
Holiday rentals in Dennis
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Top-rated holiday rentals in Dennis
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Relaxing Retreat | King Beds * Sauna * Bar Shed
Welcome to Cape Away, your charming family & pet-friendly retreat! Enjoy a fully stocked kitchen, cozy fireplaces, sauna, and outdoor shower. Unwind with dozens of board games, dart board, fire pit, and BBQ. The fully fenced private backyard offers beach gear, a bar shed and lounge area. We are perfectly located just 5–20 minutes from top rated restaurants and beaches, making it your ideal home base. With premium amenities, thoughtful touches it’s the perfect space to escape, explore and relax.

★Waterview ★Pet Friendly ★Kayaks ★Trails ★
Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

Cozy Cottage
Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property.

Romantic Cottage w/ Bikes, Paddle Boards & Kayaks
This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

Local Beach+ Fireplace + Hot Tub Under the *Stars*
Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & high-end sofas in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps 🛋️ Comfy Furnishings➕Stocked Kitchen Watch the birds, relax out back in peace & privacy or go explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

Magical Writers Cabin + hot tub in Wellfleet Woods
Escape to our unique Writer’s Cabin in the peaceful woods of Wellfleet—a magical retreat that feels like you're staying in a treehouse! You'll be surrounded by nature yet just minutes' drive from stunning beaches, crystal-clear ponds, scenic trails, and a short stroll to charming Wellfleet harbor and quaint town center. Relax and unwind at our brand-new Magnolia Spa (opening in June), featuring a hot tub and sauna. On-site massage therapy begins in July—ask us about exclusive guest rates!

Romantic getaway suite
GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

Apartment suite|Firepit|Private Deck|Pond Access
Enjoy a stylish experience at this centrally-located spot. Our newly built apartment suite is within walking distance of Dennis Port for restaurants, yoga, and an organic market. Private parking, entrance, and deck along w/ water access to Swan Pond. A full kitchen & Bath equipped with a new LG washer + dryer makes this space feel like your home away from home. Explore, play, rest & relax. We have all you need for a wonderful retreat to make your trip to the Cape an enjoyable one.

Lakefront House/Private Dock/Year Round Hot Tub/AC
Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

Cape Cod Cottage by the Bay!
Classic, beautifully crafted, newer cottage by Cape Cod Bay. All amenities. Stainless steel kitchen, Cathedral ceilings, Wide plank wood floors, water view. 2 min walk to one of the best beaches on the Cape! Quiet locale in the historic village of Quivet Neck, within East Dennis. 35 miles to Provincetown. I do not allow pets. I have family members with severe allergies who use the cottage. There is no AC at this cottage. I have 15 windows, 4 fans and an ocean breeze.

@TheCapeSummerHouse - 2bdrm Cottage in Dennisport
Explore Cape Cod from a Beautiful Cottage in Dennisport Village Freshly updated and sunny! This cozy cottage exudes coastal charm. It has a large yard perfect for the kids to play & located just .2 miles to Glendon Beach on Nantucket Sound. It’s a great place to get away for a Cape Cod vacation: central AC, fenced-in backyard with a Weber gas Grill & fire-pit, quintessential outdoor shower, WiFi, Smart TV’s, updated kitchen including a dishwasher, washer & dryer.

Fall Smores! Close to beach w/modern amenities
Just 5 minutes from the beach, this updated Cape Cod home is perfect for small families seeking a relaxing getaway. Inside, enjoy a remodeled space with modern comforts and cozy charm. Out back, unwind on the patio with a lush lawn and easy-start gas fire pit—great for dinners or s’mores under the stars. Stocked with linens, beach gear, toys, games, Wi-Fi, AC, full kitchen, and grill. Close to Holiday Hill mini golf, ice cream, and seafood shacks!
Popular amenities for Dennis holiday rentals
Other great holiday rentals in Dennis

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

Gorgeous Home 1 mi to Beach, by Cape Cod Bikepath

Claw Foot Tub & King Bed at Club Tanuki Cottage

Walk to Beach, Lake & Downtown

ONE Minute walk to BEACH! High end home special!

Nehemiahs Nest: Healing Cape Cod Pond View Cottage

Modern Luxury Apt. | 7 min from Commons

Billy's Beach Bungalow
When is the best time to visit Dennis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹20,365 | ₹21,507 | ₹21,507 | ₹21,946 | ₹22,999 | ₹26,774 | ₹31,602 | ₹30,724 | ₹23,789 | ₹20,102 | ₹20,804 | ₹21,946 |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Quick stats about holiday rentals in Dennis

Total holiday rentals
Explore 1,660 holiday rentals in Dennis

Nightly prices starting at
Dennis holiday rentals start at ₹3,511 per night before taxes and fees

Verified guest reviews
Over 51,650 verified reviews to help you choose

Family-friendly holiday rentals
1,290 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 370 rentals that welcome pets

Holiday rentals with a pool
230 properties feature pools

Rentals with dedicated workspaces
560 properties have a dedicated workspace

Wifi availability
1,640 of Dennis holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Dennis rentals

4.8 Average rating
Dennis stays are highly rated by guests – averaging 4.8 out of 5!
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- Cape Cod
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