation Rental Frequently Asked Questions

2. How many vacation rentals have private pools in Highwood?

There are 14 vacation rentals with private pools near Highwood. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Highwood are best for families?

If you are looking for a family-friendly vacation home in Highwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highwood:

4. How many Rentbyowner vacation rentals are available in Highwood?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 279 in the Highwood area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Highwood. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies by property, so it’s important to review the specific listing details. You can find this information in the rental's terms or contact the property owner directly for clarification.

6. Are there any additional fees I should be aware of when booking in this destination?

Additional fees such as cleaning fees, service charges, or local taxes are commonly applied and will be detailed on the listing page. Be sure to review all costs before completing your booking to avoid surprises.

7. What amenities are typically included with vacation rentals in this region?

Most vacation rentals in this area offer amenities like Wi-Fi, fully equipped kitchens, and parking. To ensure the property meets your needs, check the specific listing for a complete list of included amenities.

8. How can I confirm the availability of a vacation rental during my travel dates?

Availability is updated in real-time on the listing page. If your preferred dates are not available, you may contact the owner directly to inquire about alternative dates or nearby options.

9. What should I do if I need assistance during my stay in this destination?

Support is usually available through the property host or the booking platform's customer service. Contact details are provided in the listing, and reaching out promptly ensures a smooth and enjoyable stay.

Highwood Top Rated Vacation Rentals

10.0
Exceptional
(2 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $365/Night For 7 Nights US $2,554
10.0
Exceptional
(1 Review)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $355/Night For 7 Nights US $2,487
10.0
Exceptional
(1 Review)
4 Guests 1 Bedroom 1 Bathroom
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $289/Night For 7 Nights US $2,022
10.0
Exceptional
(1 Review)
2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $201/Night For 7 Nights US $1,408
9.8
Exceptional
(17 Reviews)
1 Bathroom
Couples Retreat Hotel
  • Pool
  • Breakfast
  • Parking
US $164/Night For 7 Nights US $1,150
9.4
Exceptional
(592 Reviews)
1 Bathroom
Family Friendly Hotel
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $157/Night For 7 Nights US $1,096
9.2
Exceptional
(1005 Reviews)
1 Bathroom
Family Friendly Hotel
  • Hot Tub
  • Pool
  • Breakfast
US $124/Night For 7 Nights US $865
9.0
Exceptional
(1007 Reviews)
1 Bathroom
Family Friendly Hotel
  • Hot Tub
  • Fireplace/Heating
  • Pool
US $148/Night For 7 Nights US $1,036