Best Vacation Homes in Dellwood
1350 ft²
9 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $244/Night
For 7 Nights US $1,706
1689.93 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
US $698/Night
For 7 Nights US $4,886
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $286/Night
For 7 Nights US $2,001
2131.25 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Private Beach
- Hot Tub
- Skiing
US $193/Night
For 7 Nights US $1,351
840 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Hot Tub
- Fireplace/Heating
- Ocean View
US $436/Night
For 7 Nights US $3,054
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $155/Night
For 7 Nights US $1,085
440 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $203/Night
For 7 Nights US $1,421
600 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $151/Night
For 7 Nights US $1,059
Dellwood Luxury Rentals
3003.13 ft²
16 Guests
7 Bedrooms
5 Bathrooms
Free Cancellation
House
- Hot Tub
- View
- Parking
US $873/Night
For 7 Nights US $6,112
3087 ft²
14 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $861/Night
For 7 Nights US $6,025
3000 ft²
16 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $810/Night
For 7 Nights US $5,667
US $775/Night
For 7 Nights US $5,425
15 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $737/Night
For 7 Nights US $5,160
3000 ft²
14 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Pool
US $715/Night
For 7 Nights US $5,005
14 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $711/Night
For 7 Nights US $4,975
3326.05 ft²
14 Guests
5 Bedrooms
2 Bathrooms
House
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $710/Night
For 7 Nights US $4,970
Dellwood Pet Friendly Vacation Rentals
2184 ft²
13 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $477/Night
For 7 Nights US $3,337
1194.79 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- View
US $220/Night
For 7 Nights US $1,540
2400 ft²
11 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $413/Night
For 7 Nights US $2,889
1119.45 ft²
7 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $190/Night
For 7 Nights US $1,330
3000 ft²
17 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $706/Night
For 7 Nights US $4,939
12 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $361/Night
For 7 Nights US $2,528
14 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $708/Night
For 7 Nights US $4,955
12 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $251/Night
For 7 Nights US $1,756
Dellwood Large Vacation Homes
1800 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $444/Night
For 7 Nights US $3,108
2303.48 ft²
10 Guests
1 Bedroom
2 Bathrooms
Ocean View
Apartment
- Private Beach
- Hot Tub
- Fireplace/Heating
US $470/Night
For 7 Nights US $3,287
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Hot Tub
- Fireplace/Heating
US $401/Night
For 7 Nights US $2,809
4248 ft²
15 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $624/Night
For 7 Nights US $4,369
2500 ft²
14 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $452/Night
For 7 Nights US $3,167
1800 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Oceanfront
- Hot Tub
US $526/Night
For 7 Nights US $3,683
2200 ft²
12 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $444/Night
For 7 Nights US $3,108
Why Choose Rent By Owner for your Dellwood Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Dellwood
When should you plan your Vacation Rentals stay?
Timing your visit to this charming destination can enhance your experience, so consider the seasonal changes and local climate when choosing the best time to book your vacation rentals here in Wisconsin.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours perfect for outdoor activities in this region.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn offers stunning foliage views and a pleasant climate, making it an ideal time for exploring and outdoor adventures in the area.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
The winter season transforms the destination into a snowy wonderland, perfect for quiet retreats and winter sports enthusiasts seeking tranquility.
Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 15°F
Spring (March to May)
Spring brings cooler temperatures and blooming scenery, offering a peaceful setting for those looking to escape crowds and enjoy nature at a relaxed pace.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Dellwood
How to Book Your Dellwood Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
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.
Explore and book the perfect rental in Dellwood
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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 dining spaces perfect for savoring meals amid natural surroundings.
- Take advantage of private patios or decks to relax and unwind outdoors.
- Make the most of a spacious yard suitable for outdoor games and activities.
- Explore nearby trails and pathways for scenic walks or hikes right from your rental.
- Utilize outdoor fire pits for cozy evenings under the stars with friends or family.
- Benefit from ample parking areas to easily accommodate vehicles and outdoor gear.
- Find access to lakeside or riverfront views, ideal for relaxing or water-based recreation.
Top Attractions Around Dellwood
What attractions are nearby?
While staying here, you can enjoy a variety of outdoor activities such as hiking, boating, and fishing in the nearby scenic areas, offering an authentic experience of this destination's natural beauty.
Family Activities
- Dellwood Park: Spend quality time outdoors exploring the scenic trails and picnic areas perfect for family outings in this welcoming regional park.
- Local Water Activities: Enjoy swimming, kayaking, or canoeing on nearby lakes, offering endless fun for families seeking adventure on the water.
- Family-Friendly Hiking Trails: Discover easy hiking paths suitable for all ages that wind through the area's natural beauty, providing a great way to experience the region's landscape.
- Wildlife Watching: Observe local wildlife during guided nature walks or from designated viewing spots, enriching your family’s connection with nature in this destination.
Adult Activities
- Exploring Area Waterways: Enjoy tranquil boat cruises or kayaking adventures on the scenic lakes that define this region, offering a peaceful retreat into nature.
- Hiking and Nature Trails: Discover well-maintained trails nearby that provide breathtaking views and a chance to connect with the lush landscape of the area.
- Wildlife Viewing: Observe local wildlife in their natural habitat at various parks and protected areas, perfect for nature enthusiasts seeking an authentic experience.
- Golfing Experiences: Tee off at nearby golf courses known for their picturesque fairways and challenging layouts, ideal for leisurely afternoons in the region.
Dellwood Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature: Take advantage of the scenic outdoor opportunities nearby to fully experience the natural beauty of this destination.
- Plan Ahead for Activities: Booking popular activities and excursions in advance ensures you make the most of your time here during peak seasons.
- Choose a Prime Location: Select a vacation rental close to key attractions and amenities to maximize convenience and reduce travel time.
- Engage with the Community: Connect with local events or gatherings to enrich your stay and gain authentic insights into the region.
Transportation Options
- Local Bus Service: You can rely on the regional bus system to easily access key points within the area, making it a convenient transportation option during your stay.
- Rental Car Services: Renting a vehicle provides you with flexibility and ease to explore the broader region surrounding the destination at your own pace.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options are readily available here, offering quick and reliable transportation for short trips around the area.
- Private Shuttle Services: Private shuttles operate in the region, providing comfortable and direct transfers to major points of interest nearby.
Local Customs Options
- Traditional Dairy Farming Practices: You will notice that dairy farming is an integral part of the region's heritage, reflecting local agricultural customs.
- Seasonal Festivals and Events: Participating in seasonal festivals here allows you to experience authentic community traditions and celebrate local culture.
- Respect for Nature and Outdoor Etiquette: Maintaining a respectful attitude toward outdoor spaces is highly valued, ensuring the natural beauty of the area remains pristine.
- Local Cuisine and Food Traditions: Sampling regional dishes offers insight into the area's culinary customs rooted in locally sourced ingredients and traditional recipes.
Dellwood Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Dellwood?
There are a lot of options in Dellwood. If you plan on staying in the Dellwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Dellwood:
- Pine Forest Villa w/hot tub 5 min from Lake
- Golf or Relaxing Getaway@ Northern Bay Resort!
- Peaceful retreat on large private pond just minutes to Castle Rock Lake!
- Gorgeous Lakeview Balcony with 4 Bedrooms, best location at the resort!
- New Castle Rock Lakefront Getaway w hot tub and boat slip
- Amazing cottage in a forest with great amenities
- Custom built, private home on Castle Rock Lake -with boat slip
- Guest favorite . pet friendly house,fast Wi-Fi,5min to Castle Rock Lake. Relax
- Northern Bay 4 Bdrm 3 Ba 2 Floor Condo On The Lake
- LAKEFRONT FAMILY RETREAT ON THE EASTERN SIDE OF CASTLE ROCK LAKE - PET FRIENDLY
2. Which vacation homes in Dellwood are best for families?
If you are looking for a family-friendly vacation home in Dellwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Dellwood:
3. How many Rentbyowner vacation rentals are available in Dellwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 142 in the Dellwood 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 Dellwood.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies can vary depending on the host and specific property. To understand the exact terms, please review the listing details or contact the owner directly before making your reservation.
5. Are there any additional fees I should be aware of when booking a rental here?
Additional fees such as cleaning, service charges, or security deposits are often specified in the listing. Be sure to check the detailed description and communicate with the owner for any questions regarding extra costs.
6. How do I ensure my preferred travel dates are available for booking?
Availability depends on the property's calendar provided in the listing. You can verify your dates online and reach out to the host if you have special requests or need confirmation prior to booking.
7. What amenities can I expect at vacation rentals in this destination?
Amenities vary by property but typically include essentials like Wi-Fi, kitchen access, and parking. Check the specific listing details to find out about extras like outdoor spaces, fireplaces, or water access.
8. How do I contact the property owner for further inquiries?
You can reach out to the owner through the messaging platform provided during the booking process. It’s recommended to clarify any questions about the property, policies, or local guidelines before completing your reservation.
Dellwood Top Rated Vacation Rentals
1689 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $330/Night
For 7 Nights US $2,312
1802 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $307/Night
For 7 Nights US $2,150
2515 ft²
13 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $450/Night
For 7 Nights US $3,148
10 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $453/Night
For 7 Nights US $3,170
2000 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $417/Night
For 7 Nights US $2,922
2098.96 ft²
9 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Private Beach
- Hot Tub
- Fireplace/Heating
US $356/Night
For 7 Nights US $2,490
2000 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $284/Night
For 7 Nights US $1,991
2132 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $428/Night
For 7 Nights US $2,994
