Best Vacation Homes in Dennis
Cottage
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- TV
Cottage
- Air Conditioner
- Parking
- Pet Friendly
Dennis Luxury Rentals
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- Pet Friendly
House
- Air Conditioner
- Parking
- Pet Friendly
Dennis Pet Friendly Vacation Rentals
House
- Air Conditioner
- Parking
- Pet Friendly
Cottage
- Air Conditioner
- Parking
- Pet Friendly
House
- Air Conditioner
- Parking
- Pet Friendly
House
- Air Conditioner
- Parking
- Pet Friendly
House
- Air Conditioner
- Parking
- Pet Friendly
Dennis Large Vacation Homes
House
- Air Conditioner
- Parking
- Pet Friendly
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- TV
Why Choose Rent By Owner for your Dennis 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 Dennis
When should you plan your Vacation Rentals stay?
Determining the best time to visit here depends on your preferences for weather, crowds, and local events, ensuring you select the ideal period to enjoy this destination’s unique charm and make the most of your vacation experience.
Peak Season Highlights
June to September
During the warm summer months, this destination attracts visitors seeking beach activities and outdoor adventures, making it the most popular time to book your vacation rentals.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Late June to Early September
This period marks the peak of the summer season when outdoor events and lively local gatherings draw many travelers looking for a lively coastal experience.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Off-Season Highlights
October to April
The cooler months see fewer visitors, providing a quieter environment ideal for those seeking a peaceful retreat in the region's serene surroundings.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
November to March
During this off-peak period, you can enjoy more affordable rates and less crowded accommodations while exploring the area's natural beauty in tranquility.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Dennis
How to Book Your Dennis 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 Dennis
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 grilling with a fully equipped barbecue area.
- Relax on a spacious deck or patio with comfortable seating options.
- Take advantage of a private outdoor pool during the warm summer months.
- Stroll through landscaped gardens or lush lawns surrounding your stay.
- Make the most of nearby sandy beaches with easy access from your property.
- Participate in outdoor activities such as volleyball or badminton on dedicated courts or open spaces.
- Utilize outdoor showers or changing areas for added convenience after beach visits or swimming.
Top Attractions Around Dennis
What attractions are nearby?
Within the area, you can enjoy exploring pristine beaches, engaging in water sports, or discovering charming local shops and eateries just a short drive from your Dennis vacation rental.
Family Activities
- Cape Cod Rail Trail: Explore this scenic trail perfect for family biking and walking adventures amidst the natural beauty of the region.
- Sesuit Harbor: Enjoy a day of fishing or simply relax by the harbor, soaking in the picturesque views that make this destination ideal for family outings.
- Smuggler's Beach: Spend quality time on this popular beach where you can swim, build sandcastles, or enjoy a peaceful picnic with loved ones.
- Dennis Historical Society: Discover local history through engaging exhibits and programs designed to educate and entertain families visiting here.
Adult Activities
- Visit Skaket Beach: Enjoy the tranquil, family-friendly shoreline perfect for relaxing walks and stunning sunsets in this part of Dennis.
- Explore Cape Cod Rail Trail: Cycle along the scenic trail that winds through the region, offering a great way to experience the area's natural beauty and outdoor charm.
- Discover the Heritage Museums & Gardens: Immerse yourself in art, history, and horticulture at this renowned cultural attraction located nearby in Dennis.
- Wine Tasting at Local Vineyards: Sample regional wines at nearby vineyards, making for an enjoyable adult activity in the area’s thriving wine scene.
Other Places to Stay in Dennis, MA
Josiah Dennis Manse and Old West Schoolhouse
Dennis Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Beaches: Take advantage of the region's pristine beaches to relax, swim, and enjoy the natural beauty that makes this destination so unique.
- Visit Popular Dining Spots: Discover the area's renowned eateries to experience authentic local cuisine and make your stay more memorable.
- Plan Outdoor Activities: Engage in outdoor adventures such as biking or kayaking to fully embrace the scenic landscape surrounding here.
- Attend Community Events: Check out seasonal festivals and events to immerse yourself in the local culture and vibrant community atmosphere.
Transportation Options
- Driving: Renting a car offers you the flexibility to explore Dennis and its scenic surroundings at your own pace, making it an ideal transportation option for accessing nearby beaches and local attractions.
- Public Transit: The regional bus services provide affordable and convenient transportation within the area, allowing you to easily navigate Dennis without the need for a personal vehicle.
- Taxi and Rideshare Services: Professional taxi and rideshare options such as Uber or Lyft are readily available here, offering quick and reliable transportation for short trips around the region.
- Bicycle Rentals: Given the area's welcoming bike-friendly roads and scenic routes, renting a bicycle is a healthy and enjoyable way to discover the local beauty at your leisure.
Local Customs Options
- Clam Shucking Tradition: Locals in the area have a proud history of clam shucking, which you can observe and sometimes participate in during local events or seafood festivals.
- Seafood Dining Etiquette: When enjoying fresh catches here, it’s customary to appreciate the region’s seafood heritage by dining with respect for shared meals and local culinary customs.
- Chatham Lighthouse Visits: Visiting historic lighthouses nearby is a cherished activity, where respecting maritime traditions and observing quiet reverence is appreciated.
- Community Celebrations: Participate in seasonal festivals and parades that celebrate the area's rich New England cultural heritage, fostering a sense of belonging among residents and visitors alike.
Frequently Asked Questions About Dennis?
1. What are the top vacation rentals in Dennis?
There are a lot of options in Dennis. If you plan on staying in the Dennis area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Dennis:
- Pond View~ Abuts conservation and walking trails. There is fishing at the pond
- Mermaid Cottage! beautiful propety!
- Scargo Vista ~ Professionally designed, Completely renovated craftsman home
- Compass Rose Cottage ★ Steps to Flax Pond & Nature Trails ★ Kayaks
- ⭐️ STUNNING WATERFRONT ⭐️Pet Friendly 3BDRM/2BTH*FIREPIT*KAYAKS*GAS FIREPLACE*
- Walk to Ocean Beach and Scargo Lake
- Dennis Village 3 bedroom house, walk to beach, central air, lg private setting
- Modern 4 BDR Northside Dennis Beach House w/Central A/C
- Beautiful Renovated Beach Home, located close to Dennis Beaches, north of 6A
- WALK TO MAYFLOWER BEACH! Luxury Colonial-Style Cape Cod Home with Central A/C
2. How many vacation rentals have private pools in Dennis?
There are 5 vacation rentals with private pools near Dennis. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Dennis are best for families?
If you are looking for a family-friendly vacation home in Dennis, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Dennis:
4. How many Rentbyowner vacation rentals are available in Dennis?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 206 in the Dennis 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 Dennis.
5. What is the cancellation policy for vacation rentals in Dennis, Massachusetts?
The cancellation policy varies depending on the specific property listing. You should review the details listed for each vacation rental in Dennis, Massachusetts, to understand the terms and any potential fees or refund conditions. If you have questions, reaching out directly to the property owner can provide clarity.
6. Are there any specific check-in and check-out times I should be aware of when booking in this area?
Check-in and check-out times are determined by each vacation rental’s host. You can find the specific times listed on your reservation details, or contact the property owner directly for confirmation to ensure a smooth arrival and departure process.
7. Can I see photos and read reviews before booking a vacation rental in Dennis?
Yes, detailed photos and guest reviews are available on the listing page for each property. These resources help you assess the quality and suitability of the vacation rentals here, making it easier to choose the perfect accommodation for your stay.
8. What amenities are typically included in vacation rentals in this region?
Most vacation rentals in Dennis offer amenities such as Wi-Fi, kitchen facilities, parking, and outdoor spaces. The specific amenities can vary, so it's best to check each listing for detailed information to find a property that meets your needs.
9. How do I communicate with the property owner if I have special requests or questions during my stay?
You can contact the property owner directly through the messaging system provided on the booking platform. This allows you to ask about special requests or clarify any concerns before or during your visit to ensure a comfortable stay in the area.
Dennis Top Rated Vacation Rentals
House
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- Pool
Apartment
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- Pool
