Dennis Vacation Rentals Cozy cottages, condos, and homes for rent in and around Dennis, MA. Where Massachusetts Cape Cod Area Dennis Falmouth Hyannis Yarmouth - People 1 + 2 + 3 + 4 + 5 + 6 + 7 + 8 + 9 + 10 + 11 + 12 + 13 + 14 + 15 + 16 + 17 + 18 + 19 + 20 + 21 + 22 + 23 + 24 + 25 + 26 + 27 + 28 + 29 + 30 + 31 + 32 + 33 + 34 + 35 + 36 + 37 + 38 + 39 + 40 + Search View all Mid Cape Cod Properties USA > Massachusetts > Cape Cod > Dennis Visit Dennis White picket fences, cedar shingles worn gray with sea spray, and hydrangeas spilling out of the garden. When you visit Dennis, you enter a town that begs you to slow down, dig your toes in the sand, and exhale. This mid-Cape beauty has two golf courses–Dennis Pines and Dennis Highlands–to test your skills. Splash or surf at one of the town’s shore points and then head inland for more fun at Scargo Lake. Shoppers can score coastal finds at one of Dennis’ boutiques or galleries. When you stay in Dennis, you get the best of the Cape. Find Your Dennis Rental 321 Winter St Hyannis, MA 2 Bdrms 2 Baths 6 Guests Pet Friendly From $175.00 per night + taxes & fees View Details Featured Property 4 Leeward Run Yarmouth, MA 4 Bdrms 2.5 Baths 8 Guests From $277.00 5.0 per night + taxes & fees View Details Featured Property 430 Davisville Road East Falmouth, MA 2 Bdrms 1 Baths 4 Guests Pet Friendly From $173.00 4.9 per night + taxes & fees View Details Featured Property 146 Telegraph Dennis Port, MA 3 Bdrms 2.5 Baths 6 Guests From $500.00 5.0 per night + taxes & fees View Details Search while moving Featured DennisVacation Rentals From $500 / night 146 Telegraph Dennis Port, MA 6 Guests 3 Bdrms 2.5 Baths From $277 / night 4 Leeward Run Yarmouth, MA 8 Guests 4 Bdrms 2.5 Baths From $173 / night 430 Davisville Road East Falmouth, MA 4 Guests 2 Bdrms 1 Baths Your Local TeamLocally Owned and Operated In DennisRemember, when you rent with SkyRun, you can expect superior, prompt, and personalized service that’s hard to find in a top-down rental corporation. Enjoy a personal relationship with your property manager, who can answer any questions and address all concerns promptly. Have a question about local activities, amenities, or services? Our local staff can provide recommendations for getting the most out of your stay. Our property managers are just a stone’s throw away from most of our rentals. That means they’re available to step in to help with any situation. Paul Fistori is a 20+ year Cape Cod resident who grew up in the area. Paul has had a very successful decades long career in High Tech and is transitioning to his true passion, property management. For years, he’s had a side hustle flipping houses as a licensed contractor and built up a portfolio of rental properties he manages. He enjoys boating the waters of the Cape and its glorious beaches and golf courses. Paul FistoriDennis, MAOwner, SkyRun Cape CodLet's Talk! Beaches and Areas Things to Do Check-In Instructions Property Damage Waiver Travel Insurance Chapin Memorial BeachThis spot, backed by sand dunes, opens to panoramas of Cape Cod Bay and thanks to its size, doesn’t feel crowded, even in mid-summer. Surfers love the strong tides along the ocean and tidal pools are mini-marine ecosystems to explore. Note that parking is limited and sunbathers might not enjoy the rockier beaches. Princess BeachCape Cod conjures images of oceanside play, but family-friendly Princess Beach’s home on Scargo Lake makes it an excellent choice for splashing, relaxing, and exploring. Add in a playground, grill area, and restroom access, and you’ll soon see why this spot fills up fast on warm summer days. Corporation BeachLeave the big waves to the adventures–Corporation Beach’s allure comes in the form of calm waters and rolling waves that invite kids and kids at heart to float and frolic. Take the edge off the heat with ice cream and more at the spot’s concession stand and relax–ample parking means you won’t have to fight the crowds. Make sure to stay until low tide when tidal pools emerge. Howes BeachYet another beach gem where you can spy Cape Cod Bay! Views from Howe’s Beach’s views only get better when scaling sand dunes to capture marine scenes for miles. Calm waters mean ideal swimming conditions, but note that parking fills up fast at this popular spot. Scargo BeachLake life is just minutes away from the ocean! Think less relaxing lakeside and more kayaking, paddleboarding, and water adventuring from this spot. Swimmers can splash around unencumbered in the roped-off area free of other activities. Note that this is a great option if Princess Beach’s crowds swell. Mayflower BeachBodyboarding or swimming, sandcastle construction or just splashing about, Mayflower Beach is popular with good reason. Wide beaches play host to games of frisbee and gentle waves means little ones can swim. Views of Cape Cod Bay, lots of parking (though it can fill up), lifeguards, and a concession stand add up to a perfect Cape Cod beach day. Bayview BeachLow tide means long walks and tidal pool exploration. Add in vistas of Nantucket Sound and low dunes and Bayview Beach offers a unique Dennis oceanside escape. Note that currents can be rough here and lifeguards don’t patrol this stretch. Note that the parking is for Dennis residents only. Arts and CultureCatch a show at the Cape Playhouse, America’s longest-running professional summer theater. Some of Broadway’s best light up Dennis when the temps climb and check out children’s programming, including summer arts programs. Art lovers can walk through the galleries of the Cape Cod Museum of Art and marvel at the more than 2,000 permanent installations and rotating exhibitions. Make sure to save time to stroll through the museum’s sculpture garden where flora, fauna, and creativity intersect for a total sensory experience. FishingMaybe you should plan your Dennis stay according to what fish are biting. Spring finds schools of striped bass. Summer’s heat has the bluefish and flounder biting your bait. Fall’s cooler weather means the striped bass pass through Dennis’ waters on their way to their winter homes. Another bonus? Dennis offers saltwater and freshwater fishing options at Scargo Lake, so you can see where the fish bite best. GolfingTwo Dennis golfing opportunities invite you to test your swing at Dennis Pines and Dennis Highlands. Dennis Pines will test your skills through all of its 7,000 yards. This par-72 course has the rep as one of the Cape’s best places to tee off. Dennis Highlands can’t be beaten for its natural beauty along the par-71 course, lined with rugged pines and wildflower blooms. Both courses offer year-round play, so book a tee time and see which course becomes your new favorite. For the History BuffsDennis embraces its colonial past and invites visitors to step back in time.In July and August, the West Dennis Graded School and Maritime Museum turns back time to the Cape’s 1700s maritime past. Visit the town’s namesake at the Josiah Dennis Manse and wander through the rooms to feel what early Dennis life was like. The Bass River Lighthouse illuminated the seas with a 12-miles range and today operates as an inn. ShoppingCoastal flair abounds at Dennis’ retailers, with artisan goods to one-of-a-kind boutique finds to farmers’ market favorites. Stop into the Dennis Public Market and savor local foods and load up on artisan goods. Art and antiques also abound at galleries and shops. Simply put, Dennis ticks all the retail boxes. Scargo TowerTop-notch views await climbers who scale Scargo Tower’s 30 feet–a short climb with big rewards. See from the Lower Cape all the way to Provincetown. Check the Town of Dennis for hours of operation. On the waterIn, on, or high above, Dennis’ waters mean endless adventures. Swim or kayak at Scargo Lake and of course one of the town’s shore points. Book a time parasailing high above the water or grab a kayak to explore. Fishing charters take anglers to the best spots. Hiking and BikingThe Cape Cod Rail tail winds through Dennis and walkers, bikers, and runs love to explore this part of the Cape on its paved path. Spy marshland wildlife and even see a cranberry bog. The trail even has an unpaved shoulder for horseback riders. Check-In Instructions Check-in is 4:00pm ET and check-out is 10:00am ET. A check-in instructions email will be distributed to guests 7 days prior to arrival date containing directions and access information for the property. In most cases guests will access a property via a lockbox or smart lock using the given access code. Early check-ins can only be confirmed on the day of arrival. Guests must depart the property by the check-out time unless a late checkout has been coordinated and confirmed with the SkyRun office. Late check-outs must be coordinated directly with the SkyRun office no later than 9am on the day of departure; please note that if we have an incoming guest we will not be able to accommodate a late checkout. We ask that guests remove major trash from the unit, return the furniture to it’s original location, and load and run the dishwasher. Parking Parking may be limited. The check-in instructions email will contain information regarding parking at your property. Any parking fines assessed to your vehicles during your stay will be billed to you if they are billed to us. Parking fines can be significant. Property Damage Waiver Enjoy peace-of-mind with our incidental damage protection. SkyRun includes a property damage protection waiver on each reservation. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure. It does not cover damage that is willful, the result of negligence, or damaged caused by the misuse of household items. It also doesn’t cover unreported damage. SkyRun doesn’t charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is non-refundable. If during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss”, and the property owner’s insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file. Coverage is provided to you and all travelling companions that are staying in the home overnight during your stay. Coverage is not provided for loss due to: Your intentional acts or gross negligence. Any damage that occurs if you are in violation of the terms and conditions (including but not limited to having more than maximum occupancy or having a party). Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you. Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation unless substantiated by a police report. Your Duties in the Event of Damage. You must: Take all reasonable, necessary steps to protect the property and prevent further damage to it. Report the loss in writing (email ok) prior to check-out to the SkyRun staff. Provide us documentation such as pictures to substantiate the claim. Travel Insurance Nationwide® Travel Insurance protects your vacation investment against unforeseen events like a hurricane, sickness, injury, flight cancellation, job loss and much more. Group coverage protects everyone in your traveling party for one low price. Property Management You Can Trust Owning a vacation rental shouldn’t be stressful. Let SkyRun ease your worries and increase your revenue with our vacation rental management solutions. Why choose SkyRun? As a locally owned & operated business, our homeowners are not just a number to us, they’re our neighbors. But as a franchise, we have access to tools and tech that help you stay ahead of the game. That’s why thousands of second homeowners trust us with their properties. Learn More “My property’s income has doubled in the last year! SkyRun is a great business partner to me and their willingness to listen and grow revenue has been stellar.” Kay JohnsonDestin, FL SkyRun has exceeded my expectations…The personal touch of a small business, with the professionalism, experience and technology of a big company. Can’t ask for anything better! EliasPhoenix, AZ SkyRun’s staff has always treated my properties as if they were their own, and that’s such a comforting feeling. I’m very happy with the income stream generated through SkyRun’s property management! KarenWondervu, CO Dennis Blog Do I Need Short-Term Rental Insurance for My Vacation Property? Read More How to Turn Your House into an Airbnb: A Complete Guide from Vacation Rental Experts Read More SkyRun Selects PriceLabs’ Revenue Management Platform to Maximize Vacation Rental Revenue Read More SkyRun Named Among Top New & Emerging and Fastest Growing Franchises Read More View All Explore Nearby Areas FalmouthYarmouth Dennis Frequently Asked Questions How do I know I’m getting a good vacation rental? SkyRun provides photos, virtual tours, maps, amenity details and reviews about the property you will be renting. Our staff has first-hand knowledge of each property, so don't hesitate to call us if you have any questions. What’s included? Our rentals come fully furnished including TVs, high-speed internet, linens and towels, a microwave, dishes, pots, pans, and other kitchen essentials. We sweat the details and provide supplies like shampoo, conditioner, tissues, paper towels, dishwasher detergent, soaps, trash bags, etc. We provide everything you expect from a fine hotel, and then some. Refer to individual listings to see more amenity information, and please contact us directly if you still have questions. Am I getting a good deal? When you book direct with SkyRun you avoid paying service fees that traditional listing sites like Airbnb and Vrbo charge. Our prices are also competitive with rent-from-owner rates, but we offer professional service, optional travel insurance, and immediate on-site assistance should the need arise. In addition, we offer exclusive discounts from local businesses, available only to SkyRun guests. SkyRun can help you plan and save on your entire vacation experience, not only the rental itself. We also offer a fantastic value on lodging booked within 30 - 60 days of arrival with our dynamically adjusted rates. How does travel insurance work? Travel insurance is an optional addition to your total rental charges. It is offered on our reservation form at the time of booking. It is also usually offered at the time of booking when you booked with a 3rd party booking site. You can also add travel insurance onto your reservation within 48 hours of booking with SkyRun. The cost of travel insurance varies and is usually between 7% - 9.5% of your total reservation cost depending on the coverage type. If you do not have travel insurance, you can not cancel your reservation for any reason. How do I rent a property? What are the deposit and payment terms? You can rent any of our properties by booking directly on this website using a credit card or you can call to book a reservation if you would like to speak with a vacation planner. When you book, 1/3 of your total reservation cost or a minimum of $300 is charged as a non-refundable deposit to secure your rental. 30 days before your arrival, the remaining amount is due and becomes non-refundable if you need to cancel for any reason (see travel insurance above for exceptions). At this time, the credit card we have on file will be automatically charged for the balance. How do I check-in? For most properties, SkyRun utilizes a convenient keypad lock system which allows you to enter your vacation rental using a personalized access code, as opposed to having to pick up a key and worrying about keeping track of it during your stay. This also saves you the trouble of coming to a check-in center beforehand. Your welcome packet will be in your rental upon arrival, and our staff is always only a phone call away if any questions arise. What are the house rules? No smoking and no pets (unless specifically designated as a pet-friendly property) are allowed in the rentals. House parties and exceeding the maximum occupancy at any time are prohibited. As in your own home, renters are of course subject to citations for noise violations, etc, handed down by public officials. Remember you are staying as a guest in someone's home, where much investment has been made to make your stay enjoyable; please treat all private property with the respect it deserves. Sign up for emails Trip inspiration, special offers, and vacation planning tips. Name(Required) First Last Email By submitting this form, I agree to SkyRun’s Privacy Policy Δ
